Synthesis of Nitrogen and Oxygen based Pyrazole Derivatives and Its Antitubercular and Antimicrobial Activity

Kapadiya, Khushal M.; Kavadia, Kishor M.; Manvar, Parth; Khunt, Ranjan C.

doi:10.2174/2211352513666150915235745

Cited by 16 publications

(7 citation statements)

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“…Ten alkyl protons of cyclohexane ranged from δ 2.36-1.23 ppm. 13 C NMR of 7 a showed amide carbonyl carbon signal at δ 168.…”

Section: Chemistrymentioning

confidence: 99%

“…Buff solid; Yield: 80 % ; m.p: 208-210 °C; FT-IR (KBr, cm À 1 ) ν max : 3201.2 (NÀ H), 3058.6 (=CÀ H), 2864.6 (CÀ H, alkane), 1731.3 (C=O), 1619.5 (C=C, aromatic), 1557.2 (C=N); 1 H NMR (500 MHz, DMSO-d 6 ) δ(ppm): 3.24 (t, J = 14.5 Hz, 1H, À CH), 3.26 (t, J = 11.0 Hz, 1H, À CH), 3.45 (m, 3H,), 3.76 (dd, J = 2.8, 11.0 Hz, 2H, À CH 2 ), 3.96 (t, J = 9.0 Hz, 2H, À CH 2 ), 7.22 (t, J = 7.6 Hz, 1H, ArH), 7.49 (t, J = 7.2 Hz, 1H, ArH), 7.57 (d, J = 8.3 Hz, 1H, ArH), 7.65 (d, J = 7.6 Hz, 1H, ArH), 7.72 (s, 1H, ArH), 11.43 (s, 1H, -NH), 11.63 (s, 1H, -NH); 13…”

Section: Spectral Data 1244 A-tetrahydro-2'h6h-spiro[benzo[g][14]oxaz...mentioning

confidence: 99%

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Antimycobacterial, Molecular Docking and ADME Studies of Spiro Naphthyridine Pyrimidine and N‐(Quinolin‐8‐yl)acetamide Derivatives

Sahana

Vijayakumar

Ramaiah³

2023

ChemistrySelect

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Two series of compounds viz., spiro naphthyridine pyrimidine derivatives and N-(quinolin-8-yl)acetamide derivatives which possess the quinoline core moiety were designed and synthesized. The spectral analysis viz., FT-IR, 1 H-NMR, 13 C-NMR and mass was carried out to establish the structures for the synthesized compounds. In vitro anti-tubercular activity was done against Mycobacterium tuberculosis H37Rv by following "microplate alamar blue assay (MABA)". The synthesized compounds showed good anti-tuberculosis (TB) activity with the least minimum inhibitory concentration (MIC) value of 6.25 μg/ mL. Computational molecular docking studies were performed out with Mycobacterium tuberculosis enoyl reductase (INHA) (PDB code: 4TZK) using AutoDock to predict the key binding interactions responsible for the activity and the Swiss ADME (absorption, distribution, metabolism, and excretion) tool computed the in silico drug likeliness properties. The synthesized title compounds create a way for the optimization and development of potential drugs against tuberculosis.

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“…Ten alkyl protons of cyclohexane ranged from δ 2.36-1.23 ppm. 13 C NMR of 7 a showed amide carbonyl carbon signal at δ 168.…”

Section: Chemistrymentioning

confidence: 99%

Section: Spectral Data 1244 A-tetrahydro-2'h6h-spiro[benzo[g][14]oxaz...mentioning

confidence: 99%

Antimycobacterial, Molecular Docking and ADME Studies of Spiro Naphthyridine Pyrimidine and N‐(Quinolin‐8‐yl)acetamide Derivatives

Sahana

Vijayakumar

Ramaiah³

2023

ChemistrySelect

View full text Add to dashboard Cite

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“…Many researchers have synthesized such compounds under microwave or ultrasound irradiation conditions using a one-pot procedure which was better than classical heating methods [20]. Diversely substituted pyrazolines exhibit a wide spectrum of biological activities [21] such as anticancer [22,23], antioxidant [24], antibacterial [25], antifungal [26], antidepressant [27], anti-inflammatory [28] and anti-tubercular [29].…”

Section: Introductionmentioning

confidence: 99%

A green approach for the catalyst‐free synthesis of imidazole‐bearing pyrazole moiety using PEG‐400 as an efficient recyclable medium as potential anti‐tubercular and anti‐microbial agents

Panchani¹,

Kapadiya

Joshi

2022

Journal of Heterocyclic Chem

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Polyethylene glycol-400 (PEG-400) is a recyclable and rapid reaction medium for synthesizing a new series of 4-(3-[substitutedphenyl]-4,5-dihydro-1-phenyl-1H-pyrazol-5-yl)-1H-imidazoles in two-step procedures by condensation of 1H-imidazole-4-carbaldehyde and various acetophenones to form chalcones followed by base-catalyzed cyclization employing phenyl hydrazine in a catalyst-free approach. The way of projected approach provides easy work-up, less reaction time, avoids metal-based and toxic catalysts, high yield, and reduces the use of carcinogenic organic solvents. The synthesized scaffolds have been screened for their anti-microbial and anti-tubercular activity against a set of pathogens.

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“…triazoles are an equally important type of heterocyclic compounds responsible for the supreme pharmacological effect. 11 Literature shows the diversity of both triazoles and purine compounds in the area of pharmacology due to their properties as anticancer 12 , antileukemic [13][14][15] , anti-HIV-1 16,17 , antiviral 18,19 , antitubercular 20,21 , antimicrobial agents [22][23][24] , acid base indicator 25 , and dyes 26 .…”

Section: Introductionmentioning

confidence: 99%

Regioselective synthesis of triazolo[3,4-e]purine derivatives and their anti-cancer activity against NCI-60 cell-lines

Kapadiya¹,

Kavadia²,

Gohel³

et al. 2021

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Introduction: Due to the vast medicinal importance of purine nucleoside, a hybrid molecule of triazole with purine ring might explode a lead molecule in the pharma sector and based on the last decade’s studies suggested that the nitrogen-rich molecules possess a wide range of medicinal importance. Aim: Due to the vast application of purine nucleoside itself in the field of cancer research, we synthesized triazolo[3,4-e]purines and screened them for their anti-cancer study against NCI-60 cell lines by the protocol used by NIH. Materials and methods: The targeted molecules, 4-chloro-5a,6-dihydro-8-substitutedphenyl-1H-[1,2,4]triazolo[3,4-e]purine derivatives (4a-4h) were synthesized in a two-step procedure by nucleophilic substitution (SN) at C-2 chlorine followed by formation of the triazole ring by acid-catalyzed reaction in the polar protic solvent. Results: It was observed that the regioselective approach followed in C-2 chlorine replacement instead of C-6 chlorine during SN reaction. One-dose response of selected three molecules (4a, 4b, and 4c) showed that 4b (K-562: 64.47 µM & SR: 63.38 µM; mean GI50: 99.09 µM) was found to be more potent than 4a and 4c. Conclusions: We have described in this study the general synthetic method for triazolo[3,4-e]purines as an innovative class of potential anticancer agents. The dose-response curve in the sense of mean GI50 for three compounds across all 60 cell lines, 4b can be served as lead after necessary modification.

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Synthesis of Nitrogen and Oxygen based Pyrazole Derivatives and Its Antitubercular and Antimicrobial Activity

Cited by 16 publications

References 0 publications

Antimycobacterial, Molecular Docking and ADME Studies of Spiro Naphthyridine Pyrimidine and N‐(Quinolin‐8‐yl)acetamide Derivatives

Antimycobacterial, Molecular Docking and ADME Studies of Spiro Naphthyridine Pyrimidine and N‐(Quinolin‐8‐yl)acetamide Derivatives

A green approach for the catalyst‐free synthesis of imidazole‐bearing pyrazole moiety using PEG‐400 as an efficient recyclable medium as potential anti‐tubercular and anti‐microbial agents

Regioselective synthesis of triazolo[3,4-e]purine derivatives and their anti-cancer activity against NCI-60 cell-lines

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