SYNTHESIS AND ALPHA(2)-ADRENERGIC ACTIVITY OF 2-[(METHYLENEAMINO)OXY]-N-(GUANIDINO)ETHANEIMINES - A BIOISOSTERIC REPLACEMENT OF THE ARYL OFGUANABENZ-TYPE BENZYLIDENEAMINOGUANIDINE ALPHA(2)-AGONISTS WITH THE [(METHYLENEAMINO)OXY]METHYL MOIETY (MAOMM)

Authors
BALSAMO A GENTILI D MACCHIA M MARTINOTTI E ROSSELLO A SCATIZZI R
Citation
A. Balsamo et al., SYNTHESIS AND ALPHA(2)-ADRENERGIC ACTIVITY OF 2-[(METHYLENEAMINO)OXY]-N-(GUANIDINO)ETHANEIMINES - A BIOISOSTERIC REPLACEMENT OF THE ARYL OFGUANABENZ-TYPE BENZYLIDENEAMINOGUANIDINE ALPHA(2)-AGONISTS WITH THE [(METHYLENEAMINO)OXY]METHYL MOIETY (MAOMM), European journal of medicinal chemistry, 31(9), 1996, pp. 713-716
Citations number
16
Categorie Soggetti
Chemistry Medicinal
Journal title
European journal of medicinal chemistry → ACNP
ISSN journal
02235234
Volume
31
Issue
9
Year of publication
1996
Pages
713 - 716
Database
ISI
SICI code
0223-5234(1996)31:9<713:SAAAO2>2.0.ZU;2-P
Abstract
Some 2-[(methyleneamino)oxy]-N-(guanidino)ethaneimines (10a-g) were sy nthesized as analogs of guanabenz-type benzylideneaminoguanidine alpha (2)-agonists (9) in which the aryl portion (Ar) is substituted by the [(methyleneamino)oxy]methyl moiety (MAOMM). The alpha(2)-adrenergic ac tivity of compounds 10a-g was evaluated by functional tests on guinea- pig ileum. The MAOM-derivatives 10a-g exhibited an alpha(2)-adrenergic stimulating activity fairly similar to that of the benzylideneaminogu anidine reference drug guanabenz, thus supporting the hypothesis of th e existence of a bioisoster-like relationship between the MAOMM and th e Ar in the class of guanabenz-type alpha(2)-adrenergic agonists.