3,4-O-diacetylisoproterenol. Preparation, structure proof, and beta-receptor effect.
Direct acetylation of isoproterenol by selective O-acetylation using CH3COCl/CF3COOH was shown to lead to the formation of 2-(3,4-diacetoxyphenyl)-2-chloro-N-isopropyl-1-ethanamine and not to 3,4-O-diacetylisoproterenol. The latter was prepared by reduction of 3,4-diacetoxy(2-isopropylamino)acetophenone and its structure confirmed by IR, 1H, 13C NMR, mass spectral, and elemental analysis. The two compounds were tested for activity on beta-receptors. Efficacy and affinity on beta 1-receptors were found identical with the effect of isoproterenol. So was efficacy on beta2-receptors, while affinity was lower for the chloro compounds than for isoproterenol and diacetylisoproterenol which exhibited identical affinity.
D000107:Acetylation; D000818:Animals; D001792:Blood Platelets / Q000378:metabolism; D002540:Cerebral Cortex / Q000378:metabolism; D055598:Chemical Phenomena; D002621:Chemistry; D000242:Cyclic AMP / Q000378:metabolism; D006801:Humans; D007545:Isoproterenol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051381:Rats; D011943:Receptors, Adrenergic, beta / Q000187:drug effects* / Q000502:physiology; D013329:Structure-Activity Relationship
D011943:Receptors, Adrenergic, beta; C031228:3-O,4-O-diacetylisoproterenol; C047299:2-(3,4-diacetoxyphenyl)-2-chloro-N-isopropyl-1-ethanamine; D000242:Cyclic AMP; D007545:Isoproterenol