PMID: 6402597Mar 1, 1983Paper

Pyridazinones. 2. Synthesis and antisecretory and antiulcer activities of thiourea and 2-cyanoguanidine derivatives

Journal of Medicinal Chemistry
T YamadaM Ohki

Abstract

In an effort to develop new types of antiulcer agents, we synthesized a series of novel 2-[omega-(thioureido)alkyl]- and 2-[omega-(cyanoguanidino)alkyl]-3(2H)-pyridazinone derivatives. All target compounds were evaluated for gastric antisecretory activity in the pylorus-lygated rat by the method of Shay, and selected compounds were evaluated in the stress-induced ulcer test in rats. Structure-activity relationships were established. Two series of the compounds had significant activity in antisecretory and/or antiulcer tests. The molecular features essential for the activities are a thiourea group or a 2-cyanoguanidine group, a phenyl group in the C-6 position of the 3(2H)-pyridazinone ring, a four-carbon chain length between the 3(2H)-pyridazinone ring and the functional group, and a methyl group at the N-3 position of the functional group. Among them, the three thiourea derivatives (24, 26, and 38) and the six 2-cyanoguanidine derivatives (61, 62, 65, 75, 85, and 86) had the most potent antisecretory and/or antiulcer activities. These compounds are not histamine H2-receptor antagonists.

Citations

May 1, 1997·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·K YasuharaM Takahashi
Apr 1, 2009·Nucleosides, Nucleotides & Nucleic Acids·H A El-SayedE S H El-Ashry
Apr 3, 2018·Chemical & Pharmaceutical Bulletin·Yaser Abdel-Moemen El-BadryMahr Abdel-Aziz El-Hashash

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