A convenient synthesis of acyclic adenosines with an unsaturated side chain by modification of 9-(2,3-O-isopropylidene-D-ribityl)adenine

被引：4

作者：

Hirota, K ^{[1
]}

Monguchi, Y

Sajiki, H

Yatome, C

Hiraoka, A

Kitade, Y

机构：

[1] Gifu Pharmaceut Univ, Med Chem Lab, Gifu 5020003, Japan

[2] Gifu Univ, Dept Biomol Sci, Fac Engn, Gifu 501112, Japan

来源：

NUCLEOSIDES & NUCLEOTIDES | 1998年 / 17卷 / 08期

关键词：

D O I：

10.1080/07328319808003472

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

In expectation of discovering their antiviral activity, acyclic adenosine derivatives 7, 11, 12, and 16 were designed as analogs of neplanocin A (NPA) and L-eritadenine which are strong inhibitors of S-adenosyl-L-homocysteine hydrolase. The 1',5'-seco-analog of 4'-deoxymethyl-NPA (DHCA) 7 was synthesized by dideoxygenation of 9-(2, 3-O-isopropylidene-D-ribityl)adenine (2). Acyclic DHCA analogs 11 and 16 were obtained by Wittig reaction of the aldehyde 3 with Ph3P=CHCO2Et and Ph3P=CHCN, respectively. Hydrolysis of the ester 11 afforded a vinylog of L-eritadenine 12. The synthesized acyclic nucleosides 7, 10, and 11 were evaluated for antiviral activity, however, none of them showed any significant antiviral activity.

引用

页码：1333 / 1345

页数：13

共 22 条

[21] (2R,3S,5S)-2-acetoxy-3-fluoro-5-(p-toluoyloxymethyl)tetrahydrofuran:: a key intermediate for the practical synthesis of 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (FddA)
Jin, FQ
Wang, DJ
Confalone, PN
Pierce, ME
Wang, Z
Xu, GY
Choudhury, A
Nguyen, D
TETRAHEDRON LETTERS, 2001, 42 (29) : 4787 - 4789
[22] Intramolecular cyclization of 2,7- or 2,8-bis-unsaturated esters mediated by (eta(2)-propene)Ti(O-i-Pr)(2). Facile construction of mono- and bicyclic skeletons with stereoselective introduction of a side chain. A synthesis of d-sabinene
Urabe, H
Suzuki, K
Sato, F
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (42) : 10014 - 10027

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