Synthesis of Piperidine Derivatives with a Quinazoline Ring System as Potential Antihypertensive Agents

• Published in: Chemical & pharmaceutical bulletin Vol. 34; no. 5; pp. 1907 - 1916
• Main Authors: TAKAI, HARUKI, SHUTO, KATSUICHI, TERANISHI, MASAYUKI, KUBO, KAZUHIRO, KASUYA, YUTAKA, OBASE, HIROYUKI, SHIGENOBU, KOKI, KARASAWA, AKIRA
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 01.05.1986; 公益社団法人日本薬学会; Maruzen; Japan Science and Technology Agency
• Subjects: Animals; antihypertensive activity; Antihypertensive Agents - chemical synthesis; Blood Pressure - drug effects; Chemical Phenomena; Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; indole; Male; Organic chemistry; oxidative cleavage; piperidine; Piperidines - chemical synthesis; Preparations and properties; quinazoline; Quinazolines - chemical synthesis; Quinazolines - pharmacology; Rats; Rats, Inbred SHR; Aminoketone; Nitrogen heterocycle; Six membered ring; Bicyclic compound; Antihypertensive agent; Benzenic compound; Ureas; Aromatic compound; Infrared spectrum; NMR spectrum; Biological activity
• ISSN: 0009-2363; 1347-5223; 1347-5223
• DOI: 10.1248/cpb.34.1907

A series of piperidine derivatives with a 2-oxo-1, 2, 3, 4-tetrahydro-quinazoline or 2, 4-dioxo-1, 2, 3, 4-tetrahydroquinazoline ring at the 4-position were prepared and tested for antihypertensive activity. Among the compounds tested, 1-[2-hydroxy-2-(3, 4-methylenedioxyphenyl)ethyl]-4-(2, 4-dioxo-1, 2, 3, 4-tetrahydro-3-quinazolinyl)piperidine (20) and 1-[2-(4-chlorophenyl)-2-hydroxyethyl]-4-(2-oxo-1, 2, 3, 4-tetrahydro-3-quinazolinylmethyl)piperidine (30) produced relatively strong hypotension in the spontaneously hypertensive rat model.