Synthesis and biological evaluation of benzimidazole-linked 1,2,3-triazole congeners as agents
Open Access
- 2 December 2014
- journal article
- research article
- Published by Springer Science and Business Media LLC in Organic and Medicinal Chemistry Letters
- Vol. 4 (1), 1-4
- https://doi.org/10.1186/s13588-014-0014-x
Abstract
Benzimidazoles and triazoles are useful structures for research and development of new pharmaceutical molecules and have received much attention in the last decade because of their highly potent medicinal activities. A simple and efficient synthesis of triazole was carried out by treatment of 2-(4-azidophenyl)-1H-benzo[d]imidazole (6) with different types of terminal alkynes in t-BuOH/H2O, sodium ascorbate, and Zn(OTf)2, screened for cytotoxicity assay and achieved good results. A series of new benzimidazole-linked 1,2,3-triazole (8a-i) congeners were synthesized through cyclization of terminal alkynes and azide. These synthesized congeners 8a-i were evaluated for their cytotoxicity against five human cancer cell lines. These benzimidazole-linked 1,2,3-triazole derivatives have shown promising activity with IC50 values ranging from 0.1 to 43 μM. Among them, the compounds (8a, 8b, 8c, and 8e) showed comparable cytotoxicity with adriamycin control drug. In conclusion, we have developed a simple, convenient, and an efficient convergent approach for the synthesis of benzimidazole-linked 1,2,3-triazole congeners as agents. Synthesis of 1,2,3-triazole derivativesKeywords
This publication has 15 references indexed in Scilit:
- Design and synthesis of novel 7-aminoquinazoline derivatives: Antitumor and anticonvulsant activitiesBioorganic & Medicinal Chemistry Letters, 2012
- Design, synthesis and biological evaluation of novel quinazoline derivatives as potential antitumor agents: Molecular docking studyEuropean Journal of Medicinal Chemistry, 2010
- In-vivo analgesic and anti-inflammatory activities of newly synthesized benzimidazole derivativesEuropean Journal of Medicinal Chemistry, 2010
- Synthesis and potent antimicrobial activity of some novel methyl or ethyl 1H-benzimidazole-5-carboxylates derivatives carrying amide or amidine groupsBioorganic & Medicinal Chemistry, 2005
- Pyrrolo[1,2-a]benzimidazole-Based Quinones and Iminoquinones. The Role of the 3-Substituent on CytotoxicityJournal of Medicinal Chemistry, 1995
- Effects of analogs of the DNA minor groove binder Hoechst 33258 on topoisomerase II and I mediated activitiesBiochimica et Biophysica Acta (BBA) - Gene Structure and Expression, 1992
- Phase II study of pibenzimol in pancreatic cancerInvestigational New Drugs, 1991
- 1,2,3-Triazoles and their Benzo DerivativesPublished by Elsevier BV ,1984
- 4‐Amino‐3‐mercapto‐4H‐1,2,4‐triazoles and propargyl aldehydes: A new route to 3‐R‐8‐aryl‐1,2,4‐triazolo[3,4‐b]‐1,3,4‐thiadiazepinesJournal of Heterocyclic Chemistry, 1980
- Alkylating nucleosides. 1. Synthesis and cytostatic activity of N-glycosyl(halomethyl)-1,2,3-triazoles. A new type of alkylating agentJournal of Medicinal Chemistry, 1979