A simple and efficient method for the synthesis of 5,6-dihydropyrazin-2(1H)-one O-(tert-butyl)oximes, quinoxalin-2(1H)-one O-(tert-butyl)oximes and its derivatives

Aoyama, Tadashi; Tashiro, Kenshiro; Hayakawa, Mamiko; Shimada, Shigeru; Ouchi, Akihiko

doi:10.1016/j.tetlet.2018.10.015

Cited by 2 publications

(1 citation statement)

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“…Compounds (IVa-d) were synthesized via Wittig reaction by reacting to the 4-substituted benzyltriphenylphosphonium bromide with NaH, then adding the formed ylide to the appropriate aldehyde (IIIa, b) afford the targeted compounds (VIc, d) and the alkene intermediates (IVa, b) in 78-80% yield. Compounds (Va-c) were prepared in two steps by reducing the nitro derivatives (IVa, b, c) using iron/NH 4 Cl in ethanol/H 2 O under refluxing conditions [17] followed by the nucleophilic substitution reaction of the amine with methanesulfonyl chloride (Hinsberg reaction [18]) to generate the final compounds (Va, b, c) in 40-42% yield.…”

Section: Synthesis Of Pyrazole Derivativesmentioning

confidence: 99%

Identification of novel pyrazole and benzimidazole based derivatives as PBP2a inhibitors: Design, synthesis, and biological evaluation

Shalaby

Dokla

Serya

et al. 2019

Archives of Pharmaceutical Sciences Ain Shams University

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The antibiotic resistance of methicillin-resistant Staphylococcus aureus (MRSA) is attributable to the expression of the high molecular mass transpeptidase enzyme, penicillin-binding protein 2a (PBP2a), an enzyme that catalyzes the cross-linking reaction step in the cell wall biosynthesis in the face of the challenge by β-lactam antibiotics. In the current study, ten pyrazole and benzimidazole based-compounds were designed, synthesized, and evaluated as anti-MRSA agents. These derivatives were screened for their antibacterial activity against two Staphylococcus (S.) aureus strains; methicillin-sensitive Staphylococcus aureus (MSSA) ATTC6538 and MRSA USA300 strains. Three of the tested compounds (XII, XIII, and XIV) exhibited moderate bactericidal activity against MSSA, MRSA, and vancomycinresistant Staphylococcus aureus (VRSA) strains. Docking of these compounds into the allosteric site of PBP2a showed comparable binding modes to that of the lead quinazolinone PBP2a inhibitors suggesting a similar mode of action. The present study presents a promising candidate for further optimization as a potential PBP2a inhibitor targeting MRSA infection.

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Section: Synthesis Of Pyrazole Derivativesmentioning

confidence: 99%