1,2,3-Triazolyl Phenylhydrazones as Antioxidant Agents: An Ultrasound Promoted Catalyst-Free Synthesis and Molecular Docking Study

被引：2

作者：

Khare, Smita P. ^{[1
]}

Deshmukh, Tejshri R. ^{[1
]}

Sangshetti, Jaiprakash N. ^{[2
]}

Khedkar, Vijay M. ^{[3
]}

Shingate, Bapurao B. ^{[1
]}

机构：

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

[2] YB Chavan Coll Pharm, Aurangabad, Maharashtra, India

[3] Vishwakarma Univ, Sch Pharm, Pune, Maharashtra, India

来源：

POLYCYCLIC AROMATIC COMPOUNDS | 2024年 / 44卷 / 10期

关键词：

123-Triazoles; phenylhydrazones; ultrasound irradiation; catalyst free synthesis; antioxidant activity; molecular docking; BIOLOGICAL EVALUATION; POLYETHYLENE-GLYCOL; CLICK CHEMISTRY; ANTIFUNGAL ACTIVITY; FACILE SYNTHESIS; DERIVATIVES; HYDRAZONES; DESIGN; ANTIBACTERIAL; DISCOVERY;

D O I：

10.1080/10406638.2024.2309358

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, ultrasound assisted catalyst-free, green protocol has been developed for the synthesis of 1,2,3-triazolyl phenylhydrazone derivatives under environmentally benign condition. The antioxidant activity for all the synthesized derivatives were evaluated in vitro by using 1,1-diphenylpicrylhydrazyl (DPPH) radical scavenging method. The compounds 6a, 6e, 6f, and 6i were shows an excellent antioxidant activity than the standard drug butylated hydroxy toluene with IC50 values in the range 12.03 ± 0.11–14.07 ± 0.31 µg/mL. Molecular docking study was also performed to elaborate their possible interactions with Myeloperoxidase enzyme. Furthermore, in silico ADME properties for all the compounds were also studied. © 2024 Taylor & Francis Group, LLC.

引用

页码：6885 / 6902

页数：18

共 69 条

[1] Design and synthesis of new 4-pyrazolin-3-yl-1,2,3-triazoles and 1,2,3-triazol-4-yl-pyrazolin-1-ylthiazoles as potential antimicrobial agents [J].

Abdel-Wahab, Bakr F. ;

Abdel-Latif, Ehab ;

Mohamed, Hanan A. ;

Awad, Ghada E. A. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 52 :263-268

[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, antimycobacterial activity and docking study of 2-aroyl-[1]benzopyrano[4,3-c]pyrazol-4(1H)-one derivatives and related hydrazide-hydrazones [J].

Angelova, Violina T. ;

Valcheva, Violeta ;

Pencheva, Tania ;

Voynikov, Yulian ;

Vassilev, Nikolay ;

Mihaylova, Rositsa ;

Momekov, Georgi ;

Shivachev, Boris .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (13) :2996-3002

[4] Synthesis and antifungal activity of substituted salicylaldehyde hydrazones, hydrazides and sulfohydrazides [J].

Backes, Gregory L. ;

Neumann, Donna M. ;

Jursic, Branko S. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (17) :4629-4636

[5] Synthesis and antioxidant activity evaluation of a syringic hydrazones family [J].

Belkheiri, Nadji ;

Bouguerne, Benaissa ;

Bedos-Belval, Florence ;

Duran, Hubert ;

Bemis, Corinne ;

Salvayre, Robert ;

Negre-Salvayre, Anne ;

Baltas, Michel .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (07) :3019-3026

[6] Bioactive-guided structural optimization of 1,2,3-triazole phenylhydrazones as potential fungicides against Fusarium graminearum [J].

Chen, Yiliang ;

Yao, Kaicheng ;

Wang, Kaiyan ;

Xiao, Cheng ;

Li, Ke ;

Khan, Babar ;

Zhao, Shuangshuang ;

Yan, Wei ;

Ye, Yonghao .

PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, 2020, 164 :26-32

[7]

CHORNOUS V A., 2001, Pharmaceutical Chemistry Journal, V35, P203, DOI DOI 10.1023/A:1010432029236

[8] Synthesis, tuberculosis inhibitory activity, and SAR study of N-substituted-phenyl-1,2,3-triazole derivatives [J].

Costa, Marilia S. ;

Boechat, Nubia ;

Rangel, Erica A. ;

Da Silva, Fernando de C. ;

de Souza, Alessandra M. T. ;

Rodrigues, Carlos R. ;

Castro, Helena C. ;

Junior, Ivan N. ;

Lourenco, Maria Cristina S. ;

Wardell, Solange M. S. V. ;

Ferreira, Vitor F. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (24) :8644-8653

[9] Organic reactions in water or biphasic aqueous systems under sonochemical conditions. A review on catalytic effects [J].

Cravotto, Giancarlo ;

Borretto, Emily ;

Oliverio, Manuela ;

Procopio, Antonio ;

Penoni, Andrea .

CATALYSIS COMMUNICATIONS, 2015, 63 :2-9

[10] Synthesis, antibacterial and cytotoxic activities of new biflorin-based hydrazones and oximes [J].

da S. Souza, Luciana G. ;

Almeida, Macia C. S. ;

Lemos, Telma L. G. ;

Ribeiro, Paulo R. V. ;

de Brito, Edy S. ;

Silva, Vera L. M. ;

Silva, Artur M. S. ;

Braz-Filho, Raimundo ;

Costa, Jose G. M. ;

Rodrigues, Fabio F. G. ;

Barreto, Francisco S. ;

de Moraes, Manoel O. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (02) :435-439

← 1 2 3 4 5 6 7 →