Synthesis, Anti-HBV, and Anti-HIV Activities of 3′-Halogenated Bis(hydroxymethyl)-cyclopentenyladenines

被引：6

作者：

Kumamoto, Hiroki ^{[1
]}

Imoto, Shuhei ^{[2
]}

Amano, Masayuki ^{[3
,4
]}

Kuwata-Higashi, Nobuyo ^{[5
]}

Baba, Masanori ^{[6
]}

Mitsuya, Hiroaki ^{[3
,4
,5
,7
]}

Odanaka, Yuki ^{[8
]}

Matsubayashi, Satoko Shimbara ^{[8
]}

Tanaka, Hiromichi ^{[8
]}

Haraguchi, Kazuhiro ^{[1
]}

机构：

[1] Nihon Pharmaceut Univ, 10281 Komuro, Inamachi, Saitama 3620806, Japan

[2] Sojo Univ, Fac Pharmaceut Sci, 4-22-1 Ikeda, Kumamoto 8600082, Japan

[3] Kumamoto Univ, Sch Med, Dept Infect Dis, Kumamoto 8608556, Japan

[4] Kumamoto Univ, Sch Med, Dept Hematol, Kumamoto 8608556, Japan

[5] Natl Ctr Global Hlth & Med, Clin Res Ctr, Shinjuku Ku, 1-21-1 Toyama, Tokyo 1628655, Japan

[6] Kagoshima Univ, Grad Sch Med & Dent Sci, Ctr Chron Viral Dis, Div Antiviral Chemotherapy, Kagoshima 8908544, Japan

[7] NCI, Expt Retrovirol Sect, HIV & AIDS Malignancy Branch, NIH, Bethesda, MD 20892 USA

[8] Showa Univ, Sch Pharm, Shinagawa Ku, 1-5-8 Hatanodai, Tokyo 1428555, Japan

来源：

ACS MEDICINAL CHEMISTRY LETTERS | 2018年 / 9卷 / 12期

基金：

日本学术振兴会;

关键词：

Carbocyclic nucleosides; halogeno-substituent; anti-HBV; VINYL SULFONES; STEREOSELECTIVE-SYNTHESIS; STEREOSPECIFIC SYNTHESIS; CARBOCYCLIC NUCLEOSIDES; VERSATILE INTERMEDIATE; ALKYNYLATING REAGENTS; SELECTIVE-INHIBITION; DL-CEPHALOTAXINE; ROUTE; OLEFINS;

D O I：

10.1021/acsmedchemlett.8b00374

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Synthesis of 3'-halogeno analogues (5a-d) of 9-[c-4,t-5-bis(hydroxymethyl)-cyclopent-2-en-r-1-yl]-9H-adenine (BCA, 3) was accomplished by means of dual utilization of the vinyl sulfone functional moieties in both 10 and 16 utilizing a S(N)2' conjugate-addition reaction and a sulfur-extrusive stannylation, respectively. Evaluation of the antiviral activities of 5a-d revealed that introduction of a halogeno-substituent into the 3'-position of (-)-BCA diminished its anti-HIV-1 activity but increased the inhibitory activity for the reverse transcriptase of HBV in that the 3'-fluorinated BCA 5d exhibited the highest activity without significant cytotoxicity.

引用

页码：1211 / 1216

页数：11

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