A dideazatetrahydrofolate analogue lacking a chiral center at C-6, N-[4-[2-(2-amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl] benzoyl]-L-glutamic acid, is an inhibitor of thymidylate synthase

Edward C. Taylor, Dietmar Kuhnt, Chuan Shih, Sharon M. Rinzel, Gerald B. Grindey, Julio Barredo, Julio Barredo, Richard G. Moran

Research output: Contribution to journalArticle

278 Citations (Scopus)

Abstract

N- [4-[2-(2-Amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl] benzoyl]-L-glutamic acid (15), prepared in five steps from 2-pivaloyl-7-deazaguanine, has been found to be an antitumor agent with its primary site of action at thymidylate synthase rather than purine synthesis. This compound appears to be a promising candidate for clinical evaluation.

Original languageEnglish
Pages (from-to)4450-4454
Number of pages5
JournalJournal of Medicinal Chemistry
Volume35
Issue number23
StatePublished - Dec 1 1992
Externally publishedYes

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Thymidylate Synthase
Antineoplastic Agents
Glutamic Acid
7-deazaguanine
purine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A dideazatetrahydrofolate analogue lacking a chiral center at C-6, N-[4-[2-(2-amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl] benzoyl]-L-glutamic acid, is an inhibitor of thymidylate synthase. / Taylor, Edward C.; Kuhnt, Dietmar; Shih, Chuan; Rinzel, Sharon M.; Grindey, Gerald B.; Barredo, Julio; Barredo, Julio; Moran, Richard G.

In: Journal of Medicinal Chemistry, Vol. 35, No. 23, 01.12.1992, p. 4450-4454.

Research output: Contribution to journalArticle

Taylor, Edward C. ; Kuhnt, Dietmar ; Shih, Chuan ; Rinzel, Sharon M. ; Grindey, Gerald B. ; Barredo, Julio ; Barredo, Julio ; Moran, Richard G. / A dideazatetrahydrofolate analogue lacking a chiral center at C-6, N-[4-[2-(2-amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl] benzoyl]-L-glutamic acid, is an inhibitor of thymidylate synthase. In: Journal of Medicinal Chemistry. 1992 ; Vol. 35, No. 23. pp. 4450-4454.
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