2-amino-6-mercapto-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine | 132194-26-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-amino-6-mercapto-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine
• 英文别名: 2-amino-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)purine-6-thione；2-amino-9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-6-thione
• CAS: 132194-26-4
• 化学式: C₁₀H₁₃N₅O₂S
• 分子量: 267.312
• InChiKey: VPWVDNUKBIMKBG-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2',3'-二脱氧尿苷 在 sodium hydrogensulfide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 2-amino-6-mercapto-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine
  参考文献：
  名称：

  Escherichia coli mediated biosynthesis and in vitro anti-HIV activity of lipophilic 6-halo-2',3'-dideoxypurine nucleosides

  摘要：

  A series of 6-substituted 2',3'-dideoxypurine ribofuranosides (ddP) was enzymatically synthesized with live E. coli in an effort to enhance the lipophilicity of this class of anti-human immunodeficiency virus (HIV) compounds and thereby facilitate drug delivery into the central nervous system. All 6-halo-substituted ddPs were substantially more lipophilic, as defined by their octanol-water partition coefficient (P), than their nonhalogenated congeners 2',3'-dideoxyinosine (ddI) or 2',3'-dideoxyguanosine (ddG). For this class of compounds, log P's ranged from +0.5 to -1.2 in the following order: 6-iodo, 2-amino-6-iodo > 6-bromo, 2-amino-6-bromo > 6-chloro, 2-amino-6-chloro > 6-fluoro, 2-amino-6-fluoro >> ddG > ddI. These compounds were evaluated in vitro for ability to suppress the infectivity, replication, and cytopathic effect of HIV. 2-Amino-6-fluoro-, 2-amino-6-chloro-, and 6-fluoro-ddP exhibited a potent activity against HIV comparable to that of ddI or ddG and completely blocked the infectivity of HIV without affecting the growth of target cells. The comparative order of in vitro anti-HIV activity was 2-amino-6-fluoro, 2-amino-6-chloro, 6-fluoro > 2-amino-6-bromo > 2-amino-6-iodo, 6-chloro > 6-bromo > 6-iodo. These compounds also exhibited potent in vitro activity against HIV-2 and 3'-azido-3'-deoxythymidine-resistant HIV-1 variants. All 2-amino-6-halo-ddPs and 6-halo-ddPs were substrates for adenosine deaminase (ADA) and were converted to ddG or ddI, respectively. In the presence of the potent ADA inhibitor 2'-deoxycoformycin, 6-halo-substituted ddPs failed to exert an in vitro antiretroviral effect. These dideoxypurine nucleoside analogues represent a new class of lipophilic prodrugs of ddG and ddI that possess the potential for more effective therapy of HIV-induced neurologic disorders.

  DOI：

  10.1021/jm00109a012

文献信息

• 2',3'-Dideoxypurinnucleosid/Purinnucleosid-Phosphorylase-Inhibitor Kombinationstherapie und Zusammensetzungen dafür
  申请人：CIBA-GEIGY AG

  公开号：EP0374096A1

  公开（公告）日：1990-06-20

  Es wird die Kombinationstherapie von 2′,3′-Dideoxypurinnucleosiden mit Purin­nucleosid-Phosphorylase-Inhibitoren beschrieben. Sie dient der Behandlung von auf HIV (human immunodeficiency virus) und anderen Retroviren zurückgehende Infektionen, d.h. unter anderem von AIDS. Sie dient ferner einer Verlangsamung des in-vivo-Abbaus der 2′,3′-Dideoxypurinnucleoside und einer Wirkungssteigerung der 2′,3′-Dideoxypurin­nucleoside. Zusammensetzungen, die in diesen Therapien zur Anwendung kommen, werden ebenfalls offenbart.

  介绍了 2′,3′-二脱氧嘌呤核苷与嘌呤核苷磷酸酶抑制剂的联合疗法。该疗法用于治疗由艾滋病毒（人类免疫缺陷病毒）和其他逆转录病毒引起的感染，即艾滋病等。它还能减缓 2′,3′-二脱氧嘌呤核苷的体内降解，增加 2′,3′-二脱氧嘌呤核苷的作用。还公开了用于这些疗法的组合物。
• Robins, Morris J.; Wilson, John S.; Madej, Danuta, Journal of Heterocyclic Chemistry, 2001, vol. 38, # 6, p. 1297 - 1306
  作者：Robins, Morris J.、Wilson, John S.、Madej, Danuta、Tyrrell, D. Lorne J.、Gati, Wendy P.、Lindmark、Wnuk, Stanislaw F.

  DOI：——

  日期：——
• MURAKAMI, KUNICHIKA;SHIRASAKA, TAKUMA;YOSHIOKA, HIDETOSHI;KOJIMA, EIJI;AO+, J. MED. CHEM., 34,(1991) N, C. 1606-1612
  作者：MURAKAMI, KUNICHIKA、SHIRASAKA, TAKUMA、YOSHIOKA, HIDETOSHI、KOJIMA, EIJI、AO+

  DOI：——

  日期：——
• QUADRUPLEX METHOD
  申请人：Oxford Nanopore Technologies Limited

  公开号：EP2917366A1

  公开（公告）日：2015-09-16
• METHOD
  申请人：Oxford Nanopore Technologies Limited

  公开号：EP3464616A1

  公开（公告）日：2019-04-10