Cu(I)-Promoted Regioselective Synthesis of Some New Benzimidazole-1,2,3-Triazole Frameworks as In Vitro Anticancer Agents

• Published in: Russian journal of bioorganic chemistry Vol. 47; no. 5; pp. 1028 - 1033
• Main Authors: Manmohan Reddy Depa, Potla, Suneetha, Narkhede, Umesh C., Jadhav, Vinod D., Vidavalur, Siddaiah
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01-09-2021; Springer Nature B.V
• Subjects: Alkynes; Anticancer properties; Benzonitrile; Biochemistry; Biomedical and Life Sciences; Biomedicine; Bioorganic Chemistry; Cancer; Cycloaddition; Imidazole; Life Sciences; Organic Chemistry; Regioselectivity; Synthesis; Triazoles; benzimidazole-1,2,3-triazole hybrids; anticancer activity; 1,3-dipolar cycloaddition
• ISSN: 1068-1620; 1608-330X
• DOI: 10.1134/S1068162021050228

The regioselective synthesis of twelve new benzimidazole-1,2,3-triazole hybrids through the Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction between 1-(3-azidopropyl)-1
H-
benzo[d]imidazole and several terminal alkynes was described herein. All the synthesized compounds were further evaluated for their in vitro anticancer activity against three human cancer cell lines like PC3, A549, and MCF-7 using etoposide as standard drug. Four compounds named by 1-(3-(4-(3,5-dimethoxyphenyl)-1
H
-1,2,3-triazol-1-yl)propyl)-1
H
-benzo[d]imidazole,1-(3-(4-(4-methoxyphenyl)-1
H
-1,2,3-triazol-1-yl)propyl)-1
H
benzo[d]imidazole,4-(1-(3-(1
H
-benzo[d]imidazol-1-yl)propyl)-1
H
-1,2,3-triazol-4-yl) benzonitrile and 1-(3-(4-(4-nitrophenyl)-1
H
-1,2,3-triazol-1-yl)propyl)-1
H
-benzo[d]imidazole were displayed promising activity, in those the compound was shown outstanding activity against PC3, A549, and MCF-7 with IC
50
values of 3.01, 3.82, and 2.91 μM respectively.