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Synthesis and evaluation of pyrazolo[3,4-b]quinoline ribofuranosides and their derivatives as inhibitors of oncogenic Ras

Publication ,  Journal Article
Wolin, R; Wang, D; Kelly, J; Afonso, A; James, L; Kirschmeier, P; McPhail, AT
Published in: Bioorganic and Medicinal Chemistry Letters
January 23, 1996

A series of pyrazolo[3,4-b]quinoline ribofuranosides were prepared using the glycosylation methodology of Vorbruggen. Oxidative cleavage of the ribose moiety in 6 furnished the dialdehyde intermediate 36, which cyclizes upon reductive amination providing the morpholino compound 37. Derivatives from both the ribose and morpholino series were evaluated for their ability to inhibit the nucleotide exchange process of oncogenic Ras.

Duke Scholars

Published In

Bioorganic and Medicinal Chemistry Letters

DOI

ISSN

0960-894X

Publication Date

January 23, 1996

Volume

6

Issue

2

Start / End Page

195 / 200

Related Subject Headings

  • Medicinal & Biomolecular Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 1115 Pharmacology and Pharmaceutical Sciences
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

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Wolin, R., Wang, D., Kelly, J., Afonso, A., James, L., Kirschmeier, P., & McPhail, A. T. (1996). Synthesis and evaluation of pyrazolo[3,4-b]quinoline ribofuranosides and their derivatives as inhibitors of oncogenic Ras. Bioorganic and Medicinal Chemistry Letters, 6(2), 195–200. https://doi.org/10.1016/0960-894X(95)00574-D
Wolin, R., D. Wang, J. Kelly, A. Afonso, L. James, P. Kirschmeier, and A. T. McPhail. “Synthesis and evaluation of pyrazolo[3,4-b]quinoline ribofuranosides and their derivatives as inhibitors of oncogenic Ras.” Bioorganic and Medicinal Chemistry Letters 6, no. 2 (January 23, 1996): 195–200. https://doi.org/10.1016/0960-894X(95)00574-D.
Wolin R, Wang D, Kelly J, Afonso A, James L, Kirschmeier P, et al. Synthesis and evaluation of pyrazolo[3,4-b]quinoline ribofuranosides and their derivatives as inhibitors of oncogenic Ras. Bioorganic and Medicinal Chemistry Letters. 1996 Jan 23;6(2):195–200.
Wolin, R., et al. “Synthesis and evaluation of pyrazolo[3,4-b]quinoline ribofuranosides and their derivatives as inhibitors of oncogenic Ras.” Bioorganic and Medicinal Chemistry Letters, vol. 6, no. 2, Jan. 1996, pp. 195–200. Scopus, doi:10.1016/0960-894X(95)00574-D.
Wolin R, Wang D, Kelly J, Afonso A, James L, Kirschmeier P, McPhail AT. Synthesis and evaluation of pyrazolo[3,4-b]quinoline ribofuranosides and their derivatives as inhibitors of oncogenic Ras. Bioorganic and Medicinal Chemistry Letters. 1996 Jan 23;6(2):195–200.
Journal cover image

Published In

Bioorganic and Medicinal Chemistry Letters

DOI

ISSN

0960-894X

Publication Date

January 23, 1996

Volume

6

Issue

2

Start / End Page

195 / 200

Related Subject Headings

  • Medicinal & Biomolecular Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 1115 Pharmacology and Pharmaceutical Sciences
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry