Synthesis and Crystal Structure of 3-(4-Methoxyphenyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

Saeed, Aamer; Mahmood, S.; Ishida, Hiroyuki

doi:10.3390/cryst1030171

Cited by 5 publications

(1 citation statement)

References 16 publications

(13 reference statements)

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“…The spectral data compare favorably with the literature data for the 3‐(4‐methoxyphenyl)‐2‐thioxo‐2,3‐dihydroquinazolin‐4(1 H )‐one recorded at 300 and 75 MHz in DMSO‐ d 6 . The 13 C‐NMR spectra of compounds 4a – e recorded at 125 MHz in DMSO‐ d 6 revealed the presence of carbon signals in the region 158.7–160.0 ppm and 175.4–179.0 ppm corresponding to the carbonyl (C‐4) and thiocarbonyl (C‐2) groups, respectively.…”

Section: Resultssupporting

confidence: 76%

Simple and Efficient Synthesis of Novel 3‐Substituted 2‐Thioxo‐2,3‐dihydro‐1H‐benzo[g]quinazolin‐4‐ones and Their Reactions with Alkyl Halides and α‐Glycopyranosyl Bromides

Khodair

Elsafi

Alissa

2019

Journal of Heterocyclic Chem

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A series of 3‐substituted 2‐thioxo‐2,3‐dihydro‐1H‐benzo[g]quinazolin‐4‐ones 4a–e were synthesized from the reaction of 3‐aminonaphthalene‐2‐carboxylic acid 1 with isothiocyanate derivatives 2a–e. The alkylation of 4a–e with alkyl halides gave 3‐substituted 2‐alkylsulfanyl‐2,3‐dihydro‐1H‐benzo[g]quinazolin‐4‐ones 5a–o. S‐Glycosylation was carried out via the reaction of 4a–e with glycopyranosyl bromides 7a and 7b under anhydrous alkaline conditions. The structure of the compounds was established as S‐nucleoside and not N‐nucleoside. Conformational analysis has been studied by homonuclear and heteronuclear two‐dimensional NMR methods (2D DFQ‐COSY, heteronuclear multiple quantum coherence, and heteronuclear multiple bond correlation). The S site of alkylation and glycosylation was determined from the 1H and 13C heteronuclear multiple quantum coherence experiments.

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Section: Resultssupporting

confidence: 76%

Simple and Efficient Synthesis of Novel 3‐Substituted 2‐Thioxo‐2,3‐dihydro‐1H‐benzo[g]quinazolin‐4‐ones and Their Reactions with Alkyl Halides and α‐Glycopyranosyl Bromides

Khodair

Elsafi

Alissa

2019

Journal of Heterocyclic Chem

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Synthesis and Anticonvulsant Activity Evaluation of 4‐Phenyl‐[1,2,4]triazolo[4,3‐a]quinazolin‐5(4H)‐one and Its Derivatives

Zhang

Jin

Wang

et al. 2015

Archiv der Pharmazie

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A series of 4-(substituted-phenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-ones (6a-x) with triazole and other heterocyclic substituents (7-14) were synthesized and the compounds were evaluated for their anticonvulsant activity and neurotoxicity by maximal electroshock (MES) and rotarod neurotoxicity tests. Among the compounds studied, 6o and 6q showed wide margins of safety with protective indices (PIs) that were much higher than those of currently used drugs (PI6o > 25.5, PI6q > 26.0). Compounds 6o and 6q showed significant oral activity against MES-induced seizures in mice, with ED50 values of 88.02 and 94.6 mg/kg, respectively. The two compounds were also found to have potent activity against seizures that were induced by pentylenetetrazole and bicuculline.

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Synthesis and antidepressant activities of 4-(substituted-phenyl)tetrazolo[1,5-a]quinazolin-5(4H)-ones and their derivatives

2015

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A series of novel 4-(substituted-phenyl) tetrazolo[1,5-a]quinazolin-5(4H)-ones (6a-x) and their derivatives with tetrazole and other heterocyclic substituents (7-14) were designed, synthesized, and evaluated for antidepressant activities in mice. Pharmacological tests showed that three compounds (6l, 6u, and 6v) at a dose of 50 mg/kg significantly reduced the immobility time in the forced swimming test. The most active compound was 4-(p-tolyl)tetrazolo[1,5-a]quinazolin-5(4H)-one (6v), which decreased the immobility time by 82.69 % at 50 mg/kg. Moreover, 6v did not affect spontaneous activity in the open-field test, and this effect was comparable to the antidepressant effect of fluoxetine. Noradrenaline (NE) and 5-hydroxytryptamine (5-HT) levels in the brains of mice in the test sample groups significantly increased at a dose of 50 mg/kg compared with that in the control group. The monoamine oxidase (MAO) level of all test groups was reduced, but this result was not significantly different between the groups. Therefore, we can infer that their underlying mechanisms may involve the regulation of brain monoamine neurotransmitter homeostasis, based on the detected content of NE, 5-HT, and MAO in mouse brain tissue.

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Synthesis and Crystal Structure of 3-(4-Methoxyphenyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

Cited by 5 publications

References 16 publications

Simple and Efficient Synthesis of Novel 3‐Substituted 2‐Thioxo‐2,3‐dihydro‐1H‐benzo[g]quinazolin‐4‐ones and Their Reactions with Alkyl Halides and α‐Glycopyranosyl Bromides

Simple and Efficient Synthesis of Novel 3‐Substituted 2‐Thioxo‐2,3‐dihydro‐1H‐benzo[g]quinazolin‐4‐ones and Their Reactions with Alkyl Halides and α‐Glycopyranosyl Bromides

Synthesis and Anticonvulsant Activity Evaluation of 4‐Phenyl‐[1,2,4]triazolo[4,3‐a]quinazolin‐5(4H)‐one and Its Derivatives

Synthesis and antidepressant activities of 4-(substituted-phenyl)tetrazolo[1,5-a]quinazolin-5(4H)-ones and their derivatives

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