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Biodegradable neuromuscular blocking agents 6. stereochemical studies on atracurium and related polyalkylene diesters



Biodegradable neuromuscular blocking agents 6. stereochemical studies on atracurium and related polyalkylene diesters



European Journal of Medicinal Chemistry 19(5): 441-450



Stereoisomers of atracurium (3, n = 5) and 1 of its homologues each having the configuration, RR, SS and RS at the C(1)-positions were synthesized. The ratio of cis and trans components in the RR-, SS- and RS/meso-products, which contain 3, 3 and 4 isomers, respectively, measured by 1H and13C NMR is .apprx. 3.0. The ratio of cis-cis-, cis-trans- and trans-trans-isomers in the isomer mixtures, determined by HPLC [high performance liquid chromatography], is in reasonable agreement with the cis/trans ratios found by 1H NMR. Variable temperature 13C NMR suggests that the tetrahydropapaverinium ring system undergoes fast ring inversion at ambient temperature. The relative molar neuromuscular blocking potencies of the 3 atracurium isomer products in anesthetized cats were found to be RR (231), RS/meso (133) and SS (89) compared to that of tubocurarine (100). The significance of these relative potencies is discussed in relation to the potencies of norcoralydine and tubocurarine stereoisomers.

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