Miller D D, Hamada A, Craig E C, Christoph G G, Gallucci J C, Rice P J, Banning J W, Patil P N
J Med Chem. 1983 Jul;26(7):957-63. doi: 10.1021/jm00361a005.
The optical isomers and deoxy form of 2-(3,4, alpha-trihydroxybenzyl)imidazoline hydrochloride were examined for their alpha-adrenergic activity on rat aorta. The rank order of stimulant activity was deoxy (2) congruent to (R)-(-)-1 greater than (S)-(+)-1. This is in contrast to catecholamines in which the order of activity is (R)-(-)-epinephrine greater than (S)-(+)-epinephrine = epinine (deoxyepinephrine). The relative order of potency for the isomers of 2-(3,4, alpha-trihydroxybenzyl)imidazoline is different than that predicted by the Easson--Stedman theory for stereoisomers of catecholamines. Also, substitution of the deoxy compound 2 with substituents, methyl or benzyl, in the 4-position lowers the alpha-adrenergic agonist activity, and differences observed between optical isomers were small.
研究了2-(3,4,α-三羟基苄基)咪唑啉盐酸盐的光学异构体和脱氧形式对大鼠主动脉的α-肾上腺素能活性。刺激活性的顺序为脱氧(2)≡(R)-(-)-1＞(S)-(+)-1。这与儿茶酚胺相反，儿茶酚胺的活性顺序为(R)-(-)-肾上腺素＞(S)-(+)-肾上腺素=去甲肾上腺素(脱氧肾上腺素)。2-(3,4,α-三羟基苄基)咪唑啉异构体的相对效价顺序与伊登-斯特德曼理论对儿茶酚胺立体异构体的预测不同。此外，在4位用甲基或苄基等取代基取代脱氧化合物2会降低α-肾上腺素能激动剂活性，且光学异构体之间观察到的差异较小。
