1-C-(purin-N⁹-yl)-1,2,3-dideoxy-β-D-erythro-furanose | 126502-08-7

• 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: 1-C-(purin-N⁹-yl)-1,2,3-dideoxy-β-D-erythro-furanose
• 英文别名: 9-(2,3-dideoxy-β-D-ribofuranosyl)purine；9-(2,3-Dideoxy-beta-D-ribofuranosyl)-9H-purine；[(2S,5R)-5-purin-9-yloxolan-2-yl]methanol
• CAS: 126502-08-7
• 化学式: C₁₀H₁₂N₄O₂
• 分子量: 220.231
• InChiKey: GKYNWIQWAXROLY-IONNQARKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  16
• 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：
  73.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-C-(purin-N⁹-yl)-1,2,3-dideoxy-β-D-erythro-furanose 在 盐酸 作用下， 生成 嘌呤 、 2,3-Didesoxy-β-D-glycero-pentofuranose
  参考文献：
  名称：

  Hydrolysis of dideoxygenated purine nucleosides: effect of modification of the base moiety

  摘要：

  DOI：

  10.1021/jo00298a067
• 作为产物：
  描述：

  2',3'-双脱氧腺苷 在 calf intestinal adenosine deaminase 作用下， 生成 1-C-(purin-N⁹-yl)-1,2,3-dideoxy-β-D-erythro-furanose
  参考文献：
  名称：

  异构双脱氧核苷4（S）-（6-氨基-9H-嘌呤-9-基）四氢-2（S）-呋喃甲醇的抗病毒，代谢和药代动力学特性。

  摘要：

  4（S）-（6-氨基-9H-嘌呤-9-基）四氢-2（S）-呋喃甲醇（IsoddA）是一类新型旋光异构二脱氧核苷中最抗病毒的成员从自然的1'位置转置为2'位置，并且绝对构型为（S，S）。IsoddA对人免疫缺陷病毒1型（HIV-1）（IIIB株），HIV-2（ZY株）和HIV-1临床分离株具有活性。该化合物与齐多夫定（3'-叠氮基-3'-脱氧胸苷），2'，3'-二脱氧肌苷或5-氟-2'-脱氧-3'-硫代胞苷的组合显示出对HIV的协同抑制作用。用对齐多夫定耐药的临床分离株观察到活性适度降低。通过在增加的IsoddA浓度下重复传播HIV-1（HXB2），在体外选择对IsoddA耐药的病毒（抑制浓度增加8倍）。突变病毒的逆转录酶编码区包含单个碱基变化，导致第184位密码子从Met变为Val。IsoddA在体外还具有抗乙型肝炎病毒（HBV）的活性；然而，它在体内HBV模型中缺乏实质的选择性活性。Is

  DOI：

  10.1128/aac.39.9.1993

文献信息

• Synthesis and structure-activity relationships of 6-substituted 2',3'-dideoxypurine nucleosides as potential anti-human immunodeficiency virus agents
  作者：Chung K. Chu、Giliyar V. Ullas、Lak S. Jeong、Soon K. Ahn、Bogdan Doboszewski、Zhi X. Lin、J. Warren Beach、Raymond F. Schinazi

  DOI：10.1021/jm00168a006

  日期：1990.6

  In order to study the structure-activity relationships of 2',3'-dideoxypurine nucleosides as potential anti-HIV agents, various 6-substituted purine analogues have been synthesized and examined in virus-infected and uninfected human peripheral blood mononuclear cells. N6-methyl-2',3'-dideoxyadenosine (D2MeA, 7a) was initially synthesized from adenosine via 2',3'-O-bisxanthate 3. As extension of this

  为了研究2'，3'-二脱氧嘌呤核苷作为潜在的抗HIV药物的构效关系，已经合成了多种6-取代的嘌呤类似物，并在病毒感染和未感染的人外周血单核细胞中进行了研究。N6-甲基-2'，3'-二脱氧腺苷（D2MeA，7a）最初是通过2'，3'-O-双黄药3由腺苷合成的。由于该反应扩展到其他N6-取代的化合物失败，因此采用了全合成方法利用2'，3'-二脱氧核糖衍生物9合成其他嘌呤核苷。通过与N6-甲基腺嘌呤23缩合，由合适的碳水化合物24合成了N6-甲基-2'，3'-二脱氧腺苷，2'-氟阿拉伯呋喃糖基类似物32（D2MeFA）的酸稳定衍生物。N6-甲基衍生物（D2MeA）7a被证明是最有效的抗病毒药物之一。对于6个取代的化合物，其效力顺序为NHMe大于NH2大于Cl约N（Me）2大于SMe大于OH约NHEt大于SH大于NHBn约H。 2'，3'-二脱氧嘌呤核苷的6位可能决定这些化合物的抗病毒活性。发现酸
• Purine nucleoside synthesis from uridine using immobilised Enterobacter gergoviae CECT 875 whole cells
  作者：J.A Trelles、M Fernández、E.S Lewkowicz、A.M Iribarren、J.V Sinisterra

  DOI：10.1016/s0040-4039(03)00225-9

  日期：2003.3

  Biocatalysed purine nucleoside synthesis was carried out using immobilised Enterobacter gergoviae CECT 875. Similar yields (80-95%) in adenosine were obtained with both free and immobilised cells though in the last case a long reaction time was necessary. The immobilised cells can be reused at least for more than 30 times without significant loss of enzymatic activity. The immobilised biocatalyst in agarose is active in the synthesis of unnatural nucleosides. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Escherichia coli mediated biosynthesis and in vitro anti-HIV activity of lipophilic 6-halo-2',3'-dideoxypurine nucleosides
  作者：Kunichika Murakami、Takuma Shirasaka、Hidetoshi Yoshioka、Eiji Kojima、Shizuko Aoki、Harry Ford、John S. Driscoll、James A. Kelley、Hiroaki Mitsuya

  DOI：10.1021/jm00109a012

  日期：1991.5

  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.
• Enantioselective Preparation of 2‘,3‘-Dideoxynucleosides and Their Analogues from Ring-Expansion of Cyclobutanones. 2. Synthesis of 2‘,3‘-Dideoxyribosides and (1<i>S</i>,3<i>R</i>)-1- Amino-3-(hydroxymethyl)cyclopentane¹
  作者：Edward Lee-Ruff、Feng-de Xi、Jiang Hua Qie

  DOI：10.1021/jo9517151

  日期：1996.1.1
• CHU, CHUNG K.;ULLAS, GILIYAR V.;JEONG, LAK S.;AHN, SOON K.;DOBOSZEWSKI, B+, J. MED. CHEM., 33,(1990) N, C. 1553-1561
  作者：CHU, CHUNG K.、ULLAS, GILIYAR V.、JEONG, LAK S.、AHN, SOON K.、DOBOSZEWSKI, B+

  DOI：——

  日期：——