Cyclic guanidines. IV. Synthesis of hypoglycemic N-benzhydryl bicyclic guanidines.
- 1 January 1979
- journal article
- research article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 27 (4) , 841-847
- https://doi.org/10.1248/cpb.27.841
Abstract
N-benzhydryl bicyclic guanidines (12) were synthesized. The key intermediates, 1-benzhydryl-2-N- or 3-(.omega.-hydroxyalkyl)-2-imino-1,3-diazacycloalkanes (4) and (9) were prepared. The intramolecular cyclization of 4 to 12 resulted in low yield. Intramolecular cyclization of 9 to 12 was successful. Imidazo[1,2-a][1,3,5]oxadiazocine derivative (11), a new ring system, and N1-benzhydryl-N1-[2-(1-pyrrolidinyl)ethyl]urea (13) were isolated as byproducts. The N-benzhydryl bicyclic guanidines (12) showed potent hypoglycemic activity in rats.This publication has 3 references indexed in Scilit:
- Cyclic guanidines. III. Synthesis of hypoglycemic 2-benzhydrylimino-1,3-diazacycloalkanes.CHEMICAL & PHARMACEUTICAL BULLETIN, 1979
- Cyclic guanidines. I. Synthesis of hypoglycemic 1-substituted 2-imino-1,3-diazacycloalkanes.CHEMICAL & PHARMACEUTICAL BULLETIN, 1978
- Cyclic guanidines. II. Synthesis of hypoglycemic acyl or alkyl derivatives of 1-substituted 2-imino-1,3-diazacycloalkane.CHEMICAL & PHARMACEUTICAL BULLETIN, 1978