Synthesis and antimicrobial activity of structurally flexible heterocycles with the 1,4-thiazine heterosystem

Sharma, Praveen Kumar; Fogla, Ankur; Rathore, Bhawani Singh; Kumar, M.

doi:10.1007/s11164-011-0320-0

Cited by 20 publications

(6 citation statements)

References 42 publications

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“…The various substituted ortho-aminothiophenols were synthesised in the laboratory using the previously reported method [28]. Lawesson's Reagent was purchased from Spectrochem Pvt.…”

Section: Methodsmentioning

confidence: 99%

Microwave Induced Facile One-Pot Access to Diverse 2-Cyanobenzothiazole-A Key Intermediate for the Synthesis of Firefly Luciferin

Prajapati

Vekariya

2015

ILCPA

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An eco-friendly one-step preparation of various substituted 2-cyanobenzothiazole by condensation of corresponding substituted ortho-aminothiophenol with ethyl cyanoformate, employing an effective amount of Lawesson's reagent, under microwave irradiation (MWI) and solvent free conditions is presented. The structures of the compounds were elucidated with the aid of elemental analysis, IR, 1 H-NMR and mass spectral data. The targeted various substituted 2-cyanobenzothiazole are obtained in good yields and high purity.

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“…The various substituted ortho-aminothiophenols were synthesised in the laboratory using the previously reported method [28]. Lawesson's Reagent was purchased from Spectrochem Pvt.…”

Section: Methodsmentioning

confidence: 99%

Microwave Induced Facile One-Pot Access to Diverse 2-Cyanobenzothiazole-A Key Intermediate for the Synthesis of Firefly Luciferin

Prajapati

Vekariya

2015

ILCPA

View full text Add to dashboard Cite

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“…Chemicals used in this reaction such as Ethyl cyanoformate were of analytical grade and purchased from Sigma-Aldrich, USA. The various substituted ortho-aminothiophenols were synthesised in the laboratory using the previously reported method [28]. Lawesson's Reagent was purchased from Spectrochem Pvt.…”

Section: Methodsmentioning

confidence: 99%

Microwave Induced Facile One-Pot Access to Diverse 2-Cyanobenzothiazole-A Key Intermediate for the Synthesis of Firefly Luciferin

Prajapati

Vekariya

Patel

2015

ILCPA

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An eco-friendly one-step preparation of various substituted 2-cyanobenzothiazole by condensation of corresponding substituted ortho-aminothiophenol with ethyl cyanoformate, employing an effective amount of Lawesson’s reagent, under microwave irradiation (MWI) and solvent free conditions is presented. The structures of the compounds were elucidated with the aid of elemental analysis, IR, 1H-NMR and mass spectral data. The targeted various substituted 2-cyanobenzothiazole are obtained in good yields and high purity.

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“…The difference between the complex and individual energies of the enzyme and ligands was used to compute the energy of binding. 21,22…”

Section: Docking and Molecular Modeling Studymentioning

confidence: 99%

Evaluation of DHFR Inhibition and Antimicrobial Activity of Some Newly Synthesized Quinazolin-4(3H)-one Scaffold Coupled with Benzylidene and Ethylidene Amino Motifs

Harer

Bhatia

Sonar³

2022

Int J. Pharm. Investigation

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Objectives: Substituted quinazolin-4(3H)-ones at position-3 with phenyl ring, heterocycles and aliphatic moieties, were reported to impart antimicrobial activities. In light of this, we have attempted to prepare a novel series of 2-pheny-3-substituted quinazolin-4(3H)-ones fused with an azomethine (-CH=N-) connection to Benzylidene and ethylidene motifs. Each of these motifs underwent testing to determine whether it could inhibit in-vitro microbial DHFR and the subsequent antimicrobial action. Materials and Methods: The synthesized 2-phenyl-3substituted quinazolin-4(3H)-ones were characterized by FT-IR, 1 H-NMR, 13 C-NMR, ESI-MS and elemental (C, H, N, O and X=halogen) analysis. Evaluated results of in-vitro microbial DHFR inhibition are compared with the reported drug trimethoprim. Agar disc diffusion method was used for in-vitro antimicrobial activity, performed against pathogenic Gram-positive and Gramnegative bacteria like Staphylococcus aureus, Bacillus subtilis, and Escherichia coli, Pseudomonas aeruginosa respectively, and fungi like Candida albicans, and Aspergillus niger. Results: Docking analysis of ligands with DHFR (PDB=2W3M) has shown strong hydrophobic binding interaction and confirmed a perfect fit into the active domain of the target protein. Possible antimicrobial activity was induced from microbial DHFR inhibition. The results of the tests are compared with gentamycin, ciprofloxacin, and clotrimazole. Compounds with potent antibacterial activity were QI-j, and QII-f (MIC=0.1-0.2µg/mL), and moderately active compounds were QIa-d, QIl-m, QIII-d, and QIIIe-f (MIC=0.5-2.0µg/mL). Compounds exhibited potent antifungal activity were QI-c, QII-b, and QIII-f (MIC=0.1-0.2µg/mL), moderately active compounds were QIc-e, QI-g, QIm-n, QII-d, QIII-b, and QIII-e (MIC=0.5-2.0µg/mL). Conclusion: Particularly test compounds have produced DHFR inhibition in a range of 4-24µM as compared with trimethoprim (IC 50 =10 µM). Benzylidene and ethylidene moieties attached to the quinazolin-4(3H)-one had contributed to this activity. Present series of substituted quinazolin-4(3H)-ones provide a path for the design and development of newer antimicrobial agents in the treatment of deadly pathogenic infections.

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Synthesis and antimicrobial activity of structurally flexible heterocycles with the 1,4-thiazine heterosystem

Cited by 20 publications

References 42 publications

Microwave Induced Facile One-Pot Access to Diverse 2-Cyanobenzothiazole-A Key Intermediate for the Synthesis of Firefly Luciferin

Microwave Induced Facile One-Pot Access to Diverse 2-Cyanobenzothiazole-A Key Intermediate for the Synthesis of Firefly Luciferin

Microwave Induced Facile One-Pot Access to Diverse 2-Cyanobenzothiazole-A Key Intermediate for the Synthesis of Firefly Luciferin

Evaluation of DHFR Inhibition and Antimicrobial Activity of Some Newly Synthesized Quinazolin-4(3H)-one Scaffold Coupled with Benzylidene and Ethylidene Amino Motifs

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