Structure Of 18'-Epivinblastine

Date

1991-07

Authors

Lynch, Vincent M.
Stamford, Andrew
Magnus, Philip
Davis, Brian E.

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Abstract

Methyl {3aR-[3a-alpha,4-beta,5-beta,5a-beta,9(3R*,-5S*,7R*,9R*),10bR,13a-alpha]}-4-(acetyloxy)-3a-ethyl-9-[5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino[5,4-b]indol-9-yl]-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-lH-indolizino-[8,1-c,d]carbazole-5-carboxy?? late methanol solvate, C46H58N4O9.2CH3OH (1), M(r) = 875.07, monoclinic, P2(1), a = 10.2759 (12), b = 22.353 (3), c = 10.4051 (12) angstrom, beta = 106.502 (9)-degrees, V = 2291.6 (5) angstrom 3, Z = 2, D(x) = 1.27 g cm-3, Mo K-alpha radiation, lambda = 0.7107 angstrom, mu = 0.8397 cm-1, F(000) = 940, T = 198 K, R = 0.0470 for 2751 reflections, F(o) greater-than-or-equal-to 4-sigma-(F(o)). The C ring of the vindoline moiety is in the boat conformation with the hydroxy group and the tertiary N in the bowsprit positions resulting in a fairly short intramolecular hydrogen-bonding interaction. The relevant parameters for O3-H3...N9 are O...N 2.651 (6), H...N 1.94 (5) angstrom and O-H...N 147 (5)-degrees. The D and E rings are in the sofa and envelope conformations, respectively. The piperidine ring of the catharanthine portion of the molecule assumes the chair conformation while the conformation of the azacyclononene ring is a boat-chair. An intramolecular hydrogen bond between the indolino NH of the catharanthine moiety and methoxy O (O25) of the vindoline moiety is also observed. The relevant parameters for N16'-H16'...O25 are N...O 2.827 (6), H...N2.14 (6) angstrom and O-H...N 136 (5)-degrees.

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Citation

Lynch, Vincent M., Stamford, Andrew, Magnus, Philip, Davis, Brian E., >Structure of 18'-epivinblastine,> Acta Crystallogr C. 1991 Jul 15;47 ( Pt 7):1563-6. doi: 10.1107/S010827019100029X