9-[(1′R,2′S,3′R,4′S)-4′-hydroxy-2′,3′-O-isopropylidene-cyclopentan-1′-yl]-6-chloro-9H-purine | 204379-33-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 9-[(1′R,2′S,3′R,4′S)-4′-hydroxy-2′,3′-O-isopropylidene-cyclopentan-1′-yl]-6-chloro-9H-purine
• 英文别名: (3aR,5R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol；(3aR,4S,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol；(3aR,4S,6R,6aS)-6-(6-chloropurin-9-yl)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
• CAS: 204379-33-9
• 化学式: C₁₃H₁₅ClN₄O₃
• 分子量: 310.74
• InChiKey: QZIMSKBOLKOXSR-GOZTYBTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  82.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-[(1′R,2′S,3′R,4′S)-4′-hydroxy-2′,3′-O-isopropylidene-cyclopentan-1′-yl]-6-chloro-9H-purine 在 盐酸 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 ethoxy-[[(1S,2S,3S,4R)-4-(6-ethoxypurin-9-yl)-2,3-dihydroxycyclopentyl]oxymethyl]phosphinic acid
  参考文献：
  名称：

  Preparation of carbocyclic, phosphonate analogues of cyclic adenosine monophosphate (cAMP)

  摘要：

  化合物 2 和 5 经过合成和环化形成了环状 3′,5′-腺苷酸（cAMP）类似物 3、6 和 7。在一项补充工作中，环戊二烯通过六个步骤转化成了膦酸 16。化合物 16 经过脱保护和环化，形成环状 3′,5′-腺苷单磷酸 (cAMP) 类似物 18 和 19。

  DOI：

  10.1039/a704961g
• 作为产物：
  描述：

  6-噁双环[3.1.0]-3-己烯 在 四氧化锇 、 四(三苯基膦)钯 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 9-[(1′R,2′S,3′R,4′S)-4′-hydroxy-2′,3′-O-isopropylidene-cyclopentan-1′-yl]-6-chloro-9H-purine
  参考文献：
  名称：

  Merlo, Valeria; Reece, Fiona J.; Roberts, Stanley M., Journal of the Chemical Society. Perkin transactions I, 1993, # 15, p. 1717 - 1718

  摘要：

  DOI：

文献信息

• Substrate-Dependent Dihydroxylation of Substituted Cyclopentenes:  Toward the Syntheses of Carbocyclic Sinefungin and Noraristeromycin
  作者：May Xiao-Wu Jiang、Bohan Jin、Jennifer L. Gage、Alain Priour、Gordon Savela、Marvin J. Miller

  DOI：10.1021/jo060224l

  日期：2006.5.1

  from acylnitroso cycloaddition reactions of cyclopentadiene, followed by N−O reduction and efficient enzymatic resolution. The results are directly utilized in a very efficient asymmetric synthesis of an antiviral carbocyclic nucleoside, noraristeromycin 5. Extensions toward the synthesis of carbocyclic sinefungin 7 document the importance of realizing the substituent dependence of the dihydroxylation

  碳环核苷对于开发新的治疗剂具有相当大的兴趣。制备许多此类核苷类似物的关键反应是适当取代的环戊烯的二羟基化。尽管通常被认为是常规反应，但在本文中，我们报道了取代基对二羟基化反应的面部选择性的巨大影响。取代的环戊烯底物衍生自环戊二烯的酰基亚硝基环加成反应，然后进行N-O还原和有效的酶促拆分。结果直接用于抗病毒碳环核苷诺拉霉素的非常有效的不对称合成5。扩展碳环西芬净7的合成 文献记载了实现二羟基化反应的取代基依赖性的重要性。
• Synthesis and antiviral evaluation of cyclopentyl nucleoside phosphonates
  作者：Mengmeng Wang、Puneet Srivastava、Chao Liu、Robert Snoeck、Graciela Andrei、Steven De Jonghe、Piet Herdewijn

  DOI：10.1016/j.ejmech.2018.03.008

  日期：2018.4

  The synthesis of both 2ʹ-hydroxy-3ʹ-deoxy and 2ʹ-deoxy-3ʹ-hydroxy cyclopentyl nucleoside phosphonates with the natural nucleobases adenine, thymine, cytosine and guanine from a single precursor has been performed. The guanine containing analogues showed antiviral activity. Especially the 3ʹ-deoxy congener 23 was active, displaying an EC50 of 5.35 μM against TK+ VZV strain and an EC50 of 8.83 μM against

  已由单一前体合成了具有天然核碱基腺嘌呤，胸腺嘧啶，胞嘧啶和鸟嘌呤的2′-羟基-3′-脱氧和2′-脱氧-3′-羟基环戊基核苷膦酸酯。含有鸟嘌呤的类似物显示出抗病毒活性。特别是3'-脱氧同类物23是有活性，显示EC 50 5.35μM的对TK + VZV株和EC 50 8.83μM的针对TK - VZV株，除了缺乏细胞毒性。然而，膦酰二酰胺前药策略的应用并未导致抗病毒活性的提高。
• The 4′,4′-difluoro analog of 5′-noraristeromycin: A new structural prototype for possible antiviral drug development toward orthopoxvirus and cytomegalovirus
  作者：Atanu Roy、Stewart W. Schneller、Kathy A. Keith、Caroll B. Hartline、Earl R. Kern

  DOI：10.1016/j.bmc.2005.04.044

  日期：2005.7

  As a surrogate for 4'-hydroxy-5'-noraristeromycin and related carbocyclic nucleosides, an efficient, enantiodivergent synthetic route to both enantiomers of 5-(6-amino-9H-purin-9-yl)-3,3-difluorocyclopentane-1,2-diol (6 and ent-6) has been developed from a common starting material ((+)-(IR,4S)-4-hydroxy-2-cyclopenten-1-yl acetate, 10). Both compounds were assayed versus a series of viruses. The only response found was for compound 6 toward vaccinia and cowpox (EC50 Of 143 and 94 mu M, respectively) and human cytomegalovirus (EC50 of 6.2 mu M). Both compounds were non-cytotoxic. While not as active as cidofovir toward the orthopox viruses and ganciclovir toward cytomegalovirus, compound 6 offers a new structural prototype upon which to build for uncovering new agents effective against these viral types. (c) 2005 Elsevier Ltd. All rights reserved.
• Merlo, Valeria; Reece, Fiona J.; Roberts, Stanley M., Journal of the Chemical Society. Perkin transactions I, 1993, # 15, p. 1717 - 1718
  作者：Merlo, Valeria、Reece, Fiona J.、Roberts, Stanley M.、Gredson, Mike、Storer, Richard

  DOI：——

  日期：——
• Preparation of carbocyclic, phosphonate analogues of cyclic adenosine monophosphate (cAMP)
  作者：Jennifer M. L. Hillman、Stanley M. Roberts

  DOI：10.1039/a704961g

  日期：——

  Compounds 2 and 5 have been synthesised and cyclised to form the cyclic 3′,5′-adenosine monophosphate (cAMP) analogues 3, 6 and 7. In a complementary exercise, cyclopentadiene has been converted into the phosphonic acid 16 in six steps. Compound 16 has been deprotected and cyclised to form the cyclic 3′,5′-adenosine monophosphate (cAMP) analogues 18 and 19.

  化合物 2 和 5 经过合成和环化形成了环状 3′,5′-腺苷酸（cAMP）类似物 3、6 和 7。在一项补充工作中，环戊二烯通过六个步骤转化成了膦酸 16。化合物 16 经过脱保护和环化，形成环状 3′,5′-腺苷单磷酸 (cAMP) 类似物 18 和 19。