Synthesis of isoniazid-1,2,3-triazole conjugates: Antitubercular, antimicrobial evaluation and molecular docking study

被引：21

作者：

Badar, Adinath D. ^{[1
]}

Sulakhe, Shubham M. ^{[1
]}

Muluk, Mahesh B. ^{[1
]}

Rehman, Naziya N. M. A. ^{[2
]}

Dixit, Prashant P. ^{[2
]}

Choudhari, Prafulla B. ^{[3
]}

Rekha, Estharla Madhu ^{[4
]}

Sriram, Dharmarajan ^{[4
]}

Haval, Kishan P. ^{[1
]}

机构：

[1] Dr Babasaheb Ambedkar Marathwada Univ SubCampus, Dept Chem, Osmanabad 413501, India

[2] Dr Babasaheb Ambedkar Marathwada Univ SubCampus, Dept Microbiol, Osmanabad, India

[3] Bharati Vidyapeeth Coll Pharm, Dept Pharmaceut Chem, Kolhapur, Maharashtra, India

[4] Birla Inst Technol & Sci Pilani, Dept Pharm, Hyderabad, India

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2020年 / 57卷 / 10期

关键词：

MYCOBACTERIUM-TUBERCULOSIS; 1,2,3-TRIAZOLE DERIVATIVES; BIOLOGICAL EVALUATION; IN-VITRO; DESIGN; BEARING; ANTIOXIDANT; ANTICANCER; THERAPY; AGENTS;

D O I：

10.1002/jhet.4072

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the present study, a series of new isoniazid-1,2,3-triazole conjugates (5a-k) was synthesizedviaclick chemistry approach. The newly synthesized compounds were assessed for theirin vitroantitubercular and antimicrobial activities. The compound5ghas displayed potent antitubercular activity againstMycobacterium tuberculosisH37Rv (Mtb) with MIC value 1.56 mu g/mL. The active compounds were screened for their cytotoxicity profile by MTT assay against RAW 264.7 cell line. The four compounds have shown goodin vitroantimicrobial activities against both antibacterial and antifungal pathogens. A molecular docking study was accomplished to identify the probable mode of action of synthesized derivatives. These compounds have shown excellent binding affinity towardEnoyl-acp reductase(INHA) andDNA gyrase.

引用

页码：3544 / 3557

页数：14

共 47 条

[31] Synthesis, antitubercular evaluation and molecular docking studies of phthalimide bearing 1,2,3-triazoles [J].

Phatak, Pramod S. ;

Bakale, Rajubai D. ;

Dhumal, Sambhaji T. ;

Dahiwade, Lalita K. ;

Choudhari, Prafulla B. ;

Krishna, Vagolu Siva ;

Sriram, Dharmarajan ;

Haval, Kishan P. .

SYNTHETIC COMMUNICATIONS, 2019, 49 (16) :2017-2028

[32]

Plumb LA, 2004, METH MOLEC MED, V88, P165

[33] Studies on Isoniazid Derivatives through a Medicinal Chemistry Approach for the Identification of New Inhibitors of Urease and Inflammatory Markers [J].

Rizvi, Fazila ;

Khan, Majid ;

Jabeen, Almas ;

Siddiqui, Hina ;

Choudhary, M. Iqbal .

SCIENTIFIC REPORTS, 2019, 9 (1)

[34] Modification of the NADH of the isoniazid target (InhA) from Mycobacterium tuberculosis [J].

Rozwarski, DA ;

Grant, GA ;

Barton, DHR ;

Jacobs, WR ;

Sacchettini, JC .

SCIENCE, 1998, 279 (5347) :98-102

[35] Design, synthesis and in vitro anti-tuberculosis activity of benzo [6,7]cyclohepta[1,2-b]pyridine-1,2,3-triazole derivatives [J].

Sajja, Yasodakrishna ;

Vanguru, Sowmya ;

Vulupala, Hanmanth Reddy ;

Bantu, Rajashaker ;

Yogeswari, Perumal ;

Sriram, Dharmarajan ;

Nagarapu, Lingaiah .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (23) :5119-5121

[36] Synthesis of Novel Triazole-incorporated Isatin Derivatives as Antifungal, Antitubercular, and Antioxidant Agents and Molecular Docking Study [J].

Shaikh, Mubarak H. ;

Subhedar, Dnyaneshwar D. ;

Khan, Firoz A. Kalam ;

Sangshetti, Jaiprakash N. ;

Nawale, Laxman ;

Arkile, Manisha ;

Sarkar, Dhiman ;

Shingate, Bapurao B. .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (01) :413-421

[37] Synthesis and bioactivity of novel triazole incorporated benzothiazinone derivatives as antitubercular and antioxidant agent [J].

Shaikh, Mubarak H. ;

Subhedar, Dnyaneshwar D. ;

Arkile, Manisha ;

Khedkar, Vijay M. ;

Jadhav, Nandadeep ;

Sarkar, Dhiman ;

Shingate, Bapurao B. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (02) :561-569

[38] 1,2,3-Triazole derivatives as antitubercular agents: synthesis, biological evaluation and molecular docking study [J].

Shaikh, Mubarak H. ;

Subhedar, Dnyaneshwar D. ;

Nawale, Laxman ;

Sarkar, Dhiman ;

Khan, Firoz A. Kalam ;

Sangshetti, Jaiprakash N. ;

Shingate, Bapurao B. .

MEDCHEMCOMM, 2015, 6 (06) :1104-1116

[39] Efficient synthesis and in vitro antitubercular activity of 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis [J].

Shanmugavelan, Poovan ;

Nagarajan, Sangaraiah ;

Sathishkumar, Murugan ;

Ponnuswamy, Alagusundaram ;

Yogeeswari, Perumal ;

Sriram, Dharmarajan .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (24) :7273-7276

[40] Identification and validation of novel drug targets in Mycobacterium tuberculosis [J].

Singh, Vinayak ;

Mizrahi, Valerie .

DRUG DISCOVERY TODAY, 2017, 22 (03) :503-509

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