Synthesis and Evaluation of Ethyl 2-(2-Cyano-3-(Substituted Phenyl) Acrylamido)-4,5,6,7-Tetrahydrobenzo[b]Thiophene-3-Carboxylates for Antioxidant and Antibacterial Activities

Madhavi, K.; Ramanamma, K. V.

doi:10.20546/ijcmas.2016.501.034

Cited by 7 publications

(7 citation statements)

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“…2-Aminothiophene and its derivatives demonstrate diverse array of biological/pharmacological profiles and broad spectrum of applications with remarkable potency. [5] Various biological activities of 2-aminothiophene derivatives are • Analgesic [6] • Anti-inflammatory [7] • Antioxidant and antibacterial [8] • Antiproliferative [9] • Antimicrobial [10] • Anti-leishmanial [11] • Anticonvulsant. [12]…”

Section: Chemistry Of 2-aminothiophenesmentioning

confidence: 99%

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Narender¹

2021

IJPSCR

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Heterocyclic compounds offer a high degree of structural diversity and have proven to be broadly and economically useful as therapeutic agents. Essential diet ingredients such as thiamine, riboflavin, nicotinamide, pyridoxine, and ascorbic acid are heterocyclic compounds. Thiophene is the backbone of several important products, including pharmaceuticals, dyes, and agrochemicals. In addition, this S-heterocyclic core is present in many natural products, several of which show antibacterial, antifungal, antiamoebic, antioxidant, antitumor, anticoagulant, and antithrombotic activities. 2-Aminothiophenes are important five-membered heterocyclic building blocks in organic synthesis and the chemistry of these small molecules is still developing based on the discovery of cyclization by Gewald. The most convergent and well-established approach for the preparation of 2-aminothiophenes is the Gewald method, which involves the three-component reaction of a ketone, an activated nitrile and elemental sulfur in the presence of morpholine as catalyst. In the continuation of our studies toward the development of new methodologies under green chemistry approaches, herein we reported a mild, efficient, and simple "one pot" Gewald Synthesis of tetra substituted 2-aminothiophene derivatives.

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Section: Chemistry Of 2-aminothiophenesmentioning

confidence: 99%

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Narender¹

2021

IJPSCR

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“…Substituted benzothiophene derivatives are essential compounds in agrochemical and pharmaceuticals . These compounds have been reported to have antifungal, antitubercular, − anti-inflammatory, antimicrobial, , antianxiety, antibacterial, , and anticancer efficacy. In our previous work, the 4,5,6,7-tetrahydrobenzo[ b ]thiophene-3-carboxylate derivative was identified as a potential inhibitor class against Of ChtI via structure-based virtual screening.…”

Section: Introductionmentioning

confidence: 99%

Pocket-based Lead Optimization Strategy for the Design and Synthesis of Chitinase Inhibitors

Dong

Liu

et al. 2019

J. Agric. Food Chem.

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Insect chitinases play an indispensable role in shedding old cuticle during molting. Targeting chitinase inhibition is a promising pest control strategy. Of ChtI, a chitinase from the destructive insect pest Ostrinia furnacalis (Asian corn borer), has been suggested as a potential target for designing green pesticides. A 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate scaffold was previously obtained, and further derivatization generated the lead compound 1 as Of ChtI inhibitor. Here, based on the predicted binding mode of compound 1, the pocket-based lead optimization strategy was applied. A series of analogues was synthesized, and their inhibitory activities against Of ChtI were evaluated. Compound 8 with 6-tert-pentyl showed preferential inhibitory activity with a K i value of 0.71 μM. Their structure–activity relationships suggested that the compound with larger steric hindrance at the 6-nonpolar group was essential for inhibitory activity due to its stronger interactions with surrounding amino acids. This work provides a strategy for designing potential chitinase inhibitors.

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“…The reactivity order of methylene carbon is greater than the amide nitrogen and can undergo knoevenagel condensation with substituted benzaldehydes to give 2-cyano-3-(substituted phenyl) acrylamides. Further, various 2-cyano-3-(substituted phenyl)acrylamides were reported to possess diverse pharmacological activities, of which entacapone is now clinically used as antiparkinsonism drug [8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antioxidant and Anti-Inflammatory Activities of Ethyl 2-(2-Cyano-3- (Substituted Phenyl)acrylamido)-4,5-Dimethylthiophene-3-Carboxylates

Madhavi

2017

Asian J Pharm Clin Res

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Objective: Objective of the study was to synthesize and evaluate a series of novel compounds, ethyl 2-(2-cyano-3-(substituted phenyl)acrylamido)-4,5-dimethylthiophene-3-carboxylates, for in vitro antioxidant and in vivo anti-inflammatory activities.Methods: Ethyl 2-(2-cyano-3-(substituted phenyl)acrylamido)-4,5-dimethylthiophene-3-carboxylates were synthesized by knoevenagel condensation of active methylene group of ethyl 2-(2-cyanoacetamido)-4,5-dimethylthiophene-3-carboxylate with substituted benzaldehydes. The synthesized compounds were evaluated for their in vitro antioxidant properties in three different models, viz., reduction of 1,1-diphenyl-2-pycrylhydrazyl free radical, scavenging of nitric oxide free radical, and ferric ion-induced lipid peroxidation using rat brain homogenate. Few selected compounds with good antioxidant properties were pharmacologically evaluated for anti-inflammatory activity by carrageenan-induced rat paw edema model. Results:Clean and efficient synthetic procedure was used for the preparation of series of compounds. The structures of synthesized compounds were confirmed by infrared, 1 H nuclear magnetic resonance and mass spectra. The antioxidant activity data revealed that the compounds of ethyl 2-(2-cyano-3-(substituted phenyl)acrylamido)-4,5-dimethylthiophene-3-carboxylate containing phenolic substitution showed greater antioxidant activity. Hence, the active compounds were evaluated for anti-inflammatory activity and found to possess good activity. The percentage inhibition of rat paw edema obtained for the evaluated compounds was in the range of 70.2-83.1, comparable to the standard drug diclofenac (85.0%). Conclusion:The use of inexpensive, eco-friendly and readily available reagents, easy work-up and high purity of products makes the procedure a convenient and robust method for the synthesis of title compounds. The compounds of ethyl 2-(2-cyano-3-(substituted phenyl)acrylamido)-4,5-dimethylthiophene-3-carboxylate containing phenolic substitution showed greater antioxidant and anti-inflammatory activities.

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Synthesis and Evaluation of Ethyl 2-(2-Cyano-3-(Substituted Phenyl) Acrylamido)-4,5,6,7-Tetrahydrobenzo[b]Thiophene-3-Carboxylates for Antioxidant and Antibacterial Activities

Cited by 7 publications

References 0 publications

Untitled

Untitled

Pocket-based Lead Optimization Strategy for the Design and Synthesis of Chitinase Inhibitors

Synthesis, Antioxidant and Anti-Inflammatory Activities of Ethyl 2-(2-Cyano-3- (Substituted Phenyl)acrylamido)-4,5-Dimethylthiophene-3-Carboxylates

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