Synthesis, molecular and crystal structure analysis of 2-bromo-4-chloro-6-{[4-(3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-hydrazonomethyl}-phenol by experimental methods and theoretical calculations

Güntepe, Feyizan; Saraçoğlu, Hanife; Çalışkan, Nezihe; Yüksektepe, Çiğdem; Çukurovalı, Alaaddin

doi:10.1016/j.molstruc.2012.05.002

Cited by 12 publications

(5 citation statements)

References 36 publications

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“…Computational calculations of the synthesized compounds were performed by using Gauss View molecular visualized program (İnkaya, Dinçer, Ekici, & Cukurovali, ) and Gaussian 03W package (Güntepe, Saraçoğlu, Çalışkan, Yüksektepe, & Cukurovali, ). The ground state of molecular structures of synthesized compounds were optimized by density functional theory (DFT) using B3LYP functional with 6‐311G (d,p) basis set.…”

Section: Methodsmentioning

confidence: 99%

Graph theoretical analysis, in silico modeling, prediction of toxicity, metabolism and synthesis of novel 2‐(methyl/phenyl)‐3‐(4‐(5‐substituted‐1,3,4‐oxadiazol‐2‐yl) phenyl) quinazolin‐4(3H)‐ones as NMDA receptor inhibitor

Govindaraj

Panneerselvam²,

Kunjiappan

et al. 2019

Drug Development Research

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Hit, Lead & Candidate Discovery A variety of novel 2‐(methyl/phenyl)‐3‐(4‐(5‐substituted‐1,3,4‐oxadiazol‐2‐yl)phenyl) quinazolin‐4(3H)‐ones have been synthesized by treating 3‐(4‐(5‐mercapto‐1,3,4‐oxadiazol‐2‐yl)phenyl)‐2‐(methyl/phenyl)‐quinazolin‐4(3H)‐one with a variety of secondary amines. Graph theoretical analysis was used in identification of drug target that is, NMDAR (N‐methyl‐d‐aspartate receptors). The observed reports of in silico modeling and ligand based toxicity, metabolism prediction studies were encouraging us to synthesize of title compounds and evaluate their antiepileptic effects. The title compounds were tested for its antiepileptic potency by MES and scPTZ model. Rotorod test is used to assess its neurotoxicity. In the preliminary test it was found that in MES test, analogs 6d, 6e, 6f, and 6l were potent; whereas in scPTZ test analogs 6d, 6e, 6f, and 6k displayed potent antiepileptic activity. Additionally these five derivatives were tested in rats orally at a dose of 30 mg/kg and found that compounds 2‐methyl‐3‐(4‐(5‐morpholino‐1,3,4‐oxadiazol‐2‐yl)phenyl)quinazolin‐4(3H)‐one 6e and 2‐methyl‐3‐(4‐(5‐(piperidin‐1‐yl)‐1,3,4‐oxadiazol‐2‐yl)phenyl)quinazolin‐4(3H)‐one 6f exhibited superior activity than reference Phenytoin. In MES test, these derivatives 6e and 6f showed activity at 30 mg/kg i.p. dose after 0.5 hr and 4.0 hr. In scPTZ test these derivatives 6e and 6f showed activity at 100 and 300 mg/kg i.p. dose after 0.5 hr and 4.0 hr, respectively.

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Section: Methodsmentioning

confidence: 99%

Graph theoretical analysis, in silico modeling, prediction of toxicity, metabolism and synthesis of novel 2‐(methyl/phenyl)‐3‐(4‐(5‐substituted‐1,3,4‐oxadiazol‐2‐yl) phenyl) quinazolin‐4(3H)‐ones as NMDA receptor inhibitor

Govindaraj

Panneerselvam²,

Kunjiappan

et al. 2019

Drug Development Research

View full text Add to dashboard Cite

show abstract

“…Computational calculations of the synthesized and standard compounds were performed using GaussView molecular visualized program (Güntepe, Saraçoğlu, Çalışkan, Yüksektepe, & Cukurovali, ) and Gaussian 03 W package (İnkaya, Dinçer, Ekici, & Cukurovali, ) on the personal computer (Processor [Intel(R) Core(TM)2 Duo CPU E7200 @ 2.53 DHz]). The molecular structures of the synthesized and standard in the ground state were optimized by density functional theory using B3LYP functional with 6‐311G (d,p) basis set.…”

Section: Methodsmentioning

confidence: 99%

Design, graph theoretical analysis, density functionality theories, Insilico modeling, synthesis, characterization and biological activities of novel thiazole fused quinazolinone derivatives

Govindaraj

Panneerselvam²,

Alagarsamy

et al. 2018

Drug Development Research

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Hit, Lead & Candidate Discovery A series of 2‐(2‐substituted benzylidenehydrazinyl‐2‐oxopropyl)‐3‐(4‐[4‐oxo‐2‐phenylthiazolo din‐3‐yl]phenyl)quinazolin‐4(3H)‐one 7a‐7l were synthesized and characterized by IR, 1H‐NMR, 13C‐NMR, mass spectroscopy and elemental analyses. In this present study, the density functionality theory was performed to identify drug stability. Further we introduced graph theoretical analysis by utilised Kyoto Encyclopedia of Genes and Genomes (KEGG) database and Cytoscape software to identify drug target. Based on the observed drug target insilico modeling was executed to know effective drug. The antiepileptic effects of title compounds were evaluated by using MES and subcutaneous pentylenetetrazole (scPTZ) test. Acute neurological toxicity of title compounds was studied by using standardized rotorod test. After 0.5 hr of period many of the compounds showed anticonvulsant activity at MES or scPTZ test. Comparison of the biological activity of test compounds with its chemical structures indicates that, compounds possessing electron donating group exhibited superior activity than the analogs having electron withdrawing moieties. Among the electron donating group tested, amino derivative exhibited good activity than rest of derivatives. From the study it was concluded that, the compound 7j was established as very potent compared with rest of the compounds and standard drugs subjected to biological studies. Thus the compound 2‐(2‐[4‐aminobenzylidene]hydrazinyl‐2‐oxopropyl)‐3‐(4‐[4‐oxo‐2‐phenylthiazolidin‐3‐yl]phenyl) quinazolin‐4(3H)‐one (7j) came out as pilot derivative without any neurotoxicity with a wide spectrum of antiepileptic activity. Highlights The performed work is having great significance in terms of Graph theoretical analysis used to identify drug target In silico modeling used to identify designed drug interaction with identify target Density functionality studies used to identify synthesized compound energy band gap which is correlate with enhancement of its biological activity Antiepileptic effects of entire synthesized quinazolinone scaffolds were evaluated by MES and scPTZ test 2‐(2‐[4‐aminobenzylidene]hydrazinyl‐2‐oxopropyl)‐3‐(4‐[4‐oxo‐2‐phenylthiazolidin‐3‐yl]phenyl) quinazolin‐4(3H)‐one (7j) was established as very potent compared to the rest of the compounds and standard drugs which were subjected to biological studies

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“…Gauss view molecular visualized program [29] and Gaussian 03 W package [30] was used to perform computational calculations of the test analogs. Using B3LYP functional with 6-311 G (d,p) basis set density functional theory (DFT) optimizes the ground state molecular structures of synthesized compounds.…”

Section: Density Functional Theorymentioning

confidence: 99%

Design and Synthesis of Novel 1-substituted-3-(3-(3-nitrophenyl)-4-oxo-3,4-dihydrobenzopyrimidin-2-yl amino) Isothioureas for their Anti-HIV, Antibacterial Activities, Graph Theoretical Analysis, Insilico Modeling, Prediction of Toxicity and Metabolic Studies

2020

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In the present study, we have placed the substituted thiosemicarbazide moiety at the C-2 position and 3-nitrophenyl group at N-3 position of benzopyrimidines and studied their antitubercular, anti-HIV and antibacterial activities against selected gram positive and negative bacteria. The target compounds 1-substituted-3-(3-(3-nitrophenyl)-4-oxo-3,4-dihydrobenzopyrimidin-2-ylamino) isothioureas (PTS1 – PTS15 ) were obtained by the reaction of 2-hydrazino-3-(3-nitrophenyl) benzopyrimidin-4(3 H)-one (5) with different alkyl/aryl isothiocyanates followed by methylation with dimethyl sulphate. All synthesized compounds were screened for their antitubercular, anti-HIV and antibacterial activity against selective gram positive and gram negative bacteria by agar dilution method. Among the series, compound 2-methyl-3-(3-(3-nitrophenyl)-4-oxo-3,4-dihydrobenzopyrimidin-2-ylamino)-1-(3-chlorophenyl)isothiourea (PTS14) shown most potent activity against Klebsiella pneumoniae, Proteus vulgaris and Staphylococcus aureus; PTS14 exhibited the antitubercular activity at the minimum microgram of 1.56 µg/mL and anti-HIV activity at 0.96 µg/mL against HIV1 and HIV2 and offers potential for further optimization and development to new antitubercular and anti-HIV agents. The results obtained from this study confirm that the synthesized and biologically evaluated benzopyrimidines showed promising antimicrobial, antitubercular and anti-HIV activities and are new scaffolds for antimicrobial activity.

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Synthesis, molecular and crystal structure analysis of 2-bromo-4-chloro-6-{[4-(3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-hydrazonomethyl}-phenol by experimental methods and theoretical calculations

Cited by 12 publications

References 36 publications

Graph theoretical analysis, in silico modeling, prediction of toxicity, metabolism and synthesis of novel 2‐(methyl/phenyl)‐3‐(4‐(5‐substituted‐1,3,4‐oxadiazol‐2‐yl) phenyl) quinazolin‐4(3H)‐ones as NMDA receptor inhibitor

Graph theoretical analysis, in silico modeling, prediction of toxicity, metabolism and synthesis of novel 2‐(methyl/phenyl)‐3‐(4‐(5‐substituted‐1,3,4‐oxadiazol‐2‐yl) phenyl) quinazolin‐4(3H)‐ones as NMDA receptor inhibitor

Design, graph theoretical analysis, density functionality theories, Insilico modeling, synthesis, characterization and biological activities of novel thiazole fused quinazolinone derivatives

Design and Synthesis of Novel 1-substituted-3-(3-(3-nitrophenyl)-4-oxo-3,4-dihydrobenzopyrimidin-2-yl amino) Isothioureas for their Anti-HIV, Antibacterial Activities, Graph Theoretical Analysis, Insilico Modeling, Prediction of Toxicity and Metabolic Studies

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