Rapid microwave-assisted solution phase synthesis of 6, 8-disubstituted- 2-phenyl-3-(substituted-benzothiazole-2-yl) – 4-[3H]-quinazolinone as novel anticonvulsants

Laddha, Sachin S.; Bhatnagar, Satyendra Prasad

doi:10.3390/ecsoc-10-01438

Cited by 3 publications

(4 citation statements)

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“…Details of the synthesis and characterization have been well documented (Laddha et al, 2006;Laddha and Bhatnagar, 2008). As shown in Tables 1 and 2, 13 b) Introduction of double bond across C2 and N3 nitrogen to provide rigidity.…”

Section: Chemistrymentioning

confidence: 99%

“…Based on this approach we attempted to synthesize 2-phenyl-3-(substituted benzothiazole-2-yl)-quinazol-4[3H]-one and their 6,8-dibromo analogues (Laddha et al, 2006;Laddha and Bhatnagar, 2008). The title compounds showed good antiinflammatory activity (Laddha et al, 2006), and it was anticipated that they would also show PDE inhibitory activity.…”

Section: Introductionmentioning

confidence: 99%

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cAMP-dependent phosphodiesterase inhibition and SAR studies on novel 6,8-disubstituted 2-phenyl-3-(substituted benzothiazole-2-yl)-4[3H]-quinazolinone

2008

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Two series of 6,8-disubstituted-2-phenyl-3-(substituted benzothiazole-2-yl)-4[3H]-quinazolinone (1-13 and 14-26) were synthesized by reported method and evaluated for their phosphodiesterase inhibitory activity. All test compounds exhibited good activity. The structure-activity relationships based on the results obtained for these series were also studied. In both series, electron-withdrawing substitutions showed more activity. Among the tested compounds 6,8-dibromo-2-phenyl-3-(5-chloro benzothiazole-2-yl)-4[3H]-quinazolinone (20) and 6,8-dibromo-2-phenyl-3-(6-nitro benzothiazole-2-yl)-4[3H]-quinazolinone (24) were found to be even more potent than theophylline (IC 50 of 1438 ± 85 lM for 20 and 1520 ± 48 lM for 24).

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Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

cAMP-dependent phosphodiesterase inhibition and SAR studies on novel 6,8-disubstituted 2-phenyl-3-(substituted benzothiazole-2-yl)-4[3H]-quinazolinone

2008

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“…However, all the anticonvulsant drugs currently approved, and which are already in use, have dose related toxicity and idiosyncratic side effects [4]. Therefore, the research for new antiepileptic agents with lower toxicity and fewer side effects are the challenges for medicinal chemist and a wide-variety of compounds has been synthesized for this purpose [5,6].…”

Section: Introductionmentioning

confidence: 99%

“…The quinazolinone moiety is a building block for approximately 150 naturally occurring alkaloids and drugs [7]. Literature survey reveals that natural quinazolinones and their synthetic analogs possess a variety of pharmacological activities, including PDE inhibitory activity [8][9][10][11][12], anticonvulsant [5,6], bronchodilator [13], anti-inflammatory [14,15], antimalarial [16], antituberculous [17], anti-HIV [18], narcotic antagonist [19], anti-tumor [20], tyrosine kinase inhibitor [21], adenosine antagonist [22], antimicrobial [14], etc. Similarly thienopyrimidine [23,24] and pyridopyrimidine [25], the bioisosters of quinazolinones are known to possess good anticonvulsant activity.…”

Section: Introductionmentioning

confidence: 99%

Novel Fused Quinazolinones: Further Studies on the Anticonvulsant Activity of 1,2,9,11-Tetrasubstituted- 7H -Thieno[2´,3´:4,5]Pyrimido[6,1-B]-Quinazolin-7-One and 1,3,10,12-Tetrasubstituted- 8H -Pyrido[2´,3´:4,5]Pyrimido[6,1-B]Quinazolin-8-One

Laddha

Bhatnagar

2010

Future Med. Chem.

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This study indicates that fused quinazolinones display very good anticonvulsant activity. In both series, electron-withdrawing substitutions showed more activity. Among all the compounds tested, 10,12-dibromo-1- (4-chloro-phenyl)-3- (4-tolyl)-8H-pyrido[2´,3´:4,5]pyrimido[6,1-b]quinazolin-8-one and 10,12-dibromo-3- (4-chloro-phenyl)-1-phenyl-8H-pyrido[2´,3´:4,5]pyrimido[6,1-b]quinazolin-8-one were found to be the most potent.

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In Silico Screening, Synthesis And Pharmacological Screening of Quinazolinones Containing Oxazepinone Ring as NMDA Receptor Antagonists for Anticonvulsant Activity: Part -I

Sahu¹,

Nerkar²,

Chikhale³

et al. 2014

JYP

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Background: NMDA receptor specifically NR2B subunit plays a major role in eliptogenisis. Antagonists at NR2B receptor site have importance in design of anticonvulsant agents. Some quinazolinones and oxazepine have inherent drug likeliness for anticonvulsant activity. In this research work in silico biological activity spectrum (BAS), ADME prediction, Log P predictions and docking was carried out. A library of quinazolinones with oxazepinone ring was designed, from this library 3-(6-halo-2-methyl-oxoquinazolin-3-(4H-yl)-2-(substituted phenyl)-2, 3-dihydro-1,3-oxazepine-4,7-dione (AMQ 1-5 ) were prioritized for actual synthesis and pharmacological screening for NMDA receptor antagonistic activity. Method: The prioritized molecules were synthesized and characterized by melting point, IR, 1 H-NMR, TLC and elemental analysis. AOT was performed to determine LD 50 of prioritized molecules, further compounds were evaluated for their in vivo antagonistic activity on NMDA induced convulsions in mice. Result: Prioritized molecules AMQ 1-5 exhibited potent antagonistic activity on NMDA receptor. Conclusion: The compound of series AMQ 1 and AMQ 5 were showed significant activity compared to standard memantine used in the assay.

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Rapid microwave-assisted solution phase synthesis of 6, 8-disubstituted- 2-phenyl-3-(substituted-benzothiazole-2-yl) – 4-[3H]-quinazolinone as novel anticonvulsants

Cited by 3 publications

References 0 publications

cAMP-dependent phosphodiesterase inhibition and SAR studies on novel 6,8-disubstituted 2-phenyl-3-(substituted benzothiazole-2-yl)-4[3H]-quinazolinone

cAMP-dependent phosphodiesterase inhibition and SAR studies on novel 6,8-disubstituted 2-phenyl-3-(substituted benzothiazole-2-yl)-4[3H]-quinazolinone

Novel Fused Quinazolinones: Further Studies on the Anticonvulsant Activity of 1,2,9,11-Tetrasubstituted- 7H -Thieno[2´,3´:4,5]Pyrimido[6,1-B]-Quinazolin-7-One and 1,3,10,12-Tetrasubstituted- 8H -Pyrido[2´,3´:4,5]Pyrimido[6,1-B]Quinazolin-8-One

In Silico Screening, Synthesis And Pharmacological Screening of Quinazolinones Containing Oxazepinone Ring as NMDA Receptor Antagonists for Anticonvulsant Activity: Part -I

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