Anti-Helicobacter pylori agents. 3. 2-[(Arylalkyl)guanidino]-4-furylthiazoles.
A series of 2-[(arylalkyl)guanidino]-4-[(5-acetamidomethyl)furan-2-yl]thiazole s and some 4-acetamidomethyl positional isomers were synthesized and evaluated for antimicrobial activity against Helicobacter pylori. Among the compounds that had potent antimicrobial activity (MIC < 0. 1 microgram/mL), compounds 31 and 36 additionally possessed H2 antagonist and gastric antisecretory activities. Though compound 51, an analogue incorporating a methyl group onto the furan nucleus of 36, and compound 54, a positional isomer of 51, also showed potent anti-H. pylori activity, the H2 antagonism profile was eliminated from these compounds. Thus, two types of potent anti-H. pylori agents could be derived from the same scaffold.
Katsura
Y
Y
Medicinal Chemistry Research Laboratories and Medicinal Biology Research Laboratories, Fujisawa Pharmaceutical Company, Ltd., 2-1-6, Kashima, Yodogawa-ku, Osaka 532-8514, Japan.
Nishino
S
S
Ohno
M
M
Sakane
K
K
Matsumoto
Y
Y
Morinaga
C
C
Ishikawa
H
H
Takasugi
H
H
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D016275:Atrial Function; D015169:Colony Count, Microbial; D005744:Gastric Acid / Q000378:metabolism; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006168:Guinea Pigs; D006325:Heart Atria / Q000187:drug effects; D016480:Helicobacter pylori / Q000187:drug effects*; D006635:Histamine H2 Antagonists / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D066298:In Vitro Techniques; D008297:Male; D051381:Rats; D017207:Rats, Sprague-Dawley; D011970:Receptors, Histamine H2 / Q000187:drug effects; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D006146:Guanidines; D006635:Histamine H2 Antagonists; D011970:Receptors, Histamine H2; D013844:Thiazoles