A SYNTHESIS OF 2-ENDO-AMINO-2-EXO-HYDROXYMETHYLNORBORNENES HAVING INHIBITORY ACTIVITY AGAINST PROTEIN KINASE C

A SYNTHESIS OF 2-ENDO-AMINO-2-EXO-HYDROXYMETHYLNORBORNENES HAVING INHIBITORY ACTIVITY AGAINST PROTEIN KINASE C

2-endo-Hexadecylamino-2-exo-hydroxymethylnorbornene (1a) was synthesized from 2-acetamidonorbornene-2-carboxylic acid methyl ester (2) in a good overall yield. 2-endo-Hexadecylamino-2, 3-exo-bis(hydroxymethyl)norbornene (1b) was synthesized starting from dimethyl acetamidofumarate based on Diels-Ald...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1991/02/25, Vol.39(2), pp.527-529
Hauptverfasser: IWASAKI, Tameo, YAMAZAKI, Hiroyoshi, NISHITANI, Takashi, SATO, Tadashi
Format: Artikel
Sprache:eng
Schlagworte:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
amino alcohol
aminonorbornene
Chemistry
Diels-Alder reaction
Exact sciences and technology
Norbornanes - chemical synthesis
Norbornanes - chemistry
Norbornanes - pharmacology
Organic chemistry
Preparations and properties
protein kinase C
Protein Kinase C - antagonists & inhibitors
Structure-Activity Relationship
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Zusammenfassung:2-endo-Hexadecylamino-2-exo-hydroxymethylnorbornene (1a) was synthesized from 2-acetamidonorbornene-2-carboxylic acid methyl ester (2) in a good overall yield. 2-endo-Hexadecylamino-2, 3-exo-bis(hydroxymethyl)norbornene (1b) was synthesized starting from dimethyl acetamidofumarate based on Diels-Alder strategy. 1a and 1b inhibited protein kinase C at the IC50 values of 2×10-5M and 1×10-5M, respectively, but not protein kinase A at a concentration of 1×10-3M. The structure-activity relationships are discussed.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.39.527