Synthesis of variants of 5‐benzylacyclouridine and 5‐benzyloxybenzylacyclouridine

Shih‐Hsi ‐H Chu; Zhi‐Hao ‐H Chen; Zum‐Yao ‐Y Weng; Elizabeth C. Rowe; Edward Chu; Ming‐Yu Wang Chu

doi:10.1002/jhet.5570230609

Synthesis of variants of 5‐benzylacyclouridine and 5‐benzyloxybenzylacyclouridine

Shih‐Hsi ‐H Chu, Zhi‐Hao ‐H Chen, Zum‐Yao ‐Y Weng, Elizabeth C. Rowe, Edward Chu, Ming‐Yu Wang Chu

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

A number of variations and derivatives of BAU (5‐benzylacyclouridine) and BBAU (5‐benzyloxybenzylacy‐clouridine), potent inhibitors of uridine phosphorylase were synthesized for evaluation as potential cancer chemotherapeutic agents. (“Acyclo” = 2′‐hydroxymethoxymethyl‐). These included a modification of the methylene group at N‐1, esters of the terminal hydroxyl of the acyclo group, and extension of the benzyl chain at position 5 of the uracil base. BBBAU was a very good potentiator of FUdR in cell culture.

Original language	English (US)
Pages (from-to)	1651-1655
Number of pages	5
Journal	Journal of Heterocyclic Chemistry
Volume	23
Issue number	6
DOIs	https://doi.org/10.1002/jhet.5570230609
State	Published - 1986
Externally published	Yes

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Organic Chemistry

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title = "Synthesis of variants of 5‐benzylacyclouridine and 5‐benzyloxybenzylacyclouridine",

abstract = "A number of variations and derivatives of BAU (5‐benzylacyclouridine) and BBAU (5‐benzyloxybenzylacy‐clouridine), potent inhibitors of uridine phosphorylase were synthesized for evaluation as potential cancer chemotherapeutic agents. (“Acyclo” = 2′‐hydroxymethoxymethyl‐). These included a modification of the methylene group at N‐1, esters of the terminal hydroxyl of the acyclo group, and extension of the benzyl chain at position 5 of the uracil base. BBBAU was a very good potentiator of FUdR in cell culture.",

author = "Chu, {Shih‐Hsi ‐H} and Chen, {Zhi‐Hao ‐H} and Weng, {Zum‐Yao ‐Y} and Rowe, {Elizabeth C.} and Edward Chu and Chu, {Ming‐Yu Wang}",

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doi = "10.1002/jhet.5570230609",

language = "English (US)",

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T1 - Synthesis of variants of 5‐benzylacyclouridine and 5‐benzyloxybenzylacyclouridine

AU - Chu, Shih‐Hsi ‐H

AU - Chen, Zhi‐Hao ‐H

AU - Weng, Zum‐Yao ‐Y

AU - Rowe, Elizabeth C.

AU - Chu, Edward

AU - Chu, Ming‐Yu Wang

PY - 1986

Y1 - 1986

N2 - A number of variations and derivatives of BAU (5‐benzylacyclouridine) and BBAU (5‐benzyloxybenzylacy‐clouridine), potent inhibitors of uridine phosphorylase were synthesized for evaluation as potential cancer chemotherapeutic agents. (“Acyclo” = 2′‐hydroxymethoxymethyl‐). These included a modification of the methylene group at N‐1, esters of the terminal hydroxyl of the acyclo group, and extension of the benzyl chain at position 5 of the uracil base. BBBAU was a very good potentiator of FUdR in cell culture.

AB - A number of variations and derivatives of BAU (5‐benzylacyclouridine) and BBAU (5‐benzyloxybenzylacy‐clouridine), potent inhibitors of uridine phosphorylase were synthesized for evaluation as potential cancer chemotherapeutic agents. (“Acyclo” = 2′‐hydroxymethoxymethyl‐). These included a modification of the methylene group at N‐1, esters of the terminal hydroxyl of the acyclo group, and extension of the benzyl chain at position 5 of the uracil base. BBBAU was a very good potentiator of FUdR in cell culture.

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Synthesis of variants of 5‐benzylacyclouridine and 5‐benzyloxybenzylacyclouridine

Abstract

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