Synthesis, bioevaluation and molecular docking study of new piperazine and amide linked dimeric 1,2,3-triazoles

被引：21

作者：

Deshmukh, Tejshri R. ^{[1
]}

Khare, Smita P. ^{[1
]}

Krishna, Vagolu S. ^{[2
]}

Sriram, Dharmarajan ^{[2
]}

Sangshetti, Jaiprakash N. ^{[3
]}

Khedkar, Vijay M. ^{[4
]}

Shingate, Bapurao B. ^{[1
]}

机构：

[1] Dr Babasaheb Ambedkar Marathwada Univ, Dept Chem, Aurangabad 431004, Maharashtra, India

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

[3] YB Chavan Coll Pharm, Dept Pharmaceut Chem, Aurangabad, Maharashtra, India

[4] Shri Vile Parle Kelavani Mandals Inst Pharm, Dept Pharmaceut Chem, Dhule, Maharashtra, India

来源：

SYNTHETIC COMMUNICATIONS | 2020年 / 50卷 / 02期

关键词：

Antifungal activity; antioxidant activity; antitubercular activity; dimeric; 1; 2; 3-triazoles; molecular docking study; ANTITUBERCULAR AGENTS SYNTHESIS; CLICK CHEMISTRY; TRIAZOLE DERIVATIVES; FACILE SYNTHESIS; BIOLOGICAL EVALUATION; DRUG DISCOVERY; ANTIOXIDANT; CYCLOADDITION; EPIDEMIOLOGY; INHIBITORS;

D O I：

10.1080/00397911.2019.1695275

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In search of more potent new antitubercular agents, a library of novel piperazine tethered dimeric 1,2,3-triazoles were designed by assembling 1,2,3-triazoles and piperazine in a single molecular architectural framework. The titled compounds (3a-m) were synthesized by 1,3-dipolar cycloaddition of 1,4-di(prop-2-yn-1-yl)piperazine (1) and various azides (2a-m) using click chemistry approach with good yields. All the synthesized compounds (3a-m) have been screened for their in vitro antitubercular, antifungal and antioxidant activities against their respective strains. Among them, 3b, 3d, and 3i have revealed promising antitubercular activity against Mycobacterium tuberculosis (Mtb) H37Rv with MIC 12.5 mu g/mL. Molecular docking results provided well-clustered solutions to the mode of binding for these molecules into the active site of Mtb enoyl reductase (InhA). In addition to this, most of synthesized compounds were found to have potential antifungal as well as antioxidant activity.

引用

页码：271 / 288

页数：18

共 57 条

[1] Design, synthesis and evaluation of 1,2,3-triazole-adamantylacetamide hybrids as potent inhibitors of Mycobacterium tuberculosis [J].

Addla, Dinesh ;

Jallapally, Anvesh ;

Gurram, Divya ;

Yogeeswari, Perumal ;

Sriram, Dharmarajan ;

Kantevari, Srinivas .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (08) :1974-1979

[2] Click Chemistry: 1,2,3-Triazoles as Pharmacophores [J].

Agalave, Sandip G. ;

Maujan, Suleman R. ;

Pore, Vandana S. .

CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) :2696-2718

[3] Synthesis and biological evaluation of novel 1,2,3-triazole derivatives as anti-tubercular agents [J].

Ali, Abdul Aziz ;

Gogoi, Dhrubajyoti ;

Chaliha, Amrita K. ;

Buragohain, Alak K. ;

Trivedi, Priyanka ;

Saikia, Prakash J. ;

Gehlot, Praveen S. ;

Kumar, Arvind ;

Chaturvedi, Vinita ;

Sarma, Diganta .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (16) :3698-3703

[4] A click chemistry approach for the synthesis of mono and bis aryloxy linked coumarinyl triazoles as anti-tubercular agents [J].

Anand, Ashish ;

Naik, Reshma J. ;

Revankar, Hrishikesh M. ;

Kulkarni, Manohar V. ;

Dixit, Sheshagiri R. ;

Joshi, Shrinivas D. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 105 :194-207

[5]

[Anonymous], GLOB TUB REP 2016

[6]

[Anonymous], TUB SURV RISK FUNG I

[7] The influence of lipophilicity in drug discovery and design [J].

Arnott, John A. ;

Planey, Sonia Lobo .

EXPERT OPINION ON DRUG DISCOVERY, 2012, 7 (10) :863-875

[8] COMPOUNDS DESIGNED TO FIT A SITE OF KNOWN STRUCTURE IN HUMAN HEMOGLOBIN [J].

BEDDELL, CR ;

GOODFORD, PJ ;

NORRINGTON, FE ;

WILKINSON, S ;

WOOTTON, R .

BRITISH JOURNAL OF PHARMACOLOGY, 1976, 57 (02) :201-209

[9] BENZYLATED 1,2,3-TRIAZOLES AS ANTICOCCIDIOSTATS [J].

BOCHIS, RJ ;

CHABALA, JC ;

HARRIS, E ;

PETERSON, LH ;

BARASH, L ;

BEATTIE, T ;

BROWN, JE ;

GRAHAM, DW ;

WAKSMUNSKI, FS ;

TISCHLER, M ;

JOSHUA, H ;

SMITH, J ;

COLWELL, LF ;

WYVRATT, MJ ;

FISHER, MH ;

TAMAS, T ;

NICOLICH, S ;

SCHLEIM, KD ;

WILKS, G ;

OLSON, G .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (09) :2843-2852

[10] Novel 1,2,3-Triazole Derivatives for Use against Mycobacterium tuberculosis H37Rv (ATCC 27294) Strain [J].

Boechat, Nubia ;

Ferreira, Vitor F. ;

Ferreira, Sabrina B. ;

Ferreira, Maria de Lourdes G. ;

da Silva, Fernando de C. ;

Bastos, Monica M. ;

Costa, Marilia dos S. ;

Lourenco, Maria Cristina S. ;

Pinto, Angelo C. ;

Krettli, Antoniana U. ;

Aguiar, Anna Caroline ;

Teixeira, Brunno M. ;

da Silva, Nathalia V. ;

Martins, Priscila R. C. ;

Bezerra, Flavio Augusto F. M. ;

Camilo, Ane Louise S. ;

da Silva, Gerson P. ;

Costa, Carolina C. P. .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (17) :5988-5999

← 1 2 3 4 5 6 →