<i>S</i>-Phenyl 4-methoxybenzothioate

El‐Azab, Adel S.; Abdel‐Aziz, Alaa A.‐M.; El‐Subbagh, Hussein I.; Chantrapromma, Suchada; Fun, Hoong‐Kun

doi:10.1107/s1600536812005454

Cited by 3 publications

(2 citation statements)

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“…Quinazolin‐4(3 H )‐one is an important landmark in the field of synthetic anticonvulsant as it is an important skeleton of many reported anticonvulsants . Previously our research group has synthesized a series of fused quinazolino‐benzothiazoles and evaluated them as anticonvulsants .…”

Section: Introductionmentioning

confidence: 99%

“…Following hypothesis has been considered while designing of outline derivatives. Methaqualone ( I ) is a drug bearing quinazolin‐4(3 H )‐one motif found as “master key” in anticonvulsant therapy , and its 6,7‐dimethoxy analog ( II ) proved to possess manifest anticonvulsant potential against both electroshock and chemically induced seizure tests . Piriqualone ( III ) is a candidate with quinazolin‐4(3 H )‐one scaffold known for its significant anticonvulsant properties .…”

Section: Introductionmentioning

confidence: 99%

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Structural Exploration of Quinazolin‐4(3H)‐ones as Anticonvulsants: Rational Design, Synthesis, Pharmacological Evaluation, and Molecular Docking Studies

Ugale

Bari

2016

Archiv der Pharmazie

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Anticonvulsants effective against multiple seizures are of wide interest as antiepileptic drugs, especially if active against pharmaco-resistant seizures. Herein, we synthesized 16 different, rationally designed 2-((6,7-dimethoxy-4-oxo-2-phenylquinazolin-3(4H)-yl)amino)-N-(substituted phenyl)acetamides and screened for anticonvulsant activities through in vivo experiments. Compound 4d emerged as prototype with excellent anti-seizure action in mice against electroshock, chemically induced and pharmaco-resistant 6-Hz seizure models with no symptoms of neurotoxicity and hepatotoxicity (ED = 23.5 mg/kg, MES, mice, i.p.; ED = 32.6 mg/kg, scPTZ, mice, i.p.; ED = 45.2 mg/kg, 6-Hz, mice, i.p.; TD = 325.9 mg/kg, mice, i.p.). In addition, investigation of compound 4l in mice for its pharmacological profile proved it as safer anticonvulsant, devoid of the side effects such as motor dysfunction and hepatotoxicity of classical antiepileptic drugs (ED = 26.1 mg/kg, MES, mice, i.p.; ED = 79.4 mg/kg, scPTZ, mice, i.p.; TD = 361.2 mg/kg, mice, i.p.). We also predicted physiochemical and pharmacokinetic properties of structurally optimized quinazolin-4(3H)-ones by a computational protocol. A combination of in vivo anticonvulsant profile, ex vivo toxicity, and in silico studies suggested that the synthesized compounds may be useful as broad-spectrum anti-seizure drug candidates with favorable pharmacokinetic parameters.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structural Exploration of Quinazolin‐4(3H)‐ones as Anticonvulsants: Rational Design, Synthesis, Pharmacological Evaluation, and Molecular Docking Studies

Ugale

Bari

2016

Archiv der Pharmazie

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Structures of S-(pyridin-2-yl) 4-nitrobenzothioate, S-(pyridin-2-yl) 4-methylbenzothioate and S-(pyridin-2-yl) 4-methoxybenzothioate: building blocks for low-symmetry multifunctional tetrapyrroles

2023

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The crystal structures of three S-(pyridin-2-yl) benzothioesters with varying para-phenyl substituents are presented, namely, S-(pyridin-2-yl) 4-nitrobenzothioate (1, C12H8N2O3S), S-(pyridin-2-yl) 4-methylbenzothioate (2, C13H11NO2S) and S-(pyridin-2-yl) 4-methoxybenzothioate (3, C13H11NO2S). This class of compounds are used in the mono-acylation of pyrrolic species to yield multifunctional tetrapyrroles. The structures presented herein are the first of their compound class. The dominant interactions present in this series are π–π stacking and C—H...O interactions, and as the para-phenyl motif changes from electron withdrawing (NO2, 1) to electron donating (OCH3, 3), changes are observed in the interactions present in the crystal packing, from predominant π–π stacking in 1 to exclusively C—H...O/N interactions (Caryl—H...Ocarbonyl, C—H...Omethoxy and Caryl—H...Npyridine) in 3.

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