Medicinal chemical studies on antiplasmin drugs. VII. Oxa analogs of 4-aminomethylcyclohexanecarboxylic acid.

• ISODA SUMIRO

• YAMAGUCHI HITOSHI

• SATOH YOSHINARI

• HIRATA MIYOSHI

Abstract

The two isomers of 5-aminomethyltetrahydro-2H-pyran-2-carboxylic acid (9) and those of 5-aminomethyl-1, 4-dioxane-2-carboxylic acid (18) were synthesized from 2-ethoxycarbonyl-3, 4-dihydro-2H-pyran-5-carboxylic acid chloride (2) and dimethyl 1, 4-dioxane-2, 5-dicarboxylate (15), respectively. From the aminoacetal (19) and dimethyl bis (hydroxymethyl) malonate (21), trans-2-aminomethyl-1, 3-dioxane-5-carboxylic acid (26A) was synthesized. The configurations of these isomers were determined on the basis of their nuclear magnetic resonance spectra, and the preferred conformations of the isomers in aqueous solution were similarly deduced. No compound showed antiplasmin activity more potent than that of trans-4-aminomethylcyclohexanecarboxylic acid (1A).

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 28 (8), 2329-2336, 1980

  The Pharmaceutical Society of Japan

Keywords

• conformation

Details

• CRID: 1390001204166015232
• NII Article ID: 110003624030
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.28.2329
• ISSN: 13475223
• ISSN: 00092363
• PubMed: 7428124
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/28/8/28_8_2329/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1981177644
• Text Lang: en
• Data Source:
  • JaLC
  • Crossref
  • PubMed
  • CiNii Articles
• Abstract License Flag: Disallowed