Alkaloids From Catharanthus Roseus <sup>1</sup>H NMR Study of 20′S‐Deoxyvinblastine and its N‐2′ Borane Complex

Debruyn, A.; Sleeckx, J. J. M.; Dejonghe, Jp.; Hannart, J.

doi:10.1002/bscb.19830920510

Cited by 10 publications

References 7 publications

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On the Amidation of 17‐Deacetyl‐Vinblastine With the Ethylesters of Some Aminoacids

Rao¹,

Collard²,

Trouet³

et al. 1985

Bulletin des Soc Chimique

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the 0th: esters of valine ( 2 1 , leucine (31, isoleucine (41, tryptophane ( 5 ) and valine-tryptophane (6).We describe the synthesis of amides between 17-deacetylvlnblastine (1) and Considerable attention has bean given to the alkaloids of the Uadagascar periwinkle (Catharanthus roseus G. Don) because of their antitumor activity'.It seenu that this activity can be augmented or oriented by the introduction of certain amino acids or peptide chains2-'. This could be achievad by replacing the methylester on C-16 in vinblastine by the amide formed with the chosen amino acids (2)-(6). In the present paper we describe the results of this approach with 17-deacetyl vinblastine5. the caapounds synthesized in the present study the ' H NUR spectrum of vinblas-tine6-8 was chosen as reference. the study of the changes occurring on derivatizing vinblastine. For confirmation of tho structures of ' H NnR is a sufficiently sensitive tool for

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On the Amidation of 17‐Deacetyl‐Vinblastine With the Ethylesters of Some Aminoacids

Rao¹,

Collard²,

Trouet³

et al. 1985

Bulletin des Soc Chimique

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Total assignment of the proton and carbon NMR spectra of 5′‐NOR‐anhydrovinblastine

Spitzer

Crouch

Martin

1992

Journal of Heterocyclic Chem

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Total spectral assignment of the bis‐indole alkaloid Navelbine®, 5′‐nor‐anhydrovinbIastine, was accomplished using a combination of two‐dimensional nmr techniques. Conventional homonuclear and inverse‐detected experiments were supplemented with the HMQC‐TOCSY experiment to unequivocally assign carbons directly bound to overlapped protons. In addition, the recently introduced GEM‐COSY experiment was evaluated as a technique for the identification of geminal methylene pairs. Partial assignments proposed by Potier and co‐workers, based on chemical shift considerations, are largely in agreement with the unequivocal assignments determined in this study.

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¹H NMR study and conformational aspects of 20′‐deoxy‐20′‐epivindesine

Debruyn

Verzele

Jans

et al. 1986

Magnetic Reson in Chemistry

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Alkaloids From Catharanthus Roseus ¹H NMR Study of 20′S‐Deoxyvinblastine and its N‐2′ Borane Complex

Abstract: The ' H NMR spectra of 20' S-deoxyvinblastine and its N-2' borane complex have been unraveled. 2D 6-J-resolved NMR allowed to measure the isolated peaks in the overlapping patterns of the amine borane complex. Both compounds can now easily be discriminated on basis of ' H NMR data.

Cited by 10 publications

References 7 publications

On the Amidation of 17‐Deacetyl‐Vinblastine With the Ethylesters of Some Aminoacids

On the Amidation of 17‐Deacetyl‐Vinblastine With the Ethylesters of Some Aminoacids

Total assignment of the proton and carbon NMR spectra of 5′‐NOR‐anhydrovinblastine

¹H NMR study and conformational aspects of 20′‐deoxy‐20′‐epivindesine

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Alkaloids From Catharanthus Roseus 1H NMR Study of 20′S‐Deoxyvinblastine and its N‐2′ Borane Complex

Abstract: The ' H NMR spectra of 20' S-deoxyvinblastine and its N-2' borane complex have been unraveled. 2D 6-J-resolved NMR allowed to measure the isolated peaks in the overlapping patterns of the amine borane complex. Both compounds can now easily be discriminated on basis of ' H NMR data.

Cited by 10 publications

References 7 publications

On the Amidation of 17‐Deacetyl‐Vinblastine With the Ethylesters of Some Aminoacids

On the Amidation of 17‐Deacetyl‐Vinblastine With the Ethylesters of Some Aminoacids

Total assignment of the proton and carbon NMR spectra of 5′‐NOR‐anhydrovinblastine

1H NMR study and conformational aspects of 20′‐deoxy‐20′‐epivindesine

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Alkaloids From Catharanthus Roseus ¹H NMR Study of 20′S‐Deoxyvinblastine and its N‐2′ Borane Complex

¹H NMR study and conformational aspects of 20′‐deoxy‐20′‐epivindesine