Synthesis, biological evaluation, and molecular docking study of pyridine clubbed 1,3,4-oxadiazoles as potential antituberculars

Desai, N. C.; Trivedi, Anjali; Somani, Hardik; Jadeja, Krunalsinh A.; Vaja, Darshita V.; Nawale, Laxman; Khedkar, Vijay M.; Sarkar, Dhiman

doi:10.1080/00397911.2017.1410892

Cited by 23 publications

(18 citation statements)

References 54 publications

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“…However, compared to the reference drugs isoniazid and/or rifampicin, the activity was much weaker. Additionally, active derivatives showed great potential during molecular docking studies with mycobacterial enoyl reductase (InhA) [43,44]. Alghamdi et al from Saudi Arabia (2020) received a series of aryl-1,3,4-oxadiazolebenzothiazole derivatives, which they tested for antibacterial activity.…”

Section: Antibacterial Activity Of Aryl/heteroaryl Derivatives Of 134-oxadiazolementioning

confidence: 99%

“…In addition, these compounds have potent antifungal and antitubercular effect [47]. In addition, Desai et al (2016Desai et al ( , 2018 conducted studies on the antitubercular effects of pyridine based 1,3,4-oxadiazole scaffold derivatives. The most active compounds of the series 9a, 9b, additionally containing the indole ring (Figure 5), showed strong activity against M. bovis BCG in the active and dormant state.…”

Section: Antibacterial Activity Of Aryl/heteroaryl Derivatives Of 134-oxadiazolementioning

confidence: 99%

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Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives

Glomb

Świątek

2021

IJMS

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The worldwide development of antimicrobial resistance forces scientists to search for new compounds to which microbes would be sensitive. Many new structures contain the 1,3,4-oxadiazole ring, which have shown various antimicrobial activity, e.g., antibacterial, antitubercular, antifungal, antiprotozoal and antiviral. In many publications, the activity of new compounds exceeds the activity of already known antibiotics and other antimicrobial agents, so their potential as new drugs is very promising. The review of active antimicrobial 1,3,4-oxadiazole derivatives is based on the literature from 2015 to 2021.

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Section: Antibacterial Activity Of Aryl/heteroaryl Derivatives Of 134-oxadiazolementioning

confidence: 99%

Section: Antibacterial Activity Of Aryl/heteroaryl Derivatives Of 134-oxadiazolementioning

confidence: 99%

Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives

Glomb

Świątek

2021

IJMS

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“…The synthesis of N'-(substitutedbenzylidene) isonicotinohydrazides 3a-h shown to be simple and practical, achieving a good yield, as described in previous studies [37][38][39]. On the other hand, for the series of 1-(2substituted phenyl-5-(pyridin-4-yl)-1,3,4-oxadiazol-3(2H)-yl) ethanones 4a-h were synthesized according to the previously described procedures [36][37][38][39].…”

Section: Chemistrymentioning

confidence: 99%

Synthesis of Some 2,3-Dihydro-1,3,4-Oxadiazoles and 4,5-Dihydro-1,2,4-Triazoles as Anticancer Agents

Yahya

Abdullah

2020

Int J Pharm Pharm Sci

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Objective: The main objective of this work was to synthesize and evaluate the novel 2,3-dihydro-1,3,4-oxadiazole and 4,5-dihydro-1,2,4-triazole derivatives for cytotoxic activities. Methods: The 2,3-dihydro-1,3,4-oxadiazole derivatives 4a-h were synthesized by cyclization of N'-(substituted-benzylidene) isonicotinohydrazide 3a-e in refluxing acetic anhydride. The 2,3-dihydro-1,3,4-oxadiazole derivatives 4a-h were converted into the corresponding 4,5-dihydro-1,2,4-triazoles 5a-h using ammonia. All the synthesized compounds were identified, depending on the physical and spectral data. Title compounds were assessed for their cytotoxic activity against human cancer cell line (MCF-7) by using Sulforhodamine B (SRB) colorimetric assay. Results: All the synthesized compounds showed characteristic peaks in FTIR, 1HNMR and Mass spectral analysis. The results of the in vitro cytotoxic activity revealed that the compound 4c exhibited equipotent cytotoxic activity with an IC50 value of 8.04 µM when compared with that of standard drug doxorubicin (IC50= 8.02 µM). The reminder compounds have shown good to moderate cytotoxic activities when compared with that of a reference standard. Conclusion: We synthesized a series of title compounds in quantitative yields. Most derivatives showed moderate to good cytotoxic activity.

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“…In 2018, our research group synthesized N ′‐(1‐(2‐(4‐fluorophenyl)‐2‐methyl‐5‐(pyridin‐4‐yl)‐1,3,4‐oxadiazol‐3(2 H )‐yl)ethylidene)‐(aryl)‐benzohydrazides and tested them for in vitro antitubercular efficacy (Desai et al, 2018). Antitubercular activity (3.79 μg/ml), docking score (8.096), and glide energy (−53.343 kcal/mol) were excellent.…”

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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Synthesis, biological evaluation, and molecular docking study of pyridine clubbed 1,3,4-oxadiazoles as potential antituberculars

Cited by 23 publications

References 54 publications

Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives

Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives

Synthesis of Some 2,3-Dihydro-1,3,4-Oxadiazoles and 4,5-Dihydro-1,2,4-Triazoles as Anticancer Agents

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

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