Design, synthesis, and anticancer evaluation of 1,2,4-oxadiazole functionalized quinoline derivatives

Kala, Pruthu; Sharif, Syed Khasim; Krishna, Ch. Murali; Ramachandran, D.

doi:10.1007/s00044-019-02467-6

Cited by 10 publications

(9 citation statements)

References 52 publications

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“…Kala et al ( 2020 ) have worked on the design and synthesis of 1,2,4-oxadiazoles with quinoline derivatives and evaluated anticancer activity against etoposide (Kala et al 2020 ). Etoposide is used for the treatment of non-lymphocytic leukemia, lung cancer, lymphoma, testicular cancer, and glioblastoma multiforme.…”

Section: Oxadiazolementioning

confidence: 99%

Biological activity of oxadiazole and thiadiazole derivatives

Atmaram

Roopan

2022

Appl Microbiol Biotechnol

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The 5-membered oxadiazole and thiadiazole scaffolds are the most privileged and well-known heterocycles, being a common and essential feature of a variety of natural products and medicinal agents. These scaffolds take up the center position and are the core structural components of numerous drugs that belong to different categories. These include antimicrobial, anti-tubercular, anti-inflammatory, analgesic, antiepileptic, antiviral, and anticancer agents. In this review, we mostly talk about the isomers 1,2,4-oxadiazole and 1,3,4-thiadiazole because they have important pharmacological properties. This is partly because they are chemical and heat resistant, unlike other isomers, and they can be used as bio-isosteric replacements in drug design. We are reviewing the structural modifications of different oxadiazole and thiadiazole derivatives, more specifically, the anti-tubercular and anticancer pharmacological activities reported over the last 5 years, as we have undertaken this as a core area of research. This review article desires to do a thorough study and analysis of the recent progress made in the important biological isomers 1,2,4-oxadiazole and 1,3,4-thiadiazol. This will be a great place to start for future research. Key points • Five-membered heterocyclic compound chemistry and biological activity recent survey. • Synthesis and pharmacological evolution of 1,2,4-oxadiazole and 1,3,4-thiadiazole are discussed in detail. • The value and significance of heterocyclic compounds in the field of drug designing are highlighted. Supplementary Information The online version contains supplementary material available at 10.1007/s00253-022-11969-0.

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Section: Oxadiazolementioning

confidence: 99%

Biological activity of oxadiazole and thiadiazole derivatives

Atmaram

Roopan

2022

Appl Microbiol Biotechnol

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“…Functionalized quinoline derivatives were designed to evaluate their anticancer properties. [76] The designed derivatives comprised of 5,7-dinitroquinolines appended with a 3,4,5-trimethoxyphenyl ring at 2-position. In addition, 5-aryl oxadiazole was appended at quinoline 3-position through phenoxymethylene moiety.…”

Section: Heterocyclic Ring-appended Quinolinesmentioning

confidence: 99%

“…Structures of quinoline derivatives possessing heterocyclic rings. [76][77][78][79][80][81][82][83] The evidence of anticancer properties α,β-unsaturated moiety in flavonoids was made use in the design and synthesis of chalcone-fused quinoline derivatives tethered via oxazole ring. [81] In the anticancer evaluation, an excellent anticancer profile ( A series of hybrids involving coumarin and quinoline pharmacophores was prepared.…”

Section: Compdmentioning

confidence: 99%

Report on Recently (2017–20) Designed Quinoline‐Based Human Cancer Cell Growth Inhibitors

Dorababu¹

2020

ChemistrySelect

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Quinoline has been a most essential pharmacophore, derivatization of which led to enticing pharmacological properties. Quinoline is responsible for a wide range of biological potencies such as antibacterial, antifungal, anti-leishmanial, antimalarial, antioxidant and anticancer properties. Out of these clinical importances, the anticancer property of heterocycles is of greatest concern as cancer has become a major threat globally. Since some natural products containing quinoline moiety have displayed cancer inhibition potency, quinoline has been given highest priority in the anticancer drug design and development. In addition, quinoline has got eight positions including nitrogen for substitution which may result in some potential anticancer properties. Ever since, this extraordinary potential is being utilized in anticancer drug discovery. In this review, the various trends in drug design of quinoline moiety anticipating finest anticancer properties through cancer cell growth inhibition are collated comprehensively. The review work is classified based on type of quinoline derivatives. Besides this, with the aid of structure-activity relationship discussion, the importance of structural units that contributed to strongest activity towards cancer inhibition is emphasized. The particular activity would help to bring further advanced anticancer agents in the future.

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“…1,2,4-Oxadiazole-containing compounds exhibited broadspectrum anticancer [14][15][16][17], antifungal [18], antibacterial [19], (Figure 1B) antiinflammatory [20], antioxidant [21], antiviral [22], antitubercular [23], neuroprotective [24], activities. In recent years, 1,2,4-oxadiazole rings clubbed with other heterocycles have been privileged scaffolds for the generation of new lead compounds [25].…”

Section: Introductionmentioning

confidence: 99%

An efficient synthesis of new 3,5‐bis(2‐arylthiazol‐4‐yl)‐1,2,4‐oxadiazole derivatives and their antimicrobial evaluation

Shaikh

Bhoye

Nandurkar

et al. 2023

Journal of Heterocyclic Chem

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A new series of 3,5-bis(2-arylthiazol-4-yl)-1,2,4-oxadiazole (8a-o) has been synthesized by modified reaction conditions. The reaction of ester 7a with N 0hydroxy-2-phenylthiazole-4-carboximidamide 6a using NaOH in DMSO gave the formation of product 8a up to 40% yield. In the second method, the reaction with K 2 CO 3 in toluene at reflux conditions gave a 50% yield. In the third method, the reaction condition was modified. The ester 7a was hydrolyzed to acid 9a. The reactions of acid 9a using N,N-dimethyl amino pyridine (DMAP) in N,N-dimethylformamide (DMF), followed by the addition of N-(3-dimethylaminopropyl)-N 0 -ethylcarbodiimide hydrochloride (EDCÁHCl), and then N 0hydroxy-2-phenylthiazole-4-carboximidamide 6a, furnished a 65% yield of 8a.The compounds 8b-o were synthesized using DMAP and EDCÁHCl as coupling reagents and gave 60%-72% yields. The structure of newly synthesized compounds was confirmed by spectral analysis. The synthesized compounds were screened for in vitro antimicrobial activity against Escherichia coli (NCIM 2574), Proteus mirabilis (NCIM 2388), Bacillus subtilis (NCIM2063), Staphylococcus albus (NCIM 2178), Candida albicans (NCIM 3100), and Aspergillus niger (ATCC 504). Among the 8a-o derivatives, eight compounds 8c, 8e, 8f, 8g, 8i, 8j, 8k, and 8l showed good activity S. albus with a MIC 31.25-62.5 μg/mL.

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Design, synthesis, and anticancer evaluation of 1,2,4-oxadiazole functionalized quinoline derivatives

Cited by 10 publications

References 52 publications

Biological activity of oxadiazole and thiadiazole derivatives

Biological activity of oxadiazole and thiadiazole derivatives

Report on Recently (2017–20) Designed Quinoline‐Based Human Cancer Cell Growth Inhibitors

An efficient synthesis of new 3,5‐bis(2‐arylthiazol‐4‐yl)‐1,2,4‐oxadiazole derivatives and their antimicrobial evaluation

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