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• 15580-32-2 malonanilic acid 
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• 137002-59-6 N-Phenyl-3-hydroxy-3-(4-nitrophenyl)propionamide 
• 62-53-3 aniline 
• 61921-33-3 p-nitrocinnamoyl chloride 
• 1092-69-9 3-(4-nitrophenyl)-3-oxo-N-phenylpropanamide 
• 619-89-6 p-nitrocinnamic acid 
• 103-84-4 Acetanilid 
• 22440-58-0 (E)-4-nitrocinnamic acid chloride 
• 27019-24-5 (E)-4-nitrophenyl 3-(4-nitrophenyl)acrylate 

Relevant academic research and scientific papers

Selected class of enamides bearing nitro functionality as dual-acting with highly selective monoamine oxidase-b and bace1 inhibitors

A small series of nitro group-bearing enamides was designed, synthesized (NEA1–NEA5), and evaluated for their inhibitory profiles of monoamine oxidases (MAOs) and β-site amyloid precursor protein cleaving enzyme 1 (β-secretase, BACE1). Compounds NEA3 and NEA1 exhibited a more potent MAO-B inhibition (IC50 value = 0.0092 and 0.016 μM, respectively) than the standards (IC50 value = 0.11 and 0.14 μM, respectively, for lazabemide and pargyline). Moreover, NEA3 and NEA1 showed greater selectivity index (SI) values toward MAO-B over MAO-A (SI of >1652.2 and >2500.0, respectively). The inhibition and kinetics studies suggested that NEA3 and NEA1 are reversible and competitive inhibitors with Ki values of 0.013 ± 0.005 and 0.0049 ± 0.0002 μM, respectively, for MAO-B. In addition, both NEA3 and NEA1 showed efficient BACE1 inhibitions with IC50 values of 8.02 ± 0.13 and 8.21 ± 0.03 μM better than the standard quercetin value (13.40 ± 0.04 μM). The parallel artificial membrane permeability assay (PAMPA) method demonstrated that all the synthesized derivatives can cross the blood–brain barrier (BBB) successfully. Docking analyses were performed by employing an induced-fit docking approach in the GLIDE module of Schrodinger, and the results were in agreement with their in vitro inhibitory activities. The present study resulted in the discovery of potent dual inhibitors toward MAO-B and BACE1, and these lead compounds can be fruitfully explored for the generation of newer, clinically active agents for the treatment of neurodegenerative disorders.

Green synthesis of isoxazoline derivatives using microwave irradiation and their antifungal activity

Microwave irradiation method was used for synthesis of isoxazolines. Claisen Schmidt reaction of different aromatic aldehydes with acetanilide gave acrylamides (1a-1h) which on further reaction with hydroxylamine hydrochloride (in the presence of sodium hydroxide) afforded isoxazolines (2a-2h). Physical data of all the synthesized compounds were recorded. Isoxazolines were characterized by their IR and 1H NMR spectra. All the synthesized isoxazolines were screened for their antifungal activity against fungi namely Drechslera maydis and Rhizoctonia solani isolated from maize. Isoxazolines having chloro substitution on benzene ring found to be most effective followed by fluoro and nitro substituted compounds. None of the compound was registered as effective as Bavistin.

Synthesis and structure-activity relationships of substituted cinnamic acids and amide analogues: A new class of herbicides

In the present investigation, substituted cinnamic acids (3-hydroxy, 4-hydroxy, 2-nitro, 3-nitro, 4-nitro, 3-chloro, and 4-methoxy) and their amide analogues with four different types of substituted anilines have been synthesized. The synthesized compounds have been screened for their germination inhibition activity on radish (Raphanus sativus L. var. Japanese White) seeds at 50, 100, and 200 ppm concentrations, and the activity was compared with standard herbicide, metribuzin formulation (sencor). Significant activity was exhibited by all of the compounds. It was observed that with the increase in concentration of the test solution, the activity also increased. All of the compounds showed more than 70% inhibition at 100 ppm concentration except 4-hydroxy cinnamanilide. The compound, 2-chloro (4′-hydroxy) cinnamanilide was the best among the tested compounds, and it was found to be at par with the standard, metribuzin at all concentrations. Thus, it can be concluded that substituted cinnamic acids and their amide analogues may be developed as potential herbicides.

Cinnamoyl inhibitors of tissue transglutaminase

(Figure Presented) Transglutaminases (TGases) catalyze the intermolecular cross-linking of certain proteins and tissue TGases (TG2) are involved in diverse biological processes. Unregulated, high TGase activities have been implicated in several physiological disorders, but few reversible inhibitors of TG2 have been reported. Herein, we report the synthesis of a series of novel trans-cinammoyl derivatives, discovered to be potent inhibitors of guinea pig liver transglutaminase. The most effective inhibitors evaluated can be sorted into two subclasses: substituted cinnamoyl benzotriazolyl amides and the 3-(substituted cinnamoyl)pyridines, referred to more commonly as azachalcones. Kinetic evaluation of both of these subclasses revealed that they display reversible inhibition and are competitive with acyl donor TGase substrates at IC50 values as low as 18 μM. An analysis of structure - activity relationships within these series of inhibitors permitted the identification of potentially important binding interactions. Further testing of some of the most potent inhibitors demonstrated their selectivity for TG2 and their potential for further development.

CINNAMOYL INHIBITORS OF TRANSGLUTAMINASE

A compound of Formula, (I) or Formula: (II)

Nucleophilic substitution reactions of cinnamoyl chlorides with anilines in acetonitrile and acetonitrile-methanol mixtures

Kinetic studies on the solvolysis (in MeOH-MeCN mixtures) and aminolysis (with anilines in MeCN) of cinnamoyl chlorides have been carried out at 25.0 deg C.The relatively large negative values of ρY+ = -0.9 ca. -1.5 for the methanolysis are consistent with a dissociative SN2-like mechanism.For the aminolysis, the ρy values are positive (ρY = 0.52 ca. 1.64) and ρX values range from -1.68 to -2.51 in acetonitrile.The positive values of βX = 0.6-0.9 and ρXY = 0.88 in acetonitrile, and isotope effect data suggest that the aminolysis proceeds by a stepwise mechanism with rate-limiting breakdown of the tetrahedral intermediate, T+/-.It is noted that in the acyl-transfer reactions proceeding by rate-limiting departure of the leaving group from the tetrahedral intermediate the signs of both ρY and ρXY are positive and the reactivity-selectivity principle (RSP) is valid in general.

Condensed Heterocyclic Lactams. I. Study on the Cyclization Methods Resulting in 4-Aryl-3,4-dihydroquinolin-2(1H)-ones

Cyclization reactions with polyphosphoric acid of 3-aryl-3-hydroxypropionanilides carrying a p-nitro- 7a or p-amino substituent 10 on the C-3 phenyl group were investigated.In the case of p-nitro substitution the preferred reaction is, instead of cyclizat