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Ukr. Bioorg. Acta 2020, Vol. 15, N2, 27-31.

Amino acid sulfonamides based on 4-(1-oxo-1H-isochromen-3-yl)benzene-sulfonyl chloride

Anastasiia A. Riabchenko 1, Olga V. Shablykina 1,2*, Serhiy V. Shilin 1,
Svitlana A. Chumachenko
2, Volodymyr P. Khilya 1

1 Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv, 01601, Ukraine
tel.: +380-44-239-3342; e-mail: shablykina@ukr.net
2 V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, 1 Murmanska St., Kyiv, 02094, Ukraine

ABSTRACT
The creation of new amino acid derivatives from 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride 1 was investigated. The interaction of the sulfonylchloride 1 with amino acid methyl esters (hydrochlorides) in 1,4-dioxane with triethylamine led to the corresponding amino acid sulfonamide derivatives of isocoumarin. The reaction of the sulfonchloride 1 with phenylalanine in the basic water-containing medium was complicated by the lactone system disclosure and led to 2'-carboxydeoxybenzoin ultimately (namely, 2-(2-(4-(N-(1-carboxy-2-phenyl-ethyl)sulfamoyl)phenyl)-2-oxoethyl)benzoic acid). Similar product 2-(2-(4-(N-(1-carboxy-5-methylbuhyl)sulfamoyl)phenyl)-2-oxoethyl)benzoic acid has been obtained by the alkali hydrolysis of methyl ((4-(1-oxo-1H-isochromen-3-yl)phenyl)sulfonyl)leucinate.

KEYWORDS
sulfonamides, amino acids, 3-phenylisocoumarin, sulfochlorination.

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