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Synthesis of Medicinally Relevant Phenyl Sulphonylamino Alkanamides and N-aryl P-toluenesulphonamides

عنوان مقاله: Synthesis of Medicinally Relevant Phenyl Sulphonylamino Alkanamides and N-aryl P-toluenesulphonamides
شناسه ملی مقاله: JR_JMCH-2-4_005
منتشر شده در در سال 1398
مشخصات نویسندگان مقاله:

Attah S. Izuchi - Department of Pure & Industrial Chemistry, University of Nigeria, Nsukka, ۴۱۰۰۰۱, Enugu State, Nigeria
Efeturi A. Onoabedje - Department of Pure & Industrial Chemistry, University of Nigeria, Nsukka, Nigeria
Ogechi C. Ekoh - Department of Pure & Industrial Chemistry, University of Nigeria, Nsukka, ۴۱۰۰۰۱, Enugu State, Nigeria
Sunday Okafor - Department of Pharmaceutical and Medicinal Chemistry, University of Nigeria, ۴۱۰۰۰۱, Nsukka, Enugu State, Nigeria
Uchechukwu C. Okoro - Department of Pure & Industrial Chemistry, University of Nigeria, Nsukka, ۴۱۰۰۰۱, Enugu State, Nigeria

خلاصه مقاله:
Synthesis of new medicinally important phenylsulphonyl aminoalkanamides and N-aryl p-toluene sulphonamides is reported. The reaction between benzenesulphonylchloride ۷ with valine gave ۳-methyl-۲-[phenylsulphonyl)amino]butanoic acid ۹ which is converted into ۲-[acetyl (phenylsulphonyl) amino]-۳-methyl butanoic acid ۱۰ by reaction with acetic anhydride in acetic acid. The reaction of the later with SOCl۲ and subsequently with NH۳ afforded ۲-[N-acetyl (phenylsulphonyl) amino]-۳-methyl butanamide intermediate ۱۱. The palladium catalysed reaction of the intermediate with readily available aryl chlorides and bromides afforded a variety of phenyl sulphonylaminoalkanamides ۱۳a-c. In another synthesis, p-toluenesulphonylchloride (۱۴) reacted with aqueous ammonia to give ۴-methyl benzenesulphonamide ۱۵ which is converted into N-(۴-hydroxylphenyl)-۴-methylbenzene sulphonamide ۱۷a, N-(۴-formyl phenyl)-۴-methyl benzene sulphonamide ۱۷b, N-(۴-aminophenyl)-۴-methyl benzenesulphonamide ۱۷c, ۴-methyl-N-(۲-methylphenyl) benzene sulphonamide ۱۷d, N-(۴-Methoxyphenyl)-۴-methyl benzenesulphonamide ۱۷e in good yields, by reaction with ۴-chlorophenol, ۴-bromobenzaldehyde , ۴-bromoaniline, ۲-chlorotoluene and ۱-bromo-۲-methoxybenzene, respectively. Structures of the synthesized compounds were confirmed by spectroscopic and elemental analytical data

کلمات کلیدی:
Sulphonamides, Organosulfur, Anticancer, methotrexate, Synthesis

صفحه اختصاصی مقاله و دریافت فایل کامل: https://civilica.com/doc/1324435/