Cyclohexenyl nucleosides: Synthesis and biological activity of trans-3-(purin-9-yl)-4-cyclohexenylcarbinols

Michael J. Konkel; Robert Vince

doi:10.1016/0040-4020(96)00445-0

Cyclohexenyl nucleosides: Synthesis and biological activity of trans-3-(purin-9-yl)-4-cyclohexenylcarbinols

Michael J. Konkel
, Robert Vince

Center for Drug Design

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

18 Scopus citations

Abstract

The primary alcohol of cis-3-hydroxy-4-cyclohexenylcarbinol was protected with a silyl group and then the configuration of the secondary alcohol was inverted (using Mitsunobu conditions, followed by deacylation). The secondary alcohol was converted to a carbonate, which, in turn, was converted to 6-chloropurine derivatives, using palladium coupling conditions. A modified deprotection procedure gave the free alcohol of these acid/base sensitive nucleoside analogs. The resulting 6-chloropurine derivatives were treated with ammonia, giving the 6-aminopurine derivatives which were finally converted with adenosine deaminase to the guanosine and inosine analogs.

Original language	English (US)
Pages (from-to)	8969-8978
Number of pages	10
Journal	Tetrahedron
Volume	52
Issue number	27
DOIs	https://doi.org/10.1016/0040-4020(96)00445-0
State	Published - Jul 1 1996

Bibliographical note

Funding Information:
We wish to thank Mr. Jay Brownell for conducting the P-388 mouse leukemia cytotoxicity studies, the HSV-1 antiviral studies, and for help with the adenosine deaminase reactions. This work was supported by Public Health Service Grant CA23263 from the National Cancer Institute.

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SDG 3 Good Health and Well-being

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title = "Cyclohexenyl nucleosides: Synthesis and biological activity of trans-3-(purin-9-yl)-4-cyclohexenylcarbinols",

abstract = "The primary alcohol of cis-3-hydroxy-4-cyclohexenylcarbinol was protected with a silyl group and then the configuration of the secondary alcohol was inverted (using Mitsunobu conditions, followed by deacylation). The secondary alcohol was converted to a carbonate, which, in turn, was converted to 6-chloropurine derivatives, using palladium coupling conditions. A modified deprotection procedure gave the free alcohol of these acid/base sensitive nucleoside analogs. The resulting 6-chloropurine derivatives were treated with ammonia, giving the 6-aminopurine derivatives which were finally converted with adenosine deaminase to the guanosine and inosine analogs.",

author = "Konkel, \{Michael J.\} and Robert Vince",

note = "Funding Information: We wish to thank Mr. Jay Brownell for conducting the P-388 mouse leukemia cytotoxicity studies, the HSV-1 antiviral studies, and for help with the adenosine deaminase reactions. This work was supported by Public Health Service Grant CA23263 from the National Cancer Institute.",

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doi = "10.1016/0040-4020(96)00445-0",

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T2 - Synthesis and biological activity of trans-3-(purin-9-yl)-4-cyclohexenylcarbinols

AU - Konkel, Michael J.

AU - Vince, Robert

N1 - Funding Information: We wish to thank Mr. Jay Brownell for conducting the P-388 mouse leukemia cytotoxicity studies, the HSV-1 antiviral studies, and for help with the adenosine deaminase reactions. This work was supported by Public Health Service Grant CA23263 from the National Cancer Institute.

PY - 1996/7/1

Y1 - 1996/7/1

N2 - The primary alcohol of cis-3-hydroxy-4-cyclohexenylcarbinol was protected with a silyl group and then the configuration of the secondary alcohol was inverted (using Mitsunobu conditions, followed by deacylation). The secondary alcohol was converted to a carbonate, which, in turn, was converted to 6-chloropurine derivatives, using palladium coupling conditions. A modified deprotection procedure gave the free alcohol of these acid/base sensitive nucleoside analogs. The resulting 6-chloropurine derivatives were treated with ammonia, giving the 6-aminopurine derivatives which were finally converted with adenosine deaminase to the guanosine and inosine analogs.

AB - The primary alcohol of cis-3-hydroxy-4-cyclohexenylcarbinol was protected with a silyl group and then the configuration of the secondary alcohol was inverted (using Mitsunobu conditions, followed by deacylation). The secondary alcohol was converted to a carbonate, which, in turn, was converted to 6-chloropurine derivatives, using palladium coupling conditions. A modified deprotection procedure gave the free alcohol of these acid/base sensitive nucleoside analogs. The resulting 6-chloropurine derivatives were treated with ammonia, giving the 6-aminopurine derivatives which were finally converted with adenosine deaminase to the guanosine and inosine analogs.

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U2 - 10.1016/0040-4020(96)00445-0

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JO - Tetrahedron

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ER -

Cyclohexenyl nucleosides: Synthesis and biological activity of trans-3-(purin-9-yl)-4-cyclohexenylcarbinols

Abstract

Bibliographical note

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