Synthesis of 2,5‐Disubstituted‐1,3,4‐oxadiazole Derivatives and Their Evaluation as Anticancer and Antimycobacterial Agents

Abstract

A series of regioisomeric (2,5‐dimethoxybenzoic acid, veratric acid) analogues were prepared by swapping the carboxylic motif to its oxadiazole bioisostere and have been screened for in vitro anticancer studies by using MTT (3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide) colorimetric assay. All of them were well characterized by spectroscopic techniques. Among the screened compounds, 9 i (2‐(2,5‐dimethoxyphenyl)‐5‐(5‐phenylthiophen‐2‐yl)‐1,3,4‐oxadiazole) demonstrated superior activity against MDA231 cells. Products 9 i displayed excellent activity against DU145, HCT15 and 10 i (2‐(3,4‐dimethoxyphenyl)‐5‐(5‐phenylthiophen‐2‐yl)‐1,3,4‐oxadiazole) against MDA231 cells. Structure of 10 c (2‐(3,4‐dimethoxyphenyl)‐5‐(2,4,6‐trimethoxyphenyl)‐1,3,4‐oxadiazole) was further authenticated through single crystal X‐ray diffraction. Analogue 9 i have come out to be the best anticancer and antimycobacterial agent.

1,3,4-oxadiazole/chalcone hybrids: Design, synthesis, and inhibition of leukemia cell growth and EGFR, Src, IL-6 and STAT3 activities

“…Oxadiazole derivatives are typical heterocyclic compounds that have exhibited potential as anticancer therapeutics [27–32]. The anticancer activities of 1,3,4-oxadiazole involve different mechanisms, and included inhibition of matrix metalloproteinase-9 [33], tubulin polymerization [34], growth factors [30], NF-κB signaling [35], Bcl-2 [36], cell cycle progression at G2/M phase [37], thymidine phosphorylase [38,39], and STAT3 [40–44].…”

3,5–Bis(2–Hydroxyphenyl)–1H–1,2,4–Triazole Derivatives: Synthesis, Crystal Structure and Insecticidal Activity

“…The compound possesses a stable 1,2,4‐triazole heterocyclic ring and two phenol moieties can form intermolecular hydrogen bonds with heteroatom . Based on their molecular structure and the configuration of commercial pesticides, presumably these compounds have a great insecticidal activity and no articles on their insecticidal activity have been reported so far.…”

Yeni 5-Merkapto-2-(5-metil-furan-2-il-metilidenamino)-1,3,4-tiyadiazol Molekülün Sentezi ve Teorik Analizi

“…Among these molecules, thiadiazoles, which have an important place among the 5-membered heterocyclic containing nitrogen and sulfur, are widely used in pharmaceutical chemistry, materials science and organic synthesis (Shahcheragh et al, 2017). 1,3,4-Thiadiazole and its derivatives have a broad spectrum of biological activity such as antimicrobial (El-Gohary et al, 2013), antibacterial (Li et al, 2015), antioxidant (Gür et al, 2017), anticonvulsant (Luszczki et al, 2015), analgesic (Ragab et al, 2016), and anticancer (Polkam et al, 2017). In addition, 1,3,4-thiadiazole derivatives are widely used in bactericides, insecticides, pesticides, fungicides and herbicides in many areas of agriculture and technology (Zarei, 2017;Zou et al, 2002).…”