Structural Modification of Bioactive Compounds. II. Syntheses of Aminophosphonoic Acids

To develop antagonists which show selectivity in blocking neurotransmitters, several aminophosphonoic acids, 2-amino-5-phosphonopentanoic acid (IVb), 2-amino-4-(2-phosphonomethylphenyl) butyric acid (VIII), 2-(2-amino-2-carboxy) ethylphenylphosphonic acid (XIc), and N-benzylproline-4-phosphonic acid...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 32; no. 10; pp. 3918 - 3925
Main Authors MATOBA, KATSUHIDE, YONEMOTO, HIROYO, FUKUI, MASAKO, YAMAZAKI, TAKAO
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 1984
Maruzen
Japan Science and Technology Agency
Subjects
Chemistry
Exact sciences and technology
Organic chemistry
Organometalloidal and organometallic compounds
P derivatives
Preparations and properties
pyrazole
Five membered ring
Aliphatic compound
Nitrogen heterocycle
Aminoacid
Phosphorus Organic compounds
Pyrrolidine derivatives
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Summary:To develop antagonists which show selectivity in blocking neurotransmitters, several aminophosphonoic acids, 2-amino-5-phosphonopentanoic acid (IVb), 2-amino-4-(2-phosphonomethylphenyl) butyric acid (VIII), 2-(2-amino-2-carboxy) ethylphenylphosphonic acid (XIc), and N-benzylproline-4-phosphonic acid (XIX), were synthesized. Compounds IVb, VIII, and XIc were prepared from the corresponding halides (V, Xa, and XIa, respectively) by treatment with sodium diethyl acetamidomalonate (VI). Compound XIX was synthesized via 1, 3-dipolar cycloaddition of ethyl N-benzyl-N-phenylthiomethylglycinate (XV) to diethyl vinylphosphonate (XVI).
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.32.3918