Alanine derivatives with reactive groups.

Abstract:

:The synthesis of diazoketone analogs of amino acids and associated problems were investigated with N-phthaloyl-DL-alanine serving as a model. The carboxyl was activated by conversion to the acid chloride or, under mild conditions, to the mixed anhydride obtained with ethyl chloroformate or dicyclohexylcarbodiimide; the product was reacted with diazomethane. Deblocking the phthaloyl group with hydrazine gave 3-amino-1-diazo-2-butanone as a well-characterized solid salt and as a less stable oil. Further reactions of the blocked diazoketone of DL-alanine, such as conversion to alpha-haloketones, Wolff rearrangement, and deuterium exchange on C-1 were investigated. 3-A-mino-1-diazo-2-butanone had moderate inhibitory activity against mouse mammary adenocarcinoma in cell culture.

journal_name

J Pharm Sci

authors

Paul B,Korytnyk W

doi

10.1002/jps.2600670518

subject

Has Abstract

pub_date

1978-05-01 00:00:00

pages

642-5

issue

5

eissn

0022-3549

issn

1520-6017

pii

S0022-3549(15)41997-5

journal_volume

67

pub_type

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