The structure of the bisbenzylisoquinoline alkaloid dimethylwarifteine

Borkakoti, Neera; Palmer, R. A.

doi:10.1107/s0567740878003398

Cited by 7 publications

(3 citation statements)

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“…The average C-N bond distance is in good agreement with the value found in other alkaloids, for example 1.467 A in tetrandrine (Gilmore, Bryan & Kupchan, 1976), and 1.50 A in (+)-tubocurarine dichloride (Codding & James, 1973). The C=N double bond in the 3,4-dihydroisoquinoline ring is 1.292(7) A, which compares well with the value of 1.288(13) A found in dimethylwarifteine (Borkakoti & Palmer, 1978). …”

Section: Resultssupporting

confidence: 80%

“…Chemical and mass spectral analysis of these bases (Snedden, Parker & Gorinsky, 1970), referred to as warifteine (I), methylwarifteine (II) and dimethylwarifteine (III) (Fig. 1), have been made and the crystal structure analyses of (II) (this paper) and (III) (Borkakoti & Palmer, 1978) have been successfully completed. The alkaloid cissampereine isolated from the related plant Cissampelos pareira Linn., and characterized by Kupchan, Kubota, Fujita, Kobayashi, Block & Telang (1966) is isomeric with methylwarifteine.…”

Section: Introductionmentioning

confidence: 99%

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The structure of the bisbenzylisoquinoline alkaloid methylwarifteine

Borkakoti¹,

Palmer²

1978

Acta Crystallogr Sect B

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The crystal structure of the bisbenzylisoquinoline alkaloid methylwarifteine, C37HasN206, has been determined by direct methods, using Cu K tq diffractometer data. The compound crystallizes in the orthorhombic space group P2~2~21, with unit-cell dimensions a = 17.539 (4), b = 12.224 (3), c = 14.393 (3) A, Z = 4. The structure was refined by full-matrix least-squares methods to R = 0-057, for 2508 observed reflections. The phenyl rings of the isoquinoline groups are planar and the nitrogen-containing rings are both in similar half-chair conformations, with the pseudo twofold axis bisecting two C-C bonds. The benzyltetrahydroisoquinoline residue is in an extended conformation while the benzyldihydroisoquinoline residue is folded. The two halves of the molecule thus formed are joined by an ether linkage on one side and a methoxy linkage on the other side. The dihedral angle between the two benzyl groups is 111.3 o.

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Section: Resultssupporting

confidence: 80%

Section: Introductionmentioning

confidence: 99%

The structure of the bisbenzylisoquinoline alkaloid methylwarifteine

Borkakoti¹,

Palmer²

1978

Acta Crystallogr Sect B

Self Cite

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show abstract

“…3 In addition, cissampareine was found to be isomeric with methylwarifteine and had the same skeleton since both gave dimethylwarifteine on permethylation. Since the relative positions of the OH and OMe groups on each aromatic ring of the two isoquinoline moieties were never defined, the structure of the most abundant alkaloid of C. ovalifolia, warifteine, remained unsettled even though the x-ray crystal structures of both dimethylwarifteine 4 and methylwarifteine 5 were determined. We remained interested in elucidating the complete structures of warifteine and methylwarifteine since publishing a review on bisbenzylisoquinoline alkaloids, 6 where warifteine and cissampareine were placed in a special section with one diphenyl ether and one benzyl phenyl ether linkage.…”

Section: Introductionmentioning

confidence: 99%