APPLICATIONS OF ISOQUINOLINE

AND QUINOLINE DERIVATIVES

 GENERAL PROPERTIES OF ISOQUINOLINE

GENERAL PROPERTIES OF QUINOLINE:

•It is a colorless hygroscopic liquid with a strong odor.

•Aged samples, especially if exposed to light, become yellow and later brown.
•Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents.
GENERAL PROPERTIES OF ISOQUINOLINE

•Structural isomer of quinoline, a colorless(impure samples are brownish), hygroscopic liquid at room temperature , unpleasant odor.
•A weak base, pKb of 8. 6.
•It protonates to form salts upon treatment with strong acids, such as HCl.
• It forms adducts with Lewis acids, such as BF3.
•Common organic solvents(ethanol, acetone, diethyl ether, carbon disulfide).

https://pubchem.ncbi.nlm.nih.gov/compound/isoquinoline
FIELD OF APPLICATION
• MEDICINES AND DRUGS
• DYES
• USED AS SOLEVNTS
• FLAVOURING AND FRAGRANCE AGENTS
 USE OF QUINOLNE DERIVATIVE FOR THE
PROTECTION OF CULTIVATED PLANTS FROM
HERBICIDE

REF:-USE OF QUINOLINE DERIVATIVE FOR PROTECTION OF CULTIVATED PLANTS ,ADOLF HUBELE,MEGDEN

4
INTRODUCTION
• THE PRESENT INEVENTION IS RELATED TO THE USE OF QUINOLINE DERIVATIVE
FOR PROTECTING THE CULTIVATED PLANTS FROM THE HARMFUL EFFECT OF
AGROCHEMICALS PRESENT IN THE HERBICIDE
• NOT ONLY THESE QUINOLINE DERIVATIVE ACT AS A PROTECTING AGENT FOR
CULTIVATED PLANTS,BUT ALSO THEY HELP IN REGULATING PLANT GROWTH
• THESE QUINOLINE DERIVATIVE ARE CAPABLE OF SPECIFICALLY ANTAGONISING THE
HARMFUL EFFECT OF HERBICIDE ON THE CULTIVATED PLANTS AND AT THE SAME
TIME INFLUENCING THE HERBICIDAL ACTION ON WEEDS TO BE COMBATED
• BECAUSE OF THE ABOVE MENTIONED REASONS,THE QUINOLINE DERIVATIVES ARE
ALSO CALLED AS ANTIDOTES OR SAFENERS FOR THE CULTIVATED PLANTS.ALSO
THEY PROMOTE ROOT GROWTH AND GERMINATION

REF:-USE OF QUINOLINE DERIVATIVE FOR PROTECTION OF CULTIVATED PLANTS ,ADOLF HUBELE,MEGDEN 5

 GENERAL STRUCTURE OF THE QUINOLINE
DERIVATIVE
• THE GENERAL STRUCTURE OF THE QUINOLINE WHICH ACTS AS A
PROTECTING AGENT FOR THE CULTIVATED PLANTS AGAINST HERBICIDE IS
GIVEN BY THE FORMULA

• THERE CAN BE VARIOUS TYPE OF PROTECTING AGENT WHICH CAN BE

USED FOR DIFFERENT PLANTS AND FOODCROPS.
REF:-USE OF QUINOLINE DERIVATIVE FOR PROTECTION OF CULTIVATED PLANTS ,ADOLF HUBELE,MEGDEN
6
DIFFERENT TYPES OF
SUBSTITUTION POSSIBLE ON THE
QUINOLINE DERIVATIVE
1. R1,R2,R3 ARE :- -H,-NO2,-CN,-R
2. R4,R5,R6 ARE :- -H,-HALOGEN,-
3. X:- ALIPHATIC, ACYCLIC UNSATURATED HYDROCARBON HAVING 1
TO 3 CARBON ATOM
4. Y:- SODIUM SALT OF CARBOXYLIC ACID ESTER
GROUP,CARBOXYLIC ACID THIOLESTER GROUP
THE ALKYL GROUP PRESENT CAN BE STRAIGHT OR BRANCHED CHAIN
WITH 1 TO 6 CARBON ATOM OR PREFERABLY 1 TO 3 CARBON ATOM
THE PREFERRED CARBOXYLIC ACID ESTER RADICAL IS –COOR 7 AND –
COSR8 WHERE R7 AND R8 CAN BE SATURATED OR UNSATURATED
ALKYL,ALKENYL,PHENYL RADICAL
ALSO X AND Y CAN TOGETHER BE A SUBSTITUTED OR UNSUBSTITUTED
REF:-USE OF QUINOLINE DERIVATIVE FOR PROTECTION OF CULTIVATED PLANTS ,ADOLF
TETRAHYDROFURAN-2-ONE RING 7
HUBELE,MEGDEN
QUINOLINE DERIVATIVE’S ACTION
AGAINST HERBICIDE WITH POSSIBLE
SUBSTITUTION

• THE COMPOUND OF THE GENERAL STRUCTURE ARE

PARTICUARLY SUITABLE FOR PROTECTING
CULTIVATED PLANTS FROM THE HARMFUL EFFECTS
IS GIVEN BY
• DIFFERENT SUBSTITUTION WHICH IS POSSIBLE ARE:-
• X1” AND X2” ARE HALOGEN OR HYDROGEN
• Q IS THE FRAGMENT:- =N-,=CH-
• R” IS C1 TO C4 ALKYL CHAIN

REF:-USE OF QUINOLINE DERIVATIVE FOR PROTECTION OF CULTIVATED PLANTS ,ADOLF HUBELE,MEGDEN 8

TECHNIQUES FOR PROTECTING PLANT CROPS
THERE ARE BASICALLY 4 TYPES OF METHODS FROM WHICH THE CULTIVATED PLANTS
CAN BE PROTECTED FROM THE HARMFUL EFFECT OF HERBICIDE
1. SEED DRESSING
2. APPLICATION FROM TANK MIXING
3. APPLICATION INTO THE SEED FURROW
4. CONTROLLED RELEASE OF ACTIVE SUBSTANCE

REF:-USE OF QUINOLINE DERIVATIVE FOR PROTECTION OF CULTIVATED PLANTS ,ADOLF HUBELE,MEGDEN 9

 EXPLANATION FOR THESE TECHNIQUES
1. SEED DRESSING
• DRESSING THE SEED WITH A WETTABLE POWDER FORMULATION OF THE ACTIVE SUBSTANCES BY SHAKING IN A
VESSEL UNTIL UNIFORM DISTRIBUTION OVER THE SEED SURFACE IS ACHIEVED
• 10 TO 500 g OF ACTIVE SUBSTANCE IS USED PER 100 Kg OF SEED
2. TANK MIXING
• A LIQUID MIXTURE OF ANTIDOTE AND HERBICIDE ( RATIO OF 10:1) IS USED
• SUCH A TANK MIXTURE IS APPLIED IMMEDIATELY AFTER SOWING TO A DEPTH OF 5 TO 10 cm
3. SEED FURROW
• THE ANTIDOTE IS INTRODUCED AS EMULSION/POWDER INTO SEED FURROW AND HERBICIDE IS APPLIED IN THE
NORMAL MANNER AFTER FURROW IS BEING COVERED
4. CONTROLLED RELEASE OF ACTIVE SUBSTANCE
• THE ACTIVE SUBSTANCE IS APPLIED TO GRANULES IN SOLUTION AND THEY ARE LEFT TO DRY
• A COATING IS ALSO GIVEN WHICH PERMITS RELEASE OF THE ACTIVE SUBSTANCE OVER A CERTAIN PERIOD OF TIME

USE OF QUINOLINE DERIVATIVE FOR PROTECTION OF CULTIVATED PLANTS ,ADOLF HUBELE,MEGDEN

10
EXAMPLE OF THE QUINOLINE DERIVATIVE
o Methyl-2-(8-quinolinoxy)-propionate is an example of
protecting agent for cultivated plants
o Process for the Methyl-2-(8-quinolinoxy)-propionate
1. 23.2 g of 8-hydroxyquinoline is dissolved in 400ml of
butan-2-one,heat it and add 30 g of K2CO3 in portion
2. Mixture is refluxed for 1 hr and 2 g of KI and 40 g of
methyl-2-bromopropionate is added in the period of 1
hr
3. Mixture is refluxed for more 10 hr,cool it to R.T,mixture
is poured onto 1 liter of water and then it is filtered and
dried
4. Now the solvent is evapourated and oily residue is
cyrstallised and we are left with the final product which
REF:-USE OF QUINOLINE DERIVATIVE FOR PROTECTION OF CULTIVATED
o PLANTS ,ADOLF HUBELE,MEGDEN
11
is a beige colored crystals with M.P of 70 to 72 C
SOME OTHER EXAMPLES OF PROTECTING AGENTS

REF:-USE OF QUINOLINE DERIVATIVE FOR PROTECTION OF CULTIVATED PLANTS ,ADOLF HUBELE,MEGDEN 12

APPLICATION OF QUINOLINE DERIVATIVE IN
PERFURMERY

THE QUINOLINE DERIVATIVE WHICH IS USED IN PERFUMERY USED IS 6-

(butan-2-yl)quinolone
PHYSICAL CHARACTERISTICS OF 6-(butan-2-yl)quinolone
1. APPEARANCE:-YELLOW TO DARK BROWN CLEAR LIQUID
2. SPECIFIC GRAVITY:-1.007 TO 1.015 @ 298K
3. B.P:-2880C
4. SOLUBLE IN:-WATER,ALCOHOL

THE SUPPLIER SPONSOR FOR THE PERFUME ARE:-

 BERJE
 INDUKERN
 TREATT
 SYMRISE
REF:-www.thegoodscentscompany.com/data/rw1006851.html
13
QUINOLINE BASED DYE SENSOR
• THERE HAVE BEEN MANY RESEARCH DEVELOPMENT THAT TOOK PLACE
IN THE FIELD OF ENVIORNMENTAL AND MEDICAL APPLICATION
• BECAUSE OF THE TOXIC IMPACT CREATED BY THE TRANSITION METAL
ON THE ENVIORNMENT,A GREAT EFFORT IS BEING MADE IN
DEVELOPING “SIMPLE TO MAKE AND NAKED EYE ASSESMENT TOOL
WHICH IS CARRIED OUT BY USING DYE MOLECULE FOR DETECTING
METAL
• THE QUINOLINE DERIVATIVES WHICH ARE BEING USED AS METAL
DETECTOR ARE
• 8-Hydroxy Quinoline
• 2-(2,6-Bis((E)-2-(8-Hydroxyquinolin5-Yl)vinyl)-4 H-Pyran-4-
Ylidene)malononitrile (HQM Dye)

REF:-SYNTHESIS OF CHARACTERIZATION OF QUINOLINE BASED DYE SENSOR 14

SYNTHESIS OF HQM
1. 8-hydroxyquinoline (0.035 mol, 5 g) were added in
20 ml of ethanol and refluxed. After 30 min,
aqueous sodium hydroxide was added
2. 6 ml of chloroform was then slowly dropwise over
1 h reaction. Reflux was continued for 18 h.
Ethanol and excess chloroform was evaporated
3. The reaction mixture was poured into 125 ml of
ice water and this solution was adjusted to the
acidic pH condition using hydrochloric acid. After 3
h, the mixture was filtrated, dried and purified
using column chromatography
4. The yield is 17.32%

REF:-SYNTHESIS OF CHARACTERIZATION OF QUINOLINE BASED DYE SENSOR 15

REFERENCES
• [1] Feng, K., Hsu, F. L., Bota, K., & Bu, X. R. (2005). Microchemical Journal, 81, 23.
• [2] Ding, A. L., Pei, J., Yu, W. L., Lai, T. H., & Huang, W. (2002). Thin Solid Films, 417, 198.
• [3] Li, Z., & Zhang, J. (2006). Chemical Physics, 331, 159.
• [4] Dolci, L. S., Marzocchi, E., Montalti, M., Prodi, L., Monti, D., Natale, C. D., D’Amico, A., &
Paolesse, R. (2006). Biosensors and Bioelectronics, 22, 399.
• [5] Cheng, Y., Zhang, M., Yang, H., Li, F., Yi, T., & Huang, C. (2008). Dyes and Pigments, 76, 775.
• [6] Kaur, P., Kaur, S., Mahajan, A., & Singh, K. (2008). Inorganic Chemistry Communications, 11,
626.
• [7] Mei, Y., Bentley, P. A., & Wang, W. (2006). Tetrahedron Letters, 47, 2477.
• [8] Kawakami, J., Ohta, M., Yamauchi, Y., & Ohzeki, K. (2003). Analytical Science, 19, 1353.
• [9] Goswami, A., Singh, A. K., & Venkataramani, B. (2003). Talanta, 60, 1141.
• [10] Moylan, C. R., Ermer, S., Lovejoy, S. M., McComb, I. H., Leung, D. S., Wortmann, R., Krdmer,
P., & Twing, R. J. (1996). J. Am. Chem. Soc., 118, 12950.

16
Quinoline derived Drugs

1. Chloroquine

It is used to prevent and treat malaria.

It also used as antirheumatic.

Biochemical Pharmacology ,volume 55 , 15th march 1998[1]

2. Dibucaine

It is used as local anesthetic.[2]

3. Clioquinol

It is used as wound and intestinal antiseptic.[3]

[2] Journal of pharmacy and pharmacology 38,472-475 22feb 2017
[3] Journal of pharmacology and toxicology volume 63 oct 1988
4. Quinoline compounds containing heterocyclic systems at 2 nd position shows
wide spectrum of biological activities such as cytotoxic, anti-inflammatory and
antifungal behaviour. (Compound 1)
2-heteroarylbenzofuran ring systems have been reported to have antiviral,
antioxidant and antifungal activities. (compound 2)
Methylenedioxy moiety is fundamental for cytotoxic activity. The presence of
methylenedioxy moiety in some other bioactive molecule alters their
pharmacological properties.
Compound 3 have potent cytotoxicity against human cancer cell lines.
Beilstein J. Org . Chem ,7,210-217 15 Feb 2011
Yellow solid
Soluble in water, dimethyl It is highly efficient quenching of the
sulfoxide methanol. fluorescence of 7-(diethylamino)-4-
Absorption : 430 nm methylcoumarin.
Emission : 545 nm (medium water) Industrially used for the detection of
It is used as explosives detection polymers, cracks in various materials
optical waveguides.

B. May,X.Poteau,D.Yuan,R.G.Brown,Dyes and Pigments 1999,42, 79

 Quinoline Dyes
1. Acid Yellow 3

In EU and Australia ,it is permitted in food, like sauces.

In Canada or US ,it is permitted in medicines and cosmetics
2 . Solvent Yellow 33

Horst Berneth “ Methine Dyes and Pigments in Ullmann’s Encyclopedia of Industrial chemistry
ALKALOIDS OF ISOQUINOLINE
BERBERNINE
• Due to berberine's strong yellow color,
Berberis species were used to dye wool,
leather, and wood.
• Wool is still dyed with berberine today in
northern India.
• Under ultraviolet light, berberine shows a
strong yellow fluorescence , so it is useful
in histology for staining heparin in mast
cells.
• As a natural dye, berberine has a color
index of 75160.
• Berberine was supposedly used in China
as a folk medicine by Shennong around
3000 BC.
SOURCES

European Indian
barberry or barberry,
simply "chutro" or
barberry tree turmeric,
Xanthorhiza
simplicissima
(yellowroot)
Mahonia
aquifolium
(Oregon-grape
• MECHANISM OF ACTION OF THE ALKALOID:
• After you ingest berberine, it gets taken in by the body and transported into the bloodstream. Then it travels
into the body’s cells.
• Inside the cells, it binds to several different “molecular targets” and changes their function . This is similar to
how pharmaceutical drugs work.
• However, one of the main actions of berberine is to activate an enzyme inside cells called AMP-activated
protein kinase (AMPK).
• This enzyme is sometimes referred to as a “metabolic master switch” .It is found in the cells of various organs,
including the brain, muscle, kidney, heart and liver. This enzyme plays a major role in regulating metabolism.
• Berberine also affects various other molecules inside cells, and may even affect which genes are turned on or
off.

• ADVANTAGES:
• It seems to work via multiple different mechanisms:
• Decreases insulin resistance, making the blood sugar lowering hormone insulin more effective.
• Increases glycolysis, helping the body break down sugars inside cells. Decrease sugar production in the liver.
• Slows the breakdown of carbohydrates in the gut.Increases the number of beneficial bacteria in the gut.
• OTHER HEALTH BENEFITS:
• Depression: Rat studies show that it may help fight depression.
• Cancer: Test tube and animal studies have shown that it can reduce the growth and spread of various different types of
cancer .
• Antioxidant and anti-inflammatory: It has been shown to have potent antioxidant and anti-inflammatory effects in some
studies .
• Infections: It has been shown to fight harmful microorganisms, including bacteria, viruses, fungi and parasites .
• Fatty liver: It can reduce fat build-up in the liver, which should help protect against non-alcoholic fatty liver disease.
• Heart failure: One study showed that it drastically improved symptoms and reduced risk of death in heart failure patients.

• ADVERSE EFFECTS:
• Uterine contractions and miscarriages when overdosed

• https://www.webmd.com/vitamins/ai/ingredientmono-1126/berberine
•
 CODEINE

• Codeine is also an isoquinoline alkaloid obtained from opium poppy. Codeine is the most widely used naturally
occurring opioid for its medicinal use. Codeine is a prodrug, which gets metabolized into morphine in the liver. It
can also be synthesized from morphine.
• Pain relief drug due to its conversion into morphine in human body by the enzyme called CYP2D6; often
combined with other analgesics—acetaminophen or acetylsalicylic acid
• Antitussive by the agonist activity toward opiate receptors in cough center
• Euphoric effects result from its conversion to morphine when metabolized
• Maximum oral daily dose: 60 mg/day for children, 120 mg/day for adults for codeine in the form of phosphate
salts.
• ADVERSE EFFECTS:
• Should not be used as a pain relief drug among children under 18 years of age due to respiratory depression
(obstructive sleep apnea); addictive potential; numerous drug interactions (alcohol, antiviral, antihistamines,
antidepressant, travel sickness, antifungal, anticonvulsant drugs); apathy, drowsiness, obstipation, euphoria, or
sedation, tolerance
• https://www.sciencedirect.com/topics/neuroscience/isoquinoline-alkaloid
IN THE FIELD OF
PERFUMERY USAGE AS A SOLVENT
• LEATHER SCENTS
• Group: MUSK, AMBER, ANIMALIC SMELLS
• The scent of leather lies in the midline between masculine
and feminine tones.
• Historically, leather is one of the earliest notes in perfumery,
rooted in the tradition of, a guild of Parisian glove makers who
made leather gloves for the aristocracy.
• According to the fashion of the 16th century, the gloves were
perfumed with oils, musk, ambergris and civet, to mask the
nauseating breath of animal skin.
• Due to the tanning process, the raw skin doesn’t smell so
good, and this re-odorized scent is actually what today
describes our notion of the smell of leather.
• Isoquinoline, a material first isolated from coal tar in 1885, is
also used to create leather notes and provides a synthetic
alternative to birch tar oil.
Preparation and properties of heat-sealable polyimide films
with comparable coefficient of thermal expansion and good
https://www.fragrantica.com/notes/Leather-156.html adhesion to copper matrix X. M. Zhang1, X. Xiao2 , X. Wu2, J. G.
Liu*2
ALKALOIDS HAVING A STRESS BUSTING EFFECT
• Salmonella are gram-negative, non-spore-forming, motile bacteria, causing diarrhoea,
vomiting and cramps in affected people.
• Reducing the antimicrobial resistance for example.
• Isolates of Salmonella typhimurium may possess resistance to ampicillin etc
• It is also a known fact, that stress increases pathogen shedding,infections and
increasing susceptibility to new infections .
• As transportation to the slaughterhouse is a stressful event for animals, an increased
pathogen shedding and therefore a higher carcass-contamination risk can be assumed.
• Consequently, functional feed additives like probiotics, prebiotics, or plant alkaloids
are used to battle foodborne diseases.
• One of these are isoquinoline alkaloids (IQs), taken from a selected plant. IQs are
known for their positive effect on gut health and hence animal performance
• Saliva samples were collected for cortisol measurement, an indicator for stress.
• One day before transportation to the slaughterhouse, all treatment groups had
comparable cortisol levels.
• Salmonella prevalence in the faeces of pigs fed IQs was significantly decreased
compared to control animals and carcass contamination was also significantly reduced

• https://www.allaboutfeed.net/Feed-Additives/Articles/2016/8/Reducing-Salmonella-with-isoquinoline-alkaloids-2866375W/
 NOVEL FLUORESCENT ISOQUINOLINE DERIVATIVES
• Isoquinolin-3-amines bearing an alkyl group or hydrogen atom in position 4 easily underwent
Buchwald-Hartwig coupling reactions with various substituted aryl halides.
• In the frame of the present study, unsubstituted and 4-alkyl substituted isoquinolin-3-amines
• (1, R4 = H, CH3 and CH2C6H5, respectively) were treated with various substituted
bromobenzene
• derivatives and 2,3-dibromopyridine as shown in Scheme .
• The substituents of the bromobenzene reagent involved m- and p-Cl, o-, m-, and p-Br, o- and p-
NO2, o-, m-, and pCOOEt, o-CHO moieties. As a ligand to Pd2(dba)3 JohnPhos and Xantphos
provided the best results.
• As bases, cesium carbonate and sodium t-butoxide were used. The products have been
• obtained in 46–94% yields.

Novel fluorescent isoquinoline derivatives obtained via Buchwald-Hartwig coupling of isoquinolin-3-amines József Balog, Zsuzsanna Riedl, György Hajós,* Zsombor
Miskolczy, and László Biczók
The derivatives and experimental conditions are summarized in Table
• Table 2 summarizes the photophysical parameters of the new
compounds and, for the sake of comparison, those of isoquinolin-3-
amine (1, R4 = H). The fluorescence maximum exhibits a marked
displacement to longer wavelength upon attachment of N-phenyl group
to 1a, but diminishes in the series of 2a > 2g > 2s > 2t > 1a.
• The Stokes-shift of the fluorescence band is larger when a substituted
phenyl group is attached to the isoquinolinamine skeleton indicating
that more substantial structural alteration occurs upon excitation than
in the case of 1a.
• CONCLUSIONS :
• The present results reveal that a great number of actively fluorescent
phenylamino and pyridylaminoisoquinolines can be easily obtained by
one single manipulation starting from isoquinolinamines in medium to
excellent yields. The quantum yield and lifetime of the fluorescence are
insensitive to the substituent of the N-phenyl moiety but introduction of
nitro group makes the compound practically nonfluorescent.
SYNTHESIS OF TETRONIC ACID

• Synthesis of a new class of tetronic acid derivatives: a one-pot

three-component condensation reaction between isoquinoline or
pyridine and dialkyl acetylenedicarboxylate with tetronic acid
• Reaction of the zwitterions generated from isoquinoline or
pyridine and dialkyl acetylenedicarboxylate with tetronic acid
leads to 1,2-dihydroisoquinoline or 1,2-dihydropyridine tetronic
acid derivatives without using any catalyst or activation at room
temperature.
• In organic synthesis, it is used as a precursor for other substituted
and ring-fused furans and butenolides. It is also forms the
structural core of a class of pesticides, known as tetronic acid
insecticides, which includes spirodiclofen and spiromesifen.

• Tetronic acid is a chemical compound, classified as a γ-lactone,

with the molecular formula C4H4O3.

• It interconverts between keto and enol tautomers

 PAPAVERINE
• Papaverine (Latin papaver, "poppy") is an opium alkaloid antispasmodic drug,
used primarily in the treatment of visceral spasm and vasospasm (especially
those involving the intestines, heart, or brain), and occasionally in the
treatment of erectile dysfunction.
• It is used in the treatment of acute mesenteric ischemia. While it is found in
the opium poppy, papaverine differs in both structure and pharmacological
action from the analgesic (morphine-related) opium alkaloids (opiates).

• Synthesis of Essential Drugs, pp 265-266

PHENOMELANIN
Pheomelanins (or phaeomelanins) impart a pink to red hue, depending upon the concentration.
Pheomelanins are particularly concentrated in the lips,gums, and areas of the mammary glands male and female gentalia
When a small amount of brown eumelanin in hair, which would otherwise cause blond hair, is mixed with red pheomelanin, the result is strawberry blo
Pheomelanin is also present in the skin, and redheads consequently often have a more pinkish hue to their skin as well.

https://biology.stackexchange.com/questions/17225/how-do-you-increase-eumelanin-but-not-pheomelanin
 Biomimetic oxidation of the pheomelanin precursor 5-S-
cysteinyldopa in the presence of Zn(2+) ions led to the
isolation of two isomeric products, one of which could be
identified as the benzothiazolylthiazinodihydroisoquinoline
5, while the other proved too unstable for a complete
characterization.
Compound 5 exhibited absorption characteristics similar to
those of red hair pheomelanin, including a main band
around 400 nm in acids.
Similarly to red hair pheomelanin and synthetic pigments, 5
afforded on chemical degradation a
thiazolylpyridinecarboxylic acid fragment.

covering the structure of human red hair pheomelanin: benzothiazolylthiazinodihydroisoquinolines as key building blocks.
ID: 21341762 DOI: 10.1021/np100740n
 DIMETHISOQUIN SYNTHESIS

Dimethisoquin (also known as

Quinisocaine and QUOTANE) is a
topical anesthetic used as an
antipruritic.
It was shown
that dimethisoquin inhibits nicotinic
acetylcholine receptors
 DISINFECTANTS AND ANTIFUNGAL AGENTS OBTAINED
• Antifungal agents, such as 2,2'- Disinfectants, like N-Laurylisoquinoliniumbromide is prepared
Hexadecamethylenediisoquinolinium by simple N-alkylation of isoquinoline
• dichloride, which is also used as a topical
antiseptic.
• This derivative, shown below,is prepared
by N-alkylation of isoquinoline with the
appropriate dihalide.
 CYANINE DYES
Here are three types of cyanines:
Streptocyanines or open chain cyanines:
R2N+=CH[CH=CH]n-NR2 (I)
Hemicyanines:
Aryl=N+=CH[CH=CH]n-NR2 (II)
Closed chain cyanines:
Aryl=N+=CH[CH=CH]n-N=Aryl (III)
where two quaternary nitrogens are joined by a polymethine chain.
Both nitrogens may each be independently part of a heteroaromatic
moiety, such as pyrrole, imidazole, thiazole, pyridine, quinoline,
indole, benzothiazole, etc.
Cyanine dyes are used to label proteins, antibodies, peptides,
nucleic acid probes, and any kind of other biomolecules to be used
in a variety of fluorescence detection techniques: Flow
cytometry, Microscopy (mainly Visible range, but also UV, IR),
Microplate assays, Microarrays, as well as "light-up Probes"
STYRYLISOQUINOLINE DYES

• wherein R and R1 each represents an alkyl group, i. e. an alcohol radical, methyl, ethyl, n propyl, isobutyl, n-butyl, 3-
hydroxyethyl, 5-eth oxyethyl, allyl, benzyl, g-phenylethyl, 3-acetyl ethyl, 6-acetoxyethyl, etc.
• X represents an anion e. g. chloride, bromide, iodide, p-toluene sulfonate, methylsulfate, ethylsulfate, benzene Sulfonate,
acetate, perchlorate, thiocyaiiate, etc.
• n represents a positive iteger of from 1 to 2. h
 PYRROLOCARBOCYANINE SALTS (OR DYES)
• We have also found that 3-methylisoquinoline alkyl quaternary salts can be condensed with pyrrole aldehydes to which can be
represented by the following general formula:

• R2 and R3 each represents an alkyl group, especially a methyl group.

• R4 represents an alkyl group, e. g. methyl, ethyl, n-butyl, isobutyl, n-heptyl, lauryl, cetyl, benzyl, etc. or an aryl group, e.g. phenyl.
• wherein R represents an alkyl group, i. e. an alcohol radical, methyl, ethyl, n propyl, isobutyl, n-butyl, 3-hydroxyethyl, 5-eth
oxyethyl, allyl, benzyl, g-phenylethyl, 3-acetyl ethyl, 6-acetoxyethyl, etc.
• X represents an anion e. g. chloride, bromide, iodide, p-toluene sulfonate, methylsulfate, ethylsulfate, benzene Sulfonate, acetate,
perchlorate, thiocyaiiate, etc.
• The condensations are advantageously carried out in the presence of an amine, e. g. piperidine, or a carboxylic anhydride, e.g.
acetic anhydride.
THANKYOU 