title: Synthesis and crystal structure of optically active 2-[benzyl(phenyl)amino]ethyl 5-(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydro-2,6-dim ethyl-4-(3-nitrophenyl)-3-pyridinecarboxylate (NZ-105).
abstract: (S)-2-[Benzyl(phenyl)amino]ethyl 5-(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydro-2, 6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylate ((S)-NZ-105) and R isomer were synthesized through the fractional crystallization of (S)-2-Methoxy-2-phenylethyl 5-(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydro-2, 6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylate. Calcium antagonism activity was found to reside in the S isomer from single crystal X-ray diffraction analysis.
authors.affiliation: Central Research Institute, Nissan Chemical Ind. Ltd., Chiba, Japan.
authors.forename: R
authors.initials: R
authors.lastname: Sakoda
authors.forename: H
authors.initials: H
authors.lastname: Matsumoto
authors.forename: K
authors.initials: K
authors.lastname: Seto
mesh_terms: D000818:Animals; D000959:Antihypertensive Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002121:Calcium Channel Blockers / Q000138:chemical synthesis* / Q000494:pharmacology; D003460:Crystallization; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000494:pharmacology; D066298:In Vitro Techniques; D008968:Molecular Conformation; D009596:Nitrophenols; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D013237:Stereoisomerism; D014961:X-Ray Diffraction
chemical_list: D000959:Antihypertensive Agents; D002121:Calcium Channel Blockers; D004095:Dihydropyridines; D009596:Nitrophenols; D009943:Organophosphorus Compounds; C066425:efonidipine