Synthesis of novel indole, 1,2,4-triazole derivatives as potential glucosidase inhibitors

Gani, Ramesh S.; Timanagouda, Karabasanagouda; Madhushree, S.; Joshi, Shrinivas D.; Hiremath, Murigendra B; Mujawar, Salma Begum Hussain; Kudva, Avinash K.

doi:10.1016/j.jksus.2020.09.026

Cited by 17 publications

(5 citation statements)

References 38 publications

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“…In addition, the synthesis of 1,2,4-triazoles has drawn a lot of interest because of the diverse range of pharmacological applications, such as antibacterial, antimycobacterial, antifungal, anti-inflammatory, anticancer, antidiabetic, anti-tubercular, anxiolytics, and anticonvulsants [37][38][39][40]. According to a recent literature review, 1,2,4-triazolo [3,4-b][1,3,4]thiadiazine derivatives have promising biological activities including antibacterial, antifungal, anticancer, anti-HIV, antitubercular, CNS stimulant, antioxidant, anti-inflammatory hypoglycemic, diuretic, and anti-candidal activity [35,[41][42][43][44][45][46]. The above-mentioned observations prompted us to design, synthesis, and test the antibacterial and antifungal activity properties of a series 1,2,3-triazole containing 1,3,4-oxadiazoles with general formula 5 and 1,2,4triazole containing 1,3,4-thiadiazines with general formula 3.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antimicrobial activity, and in silico studies of fluoroquinolones bearing 1,3,4‐oxadiazolyl‐triazole derivatives

Venkateswara Rao,

Allaka,

Gandla

et al. 2023

Journal of Heterocyclic Chem

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Compounds containing fluoroquinolone (FQ) moiety occupy privileged chemical space for discovering novel bioactive substances. In continuation of our research work, a new series of FQs linked to triazolyl–thiadiazine hybrids (3a–f) and triazolyl–oxadiazoles (5a–f) were developed as a new antimicrobial agent targeting DNA gyrase of Staphylococcus aureus. All the novel compounds have been characterized with IR, 1H NMR, 13C NMR, mass spectral analysis and elemental analysis. All the synthesized derivatives were investigated for their antibacterial effect against various bacterial and fungal strains. Against Gram‐positive bacteria S. aureus, compounds 3e, 5a, and 5d showed the highest antibacterial activity with minimum inhibitory concentrations (MIC) values 5.0 ± 0.04, 8.6 ± 0.03, and 6.1 ± 0.02 μg/mL, respectively. FQ derivatives 3a, 5c had the most potent antibacterial activity against Klebsiella pneumonia bacteria with MICs 6.4 ± 0.01, 4.1 ± 0.01 μg/mL and compounds 3e, 5d are active against Gram‐negative bacteria Bacillus cereus with MICs 8.3 ± 0.02, 10.0 ± 0.02 μg/mL, respectively. Interestingly, the molecules 3e were slightly more selective towards antifungal activity against Fusarium oxysporum (MIC 4.2 ± 0.01 μg/mL), compared to fluconazole (MIC 3.5 ± 0.01 μg/mL). In addition, a fascinating molecular modeling investigation showed that our FQs 3, 5 demonstrated good binding inhibition of S. aureus complex in DNS gyrase (2XCT) towards advancing an efficient medication against antibacterial disease. The prepared ligand 3c forms three hydrogen bonds with amino acid residues LysB:1043 (N23…NZ), ArgB:1092 (O20…NH), GlyB:1082 (O…N) with bond lengths 3.13, 2.15, 2.76 A°, respectively.

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Section: Introductionmentioning

confidence: 99%

Synthesis, antimicrobial activity, and in silico studies of fluoroquinolones bearing 1,3,4‐oxadiazolyl‐triazole derivatives

Venkateswara Rao,

Allaka,

Gandla

et al. 2023

Journal of Heterocyclic Chem

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“…The 1,2,4-triazoles derivatives have been found to possess wide spectrum of biological activities [30][31][32][33]. Numerous triazole-based drugs has been developed as antibacterial [34], antifungal [35], anti-malarial [36], anticancer [37], antidiabetic [38].…”

Section: Introductionmentioning

confidence: 99%

Syntheses and Antioxidant Activity of 1-Isonicotinoyl-4-phenylthiosemicarbazide and Crystal Structures of N-Phenyl-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine Hydrochloride and 4-Phenyl-3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione derived from 1 Isonicotinoyl-4-phenylthiosemicarbazide

Faye

Mbow

Gaye

et al. 2022

EJCS

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The title compound C13H12N4OS (I) is synthetized from isonicotinic hydrazide and isothiocynate. Compounds C13H11N4OCl (II) and C13H10N4S (III) where obtained upon reaction of (I) with Fe(II) or Mn(II) salts. Compound (II) is heterocyclic 1,3,4-oxadiazole while compound (III) is heterocyclic 1,2,4-triazole. The 1,3,4-oxadiazol derivative is almost planar with dihedral angle of 2.66 (8) and 5.14 (8)° between 1,3,4-oxadiazole ring and phenyl and pyridinium rings respectively; the dihedral angle between the phenyl and pyridinium rings is 3.92 (8)°. The 1,2,4-triazole derivative is non-planar. The phenyl and pyridyl rings form dihedral angles of 58.35 (5) and 58.33 (5)°, respectively, with the 1,2,4-triazole ring; the dihedral angle between the phenyl and pyridyl rings is 36.85 (4)°. In the compound (II) intramolecular hydrogen bonds of type N—H···Cl, C—H···N and C—H···Cl resulting in S(6) ring stabilize the structure. Intermolecular hydrogen bonds of type N—H···N, C—H···N, C—4···Cl link the molecule thus forming a three-dimensional network. In the structure of compound (III), intermolecular hydrogen bonds of type N—H···N, C—H···N, C—H···S1,link the monomer in a three-dimensional network.

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“…1,2,4-triazole possesses a wide variety of pharmacological activity including antimicrobial, anti-cancer, anti-diabetic, anti-tubercular, anxiolytics, anticonvulsants, etc. [25][26][27][28][29][30]. Schiff base ligands having triazole ring can be considered as "privileged structures" and are widely used due to their novel structural features.…”

Section: Introductionmentioning

confidence: 99%

Transition metal complexes of triazole-based bioactive ligands: synthesis, spectral characterization, antimicrobial, anticancer and molecular docking studies

et al. 2021

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Synthesis of novel indole, 1,2,4-triazole derivatives as potential glucosidase inhibitors

Cited by 17 publications

References 38 publications

Synthesis, antimicrobial activity, and in silico studies of fluoroquinolones bearing 1,3,4‐oxadiazolyl‐triazole derivatives

Synthesis, antimicrobial activity, and in silico studies of fluoroquinolones bearing 1,3,4‐oxadiazolyl‐triazole derivatives

Syntheses and Antioxidant Activity of 1-Isonicotinoyl-4-phenylthiosemicarbazide and Crystal Structures of N-Phenyl-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine Hydrochloride and 4-Phenyl-3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione derived from 1 Isonicotinoyl-4-phenylthiosemicarbazide

Transition metal complexes of triazole-based bioactive ligands: synthesis, spectral characterization, antimicrobial, anticancer and molecular docking studies

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