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具有二卤乙烯基单元的腺苷开链碳环类似物作为S-腺苷-L-高半胱氨酸水解酶的潜在抑制剂。

Open-chain carbocyclic analogs of adenosine with dihalovinyl unit as potential inhibitors of S-adenosyl-L-homocysteine hydrolase.

作者信息

Lewandowska Elzbieta, Lalama Jennifer, Yuan Chong-Sheng, Wnuk Stanislaw F

机构信息

Department of Chemistry, Florida International University, Miami, Florida 33199, USA.

出版信息

Nucleosides Nucleotides Nucleic Acids. 2003 Sep;22(9):1747-55. doi: 10.1081/NCN-120023270.

DOI:10.1081/NCN-120023270
PMID:14533879
Abstract

Vinylogously extended deoxyeritadenine derivatives were synthesized as acyclic/ carbocyclic analogues of the 6'-halo(homovinyl)adenosines, which are known to be potent inhibitors of S-adenosyl-L-homocysteine hydrolase. Swern oxidation of 9-[3-(t-butyldimethylsilyloxy)-4-hydroxybutyl]adenine (4) followed by Wittig olefination and desilylation gave access to ethyl 6-(adenin-9-yl)-4-hydroxy-2(E)-hexenoate (7) and 5-(adenin-9-yl)-1,1-dibromo-1-penten-3-ol (9). No inhibition of AdoHcy Hydrolase was observed with 7 and 9.

摘要

乙烯基类似物扩展的脱氧艾瑞腺苷衍生物被合成为6'-卤代（高乙烯基）腺苷的无环/碳环类似物，已知这些类似物是S-腺苷-L-高半胱氨酸水解酶的有效抑制剂。9-[3-(叔丁基二甲基硅氧基)-4-羟基丁基]腺嘌呤（4）经斯文氧化，然后进行维蒂希烯烃化和脱硅反应，得到6-(腺嘌呤-9-基)-4-羟基-2(E)-己烯酸乙酯（7）和5-(腺嘌呤-9-基)-1,1-二溴-1-戊烯-3-醇（9）。未观察到7和9对腺苷高半胱氨酸水解酶有抑制作用。

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1
Open-chain carbocyclic analogs of adenosine with dihalovinyl unit as potential inhibitors of S-adenosyl-L-homocysteine hydrolase.具有二卤乙烯基单元的腺苷开链碳环类似物作为S-腺苷-L-高半胱氨酸水解酶的潜在抑制剂。
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2
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8
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9
Inactivation of S-adenosyl-L-homocysteine hydrolase by amide and ester derivatives of adenosine-5'-carboxylic acid.腺苷-5'-羧酸的酰胺和酯衍生物对S-腺苷-L-高半胱氨酸水解酶的失活作用。
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