تحضير ثايودايزول 2

Synthesis and Biological Evaluation of 5-Fatty-acylamido-1, 3, 4-
Thiadiazole-2-Thioglycosides
Srikanth Vudhgiria, c, Dhevendar Koudeb, c, Dileep Kumar Veeragonib, c, Sunil Misrab, c,
R. B. N. Prasada, c, Ram Chandra Reddy Jala* a, c
a
Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad-
500007, India
b
Pharmacology & Toxicology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka,
Hyderabad-500007, India
c
Academy of Scientific and Innovative Research, New Delhi, India
Correspondence:
Dr. Ram Chandra Reddy Jala
Centre for Lipid Research
CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500007, India
E-mail: jrcreddy10@gmail.com, ramchandra@iict.res.in
Tel.: +91-40-27191838
EXPERIMENTAL
Materials and General Experimental Procedures
All the chemicals were of analytical grade obtained from different commercial sources and
used without any further purification. All the dry reactions were carried out under nitrogen
atmosphere using anhydrous freshly distilled solvents and sieved through molecular sieves (4
Å) in flame dried glassware using standard gas-light syringes and septa. Reactions were
monitored on TLC plates (Coated with TLC grade silica gel, obtained from Merck) and the
spots were detected by iodine vapours. Column chromatography was performed on silica gel
(100-200 mesh) procured from Qualigens (India) using freshly distilled solvents. All the 1H-
NMR and 13C-NMR spectra were recorded on a Bruker UXNMR (Operating for 1H-NMR at
13
300 MHz, 500 MHz, 400 MHz and for C-NMR at 75 MHz, 100 MHz, 125 MHz)
spectrometer using TMS (δ = 0) as an internal standard for chemical shifts (δ) in CDCl3,
CD3OD, CF3COOD and DMSO – d6 at 25 °C. Mass spectra were recorded with HRMS, ESI-
MS (Electron Spray Ionization Technique). IR spectra were recorded with a Perkin-Elmer
FT-IR spectrum BX. The melting points were determined on a Barnstead Electrothermal
9200 instrument.
General Procedure for the Synthesis of Fatty Acid Chlorides (2a–2j)
To a stirred solution of fatty acid in dichloromethane (DCM), catalytic amount of dimethyl

formamide (DMF) was added and the contents were stirred at 0 °C. Oxalyl chloride was
added under nitrogen atmosphere and the reaction mixture was further stirred at 0 °C for 3 h.
Then reaction mixture was concentrated under reduced pressure to remove DCM and excess
oxalyl chloride. Later crude acid chloride dissolved in DCM was used for the next step
directly under nitrogen atmosphere.
5-Amino-1, 3, 4-thiadiazole-2-thiol (3)
Anhydrous sodium carbonate (5.27 g) and carbon disulphide (8.33 g, 109 mmol) were added
slowly to a stirred solution of thiosemicarbazide (10 g, 109 mmol) in absolute ethanol. The
mixture was stirred under reflux for 1 h and it was later heated at 75–80 oC for 4 h. Then
solvent was removed under reduced pressure and the residue was dissolved in water (50 mL)
and acidified with conc. HCl to give a desired product with 84% yield (5.4 g). Mp: 234-236
o
C. 1H-NMR (300 MHz, CDCl3+DMSO-d6) δ (ppm) = 13.12 (s, 1H), 6.98 (s, 2H); 13
C-
1
NMR (75 MHz, CDCl3+DMSO-d6) δ (ppm) = 181.1, 161.6; IR (KBr): 3331, 3265, 2751,
2548, 1556 cm-1; ESI-MS: m/z at 131 [M - H].
General Procedure for the Synthesis of 5-Fatty-acylamido-1, 3, 4-thiadiazole-2-thiols

(4a-4j)
To a stirred solution of 5-amino-1, 3, 4-thiadiazole-2-thiol (3) (1 eq.) in DCM (5 mL) and
triethyl amine (0.5 eq.), acid chloride (1 eq.) was added dropwise under nitrogen atmosphere.
Then the reaction mixture was stirred at room temperature for 6 h. The progress of reaction
was monitored by TLC with UV detection. After complete conversion, water was added and
the crude product was extracted with DCM and purified by column chromatography to get
the desired product with 80 – 88% yield.
5-Hexanamido-1, 3, 4-thiadiazole-2-thiol (4a)
This crude compound was subjected to silica gel column chromatography and the required
product was eluted in solvent mixture (hexane: EtOAc, 70: 30, v/v) as a white solid with 84%
yield. 1H-NMR (400 MHz, CDCl3+DMSO-d6) δ (ppm) = 13.48 (s, 1H), 11.48 (s, 1H), 2.48
(t, J = 7.45 Hz, 2H), 1.70 – 1.77 (m, 2H), 1.32 – 1.37 (m, 4H), 0.91 (t, J = 6.96 Hz, 3H); 13C-
NMR (75 MHz, CDCl3+DMSO-d6) δ (ppm) = 182.3, 170.6, 170.3, 159.9, 150.7, 44.3, 33.3,
33.2, 29.1, 22.6, 22.6, 20.3, 12.1, 7.0; IR (KBr): 3406, 3163, 2925, 2854, 1687, 1572, 1310,
1067, 670 cm-1; ESI-MS: m/z at 230 [M - H].
5-Octanamido-1, 3, 4-thiadiazole-2-thiol (4b)
13C-NMR
(t, J = 7.42 Hz, 2H), 1.63 (m, 2H), 1.28 (m, 8H), 0.87 (t, J = 6.60 Hz, 3H); (75
MHz, CDCl3+DMSO-d6) δ (ppm) = 182.9, 171.1, 151.3, 33.8, 30, 27.4, 27.3, 23.3, 21, 12.6;
IR (KBr): 3417, 3169, 2922, 2852, 1686, 1581, 1466, 1304, 1217, 1064, 770 cm-1; ESI-MS:
m/z at 258 [M - H].
5-Decanamido-1, 3, 4-thiadiazole-2-thiol (4c)
2
13C-NMR
(t, J = 7.45 Hz, 2H), 1.65 (m, 2H), 1.25 (m, 12H), 0.87 (t, J = 7.21 Hz, 3H); (75
MHz, CDCl3+DMSO-d6) δ (ppm) = 182.9, 171.1, 151.4, 33.8, 30.2, 27.8, 27.6, 27.5, 23.4,
21.1, 12.7; IR (KBr): 3418, 2932, 2856, 1687, 1578, 1483, 1303, 1218, 771 cm-1; ESI-MS:
m/z at 286 [M -H].
N-(5-Mercapto-1, 3, 4-thiadiazol-2-yl) undec-10-enamide (4d)
– 5.85 (m, 1H), 4.89 – 5.00 (m, 2H), 2.41 (t, J = 7.42 Hz, 2H), 1.99 – 2.05 (m, 2H), 1.63 (m,
2H), 1.29 (m, 10H); 13C-NMR (75 MHz, CDCl3+DMSO-d6) δ (ppm) = 183.8, 172.0, 171.8,
152.2, 138.5, 114.1, 34.7, 33.2, 28.6, 28.4, 28.2, 24.3; IR (KBr): 3441, 3112, 2922, 2852,
1698, 1573, 1379, 1215, 1065, 759, 553 cm-1; ESI-MS: m/z at 298 [M - H].
5-Dodecanamido-1, 3, 4-thiadiazole-2-thiol (4e)
yield. 1H-NMR (300 MHz, CDCl3+CF3COOD-d) δ (ppm) = 2.64 (t, J = 7.42 Hz, 2H), 1.78
(m, 2H), 1.29 (m, 16H), 0.89 (t, J = 5.77 Hz, 3H); 13C-NMR (75 MHz, CDCl3+CF3COOD-
d) δ (ppm) = 175.7, 36.3, 32.0, 29.7, 29.4, 29.2, 29.0, 25.2, 22.7, 13.7; IR (KBr): 3407, 3019,
2918, 2850, 1696, 1580, 1468, 1312, 1164, 1063, 669 cm-1; ESI-MS: m/z at 314 [M - H].
5-Tetradecanamido-1, 3, 4-thiadiazole-2-thiol (4f)
13C-NMR
- 1.79 (m, 2H), 1.27 (m, 20H), 0.88 (t, J = 6.05 Hz, 3H); (75 MHz,
CDCl3+CF3COOD-d) δ (ppm) = 174.7, 36.1, 31.9, 29.6, 29.6, 29.5, 29.3, 29.3, 29.1, 28.9,
25.0, 22.7, 13.9; IR (KBr): 3408, 3175, 2919, 2850, 1698, 1582, 1482, 1383, 1216, 1114
1063, 771 cm-1; ESI-MS: m/z at 342 [M - H].
5-Hexadecanamido-1, 3, 4-thiadiazole-2-thiol (4g)
3
d) δ (ppm) = 175.4, 36.2, 32.1, 29.8, 29.7, 29.6, 29.5, 29.4, 29.2, 29.0, 25.1, 22.8, 13.8; IR
(KBr): 3156, 3015, 2922, 2852, 1698, 1573, 1467, 1310, 1065, 759 cm-1; ESI-MS: m/z at
370 [M - H].
5-Octadecanamido-1, 3, 4-thiadiazole-2-thiol (4h)
d) δ (ppm) = 174.7, 36.2, 34.1, 32.0, 29.8, 29.5, 29.4, 29.2, 29.1, 29.1, 29.0, 24.9, 24.7, 22.7,
13.8; IR (KBr): 3407, 3107, 2918, 2850, 1696, 1581, 1468, 1216, 1063, 772, 669 cm-1; ESI-
MS: m/z at 398 [M - H].
5-Oleylamido-1, 3, 4-thiadiazole-2-thiol (4i)
– 5.42 (m, 2H), 2.41 (t, J = 7.42 Hz, 2H), 1.96 (m, 4H), 1.64 (m, 2H), 1.26 (m, 20H), 0.87 (t,
J = 6.87 Hz, 3H); 13C-NMR (75 MHz, CDCl3+DMSO-d6) δ (ppm) = 183.6, 171.6, 152.0,
129.3, 129.1, 34.3, 31.4, 30.7, 28.5, 28.3, 28.1, 27.9, 27.8, 26.1, 23.8, 21.5, 13.1; IR (KBr):
3441, 3111, 2922, 2851, 1698, 1573, 1410, 1310, 1215, 1170, 963, 758, 669 cm-1; ESI-MS:
m/z at 396 [M - H].
5-Erucylamido-1, 3, 4-thiadiazole-2-thiol (4j)
– 5.37 (m, 2H), 2.41 (t, J = 7.42 Hz, 2H), 1.94 – 2.01 (m, 4H), 1.61 – 1.66 (m, 2H), 1.25 (m,
28H), 0.87 (t, J = 6.87 Hz, 3H); 13C-NMR (75 MHz, CDCl3+DMSO-d6) δ (ppm) = 183.3,
171.3, 151.7, 129.04, 128.5, 34.1, 31.2, 30.5, 28.2, 28.1, 27.9, 27.8, 25.8, 23.6, 21.3, 12.9; IR
(KBr): 3442, 3156, 2922, 2852, 1698, 1573, 1467, 1379, 1216, 1065, 759, 669 cm-1; ESI-
MS: m/z at 452 [M - H].
4
1, 2, 3, 4, 6-Penta-O-acetyl-β-D-galactopyranoside (5)
A mixture of galactose (8.0 g, 44.43 mmol) and sodium acetate (10.92 g, 133.29 mmol) was
dissolved in acetic anhydride (68.8 mL, 458 mmol). The reaction mixture was refluxed for 4
h at 90 °C and it was cooled to room temperature and then poured into the beaker containing
crushed ice (500 mL) under stirring conditions. The penta acetate was precipitated and the
ppt was filtered and washed with ice-cold water until the odour of the acetic acid was
disappeared. The crude product was purified by recrystalization from MeOH to afford the
title compound (15.93 g, 92 %) as a white crystalline solid. Mp: 142 - 145 oC; 1H-NMR (400
MHz, CDCl3) δ (ppm) = 5.71 (d, J = 8.31 Hz, 1H), 5.43 (m, 1H), 5.33 (t, J = 8.31 Hz, 1H),
5.09 (dd, J = 3.42, 10.39 Hz, 1H), 4.1 – 4.19 (m, 2H), 4.04 – 4.08 (m, 1H), 2.16 (s, 3H), 2.12
(s, 3H), 2.04 (s, 6H), 1.99 (s, 3H); C-NMR (100 MHz, CDCl3) δ (ppm) = 170, 169.8,
13
169.6, 169.1, 168.7, 91.8, 71.4, 70.5, 67.6, 66.6, 60.8, 20.5, 20.4, 20.3; IR (CHCl3): 3027,
2969, 2951, 2907,1756, 1743, 1422, 1371, 1322, 1225, 1067,1048, 912, 756, 704, 641,599
cm -1; HRMS (ESI) m/z [M + Na]-calc for C16H22O11Na 413.10543 found 413.10449.
2, 3, 4, 6-Tetra-O-acetyl-galactopyranose hemiacetal (6)
Hydrazine acetate (2 g, 22.56 mmol) was added to a solution of 1, 2, 3, 4, 6-penta-O-acetyl-β-

D-galactopyranoside (8 g, 20.5 mmol) in DMF (80 mL) at 50 °C and stirred the reaction
mixture for 2 h under N2. When TLC (hexane: EtOAc, 1:1, v/v) showed the formation of
product and the disappearance of starting materials, the mixture was diluted with EtOAc,
washed with aqueous 5% NaCl and water, dried over anhydrous Na 2SO4 and concentrated
successively to give yellow oil. This crude oil was subjected to silica gel column
chromatography. The required product was eluted in solvent mixture (EtOAc: hexane, 35: 65,
v/v) as a syrup (92%, 6.56 g). 1H-NMR (500 MHz, CDCl3) δ (ppm) = 5.54 (t, J = 9.9 Hz,
1H), 5.46 (d, J = 2.8 Hz, 1H), 5.09 (t, J = 9.4 Hz, 1H), 4.8 - 4.9 (m, 1H), 4.22 - 4.29 (m, 2H),
4.10 – 4.16 (m, 1H), 2.10 (s, 3H), 2.08 (s, 3H), 2.04 (s, 3H), 2.02 (s, 3H); 13
C-NMR (75
MHz, CDCl3) δ (ppm) = 171.06,170.5 170.3, 169.7, 95.3, 89.9 72.9, 72.4, 71.8, 71.1, 69.9,
68.4, 66.9, 61.9, 60.5, 30.1, 29.6, 20.68, 20.6; IR (CHCl3): 3460.6, 3024.4, 1748.8, 1369.5,
1235.7, 1038.6, 756 cm-1; HRMS (ESI) m/z [M + Na]-calc for C14H20O10Na = 371.09487
found 371.09459.
5
2, 3, 4, 6-Tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate (7)
2, 3, 4, 6-Tetra-O-acetyl-galactopyranose hemiacetal (2) (6 g, 17.24 mmol) was treated with

trichloroacetonitrile (17.2 mL, 172.4 mmol) and DBU (0.52 mL, 6.88 mmol) in anhydrous
DCM (60 mL) and stirred for 2 h at room temperature. After 2 h, the reaction mixture was
concentrated under reduced pressure and purified by silica gel column chromatography. The
required product was eluted in solvent mixture (EtOAc: hexane, 20: 80, v/v) with good yield
(77%, 6.52 g). 1H-NMR (400 MHz, CDCl3) δ (ppm) = 8.6 (s, 1H), 6.61 (d, J = 2.32 Hz, 1H),
5.57 (br s, 1H), 5.34 - 5.45 (m, 2H), 4.45 (t, J = 6.35 Hz, 1H), 4.06 – 4.19 (m, 2H), 2.18 (s,
3H), 2.02 (2s, 9H); 13
C-NMR (CDCl3, 100 MHz): δ (ppm) = 170.1, 169.9, 169.8, 169.7,
160.6, 93.3, 90.5, 68.8, 67.3, 67.2, 66.7, 61, 20.4, 20.3; IR (CHCl3): 3478, 3347, 2135,
1748.8, 1676.44, 1371, 1218, 1073, 756 cm-1;
General Procedure for Synthesis of N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-

galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) fatty-acylamides (8a-8j)
Imidate (7) (1 mmol), 5-fatty-acylamido-1, 3, 4-thiadiazole-2-thiols (4a-4j) (1.2 mmol) and
molecular sieves (4 Å) were taken in freshly distilled DCM (10 mL) at 0 °C and stirred for 30
min under nitrogen atmosphere. To this reaction mixture, trimethylsilyl
trifluoromethanesulfonate (TMSOTf, 0.3 eq.) was added dropwise at 0 °C and slowly
allowed the reaction mixture to room temperature and stirred for overnight. After completion
of all the starting materials, the reaction mixture was filtered and dissolved in CHCl 3 (30
mL). The organic layer was extracted with aq. NaHCO 3 solution, dried over anhydrous
Na2SO4 and concentrated under reduced pressure successively. The crude mixture was
purified by silica gel column chromatography. The required spot was eluted in solvent
mixture (hexane: EtOAc, 65:35, v/v) with 72 – 80 % yield.
N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)

hexanamide (8a)
yield. 1H-NMR (500 MHz, CDCl3) δ (ppm) = 5.47 (d, J = 3.35 Hz, 1H), 5.33 (t, J = 10.07
Hz, 1H), 5.10 (dd, J = 3.35, 10.07 Hz, 1H), 4.97 – 4.99 (m, 1H), 4.20 (d, J = 6.41 Hz, 2H),
4.04 (t, J = 6.41 Hz, 1H), 2.67 – 2.70 (m, 2H), 2.17 (s, 3H), 2.10 (s, 3H), 2.08 (s, 3H), 1.99 (s,
3H), 1.73 – 1.79 (m, 2H), 1.37 (m, 4H), 0.90 (t, J = 7.02 Hz, 3H); 13
C-NMR (100 MHz,
CDCl3) δ (ppm) = 171.9, 170.5, 170.1, 169.8, 169.2, 162.6, 154.8, 84.3, 75.1, 71.5, 67, 66.8,
6
61.5, 35.9, 31.1, 24.7, 22.2, 20.6, 20.4, 13.8; IR (CHCl3): 3420, 2930, 2858, 1752, 1698,
1548, 1434, 1220, 1085, 917, 769 cm-1; ESI-MS: m/z at 584 [M + Na].

octanamide (8b)
yield. 1H-NMR (400 MHz, CDCl3) δ (ppm) = 12.79 (s, 1H), 5.48 (d, J = 3.36 Hz, 1H), 5.33
(t, J = 10.02 Hz, 1H), 5.10 (dd, J = 3.30, 9.90 Hz, 1H), 4.97 (d, J = 10.02 Hz, 1H), 4.21 (d, J
= 6.35 Hz, 2H), 4.06 (t, J = 6.48 Hz, 1H), 2.69 (t, J = 6.96 Hz, 2H), 2.17 (s, 3H), 2.10 (s, 3H),
2.09 (s, 3H), 1.99 (s, 3H), 1.72 – 1.79 (m, 2H), 1.25 – 1.41 (m, 8H), 0.87 (t, J = 7.09 Hz, 3H);
13C-NMR (125 MHz, CDCl3) δ (ppm) = 172, 170.5, 170.1, 169.8, 169.2, 162.6, 154.7, 84.3,
75.1, 71.5, 67, 66.8, 61.5, 35.9, 31.7, 29.3, 29.2, 29.1, 29, 25.1, 22.5, 20.7, 20.6, 20.5, 20.4,
14; IR (CHCl3): 3422, 2931, 2858, 1753, 1547, 1371, 1218, 1058, 757 cm-1; ESI-MS: m/z at
612 [M + Na].

decanamide (8c)
(t, J = 9.91 Hz, 1H), 5.10 (dd, J = 3.35, 9.91 Hz, 1H), 4.97 (d, J = 10.07 Hz, 1H), 4.21 (d, J =
6.41 Hz, 2H), 4.05 (t, J = 6.25 Hz, 1H), 2.68 (t, J = 7.32 Hz, 2H), 2.17 (s, 3H), 2.10 (s, 3H),
2.08 (s, 3H), 1.99 (s, 3H), 1.72 – 1.78 (m, 2H), 1.25 – 1.40 (m, 12H), 0.87 (t, J = 7.17 Hz,
3H); 13C-NMR (125 MHz, CDCl3) δ (ppm) = 171.9, 170.5, 170.1, 169.8, 169.2, 162.6,
154.7, 84.3, 75.1, 71.5, 67, 66.8, 61.5, 35.9, 31.7, 29.3, 29.2, 29.1, 29, 25.1, 22.5, 20.7, 20.6,
20.5, 20.4, 14; IR (CHCl3): 3421, 2923, 2858, 1753, 1699, 1548, 1370, 1220, 1058, 917,
770, 627 cm-1; ESI-MS: m/z at 640 [M + Na].
N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) 10-

undecenamide (8d)
yield. 1H-NMR (500 MHz, CDCl3) δ (ppm) = 12.51 (s, 1H), 5.76 – 5.84 (m, 1H), 5.48 (d, J
= 3.35 Hz, 1H), 5.33 (t, J = 9.91 Hz, 1H), 5.10 (dd, J = 3.35, 9.91 Hz, 1H), 5.01 (m, 1H),
4.97 (d, J = 10.07 Hz, 1H), 4.91 – 4.93 (m, 1H), 4.21 (d, J = 6.56 Hz, 2H), 4.05 (t, J = 6.25
7
Hz, 1H), 2.68 (t, J = 7.32 Hz, 2H), 2.17 (s, 3H), 2.10 (s, 3H), 2.08 (s, 3H), 1.99 (s, 3H), 1.72
– 1.78 (m, 2H), 1.29 – 1.39 (m, 10H); 13C-NMR (100 MHz, CDCl3) δ (ppm) = 171.9, 170.5,
170.1, 169.8, 169.2, 162.5, 154.8, 139, 114.1, 84.3, 75.1, 71.5, 67, 66.8, 61.5, 35.9, 33.6,
29.2, 29, 28.8, 25.1, 20.6, 20.5, 20.4; IR (CHCl3): 3456, 3022, 2930, 2856, 1752, 1697,
1547, 1371, 1218, 1059, 916, 756 cm-1; ESI-MS: m/z at 652 [M + Na].

dodecanamide (8e)
(t, J = 10.02 Hz, 1H), 5.11 (dd, J = 3.18, 9.78 Hz, 1H), 4.97 (d, J = 10.02 Hz, 1H), 4.22 (d, J
= 6.48 Hz, 2H), 4.06 (t, J = 6.48 Hz, 1H), 2.70 (t, J = 7.45 Hz, 2H), 2.17 (s, 3H), 2.10 (s, 3H),
2.09 (s, 3H), 1.99 (s, 3H), 1.71 – 1.79 (m, 2H), 1.25 – 1.41 (m, 16H), 0.87 (t, J = 6.72 Hz,
154.8, 84.4, 75.1, 71.5, 67, 66.8, 61.5, 35.9, 31.8, 29.5, 29.4, 29.2, 29.1, 25.1, 22.6, 20.6,
20.5, 20.4, 14; IR (CHCl3): 3423, 3161, 2930, 2858, 1753, 1640, 1433, 1370, 1220, 1085,
917, 769 cm-1. ESI-MS: m/z at 668 [M + Na].

tetradecanamide (8f)
(t, J = 9.90 Hz, 1H), 5.11 (dd, J = 3.30, 9.90 Hz, 1H), 4.97 (d, J = 10.02 Hz, 1H), 4.21 (d, J =
6.35 Hz, 2H), 4.05 (t, J = 6.60 Hz, 1H), 2.69 (t, J = 7.45 Hz, 2H), 2.17 (s, 3H), 2.10 (s, 3H),
2.09 (s, 3H), 1.98 (s, 3H), 1.71 – 1.79 (m, 2H), 1.25 – 1.39 (m, 20H), 0.87 (t, J = 6.60 Hz,
154.7, 84.3, 75.1, 71.5, 67, 66.8, 61.5, 35.9, 31.8, 29.5, 29.4, 29.2, 29, 25.1, 22.6, 20.6, 20.5,
20.4, 14; IR (CHCl3): 3020, 2928, 2856, 1751, 1698, 1546, 1433, 1371, 1216, 1059, 918,
757 cm-1; ESI-MS: m/z at 696 [M + Na].

hexadecanamide (8g)
8
yield. 1H-NMR (400 MHz, CDCl3) δ (ppm) = 12.18 (s, 1H), 5.48 (m, 1H), 5.33 (t, J = 9.91
Hz, 1H), 5.10 (dd, J = 3.30, 9.91 Hz, 1H), 4.97 (d, J = 10.07 Hz, 1H), 4.20 (d, J = 6.41 Hz,
2H), 4.05 (t, J = 6.41 Hz, 1H), 2.66 (t, J = 7.32 Hz, 2H), 2.17 (s, 3H), 2.10 (s, 3H), 2.08 (s,
3H), 1.98 (s, 3H), 1.71 – 1.77 (m, 2H), 1.25 – 1.40 (m, 24H), 0.87 (t, J = 6.86 Hz, 3H); 13C-
NMR (100 MHz, CDCl3) δ (ppm) = 172, 170.5, 170.1, 169.8, 169.2, 162.6, 154.8, 84.4,
75.1, 71.5, 67, 66.8, 61.5, 35.9, 31.8, 29.5, 29.4, 29.2, 29.1, 25.1, 22.6, 20.6, 20.5, 20.4, 14;
IR (CHCl3): 3021, 2928, 2856, 1751, 1698, 1546, 143, 1371, 1216, 1060, 918, 753, 668 cm-
1
; ESI-MS: m/z at 724 [M + Na].

octadecanamide (8h)
yield. 1H-NMR (500 MHz, CDCl3) δ (ppm) = 5.48 (d, J = 3.35 Hz, 1H), 5.33 (t, J = 9.91 Hz,
1H), 5.10 (dd, J = 3.20, 9.91 Hz, 1H), 4.97 (d, J = 10.07 Hz, 1H), 4.20 (d, J = 6.41 Hz, 2H),
4.04 (t, J = 6.41 Hz, 1H), 2.65 (t, J = 7.32 Hz, 2H), 2.17 (s, 3H), 2.10 (s, 3H), 2.08 (s, 3H),
1.98 (s, 3H), 1.71 – 1.77 (m, 2H), 1.25 – 1.38 (m, 28H), 0.87 (t, J = 6.86 Hz, 3H); 13C-NMR
(125 MHz, CDCl3) δ (ppm) = 171.9, 170.5, 170.1, 169.8, 169.2, 162.6, 154.8, 84.4, 75.2,
71.5, 67, 66.8, 61.5, 36, 31.8, 29.6, 29.4, 29.3, 29.1, 25.1, 22.6, 20.6, 20.5, 20.4, 14; IR
(CHCl3): 3020, 2927, 2855, 1751, 1698, 1546, 1433, 1371, 1216, 1059, 918, 770 cm-1; ESI-
MS: m/z at 752 [M + Na].

oleoylamide (8i)
– 5.38 (m, 2H), 5.33 (t, J = 10.07 Hz, 1H), 5.10 (dd, J = 3.35, 10.07 Hz, 1H), 4.97 (d, J =
10.07 Hz, 1H), 4.20 (d, J = 6.56 Hz, 2H), 4.05 (t, J = 6.41 Hz, 1H), 2.68 (t, J = 7.32 Hz, 2H),
2.17 (s, 3H), 2.10 (s, 3H), 2.08 (s, 3H), 1.98 (s, 3H), 1.92 – 1.96 (m, 4H), 1.72 – 1.78 (m,
2H), 1.25 – 1.39 (m, 20H), 0.87 (t, J = 6.71 Hz, 3H); 13C-NMR (100 MHz, CDCl3) δ (ppm)
= 171.9, 170.5, 170.1, 169.8, 169.2, 162.5, 154.7, 130.4, 130., 84.3, 75.1, 71.5, 67, 66.8, 61.5,
35.9, 32.5, 31.7, 29.5, 29.3, 29.2, 29.1, 29, 28.9, 27.1, 25, 22.5, 20.7, 20.6, 20.5, 20.4, 14; IR
(CHCl3): 3441, 2925, 2854, 1752, 1639, 1549, 1370, 1224, 1058 cm-1; ESI-MS: m/z at 750
[M + Na].
9
erucoylamide (8j)
– 5.37 (m, 3H), 5.10 (dd, J = 3.35, 10.07 Hz, 1H), 4.97 (d, J = 9.91 Hz, 1H), 4.20 (d, J = 6.41
Hz, 2H), 4.05 (t, J = 6.41 Hz, 1H), 2.68 (t, J = 7.32 Hz, 2H), 2.17 (s, 3H), 2.10 (s, 3H), 2.08
(s, 3H), 1.99 – 2.03 (m, 4H), 1.98 (s, 3H), 1.72 – 1.78 (m, 2H), 1.26 – 1.38 (m, 28H), 0.87 (t,
J = 6.71 Hz, 3H); 13C-NMR (100 MHz, CDCl3) δ (ppm) = 171.8, 170.5, 170.1, 169.8, 169.2,
162.4, 154.8, 130.2, 129.8, 84.4, 75.2, 71.5, 67, 66.8, 61.5, 36, 32.5, 31.8, 29.6, 29.4, 29.3,
29.1, 27.1, 25, 22.6, 20.6, 20.5, 14; IR (CHCl3): 3442, 2925, 2852, 1753, 1692, 1552, 1370,
1223, 1058, 917, 721, 556 cm-1; ESI-MS: m/z at 806 [M + Na].
General Procedure for Synthesis of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-

2-yl) fatty-acylamides (9a-9j)
Compounds 8a-8j were dissolved in dry methanol that contained a catalytic amount of
sodium methoxide (Zemplen deacetylation). The reaction mixture was allowed to stir at
ambient temperature for 30 min under nitrogen atmosphere. After total consumption of
starting material, the reaction mixture was neutralized by the addition of Amberlite IR-120
(H+) resin. The reaction mixture was filtered and concentrated under reduced pressure to
obtain a crude product. This crude product was purified by silica gel column chromatography
using a solvent mixture (chloroform: methanol, 92:8, v/v) to give title compounds as white
solids with 95-97 % yield.
N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) hexanamide (9a)
product was eluted in solvent mixture (chloroform: methanol, 92: 8, v/v) as a white solid with
96% yield. 1H-NMR (300 MHz, CDCl3+CD3OD) δ (ppm) = 4.74 (d, J = 9.35 Hz, 1H), 3.99
– 4.00 (m, 1H), 3.76 - 3.82 (m, 2H), 3.62 – 3.68 (m, 1H), 3.53 – 3.57 (m, 1H), 3.39 – 3.42 (m,
1H), 2.51 (t, J = 7.42 Hz, 2H), 1.70 – 1.75 (m, 2H), 1.35 – 1.38 (m, 4H), 0.92 (t, J = 6.60 Hz,
3H); 13C-NMR (100 MHz, CDCl3+CD3OD) δ (ppm) = 184.7, 172.5, 153.1, 146.1, 99.5,
74.3, 73.2, 72.2, 70.9, 69.9, 68.9, 61.4, 60.9, 35.1, 30.8, 24.2, 21.9, 13.3; IR (KBr): 3406,
2917, 2850, 1714, 1638, 1538, 1470, 1306, 1156, 1064, 773 cm-1; HRMS (ESI) m/z [M +
H]-calc for C14H24O6N3S2 = 394.1101 found 394.1098.
10
N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) octanamide (9b)
97% yield. 1H-NMR (300 MHz, CDCl3+DMSO-d6) δ (ppm) = 13.94 (s, 1H), 4.61 (d, J =
9.62 Hz, 1H), 3.87 - 3.90 (m, 1H), 3.44 – 3.65 (m, 4H), 3.34 – 3.41 (m, 1H), 2.40 (t, J = 7.42
13C-NMR
Hz, 2H), 1.59 (m, 2H), 1.27 (m, 12H), 0.87 (t, J = 6.05 Hz, 3H); (75 MHz,
CDCl3+DMSO-d6) δ (ppm) = 182.4, 170.8, 151, 95.8, 73.4, 72, 70.8, 69.1, 68.6, 67.5, 67,
59.3, 33.4, 29.7, 27.1, 23, 20.7; IR (KBr): 3509, 2918, 2852, 1715, 1639, 1582, 1470, 1078,
1037 cm-1; HRMS (ESI) m/z [M + H]-calc for C16H28O6N3S2 = 422.1414 found 422.1403.
N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) decanamide (9c)
9.62 Hz, 1H), 3.97 (m, 1H), 3.71 - 3.74 (m, 2H), 3.66 (t, J = 9.62 Hz, 1H), 3.58 (t, J = 6.05
Hz, 1H), 3.51 (m, 1H), 2.48 (t, J = 7.42 Hz, 2H), 1.66 (m, 2H), 1.26 (m, 12H), 0.87 (t, J =
6.05 Hz, 3H); 13C-NMR (75 MHz, CDCl3+DMSO-d6) δ (ppm) = 172.5, 172.1, 156.5, 152.8,
99.4, 86.6, 78.9, 74.2, 69.8, 69.3, 68.5, 68.4, 61.2, 60.7, 35, 34.9, 31.3, 28.5, 28.6, 24.5, 24.4,
22.1, 13.3; IR (KBr): 3406, 2917, 2850, 1714, 1640, 1537, 1409, 1271, 1064, 773, 528 cm-1;
HRMS (ESI) m/z [M + H]-calc for C18H32O6N3S2 = 450.1727 found 450.1712.
N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) 10-undecenamide (9d)
98% yield. 1H-NMR (300 MHz, CDCl3+DMSO-d6) δ (ppm) = 12.27 (s, 1H), 5.72 – 5.86
(m, 1H), 4.89 – 5.01 (m, 2H), 4.81 (d, J = 9.62 Hz, 1H), 4.03 (m, 1H), 3.78 - 3.80 (m, 2H),
3.72 (t, J = 9.62 Hz, 1H), 3.62 (t, J = 5.77 Hz, 1H), 3.55 (dd, J = 3.02, 9.07 Hz, 1H), 2.49 (t, J
= 7.42 Hz, 2H), 1.99 – 2.06 (m, 2H), 1.68 (m, 2H), 1.30 (m, 10H); 13C-NMR (75 MHz,
CDCl3+DMSO-d6) δ (ppm) = 172.1, 138.7, 113.6, 99.5, 86.6, 78.9, 74.3, 69.8, 69.3, 68.5,
60.9, 35.2, 33.3, 28.8, 28.7, 28.5, 24.6, 24.5; IR (KBr): 3407, 2920, 2850, 1707, 1525, 1406,
1294, 1143, 1056, 759, 669 cm-1; HRMS (ESI) m/z [M + H]-calc for C19H32O6N3S2 =
462.1727 found 462.1712.
11
N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) dodecanamide (9e)
9.62 Hz, 1H), 3.99 (m, 1H), 3.73 -3.75 (m, 2H), 3.69 – 3.71 (m, 1H), 3.64 -3.67 (m, 1H), 3.57
– 3.60 (m, 1H), 2.41 (t, J = 7.42 Hz, 2H), 1.64 (m, 2H), 1.25 (m, 16H), 0.87 (t, J = 6.87 Hz,
3H); 13C-NMR (75 MHz, CDCl3+DMSO-d6) δ (ppm) = 183.1, 171.3, 151.6, 85.9, 78.1,
73.6, 71.4, 68.7, 59.3, 34, 30.4, 28.1, 28, 27.8, 27.6, 23.5, 21.2, 12.8; IR (KBr): 3423, 2918,
2850, 1697, 1639, 1537, 1215, 1064, 757, 669 cm-1; HRMS (ESI) m/z [M + H]-calc for
C20H36O6N3S2 = 478.2030 found 478.2040.
N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) tetradecanamide (9f)
9.62 Hz, 1H), 4.01 (m, 1H), 3.76 -3.78 (m, 2H), 3.69 (t, J = 9.07 Hz, 1H), 3.57 -3.61 (m, 1H),
3.52 (dd, J = 2.47, 9.07 Hz, 1H), 2.48 (t, J = 7.42 Hz, 2H), 1.67 (m, 2H), 1.25 (m, 20H), 0.87
(t, J = 6.61 Hz, 3H); 13C-NMR (75 MHz, CDCl3+DMSO-d6) δ (ppm) = 171.6, 160.4, 155.9,
86.6, 78.8, 74.4, 69.6, 68, 60.3, 34.9, 31.3, 29, 28.9, 28.7, 28.5, 24.5, 22.1, 13.6; IR (KBr):
3422, 2918, 2850, 1713, 1639, 1537, 1215, 1064, 770, 669 cm-1; HRMS (ESI) m/z [M + H]-
calc for C22H40O6N3S2 = 506.2353 found 506.2339.
N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) hexadecanamide (9g)
9.62 Hz, 1H), 4.00 (m, 1H), 3.76 (m, 2H), 3.65 - 3.69 (m, 1H), 3.57 -3.61 (m, 1H), 3.53 (m,
1H), 2.48 (t, J = 7.70 Hz, 2H), 1.67 (m, 2H), 1.25 (m, 24H), 0.87 (t, J = 6.87 Hz, 3H); 13C-
NMR (75 MHz, CDCl3+DMSO-d6) δ (ppm) = 170.4, 159.2, 154.9, 85.7, 78.1, 73.4, 68.5,
66.8, 59.1, 33.8, 30.2, 27.9, 27.8, 27.6, 27.5, 27.4, 23.5, 23.3, 21, 12.7; IR (KBr): 3423,
2918, 2851, 1640, 1537, 1215, 1079, 770, 669 cm-1; HRMS (ESI) m/z [M + H]-calc for
C24H44O6N3S2 = 534.2666 found 534.2656.
12
N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) octadecanamide (9h)
9.62 Hz, 1H), 3.96 (m, 1H), 3.69 - 3.72 (m, 1H), 3.57 - 3.64 (m, 4H), 2.47 (t, J = 7.70 Hz,
13C-NMR
2H), 1.65 (m, 2H), 1.25 (m, 28H), 0.87 (t, J = 6.87 Hz, 3H); (75 MHz,
CDCl3+DMSO-d6) δ (ppm) = 171.4, 160.2, 156, 86.7, 79, 74.4, 69.6, 67.9, 60.1, 34.9, 31.2,
29, 28.8, 28.7, 28.5, 24.5, 22, 13.7; IR (KBr): 3422, 2918, 2850, 1714, 1697, 1537, 1307,
1216, 1064, 771, 669 cm-1; HRMS (ESI) m/z [M + H]-calc for C26H48O6N3S2 = 562.2979
found 562.2965.
N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) oleoylamide (9i)
97% yield. 1H-NMR (300 MHz, CDCl3+DMSO-d6) δ (ppm) = 12.05 (s, 1H), 5.36 (m, 2H),
4.80 (d, J = 9.64 Hz, 1H), 4.01 (m, 1H), 3.96 (m, 1H), 3.77 – 3.82 (m, 2H), 3.59 - 3.68 (m,
2H), 2.48 (t, J = 7.42 Hz, 2H), 1.95 (m, 4H), 1.66 (m, 2H), 1.25 - 130 (m, 20H), 0.87 (t, J =
6.87 Hz, 3H); 13C-NMR (75 MHz, CDCl3+DMSO-d6) δ (ppm) = 183.3, 171.4, 151.7, 129.1,
128.9, 98.9, 69.3, 69.1, 68.2, 67.9, 60.2, 53.8, 34.1, 31.2, 30.5, 28.3, 28.1, 27.9, 27.8, 27.6,
25.8, 23.6, 21.3, 12.9; IR (KBr): 3407, 2977, 2850, 1707, 1642, 1525, 1406, 1368, 1294,
found 560.2822.
N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) erucoylamide (9j)
96% yield. 1H-NMR (300 MHz, CDCl3+DMSO-d6) δ (ppm) = 12.36 (s, 1H), 5.30 – 5.35
(m, 2H), 4.78 (d, J = 9.62 Hz, 1H), 3.97 (m, 1H), 3.71 -3.73 (m, 2H), 3.62 – 3.67 (m, 1H),
3.52 -3.59 (m, 1H), 3.49 - 3.52 (m, 1H), 2.48 (t, J = 7.52 Hz, 2H), 1.96 – 2.00 (m, 4H), 1.66
(m, 2H), 1.26 (m, 28H), 0.87 (t, J = 6.32 Hz, 3H); 13C-NMR (75 MHz, CDCl3+DMSO-d6) δ
(ppm) = 171.5, 160.3, 156, 129.7, 129.3, 86.7, 78.9, 74.5, 69.6, 68, 60.2, 34.9, 31.9, 31.2,
29.1, 29, 28.9, 28.8, 28.6, 26.6, 24.5, 22, 13.7; IR (KBr): 3345, 2920, 2850, 1707, 1526,
13
found 616.3443.
Biological Activities
Cytotoxicity Assay (MTT Assay)
Cytotoxicity assay (MTT assay) was evaluated for the compounds 8a-8j and 9a-9j as per our
earlier study1. Four different cancer cell lines and one normal cell line namely, SKOV3-
Ovarian cancer (ATCC® HTB 77™), HeLa-Cervical cancer (ATCC® CCL2™), MDAMB-
231-Breast cancer (ATCC® HTB26™), DU145-Prostate cancer (ATCC ® HTB81™) and
CHO-K1-Normal Chinese hamster ovary cell line (ATCC® CCL-61™) were obtained from
the ATCC (Bethesda, MD, USA) and maintained in DMEM supplemented with 10 % FBS, 2
mM l-glutamine, 100 U/mL penicillin, and 100 μg/mL streptomycin at 37 °C in a 5 % CO 2
incubator. After seeding of cells in 96 well culture plate, allowed to attach properly. Test
compounds of different concentrations ranging from 1 to 50 µM were added in triplicates and
incubated for 24 h. The cells were then incubated with MTT (0.5 mg/mL) for 3 h and to
dissolve the insoluble formazan crystals 100 µL DMSO was added to each well. Finally, the
absorbance of the plates was measured using a Synergy H1 multi-mode plate reader, USA.
Doxorubicin was used as a positive control for the comparison.
Antibacterial Activity
Antibacterial activity was conducted against an array of 6 bacterial strains (obtained from the
Microbial Type Culture Collection MTCC), which are as follows: Staphylococcus aureus
(MTCC 96), Staphylococcus epidermidis (MTCC 9041) and Bacillus subtilis (MTCC 441) as
Gram-positive bacteria; Escherichia coli (MTCC 443), Pseudomonas aeruginosa (MTCC
1688) and Klebsiella pneumoniae (MTCC 618) as Gram-negative bacteria. The inhibitory
zones (in mm) were determined by agar well method2 (cup plate method). Antibiotics
Streptomycin and Penicillin were used as positive controls against bacteria. Each experiment
was assessed in triplicates and all values are expressed as means ± standard error.
References
1. Vishnu Sravan, B.; Susheel Kumar, N.; Rama Krishna, D.; Nageshwara Rao, S. S.;
Misra, S.; Ranjan Patra, C. Nanotoxicology 2016, 10, 413.
2. Braude, A. I.; W. B. Sauders Company, London, Microbiology 1982.
14
Spectra
1H-NMR Spectrum of 5-Amino-1, 3, 4-thiadiazole-2-thiol (3)
13C-NMR Spectrum of 5-Amino-1, 3, 4-thiadiazole-2-thiol (3)
15
1H-NMR Spectrum of 5-Hexanamido-1, 3, 4-thiadiazole-2-thiol (4a)
13C-NMR Spectrum of 5-Hexanamido-1, 3, 4-thiadiazole-2-thiol (4a)
16
1H-NMR Spectrum of 5-Octanamido-1, 3, 4-thiadiazole-2-thiol (4b)
13C-NMR Spectrum of 5-Octanamido-1, 3, 4-thiadiazole-2-thiol (4b)
17
1H-NMR Spectrum of 5-Decanamido-1, 3, 4-thiadiazole-2-thiol (4c)
13C-NMR Spectrum of 5-Decanamido-1, 3, 4-thiadiazole-2-thiol (4c)
18
1H-NMR Spectrum of N-(5-Mercapto-1, 3, 4-thiadiazol-2-yl) undec-10-enamide (4d)
13
C-NMR Spectrum of N-(5-Mercapto-1, 3, 4-thiadiazol-2-yl) undec-10-enamide (4d)
19
1H-NMR Spectrum of 5-Dodecanamido-1, 3, 4-thiadiazole-2-thiol (4e)
13C-NMR Spectrum of 5-Dodecanamido-1, 3, 4-thiadiazole-2-thiol (4e)
20
1H-NMR Spectrum of 5-Tetradecanamido-1, 3, 4-thiadiazole-2-thiol (4f)
13C-NMR Spectrum of 5-Tetradecanamido-1, 3, 4-thiadiazole-2-thiol (4f)
21
1H-NMR Spectrum of 5-Hexadecanamido-1, 3, 4-thiadiazole-2-thiol (4g)
13
C-NMR Spectrum of 5-Hexadecanamido-1, 3, 4-thiadiazole-2-thiol (4g)
22
1H-NMR Spectrum of 5-Octadecanamido-1, 3, 4-thiadiazole-2-thiol (4h)
13C-NMR Spectrum of 5-Octadecanamido-1, 3, 4-thiadiazole-2-thiol (4h)
23
1H-NMR Spectrum of 5-Oleylamido-1, 3, 4-thiadiazole-2-thiol (4i)
13C-NMR Spectrum of 5-Oleylamido-1, 3, 4-thiadiazole-2-thiol (4i)
24
1H-NMR Spectrum of 5-Erucylamido-1, 3, 4-thiadiazole-2-thiol (4j)
13
C-NMR Spectrum of 5-Erucylamido-1, 3, 4-thiadiazole-2-thiol (4j)
25
1H-NMR Spectrum of 1, 2, 3, 4, 6-Penta-O-acetyl-β-D-galactopyranoside (5)
13C-NMR Spectrum of 1, 2, 3, 4, 6-Penta-O-acetyl-β-D-galactopyranoside (5)
26
1H-NMR Spectrum of 2, 3, 4, 6- Tetra-O- acetyl-galactopyranose hemiacetal (6)
13C-NMR Spectrum of 2, 3, 4, 6- Tetra-O- acetyl-galactopyranose hemiacetal (6)
27
1H-NMR Spectrum of 2, 3, 4, 6-Tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate
(7)
13C-NMR Spectrum of 2, 3, 4, 6-Tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate

(7)
28
1H-NMR Spectrum of N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3,
4-thiadiazol-2-yl) hexanamide (8a)
13
C-NMR Spectrum of N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3,
4-thiadiazol-2-yl) hexanamide (8a)
29
4-thiadiazol-2-yl) octanamide (8b)
13
4-thiadiazol-2-yl) octanamide (8b)
30
4-thiadiazol-2-yl) decanamide (8c)
13C-NMR Spectrum of N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3,

4-thiadiazol-2-yl) decanamide (8c)
31
4-thiadiazol-2-yl) 10-undecenamide (8d)

4-thiadiazol-2-yl) 10-undecenamide (8d)
32
4-thiadiazol-2-yl) dodecanamide (8e)
13
4-thiadiazol-2-yl) dodecanamide (8e)
33
4-thiadiazol-2-yl) tetradecanamide (8f)

4-thiadiazol-2-yl) tetradecanamide (8f)
34
4-thiadiazol-2-yl) hexadecanamide (8g)

4-thiadiazol-2-yl) hexadecanamide (8g)
35
4-thiadiazol-2-yl) octadecanamide (8h)
13
4-thiadiazol-2-yl) octadecanamide (8h)
36
4-thiadiazol-2-yl) oleoylamide (8i)
13
4-thiadiazol-2-yl) oleoylamide (8i)
37
4-thiadiazol-2-yl) erucoylamide (8j)

4-thiadiazol-2-yl) erucoylamide (8j)
38
1H-NMR Spectrum of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)
hexanamide (9a)
13C-NMR Spectrum of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)

hexanamide (9a)
39
HRMS of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) hexanamide (9a)
1
H-NMR Spectrum of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)
octanamide (9b)
40
octanamide (9b)
HRMS of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) octanamide (9b)
41
1
decanamide (9c)

decanamide (9c)
42
HRMS of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) decanamide (9c)
1H-NMR Spectrum of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) 10-

undecenamide (9d)
43
13C-NMR Spectrum of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) 10-
undecenamide (9d)
HRMS of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) 10-undecenamide

(9d)
44
dodecanamide (9e)
13
C-NMR Spectrum of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)
dodecanamide (9e)
45
HRMS of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) dodecanamide (9e)
1
46
HRMS of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) tetradecanamide (9f)
47
hexadecanamide (9g)

hexadecanamide (9g)
48
HRMS of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) hexadecanamide (9g)
1
octadecanamide (9h)
49
octadecanamide (9h)
HRMS of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) octadecanamide (9h)
50
oleoylamide (9i)

oleoylamide (9i)
51
HRMS of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-Thiadiazol-2-yl) Oleoylamide (9i)

erucoylamide (9j)
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erucoylamide (9j)
HRMS of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-Thiadiazol-2-yl) Erucoylamide (9j)
53

تحضير ثايودايزول 2

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تحضير ثايودايزول 2

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Synthesis and Biological Evaluation of 5-Fatty-acylamido-1, 3, 4-

General Procedure for the Synthesis of Fatty Acid Chlorides (2a–2j)

To a stirred solution of fatty acid in dichloromethane (DCM), catalytic amount of dimethyl

5-Amino-1, 3, 4-thiadiazole-2-thiol (3)

General Procedure for the Synthesis of 5-Fatty-acylamido-1, 3, 4-thiadiazole-2-thiols

5-Hexanamido-1, 3, 4-thiadiazole-2-thiol (4a)

5-Octanamido-1, 3, 4-thiadiazole-2-thiol (4b)

5-Decanamido-1, 3, 4-thiadiazole-2-thiol (4c)

N-(5-Mercapto-1, 3, 4-thiadiazol-2-yl) undec-10-enamide (4d)

5-Dodecanamido-1, 3, 4-thiadiazole-2-thiol (4e)

5-Tetradecanamido-1, 3, 4-thiadiazole-2-thiol (4f)

5-Hexadecanamido-1, 3, 4-thiadiazole-2-thiol (4g)

5-Octadecanamido-1, 3, 4-thiadiazole-2-thiol (4h)

5-Oleylamido-1, 3, 4-thiadiazole-2-thiol (4i)

5-Erucylamido-1, 3, 4-thiadiazole-2-thiol (4j)

2, 3, 4, 6-Tetra-O-acetyl-galactopyranose hemiacetal (6)

Hydrazine acetate (2 g, 22.56 mmol) was added to a solution of 1, 2, 3, 4, 6-penta-O-acetyl-β-

2, 3, 4, 6-Tetra-O-acetyl-galactopyranose hemiacetal (2) (6 g, 17.24 mmol) was treated with

General Procedure for Synthesis of N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-

N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)

N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)

N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)

N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) 10-

N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)

N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)

N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)

N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)

N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)

General Procedure for Synthesis of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-

N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) hexanamide (9a)

N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) decanamide (9c)

N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) 10-undecenamide (9d)

N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) tetradecanamide (9f)

N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) hexadecanamide (9g)

N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) oleoylamide (9i)

N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) erucoylamide (9j)

1H-NMR Spectrum of 5-Amino-1, 3, 4-thiadiazole-2-thiol (3)

13C-NMR Spectrum of 5-Amino-1, 3, 4-thiadiazole-2-thiol (3)

13C-NMR Spectrum of 5-Hexanamido-1, 3, 4-thiadiazole-2-thiol (4a)

13C-NMR Spectrum of 5-Octanamido-1, 3, 4-thiadiazole-2-thiol (4b)

13C-NMR Spectrum of 5-Decanamido-1, 3, 4-thiadiazole-2-thiol (4c)

13C-NMR Spectrum of 5-Dodecanamido-1, 3, 4-thiadiazole-2-thiol (4e)

13C-NMR Spectrum of 5-Tetradecanamido-1, 3, 4-thiadiazole-2-thiol (4f)

13C-NMR Spectrum of 5-Octadecanamido-1, 3, 4-thiadiazole-2-thiol (4h)

13C-NMR Spectrum of 5-Oleylamido-1, 3, 4-thiadiazole-2-thiol (4i)

13C-NMR Spectrum of 1, 2, 3, 4, 6-Penta-O-acetyl-β-D-galactopyranoside (5)

13C-NMR Spectrum of 2, 3, 4, 6- Tetra-O- acetyl-galactopyranose hemiacetal (6)

13C-NMR Spectrum of 2, 3, 4, 6-Tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate

13C-NMR Spectrum of N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3,

13C-NMR Spectrum of N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3,

13C-NMR Spectrum of N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3,

13C-NMR Spectrum of N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3,

13C-NMR Spectrum of N-(5-(2ʹ, 3ʹ, 4ʹ, 6ʹ-Tetra-O-acetyl-β-D-galactopyranosylthio)-1, 3,

13C-NMR Spectrum of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)

HRMS of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) octanamide (9b)

13C-NMR Spectrum of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)

1H-NMR Spectrum of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) 10-

HRMS of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) 10-undecenamide

HRMS of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) tetradecanamide (9f)

13C-NMR Spectrum of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)

HRMS of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl) octadecanamide (9h)

13C-NMR Spectrum of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)

1H-NMR Spectrum of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-thiadiazol-2-yl)

HRMS of N-(5-(β-D-Galactopyranosylthio)-1, 3, 4-Thiadiazol-2-yl) Erucoylamide (9j)