Design and synthesis of 1,2,3-triazole–etodolac hybrids as potent anticancer molecules

Abstract

A series of novel 1,2,3-triazole-etodolac hybrids (6a-l) were designed and synthesized as potent anticancer molecules. The synthesis strongly relied on Huisgen's 1,3-dipolar cycloaddition between etodolac azide 3 and substituted terminal alkynes 5a-l. The use of CH 2 Cl 2 as a co-solvent with H 2 O increased the reaction rate and provided the corresponding 1,2,3-triazole-etodolac hybrids (6a-l) in excellent yields compared to other organic co-solvent systems. All the compounds were screened for their in vitro anticancer activity against human A549 cell lines and compounds 6e, 6f, 6h, 6j, and 6l were found to be the best anti-cancer molecules as compared to the marketed drug doxorubicin. Kukatpally,

1,2,3-Triazole-Containing Compounds as Anti–Lung Cancer Agents: Current Developments, Mechanisms of Action, and Structure–Activity Relationship

“…An antiproliferative SAR study of 1,2,3-triazole-containing etodolac derivatives 13 (Figure 4, IC 50 : 3.29-10.71 μm, MTT assay) against A549 cells revealed that the phenyl ring is crucial for the activity, and replacement by the naphthyl group results in loss of activity (Kummari et al, 2017). Introduction of substituents into the phenyl ring is generally detrimental to the activity, whereas methyl at the para position could enhance the activity slightly.…”

Novel anticancer and antibacterial organometallic polymer based on ferrocene as a building block and xanthone bioactive scaffolds: Synthesis, characterization, and biological study

“…Based on the best knowledge, ferrocene, xanthone, azine, and triazole bearing compounds have the good anticancer activity, individually. Now, it has been possible that these frameworks were together in the polymer backbone and show the synergic effect.…”

An Overview of Recent Advances in the Applications of Click Chemistry in the Synthesis of Bioconjugates with Anticancer Activities

“…Kummari et al . have prepared a range of new 1,2,3‐triazole–etodolac hybrids ( 91 ) by this procedure that to a solution of 2‐(1,8‐diethyl‐1,3,4,9‐tetrahydropyrano[3,4‐ b ]indol‐1‐yl)acetic acid ( 88 ) in dry THF at 0 ° C, a stirred solution of LiAlH 4 in dry THF was added and the mixture was stirred at r.t. After completion and purification, compound 89 was produced.…”