Design, synthesis and characterization of novel 2-(2, 3-dichlorophenyl)-5-aryl-1,3,4-oxadiazole derivatives for their anti-tubercular activity against Mycobacterium tuberculosis

Ningegowda, Raghu; Chandrashekharappa, Sandeep; Singh, Vinayak; Mohanlall, Viresh; Venugopala, Katharigatta N.

doi:10.1016/j.cdc.2020.100431

Cited by 28 publications

(11 citation statements)

References 18 publications

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“…synthesised a series of 2–(2,3-dichlorophenyl)-5-aryl- 1,3,4-oxadiazole derivatives and assessed their antimycobacterial activity against Mycobacterium tuberculosis H37RvMa strain. Compound 13 ( Figure 1 ) exhibited good anti-tuberculosis activity at a concentration of 62.5 μg/mL, and its pharmacophore can be optimised to generate a series of improved anti-tuberculosis lead compounds containing the 1,3,4-oxadiazole ring 21 .…”

Section: Oxadiazolementioning

confidence: 99%

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Wang

Sun

Jia

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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Oxadiazole is a five-membered heterocyclic compound containing two nitrogen atoms and one oxygen atom. The 1,3,4-oxadiazole and 1,2,4-oxadiazole have favourable physical, chemical, and pharmacokinetic properties, which significantly increase their pharmacological activity via hydrogen bond interactions with biomacromolecules. In recent years, oxadiazole has been demonstrated to be the biologically active unit in a number of compounds. Oxadiazole derivatives exhibit antibacterial, anti-inflammatory, anti-tuberculous, anti-fungal, anti-diabetic and anticancer activities. In this paper, we report a series of compounds containing oxadiazole rings that have been published in the last three years only (2020–2022) as there was no report or their activities described in any article in 2019, which will be useful to scientists in research fields of organic synthesis, medicinal chemistry, and pharmacology.

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Section: Oxadiazolementioning

confidence: 99%

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Wang

Sun

Jia

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…202213101 1,3,4-oxadiazole containing molecules showed wide range of biological activities viz. anti-inflammatory [14,15], antioxidant [14,[16][17], anticonvulsant [18,19], antibacterial [20,21], antiviral [22], anticancer [23][24][25][26], antifungal [21,27], anti-HIV [28,29], antituberculosis [30,31], antimalarial [32,33], insecticidal [34,35], herbicidal [36,37], analgesic [38], ulcerogenic liability [39], muscle relaxant [40], antidepressant agents [41] and sedative-hypnotic [42]. However, more emphasis is reported on the molecules relevant to medicinal chemistry, specifically in the discovery of new chemical entities with antiparasitic [12] and antimicrobial properties [43].…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial Activity and Sar of 2,5-Disubstituted 1,3,4-Oxadiazole Derivatives

Kumar

Narang

Devgun

et al. 2022

JASR

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1,3,4-oxadiazole is a five membered heterocyclic aromatic moiety, present in a number of antimicrobial agents. 2,5- disubstituted 1,3,4-oxadiazole derivatives have shown broad spectrum of antibacterial and antifungal activities. Many scientific groups have synthesized and screened their antimicrobial potential. Reported activity data showed that some 1,3,4-oxadiazole derivatives exhibited better activity than already known antibiotics. Hence, they can be used as lead for development of promising antimicrobial agents. In present review, antimicrobial activities and SAR of 2,5-disubstituted 1,3,4-oxadiazole derivatives reported by different research groups in last ten years have been summarized.

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“…The pharmacological activity linked with 1,3,4‐oxadiazole has intrigued researchers, and certain commercially available drugs such as Raltegravir, Furamizole, Nesapidil, Tiodazosin, and Zibotentan contain this scaffold. The antitubercular activity of 1,3,4‐oxadiazole may be due to its core structure, which contains two nitrogen atoms and one oxygen atom (Ambhore et al, 2019; Dhumal et al, 2016; El‐Etrawy & Sherbiny, 2021; Khan et al, 2017; Ningegowda et al, 2020). Similarly, because it is present in the Lampit, which the FDA in 2020, the furan nucleus, approved has demonstrated its efficacy and medical relevance.…”

Section: Introductionmentioning

confidence: 99%

Conventional and microwave‐assisted organic synthesis of novel antimycobacterial agents bearing furan and pyridine hybrids

Desai

Bhatt

Jadeja

et al. 2021

Drug Development Research

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Drug resistance in tuberculosis poses a serious threat to humanity because currently available antitubercular drugs are ineffective against Mycobacterium tuberculosis (M. tuberculosis). As a result, the approval of Bedaquiline and Delamanid for the treatment of drug‐resistant tuberculosis was accelerated. Still, there is an urgent need to search for new antitubercular drugs with novel mechanisms of action (MoA). Due to this, we have designed a synthetic strategy by utilizing microwave‐assisted organic synthesis. We have compared our method with the conventional procedure, and the data show that our procedure is more effective in the preparation of title compounds. A unique series of 1‐(2‐(furan‐2‐yl)‐5‐(pyridin‐4‐yl)‐1,3,4‐oxadiazol‐3(2H)‐yl)‐3‐(aryl)‐prop‐2‐en‐1‐ones (5a‐o) was synthesized utilizing conventional and microwave‐assisted techniques. Synthetic compounds were investigated for antitubercular activity against Mycobacterium TB H37Ra and Mycobacterium bovis (M. bovis). Compound 5b was reported to be the most effective against M. tuberculosis H37Ra (97.69 percent inhibition at 30 μg/ml) and M. bovis (97.09 percent inhibition at 30 μg/ml). An in silico binding affinity study of mycobacterial enoyl‐acyl carrier protein reductase (InhA) reveals the binding mechanism and thermodynamic interactions that determine these molecule's binding affinity. Compound 5b had a high glide score of −8.991 and low glide energy of −49.893 kcal/mol.

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Design, synthesis and characterization of novel 2-(2, 3-dichlorophenyl)-5-aryl-1,3,4-oxadiazole derivatives for their anti-tubercular activity against Mycobacterium tuberculosis

Cited by 28 publications

References 18 publications

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Antimicrobial Activity and Sar of 2,5-Disubstituted 1,3,4-Oxadiazole Derivatives

Conventional and microwave‐assisted organic synthesis of novel antimycobacterial agents bearing furan and pyridine hybrids

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