UNIVERSIDAD AUTÓNOMA DEL ESTADO DE MORELOS

Facultad de Ciencias Químicas e Ingeniería

CO MUNI CA CI Ó N Y EX P RES I Ó N O RAL

FRUTAS CON ESCUDOS

Experimento No. X
Nombre de autor(es): Carmona Giles Yanea Yamilett
Fecha de realización del experimento:

Resumen: Golpes, microorganismos como moho o bacterias, son las principales causas que afectan a la fruta de los cultivadores
y al consumidor, para minimizar estos riesgos se ha buscado la implementación de métodos tecnológicos para la conservación
de estas evitando la contaminación ambiental y reducción de costos que logren competir con los empaques de platicos
actualmente utilizados y no pierdan su calidad.

Abstract: Blows, microorganisms such as mold or bacteria, are the main causes that affect the fruit of the growers and the
consumer, to minimize these risks, the implementation of technological methods for their conservation has been sought, avoiding
environmental contamination and reducing costs that manage to compete with the plastic packages currently used and do not
lose their quality.

Objetivos:
1. XXX
2. XXXX

Palabras clave:

Justificación
Hipótesis
1. Introducción (máximo 4500 caracteres con espacio)
Inflammation is a physiological and adaptive tissue response
mechanism to harmful stimuli (e.g. pathogens, mechanical trauma,
ischemia, chemicals or antigens), that ultimately lead to the restoration
of affected tissues to their normal structural and functional state, and/or
the elimination of invading organisms.1 In this dynamic and highly
regulated mechanism, the cells such as neutrophils, macrophages, and
pro-inflammatory mediators collaborate to neutralize and eliminate the
damaging stimuli to restore homeostasis. 2 The resolution of
inflammation is central to human health, if unresolved, inflammation
itself can lead to further tissue damage that can eventually contribute to
the pathogenesis of chronic inflammatory and autoimmune diseases
such as asthma, psoriasis, rheumatoid arthritis, 3 cardiovascular
diseases (e.g. atherosclerosis),4 CNS neurological disorders, including
Parkinson, Alzheimer, multiple sclerosis,5 inflammatory bowel diseases
involving Crohn´s disease and ulcerative colitis,6 cancer7 and obesity.8
All of these diseases are a significant worldwide public health
concern that affects millions of people and place considerable financial
burden to the society. Management of inflammatory disorders involves
the use of therapeutic agents for relieving pain and reducing
inflammation either decreasing and/or neutralizing the levels of pro-
inflammatory mediators or inhibiting the recruitment of leukocytes and
their activation. These therapeutics include non-steroidal anti-inflammatory
drugs (NSAIDs), glucocorticoid receptor agonists (synthetic GCs), disease
modifying anti-rheumatic drugs (DMARDs), and antibodies or inhibitors
targeting specific cytokines, such as tumor necrosis factor (TNF)-α and
interleukin (IL)-1.9 Although the therapy with these drugs, alone or
combined, has shown effectiveness, there is a growing concern about
their side effects especially in prolonged treatments. For this reason,
there is a need for developing new anti-inflammatory agents with better
efficacy and greater safety profile. In this context, the α-
aminophosphonates, emerged as a promising new class of drugs
because they exhibit a variety of pharmacological activities of great
medical interest.10 Their most promising applications are as
antibacterials,11 antitumorals,12 antivirals,13 antifungals,14 and
neuromodulators.15 The α-aminophosphonic acids are considered the
most important analogues of the α-amino acids obtained by isosteric
substitution of the planar and less bulky carboxylic acid (CO2H) by a
tetrahedral phosphonic acid functionality (PO3H2).16 Their similitude with
the natural α-amino acids makes them extremely important
antimetabolites, which compete with their carboxylic counterparts for the
active sites of several enzymes classes and other cell receptors. 17 In this
sense, recently has been reported that aminophosphonic-type activity-
based probes can inhibit Neutrophil Serine Proteases.18 This proteolytic
enzymes regulate the inflammatory response by specifically altering the
function of cytokines and chemokines. 19 Thus, this feature suggests that
α-aminophosphonates may have the potential to modulate the
inflammatory process. Consequently, had been reported that some of α-
aminophosphonates inhibit carrageenan induced inflammation in rats.20
2. Resultados y discusión
The synthesis of the target α-methyl phosphoserine derivatives 1a-f was
carried out according to our previous reports22 (Scheme 1).
3. Conclusiones
In summary, we have developed a straightforward one-pot three-
component method catalyzed by phenylphosphonic acid, for the
synthesis of α-methyl phosphoserine derivatives 1a-f, 2a-c and the α-
hydroxyphosphonate 3. These compounds significantly decreased TPA
induced-ear inflammation and this effect is mainly due to the ability of
the compounds to decrease the influx of neutrophils and monocytes.
QSAR analysis show that a spherical shape for the α-methyl
phosphoserine derivatives favors their anti-inflammatory activity,
increasing the alkyl chain allows the compounds to bend over
themselves to adopt this form, like in 1c and 2b. In the same manner,
the introduction of the methyl group between the amino and phenyl
improves the spherical shape of the molecule.
4. Sección experimental

Información general:

Reactivos

Materiales
Esquema 1. Three-component synthesis of 1a-f.
Cálculos estequiométricos
Thus, the three-component reaction of acetoxyacetone with diverse
aliphatic amines and dimethyl phosphite in the presence of 10 mol% of
phenylphosphonic acid, was performed under solvent-free conditions. The Referencias (De acuerdo a la ACS)
expected α-aminophosphonates 1a-f were obtained in 45 to 73% yield.
However, when the three-component reaction was performed using tert- Nota: Solo son válidas referencias bibliográficas de libros y
butylamine as the aliphatic amine, the α-hydroxymethylphosphonate 3 artículos científicos
was isolated in 89% yield (Scheme 1).

In a similar way, the three-component reaction of hydroxyacetone
with different amines and dimethyl phosphite in the presence of 10 mol%
of phenylphosphonic acid, afforded the corresponding α-methyl
phosphoserine derivatives 2a-c in 48 to 75% yield (Scheme 2).
Tabla 1
Efficacy (maximal efficacy), potency (ED50), and relative potency values
of the new α-methyl phosphoserine derivatives on TPA-induced ear
edema.
1. Abdulkhaleq LA, Assi MA, Abdullah R, Zamri-Saad M, Taufiq-
Yap YH, Hezmee MNM. Vet. World. 2018;11: 627–635.
2. Lang Y, Chu F, Shen D, Zhang W, Zheng C, Zhu J, Cui L.
Mediators Inflamm. 2018; 2018:1–11.
3. Siti HN, Kamisah Y, Kamsiah J. Vascul. Pharmacol. 2015;
71:40–56.
4. Stephenson J, Nutma, E, van der Valk P, Amor S. Immunology.
2018; 154:204–219.

Compound Maximal ED50b Relative

efficacy (%)a (mg/ear) potencyc
Indomethacin 99.34±1.99 0.49 1.0
1f 96.9±2.30 0.73 1.51
1d 92.98±3.92 0.97 1.97
2b 94.58±1.96 1.01 2.07
2c 95.0±3.09 1.06 2.18
1c 97.04±3.23 1.29 2.67
1a 97.58±1.38 1.46 3.02
1e 73.15±3.54 1.69 3.47
1b 66.14±9.36 1.74 3.58
2a 81.56±6.50 3.63 7.48

The physical interpretation to SPAN can be viewed as an effective rotational

radius. It is a very useful molecular descriptor especially for the analysis of
configurational