Synthesis and Biological Activity of β-Aminoketones, Secondary Aminopropanols and Oximes of 2-Aminothiophene Series

Recent progress in the chemistry of β-aminoketones

“…Among them, compound 142 presented the greatest sensitivity against blood coagulation, while compounds 143 , 144 , and 147–151 had reduced activity compounds 145 , 146 , and 152 were inactive. 154…”

“…Owing to the privileged biological potency of tertiary amino alcohols, 155,156 Gevorgyan et al 154 synthesized a series of tertiary piperazinyl amino alcohols 160–172 by the reaction of β-aminoketones 158 and 159 with a Grignard reagent “prepared from metallic magnesium with alkyl(aryl)halide in anhydrous diethyl ether”. The dihydrochloride salts of some of these compounds 173–178 were prepared by treatment with hydrochloric acid (Scheme 50).…”

“…Gevorgyan et al 154 also developed the synthesis of a series of β-aminoketones 136–141 in a mixture of water and alcohol after a short time. Thus, 3-(diethylamino)-1-(aryl)propan-1-one hydrochlorides 246 reacted with tetrahydrobenzo[ b ]-thiophenes 247 under free-catalyst conditions to afford the desired β-aminoketones 136–141 (Scheme 60).…”

“…Among them, compound 142 presented the greatest sensitivity against blood coagulation, while compounds 143, 144, and 147-151 had reduced activity compounds 145, 146, and 152 were inactive. 154 The respective b-aminoketone "methyl esters of isosteviol" 29-33 underwent selective reduction by treatment with sodium borohydride in dry methanol under mild reaction conditions to give 1,3-amino alcohols 153-157 through hydroxy-formylation processes. The 1,3-amino alcohol products are diastereomeric mixtures in some cases.…”

“…In addition, the incorporation of N-benzyl substituents in the amino group is crucial for improved cytotoxic inuence and privileged antiproliferative characters. 107 Owing to the privileged biological potency of tertiary amino alcohols, 155,156 Gevorgyan et al 154…”