Microwave-assisted organic synthesis, antimycobacterial activity, structure–activity relationship and molecular docking studies of some novel indole-oxadiazole hybrids

Desai, N. C.; Somani, Hardik; Mehta, Harsh K.; Jadeja, Dharmpalsinh J.; Khasiya, Ashvinkumar G.; Khedkar, Vijay M.

doi:10.1080/1062936x.2022.2032333

Cited by 6 publications

(5 citation statements)

References 28 publications

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“…120.8,122.3,124.7,127.7,128.1,128.8,129.0,129.2,129.4,129.8 (C 3 of pyrazole),132.2,133.4,134.4,136.3,137.7 (C 4 of pyrazole), 120. 7,120.8,122.2,123.5,125.1,128.1,128.6,128.9,129.2 (C 3 of pyrazole),129.8,130.3,131.6,132.4,133.6,134.6,136.2,138.7 (C 5 of pyrazole),148.8,150.7,3, -1,3,4oxadiazole), 120.8 (C 4 of pyrazole), 120.5, 120.9, 122.4, 124.7, 127.6, 128.6,129.2,129.4,129.5 (C 3 of pyrazole),129.6,130.2,132.4,133.6,134.4,134.5,134.8,136.6 70.39;H,4.43;N,12.83%. Found: C,70.37;H,4.46; N, 12.81%.…”

Section: Materials and Instrumentsmentioning

confidence: 99%

“…4 | 1-(2-(4-Chlorophenyl)-5-(pyridin-3-yl)-1,3,4oxadiazol-3(2H)-yl)-3-(1-phenyl-3-(p-tolyl)-1H-pyrazol-4-yl)prop-2-en-1-one (6d (C 4 of pyrazole), 120. 7,120.8,122.2,124.9,127.7,128.7,129.1,129.2,129.6 (C 3 of pyrazole),129.8,130.3,132.2,133.8,134.2,134.3,134.7,136.9 (-C-CH═), 138. 5,120.9,121.4,125.6,125.9,128.6,128.7,128.8,129.1 (C 3 of pyrazole), 129.6, 131.3, 131.5, 132.4, 133.2, 133.6, 137.3 script from Gaussian outputs to correlate with drug properties.…”

Section: Materials and Instrumentsmentioning

confidence: 99%

“…1,3,4-Oxadiazole is an active scaffold as antitubercular, antiinflammatory, anticancer, and antimicrobial. [3][4][5][6][7][8] Pyridine moiety is active as an antidepressant, antitubercular, antimicrobial, and antioxidant. [9][10][11][12][13][14][15] Pyrazole moiety is active as an antiviral, antitubercular, and antiproliferative.…”

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confidence: 99%

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Design, synthesis, antimicrobial activity, DFT, and molecular docking studies of pyridine‐pyrazole‐based dihydro‐1,3,4‐oxadiazoles against various bacterial and fungal targets

Desai

Jadeja

Monapara

et al. 2023

J Biochem & Molecular Tox

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Antimicrobial resistance which is increasing at an alarming rate is a severe public health issue worldwide. Hence, the development of novel antibiotics is an urgent need as microbes have developed resistance against available antibiotics. In search of novel antimicrobial agents, a convenient route for the preparation of substituted 3‐(1‐phenyl‐3‐(p‐tolyl)‐1H‐pyrazol‐4‐yl)‐1‐(2‐phenyl‐5‐(pyridin‐3‐yl)‐1,3,4‐oxadiazol‐3(2H)‐yl)prop‐2‐en‐1‐ones (6a–6o) has been adopted by using pyridine‐3‐carbohydrazide and various aromatic aldehydes. The newly synthesized compounds were characterized by using various spectral techniques, for example, IR, 1H NMR, 13C NMR, and mass spectroscopy. Synthesized hybrids were studied for in vitro antimicrobial potency against various bacterial and fungal strains. Antibacterial results revealed that compounds 6e, 6h, 6i, 6l, and 6m were found to be most active against bacterial strains as they showed minimum inhibitory concentration (MIC) value of 62.5 μg/mL while compounds 6d, 6e, and 6h showed MIC value of 200 μg/mL against Candida albicans. The quantum parameters that relate to the bioavailability of the compounds were computed, followed by docking with different bacterial and fungal targets like sortase A, dihydrofolate reductase, thymidylate kinase, gyrase B, sterol 14‐alpha demethylase. The experimental and computational results are in good agreement.

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Section: Materials and Instrumentsmentioning

confidence: 99%

Section: Materials and Instrumentsmentioning

confidence: 99%

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Design, synthesis, antimicrobial activity, DFT, and molecular docking studies of pyridine‐pyrazole‐based dihydro‐1,3,4‐oxadiazoles against various bacterial and fungal targets

Desai

Jadeja

Monapara

et al. 2023

J Biochem & Molecular Tox

Self Cite

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“…9, Table 9) showed 90.4% inhibition against the M. tuberculosis strain, and rifampin was 99.5%. 111 Derivative 68 (Fig. 9, Table 9, IC 50 : 50.98 μM) showed excellent DPPH radical scavenging activity, and was found to have a higher ability to neutralize free radical cation ABTS˙ + than Trolox with an IC 50 value of 19.49 μM, while the IC 50 value of Trolox was 29.62 μM.…”

Section: Phenylpropanoid-indole Derivativesmentioning

confidence: 99%

Research status of indole-modified natural products

Duan,

Song,

Guo

et al. 2023

RSC Med. Chem.

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“… 14 Moreover, pyridine is a is a six-membered heterocyclic entity containing nitrogen atoms while pyrimidine has two nitrogen atoms at its adjacent carbon. Pyridine and pyrimidine derivatives have a wide range of biological activities, i.e., antimicrobial, 15 , 16 anti-inflammatory, 17 antitumor, 18 anticancer, 19 antitubercular, 20 , 21 etc.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antifungal Ergosterol Inhibition, Antibiofilm Activities, and Molecular Docking on β-Tubulin and Sterol 14-Alpha Demethylase along with DFT-Based Quantum Mechanical Calculation of Pyrazole Containing Fused Pyridine–Pyrimidine Derivatives

Desai,

Khasiya,

Jadeja

et al. 2023

ACS Omega

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Multidrug-resistant fungal infections have become much more common in recent years, especially in immune-compromised patients. Therefore, researchers and pharmaceutical professionals have focused on the development of novel antifungal agents that can tackle the problem of resistance. In continuation to this, a novel series of pyrazole-bearing pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione derivatives (4a–4o) have been developed. These compounds have been screened against Candida albicans, Aspergillus niger, and Aspergillus clavatus. The synthesized compounds were characterized by well-known spectroscopic techniques, i.e., IR, 1H NMR, 13C NMR, and mass spectrometry. In vitro antifungal results revealed that compound 4n showed activity against C. albicans having MIC value of 200 μg/mL. To know the plausible mode of action, the active derivatives were screened for anti-biofilm and ergosterol biosynthesis inhibition activities. The compounds 4h, 4j, 4k, and 4n showed greater ergosterol biosynthesis inhibition than the control DMSO. To comprehend how molecules interact with the receptor, studies of molecular docking of 4k and 4n have been performed on the homology-modeled protein of β-tubulin. The molecular docking revealed that the active compounds 4h, 4j, 4k, 4l, and 4n interacting with the active site amino acid of sterol 14-alpha demethylase (PDB ID: 5v5z) indicate one of the possible modes of action of ergosterol inhibition activity. The synthesized compounds 4c, 4e, 4h, 4i, 4j, 4k, 4l, and 4n inhibited biofilm formation and possessed the potential for anti-biofilm activity. DFT-based quantum mechanical calculations were carried out to optimize, predict, and compare the vibration modes of the molecule 4a.

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Microwave-assisted organic synthesis, antimycobacterial activity, structure–activity relationship and molecular docking studies of some novel indole-oxadiazole hybrids

Cited by 6 publications

References 28 publications

Design, synthesis, antimicrobial activity, DFT, and molecular docking studies of pyridine‐pyrazole‐based dihydro‐1,3,4‐oxadiazoles against various bacterial and fungal targets

Design, synthesis, antimicrobial activity, DFT, and molecular docking studies of pyridine‐pyrazole‐based dihydro‐1,3,4‐oxadiazoles against various bacterial and fungal targets

Research status of indole-modified natural products

Synthesis, Antifungal Ergosterol Inhibition, Antibiofilm Activities, and Molecular Docking on β-Tubulin and Sterol 14-Alpha Demethylase along with DFT-Based Quantum Mechanical Calculation of Pyrazole Containing Fused Pyridine–Pyrimidine Derivatives

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