Benzimidazole‐1,3,4‐Oxadiazole Hybrids: Synthesis, Anticancer Evaluation, Docking and DFT Studies

Abstract

In the present work, new benzimidazole based 1,3,4-oxadiazole linked thioacetamide conjugates have been synthesized and evaluated for antiproliferative activity. Formation of all the target molecules were elucidated by NMR ( 1 H & 13 C), FTIR, mass spectrometry and other techniques. The compounds displayed significant to moderate cytotoxicity towards MCF-7, HepG2 and HCT-116 cancerous cell lines. Among all the compounds, compound 11, 12 and 13 showed promising cytotoxicity with IC 50 2.39-10.98 μM, 4.57-16.35 μM and 3.10-15.58 μM towards MCF-7, HepG2 and HCT-116, respectively. Also, compound 11, 12 and 13 inhibited EGFR with IC 50 0.91-2.1 μM and exhibited high binding energy of À 8.34, À 8.06 & À 8.08 Kcal/mol, respectively against EGFR protein in docking study. The DFT study was also found to be consistent with the anticancer results of these newly synthesized compounds. It can be concluded that these 1,3,4-oxadiazole based benzimidazole derivatives possess promising anticancer properties and could be used as anticancer leads. Results and DiscussionChemistry ortho-Phenylenediamine 1 was the main raw material for the preparation of all the final compound 7-17. All the intermedi-[a] S.

Biological Activities, DFT Calculations, and Molecular Docking Simulation of Thymol‐Based Compounds

“…Compound 3 d showed the highest antioxidant activity in good agreement with the lower value of electronic chemical potential calculated (Table 1). [38] …”

“Synergistic Innovation: Crafting Indazole Derivatives for Advanced Anticancer, Antioxidant, and Antimicrobial Efficacy through Integrative Design and Holistic Evaluation”

“…The indazole nucleus, distinguished by its five-membered heterocyclic structure, has become a focal point of interest owing to its remarkable spectrum of pharmacological activities, spanning anticancer, antioxidant and antimicrobial properties. [2,3] The allure of indazole lies in its capacity to open up new vistas in therapy, presenting the tantalizing prospect of pioneering medications that have the potential to revolutionize the healthcare landscape. Its ubiquitous presence in nature establishes indazole as a pivotal scaffold for numerous indispensable molecules in the realms of biology and medicine.…”

“…Among the myriad of compounds under scrutiny, indazole derivatives have emerged as a particularly compelling class, captivating substantial attention for their auspicious pharmacological applications. The indazole nucleus, distinguished by its five‐membered heterocyclic structure, has become a focal point of interest owing to its remarkable spectrum of pharmacological activities, spanning anticancer, antioxidant and antimicrobial properties [2,3] . The allure of indazole lies in its capacity to open up new vistas in therapy, presenting the tantalizing prospect of pioneering medications that have the potential to revolutionize the healthcare landscape.…”

Synthesis, Antioxidant, and Anticancer Studies of New 1,3,4‐Oxadiazole Derivatives Linked to Benzoquinoline

“…[19,20] The broad and potent activity of 1,3,4-oxadiazole and their derivatives has established them as important pharmacological scaffolds, especially in the treatment of cancer disease. [21][22][23][24] For example, Zibotentan, an FDAapproved anticancer drug, is a 1,3,4-oxadiazole nucleus that contains the most exclusive derivatives on the market [20] Figure 1.…”

“…Figure 1 shows some drugs with 1,3,4‐oxadiazole scaffold, for example, Furamizole (a nitrofuran derivative with potent antibacterial activity), Nesapidil (vasodilator agent), Raltegravir (antiviral)and Tiodazosin (antihypertensive agent) [19,20] . The broad and potent activity of 1,3,4‐oxadiazole and their derivatives has established them as important pharmacological scaffolds, especially in the treatment of cancer disease [21–24] . For example, Zibotentan, an FDA‐approved anticancer drug, is a 1,3,4‐oxadiazole nucleus that contains the most exclusive derivatives on the market [20] Figure 1.…”