Click synthesis, antimicrobial, DNA photocleavage and computational studies of oxindole-tethered 1H-1,2,3-triazoles

被引:12
作者
Kumar, Vijay [1 ]
Lal, Kashmiri [1 ]
Kumar, Ravinder [2 ]
Kumar, Anil [2 ]
Mathpati, Ramling S. [3 ]
Singh, Madhur Babu [4 ]
Kumari, Kamlesh [5 ]
机构
[1] Guru Jambheshwar Univ Sci & Technol, Dept Chem, Hisar 125001, Haryana, India
[2] Guru Jambheshwar Univ Sci & Technol, Dept Bio & Nano Technol, Hisar 125001, Haryana, India
[3] Natl Inst Technol, Dept Chem, Kurukshetra 136119, Haryana, India
[4] Univ Delhi, Atma Ram Sanatan Dharma Coll, Dept Chem, New Delhi 110021, India
[5] Univ Delhi, Dept Zool, Delhi 110007, India
关键词
antimicrobial; click chemistry; DNA photocleavage; docking; 1; 2; 3-triazole; oxindole; x-ray diffraction; CYCLOADDITION EN-ROUTE; ANTIBACTERIAL; UPDATE; ISATIN; DERIVATIVES; ANTIFUNGAL; CHEMISTRY; DOCKING; DESIGN; ACID;
D O I
10.4155/fmc-2023-0075
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Aim: To obtain new hybrids derived from isatin and triazole. Materials & methods: A series of oxindole-1-H-1,2,3-triazole hybrids (4a-l) were synthesized from 3-sulfenylated N-propargylated oxindoles and organic azides employing Cu(I)-catalyzed azide-alkyne cycloaddition. These compounds were evaluated in vitro for antimicrobial activity by the standard serial dilution method and DNA photocleavage activity. Results: Antimicrobial assay revealed that compounds 4l and 4f exhibited promising efficacy against Candida albicans and Rhizopus oryzae, respectively, with a minimum inhibitory concentration (MIC) value of 0.0008 & mu;mol/mL. Compounds 4h and 4k completely degraded plasmid DNA. Further molecular docking of compounds with 1KZN (4j and 4k) and 5TZ1 (4h and 4l) revealed good binding interactions. Conclusion: Results of the current research can help in the development of new antimicrobial agents with high efficacy.
引用
收藏
页码:1115 / 1131
页数:17
相关论文
共 84 条
[1]  
Adki N., 2022, CURR CHEM LETT, V11, P139, DOI DOI 10.5267/J.CCL.2021.8.001
[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]   1,2,3-Triazole-Benzofused Molecular Conjugates as Potential Antiviral Agents against SARS-CoV-2 Virus Variants [J].
Al-Humaidi, Jehan Y. ;
Shaaban, Marwa M. ;
Rezki, Nadjet ;
Aouad, Mohamed R. ;
Zakaria, Mohamed ;
Jaremko, Mariusz ;
Hagar, Mohamed ;
Elwakil, Bassma H. .
LIFE-BASEL, 2022, 12 (09)
[4]   1,2,3-Triazole hybrids as anticancer agents: A review [J].
Alam, Mohammad Mahboob .
ARCHIV DER PHARMAZIE, 2022, 355 (01)
[5]   Comparative Investigation on the Crystal Structures, Hirshfeld Surface Analysis, Antitubercular Assays, and Molecular Docking of Regioisomeric 1,2,3-Triazoles [J].
Anand, Ashish ;
Sindogi, Kishorkumar ;
Dixit, Sheshagiri R. ;
Shetty, Richa P. ;
Pujar, Gurubasavaraj, V ;
Kulkarni, Manohar, V ;
Row, Tayur N. Guru .
CHEMISTRYSELECT, 2022, 7 (15)
[6]   Microwave-assisted synthesis, antioxidant and antimicrobial evaluation of 2-indolinone-based bis-1,2,3-triazole derivatives [J].
Ashok, Dongamanti ;
Gundu, Srinivas ;
Aamate, Vikas Kumar ;
Devulapally, Mohan Gandhi .
MOLECULAR DIVERSITY, 2018, 22 (01) :57-70
[7]   Methods for in vitro evaluating antimicrobial activity: A review [J].
Balouiri, Mounyr ;
Sadiki, Moulay ;
Koraichi Ibnsouda, Saad .
JOURNAL OF PHARMACEUTICAL ANALYSIS, 2016, 6 (02) :71-79
[8]   Synthesis and antimalarial activity of 7-chloroquinoline-tethered sulfonamides and their [1,2,3]-triazole hybrids [J].
Batra, Neha ;
Agarwal, Drishti ;
Wadi, Ishan ;
Tekuri, Chandra Sekhar ;
Gupta, Rinkoo D. ;
Nath, Mahendra .
FUTURE MEDICINAL CHEMISTRY, 2022, 14 (23) :1725-1739
[9]   Design and synthesis, biological evaluation of bis-(1,2,3-and 1,2,4)-triazole derivatives as potential antimicrobial and antifungal agents [J].
Bitla, Sampath ;
Gayatri, Akkiraju Anjini ;
Puchakayala, Muralidhar Reddy ;
Bhukya, Vijaya Kumar ;
Vannada, Jagadeshwar ;
Dhanavath, Ramulu ;
Kuthati, Bhaskar ;
Kothula, Devender ;
Sagurthi, Someswar Rao ;
Atcha, Krisham Raju .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2021, 41
[10]   Bad Bugs, No Drugs: No ESKAPE! An Update from the Infectious Diseases Society of America [J].
Boucher, Helen W. ;
Talbot, George H. ;
Bradley, John S. ;
Edwards, John E., Jr. ;
Gilbert, David ;
Rice, Louis B. ;
Scheld, Michael ;
Spellberg, Brad ;
Bartlett, John .
CLINICAL INFECTIOUS DISEASES, 2009, 48 (01) :1-12