Acetic Acid-Driven One-Pot Synthesis of 4,7-dihydro-[1,2,3]thiadiazolo[5,4-b]pyridine-6-carboxamides and Pharmacological Evaluations

被引：0

作者：

Bhalodiya, Savan S. ^{[1
]}

Parmar, Mehul P. ^{[1
]}

Patel, Chirag D. ^{[1
]}

Patel, Subham G. ^{[1
]}

Vala, Disha P. ^{[1
]}

Suresh, Nandhakumar ^{[2
]}

Jayachandran, Bhuvaneshwari ^{[2
]}

Arumugam, Madan Kumar ^{[2
]}

Narayan, Mahesh ^{[3
]}

Patel, Hitendra M. ^{[1
]}

机构：

[1] Sardar Patel Univ, Dept Chem, Vallabh Vidyanagar 388120, Gujarat, India

[2] Sathyabama Inst Sci & Technol, Ctr Mol & Nanomed Sci, Canc Biol Lab, Chennai 600119, Tamil Nadu, India

[3] Univ Texas El Paso, Dept Chem & Biochem, Biochem Div, CCSB 2 0202, 500 W Univ Ave, El Paso, TX 79968 USA

来源：

CHEMMEDCHEM | 2025年 / 20卷 / 02期

关键词：

Multicomponent reaction; 4,7-dihydro-[1,2,3]thiadiazolo[5,4-b]pyridine-6-carboxamides; Antimicrobial; Molecular docking; ANTIMICROBIAL EVALUATION; BIOLOGICAL EVALUATION; DERIVATIVES; DESIGN;

D O I：

10.1002/cmdc.202400595

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A diverse set of 4,7-dihydro-[1,2,3]thiadiazolo[5,4-b]pyridine-6-carboxamides 4(a–o) was synthesized via a one-pot reaction of 5-amino-[1,2,3]thiadiazole, various aromatic aldehydes, and different acetoacetanilides, using glacial acetic acid. The resulting compounds were obtained in moderate to good yields. All the newly synthesized compounds were evaluated for their antimicrobial activity. Among them, compound 4 e demonstrated superior efficacy against the Salinivibrio proteolyticus strain of Gram-negative bacteria compared to ciprofloxacin. Compound 4 d exhibited the highest potency against the fungal strain Candida albicans, surpassing amphotericin B. The physicochemical characteristics of 4 d and 4 e were assessed. According to docking analysis, DHTDAPy 4 e shows a higher binding affinity of −7.2 kcal/mol in the binding cavity of the receptor. These findings illustrate the safety, tolerability, and potency of the newly synthesized DHTDAPy compounds against fungal and bacterial infections. © 2024 Wiley-VCH GmbH.

引用

页数：9

共 50 条

[11] One-Pot Three-Component Domino Synthesis of Isoxazolo[5,4-b]pyrano[2,3-f]quinolines: An Efficient Fluorescent Turn-off Chemosensor for Picric Acid
Rubina, Stephen Raja
Leka, Sivakumar Indhu
Priya, Karthikeyan Sathya
Kumar, Raju Ranjith
Murugesan, Sepperumal
CHEMISTRYSELECT, 2022, 7 (45):
[12] Microwave-assisted One-pot Synthesis of [1,2,3]Triazolo[4′,5′:4,5] Pyrano[2,3-d] pyrimidines and their Biological Evaluation
Venkatesh, Egurapu
Narsimha, Sirassu
Reddy, Nagavelli Vasudeva
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2021, 31 (01) : 125 - 130
[13] One-Pot Multicomponent Synthesis of 1-Aryl-5-methyl-N-R2-1H-1,2,3-triazole-4-carboxamides: An Easy Procedure for Combinatorial Chemistry
Pokhodylo, Nazariy T.
Matiychuk, Vasyl S.
Obushak, Mykola D.
JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (03): : 481 - 485
[14] One-pot synthesis of spiro(indoline-3,4-pyrazolo[3,4-b]pyridine)-5-carbonitriles as p53-MDM2 interaction inhibitors
Ibrahim, Hany S.
Eldehna, Wagdy M.
Fallacara, Anna Lucia
Ahmed, Esam R.
Ghabbour, Hazem A.
Elaasser, Mahmoud M.
Botta, Maurizio
Abou-seri, Sahar M.
Abdel-Aziz, Hatem A.
FUTURE MEDICINAL CHEMISTRY, 2018, 10 (24) : 2771 - 2790
[15] New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones
Shuvalov, Vladislav Yu.
Vlasova, Ekaterina Yu.
Zheleznova, Tatyana Yu.
Fisyuk, Alexander S.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2023, 19 : 1155 - 1160
[16] Magnetic biochar-supported ZrO2 as an efficient catalyst for one-pot synthesis of 1′,4′-dihydro-3H,3′H-spiro[furo[3,4-b]quinoline-9,2′-quinoxaline]-1,3′(4H)-diones
Zhang, Shuai-Zheng
Dong, Li-Na
Mo, Li-Ping
Zhang, Zhan-Hui
APPLIED ORGANOMETALLIC CHEMISTRY, 2023, 37 (02)
[17] Ultrasound-assisted one-pot, three-component synthesis of spiro[indoline-3,4′-pyrazolo[3,4-b]pyridine]-2,6′(1′H)-diones in water
Bazgir, Ayoob
Ahadi, Somayeh
Ghahremanzadeh, Ramin
Khavasi, Hamid Reza
Mirzaei, Peiman
ULTRASONICS SONOCHEMISTRY, 2010, 17 (02) : 447 - 452
[18] Microwave Assisted One-Pot Synthesis of Fused[1,2,3]Triazolo[4′,5′:3,4]Pyrrolo[1,2-c]Pyrimidines as Potent Anticancer Agents
Thatikonda, Raveendar Reddy
Merugu, Karuna Sree
CHEMISTRYSELECT, 2024, 9 (44):
[19] SILICA SULFURIC ACID AS A SOLID ACID CATALYZED SYNTHESIS OF 4,5,6,7-TETRAHYDRO-2H-PYRAZOLO[3,4-b]PYRIDINE-5-CARBONITRILES AND 1,4-DIARYL-4,5-DIHYDRO-3-METHYL-1H-PYRAZOLO[3,4-b]PYRIDINE-6(7H)-ONES
Mahdavinia, Gholam Hossein
Rahmati, Abbas
REVUE ROUMAINE DE CHIMIE, 2015, 60 (11-12) : 1025 - 1032
[20] One-Pot Synthesis of New (1,3-Thiazolo[5,4-b]pyridin-2-yl)benzenediols and Their Antiproliferative Activities against Human Cancer Cell Lines
Matysiak, Joanna
Karpinska, Monika M.
Niewiadomy, Andrzej
Wietrzyk, Joanna
Klopotowska, Dagmara
CHEMISTRY & BIODIVERSITY, 2012, 9 (01) : 48 - 57

← 1 2 3 4 5 →