Synthesis and Structure-Activity Study of Protease Inhibitors. III. Amidinophenols and Their Benzoyl Esters

Synthesis and Structure-Activity Study of Protease Inhibitors. III. Amidinophenols and Their Benzoyl Esters

Various amidinophenol derivatives (27-47) and their benzoates (4-26) were synthesized and evaluated for inhibitory activities against trypsin, plasmin, kallikrein, thrombin, Clr and Cls as well as in vitro complement-mediated hemolysis. 4-(β-Amidinoethenyl) phenyl 4-guanidinobenzoate (15) and 4-amid...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1984/11/25, Vol.32(11), pp.4466-4477
Hauptverfasser: YAEGASHI, TAKASHI, NUNOMURA, SHIGEKI, OKUTOME, TOSHIYUKI, NAKAYAMA, TOYOO, KURUMI, MASATERU, SAKURAI, YOJIRO, AOYAMA, TAKUO, FUJII, SETSURO
Format: Artikel
Sprache:eng
Schlagworte:
Amidines - chemical synthesis
Amidines - pharmacology
amidinophenols
Animals
Benzoates - chemical synthesis
Benzoates - pharmacology
benzoic acid
Chemical Phenomena
Chemistry
complement component C1s
Exact sciences and technology
Hemolysis - drug effects
In Vitro Techniques
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Protease Inhibitors - chemical synthesis
Protease Inhibitors - pharmacology
Sheep
Structure-Activity Relationship
trypsin
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Zusammenfassung:Various amidinophenol derivatives (27-47) and their benzoates (4-26) were synthesized and evaluated for inhibitory activities against trypsin, plasmin, kallikrein, thrombin, Clr and Cls as well as in vitro complement-mediated hemolysis. 4-(β-Amidinoethenyl) phenyl 4-guanidinobenzoate (15) and 4-amidino-2-benzoylphenyl 4-guanidinobenzoate (26) were found to have potent inhibitory activities with IC50s of 9×10-8M (trypsin) and 2×10-7M (Cls) for the former and 3×10-8M (trypsin) and 2×10-7M (Cls) for the latter.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.32.4466