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Antineoplastic agents. 595. Structural modifications of betulin and the X-ray crystal structure of an unusual betulin amine dimer.
J Nat Prod. 2014 Apr 25; 77(4):863-72.JN

Abstract

The lupane-type triterpene betulin (1) has been subjected to a series of structural modifications for the purpose of evaluating resultant cancer cell growth inhibitory activity. The reaction sequence 7→11→12 was especially noteworthy in providing a betulin-derived amine dimer. Other unexpected synthetic results included the 11 and 13/14→17 conversions, which yielded an imidazo derivative. X-ray crystal structures of dimer 12 and intermediate 25 are reported. All of the betulin modifications were examined for anticancer activity against the P388 murine and human cell lines. Significant cancer cell growth inhibition was found for 4, 8, 9, 15/16, 19, 20, 24, and 26, which further defines the utility of the betulin scaffold.

Authors+Show Affiliations

Department of Chemistry and Biochemistry, Arizona State University , P.O. Box 871604, Tempe, Arizona 85287-1604, United States.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

24694263

Citation

Pettit, George R., et al. "Antineoplastic Agents. 595. Structural Modifications of Betulin and the X-ray Crystal Structure of an Unusual Betulin Amine Dimer." Journal of Natural Products, vol. 77, no. 4, 2014, pp. 863-72.
Pettit GR, Melody N, Hempenstall F, et al. Antineoplastic agents. 595. Structural modifications of betulin and the X-ray crystal structure of an unusual betulin amine dimer. J Nat Prod. 2014;77(4):863-72.
Pettit, G. R., Melody, N., Hempenstall, F., Chapuis, J. C., Groy, T. L., & Williams, L. (2014). Antineoplastic agents. 595. Structural modifications of betulin and the X-ray crystal structure of an unusual betulin amine dimer. Journal of Natural Products, 77(4), 863-72. https://doi.org/10.1021/np400947d
Pettit GR, et al. Antineoplastic Agents. 595. Structural Modifications of Betulin and the X-ray Crystal Structure of an Unusual Betulin Amine Dimer. J Nat Prod. 2014 Apr 25;77(4):863-72. PubMed PMID: 24694263.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Antineoplastic agents. 595. Structural modifications of betulin and the X-ray crystal structure of an unusual betulin amine dimer. AU - Pettit,George R, AU - Melody,Noeleen, AU - Hempenstall,Frank, AU - Chapuis,Jean-Charles, AU - Groy,Thomas L, AU - Williams,Lee, Y1 - 2014/04/02/ PY - 2014/4/4/entrez PY - 2014/4/4/pubmed PY - 2014/7/30/medline SP - 863 EP - 72 JF - Journal of natural products JO - J Nat Prod VL - 77 IS - 4 N2 - The lupane-type triterpene betulin (1) has been subjected to a series of structural modifications for the purpose of evaluating resultant cancer cell growth inhibitory activity. The reaction sequence 7→11→12 was especially noteworthy in providing a betulin-derived amine dimer. Other unexpected synthetic results included the 11 and 13/14→17 conversions, which yielded an imidazo derivative. X-ray crystal structures of dimer 12 and intermediate 25 are reported. All of the betulin modifications were examined for anticancer activity against the P388 murine and human cell lines. Significant cancer cell growth inhibition was found for 4, 8, 9, 15/16, 19, 20, 24, and 26, which further defines the utility of the betulin scaffold. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/24694263/Antineoplastic_agents__595__Structural_modifications_of_betulin_and_the_X_ray_crystal_structure_of_an_unusual_betulin_amine_dimer_ L2 - https://doi.org/10.1021/np400947d DB - PRIME DP - Unbound Medicine ER -