(1'R,4'S)-2-Amino-6-chloro-9-[4'-(acetoxymethyl)cyclopent-2'-en-1'-yl]purine | 162992-44-1

• 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: (1'R,4'S)-2-Amino-6-chloro-9-[4'-(acetoxymethyl)cyclopent-2'-en-1'-yl]purine
• 英文别名: (-)-(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentenylacetylcarbinol；(-)-(1S,4R)-4-(2-amino-6-chloro-9H-pyrinyl-9-yl)-2-cyclopentenylacetylcarbinol；9-[cis-(1'R,4'S)-4'-acetoxymethyl-2'-cyclopenten-1'-yl]-9H-2-amino-6-chloropurine；((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl acetate；(1S,4R)-[4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methyl acetate；[(1S,4R)-4-(2-amino-6-chloropurin-9-yl)cyclopent-2-en-1-yl]methyl acetate
• CAS: 162992-44-1
• 化学式: C₁₃H₁₄ClN₅O₂
• 分子量: 307.739
• InChiKey: JFKKQCVMHDUETL-BDAKNGLRSA-N

物化性质

• 沸点：
  539.9±60.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  95.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1'R,4'S)-2-Amino-6-chloro-9-[4'-(acetoxymethyl)cyclopent-2'-en-1'-yl]purine 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 阿巴卡韦
  参考文献：
  名称：

  碳环核苷的高效，一般不对称合成：不对称醛醇/环封闭复分解策略的应用。

  摘要：

  已经开发了碳环和己吡喃糖基核苷的一般有效合成方法。该策略结合了三个关键的转变：不对称的醛醇加成物以建立假糖的相对和绝对构型，闭环易位以构建假糖环，以及Trost型钯（0）介导的取代以组装假糖和糖。芳香基。Carbovir，abacavir及其2'-甲基衍生物以及己吡喃糖基核苷类似物已通过该序列制备。

  DOI：

  10.1021/jo005535p
• 作为产物：
  描述：

  (-)-文斯内酯 在 4-二甲氨基吡啶 、 二碳酸二叔丁酯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正丁醇 为溶剂， 反应 81.5h， 生成 (1'R,4'S)-2-Amino-6-chloro-9-[4'-(acetoxymethyl)cyclopent-2'-en-1'-yl]purine
  参考文献：
  名称：

  [EN] MODIFIED NUCLEOSIDES AND NUCLEOTIDES ANALOGS AS ANTIVIRAL AGENTS FOR CORONA AND OTHER VIRUSES
  [FR] ANALOGUES DE NUCLÉOSIDES ET DE NUCLÉOTIDES MODIFIÉS UTILISÉS EN TANT QU'AGENTS ANTIVIRAUX CONTRE LE CORONAVIRUS ET D'AUTRES VIRUS

  摘要：

  Compounds, compositions and methods for preventing, treating or curing a coronavirus infection in human subjects or other animal hosts. In one embodiment, the compounds can be used to treat an infection with a severe acute respiratory syndrome virus, such as human coronavirus 229E, SARS, MERS, SARS-CoV-1 (OC43), and SARS-CoV-2. In another embodiment, the methods are used to treat a patient infected with a Flavivirus, Picornavus, Togavirus, or Bunyavirus.

  公开号：

  WO2022217154A2

文献信息

• Therapeutic nucleosides
  申请人：Burroughs Wellcome Co.

  公开号：US05034394A1

  公开（公告）日：1991-07-23

  The present invention relates to 6-substituted purine carbocyclic nucleosides and their use in medical therapy particularly in the treatment of HIV and HBV infections. Also provided are pharmaceutical formulations and processes for the preparation of compounds according to the invention.

  本发明涉及6-取代嘌呤环核苷和它们在医学治疗中的应用，特别是在治疗HIV和HBV感染方面。还提供了根据本发明制备化合物的药物配方和工艺。
• Facile conversion of 4-endo-hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one into carbocyclic 2′-deoxyribonucleoside analogues
  作者：Anupma Dhanda、Lars J. S. Knutsen、May-Britt Nielsen、Stanley M. Roberts、David R. Varley

  DOI：10.1039/a906464h

  日期：——

  furnish the bromoacetates 14–18 in good yields. A plausible explanation for the observed selectivity is proposed. Hydrodebromination of compounds 14, 17, 18 and 19 provided the corresponding 2′-deoxyribonucleoside analogues 20–23.

  易于获得的3,5-顺式双取代的环戊烯9-13与N-溴丁二酰亚胺（或N-溴乙酰胺）和乙酸银在冰醋酸中以高度立体选择性的方式反应，以高收率提供溴乙酸酯14-18。对于观察到的选择性提出了合理的解释。化合物14、17、18和19的加氢脱溴作用提供了相应的2'-脱氧核糖核苷类似物20-23。
• 6-Deoxycarbovir: A Xanthine Oxidase Activated Prodrug of Carbovir
  作者：Robert Vince、Jay Brownell、Scott A. Beers

  DOI：10.1080/15257779508014651

  日期：1995.2

  (-)-(cis)-4-(2-Amino-9H-purin-9-yl)-2-cyclopentenyl carbinol (6-deoxycarbovir) was prepared in order to evaluate prodrug approaches to increased bioavailability of the anti-HN agent, (-)-carbovir. Incubation experiments demonstrated that 6-deoxycarbovir was rapidly converted to (-)-carbovir by the enzyme, xanthine oxidase. Since xanthine oxidase activity is present in both the intestine and liver, a high first pass conversion to carbovir would be expected in vivo.

  (-)-(顺式)-4-(2-氨基-9H-嘌呤-9-基)-2-环戊烯基乙醇（6-去氧碳普维）被制备出来，以评估增加抗HN剂(-)-碳普维生物利用度的前药方法。温育实验表明，6-去氧碳普维在黄嘌呤氧化酶的作用下迅速转化为(-)-碳普维。由于黄嘌呤氧化酶的活性存在于肠道和肝脏中，在体内可预期高首次通过转化为碳普维。
• An Efficient Asymmetric Approach to Carbocyclic Nucleosides:  Asymmetric Synthesis of 1592U89, a Potent Inhibitor of HIV Reverse Transcriptase
  作者：Michael T. Crimmins、Bryan W. King

  DOI：10.1021/jo960708p

  日期：1996.1.1
• A short and efficient synthesis of 5-hydroxymethylcyclopent-2-enol from d-glucose and its elaboration to the carbanucleoside (−)-carbovir
  作者：Biswajit G. Roy、Prithwish K. Jana、Basudeb Achari、Sukhendu B. Mandal

  DOI：10.1016/j.tetlet.2007.01.016

  日期：2007.2

  Introduction of an allyl functionality at C-3 of 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose followed by olefination at C-5 and C-6 provided 1,6-diene 5 which, upon ring closing metathesis and subsequent functional group manipulation, furnished the key cyclopentene diacetate 7, which was elaborated to carbanucleoside (-)-carbovir 1. (c) 2007 Elsevier Ltd. All rights reserved.