Synthesis of 2-Methylidene Spermidine and its N1-Acetylated Derivative

— Simple and practical synthetic protocols have been developed for the preparation of earlier unknown 2-methylidene derivatives of spermidine and N 1 -Ас-spermidine, i.e., 1,8-diamino-2-methylidene-4-azaoctane (2-Met-Spd) and N 1 -(acetyl)-1,8-diamino-2-methylidene-4-azaoctane ( N 1 -Ас-2-Met-Spd),...

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Bibliographic Details
Published in:	Russian journal of bioorganic chemistry Vol. 48; no. 6; pp. 1202 - 1208
Main Authors:	Khomutov, M. A., Khomutov, A. R.
Format:	Journal Article
Language:	English
Published:	Moscow Pleiades Publishing 2022 Springer Nature B.V
Subjects:	Biochemistry Biomedical and Life Sciences Biomedicine Bioorganic Chemistry Life Sciences Organic Chemistry Polyamines acetylpolyamine oxidase spermidine analogs polyamines
Online Access:	Get full text
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Summary:	— Simple and practical synthetic protocols have been developed for the preparation of earlier unknown 2-methylidene derivatives of spermidine and N 1 -Ас-spermidine, i.e., 1,8-diamino-2-methylidene-4-azaoctane (2-Met-Spd) and N 1 -(acetyl)-1,8-diamino-2-methylidene-4-azaoctane ( N 1 -Ас-2-Met-Spd), respectively. Target compounds were obtained each in seven steps with high overall yields starting from the commercially available 2-chloromethyl-3-chloropropene-1. Possible application of newly synthesized spermidine analogs for the inhibition of FAD-dependent N 1 -acetyl polyamine oxidase is discussed.
ISSN:	1068-1620 1608-330X
DOI:	10.1134/S1068162022060140