(1R,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl acetate | 150025-30-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (1R,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl acetate
• 英文别名: (1R,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-enyl acetate；[(1R,4R)-4-(6-chloropurin-9-yl)cyclopent-2-en-1-yl] acetate
• CAS: 150025-30-2
• 化学式: C₁₂H₁₁ClN₄O₂
• 分子量: 278.698
• InChiKey: AUTHPZRHXUJHSH-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1R,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl acetate 在 potassium cyanide 、 ruthenium trichloride 、 sodium periodate 、 偶氮二甲酸二苄酯 、 氨 、 乙酰氯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 39.04h， 生成 (1R,2S,3R,5S)-3-(6-Amino-purin-9-yl)-5-hydroxyamino-cyclopentane-1,2-diol; hydrochloride
  参考文献：
  名称：

  Syntheses of novel hydroxylamine carbanucleosides

  摘要：

  Enantiomerically pure 4'-hydroxylamino-adenine-derived carbanucleosides have been synthesized as isosteric 4'-hydroxymethyl analogs to carbovir, ddA, and aristeromycin. The key steps in the syntheses involved an enzymatic desymmetrization, two subsequent Mitsunobu reactions, and a highly diastereoselective ruthenium tetroxide-mediated dihydroxylation, overcoming the syn-directing effect seen in osmium tetroxide-mediated dihydroxylations. Hydroxylamino-propane analogs were also synthesized through similar methodology to afford adenine and cyclopropylamino purine analogs to acyclovir. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00359-7
• 作为产物：
  描述：

  (1S,4R)-顺式-4-乙酰氧基-2-环戊烯-1-醇 、 6-氯嘌呤 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成 (1R,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl acetate
  参考文献：
  名称：

  从一种常见的对映体纯的起始原料合成四种可能的立体异构5'-碳环核苷

  摘要：

  从常见的对映体纯的烯丙基单乙酸酯1开始，已开发出四种立体异构体对映体纯的5'-去碳环核苷2b，ent - 2b，3b和ent - 3b的灵活合成方法。

  DOI：

  10.1016/s0040-4039(00)73022-x

文献信息

• Stereocontrolled synthesis of the four stereoisomeric diphosphorylphosphonates of carbocyclic 2′,3′-dideoxy-2′,3′-didehydro-5′-noradenosine
  作者：Natalia B. Dyatkina、Fritz Theil、Martin von Janta-Lipinski

  DOI：10.1016/0040-4020(94)00986-5

  日期：1995.1

  A flexible synthesis of the four stereoisomeric enantiomerically pure 5′-nor carbocyclic adenosine analogues 4b, ent-4b, 5b and ent-5b starting from the common enantio-merically pure allylic monoacetate 3 has been developed. Each of the nucleoside analogues was transformed into the corresponding 4′-phosphonates and subsequently into the diphosphoryl-phosphonates 4e, ent-4e, 5e, and ent-5e, respectively

  已经开发了从常见的对映体纯的烯丙基单乙酸酯3开始的四个立体异构对映体纯的5'-去碳环腺苷类似物4b，ent - 4b，5b和ent - 5b的灵活合成。将每个核苷类似物分别转化为相应的4'-膦酸酯，然后分别转化为二磷酸基膦酸酯4e，ent - 4e，5e和ent - 5e。
• Enantiospecific synthesis of the fluoro and epimeric derivatives of 5′-noraristeromycin
  作者：Suhaib M. Siddiqi、Frank P. Oertel、Xing Chen、Stewart W. Schneller

  DOI：10.1039/c39930000708

  日期：——

  The synthesis of derivatives of 5′-noraristeromycin 1 in which its C-4′ hydroxy group has been (i) replaced by a fluorine atom (5) and (ii) inverted (6) is described starting from the diacetate of (Z)-cyclopentene-3,5-diol.

  的5'-noraristeromycin衍生物的合成1在其C-4'羟基基团被（我）代替被氟原子（5）和（II）反转（6）从的二乙酸酯开始描述（Ž） -环戊烯-3,5-二醇。
• An Epimer of 5'-Noraristeromycin and Its Antiviral Properties
  作者：Suhaib M. Siddiqi、Xing Chen、Stewart W. Schneller、Satoru Ikeda、Robert Snoeck、Graciela Andrei、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm00035a020

  日期：1994.4

  virus, reovirus, and cytomegalovirus. A similar antiviral activity spectrum was shown by the S-adenosylhomocysteine hydrolase inhibitors neplanocin A and carbocyclic 3-deazaadenosine. While equally potent as neplanocin A against most of the viruses tested, compound (-)-3 was significantly less cytotoxic. The results of this study suggest that (-)-3 should be pursued for the treatment of those virus infections

  从（+）-（（（1R，4S）-4-羟基-2-环戊烯-1）三个步骤对映体制备5'-noraristeromycin差向异构体（（-）-3）的衍生物评估了乙酸-乙酸乙酯对多种病毒的抗病毒活性，发现其对水痘带状疱疹病毒，牛痘病毒，水疱性口炎病毒，副流感病毒，呼肠孤病毒和巨细胞病毒显示出显着活性。 S-腺苷同型半胱氨酸水解酶抑制剂neplanocin A和碳环3-deazaadenosine均显示出抗病毒活性谱，尽管与neplanocin A一样有效，但化合物（-）-3的细胞毒性却较小。应该采用（-）-3来治疗那些病毒感染[即痘（VV），弹状病毒（VSV），副粘病毒（副流感）和reo]似乎对该化合物非常敏感。
• Design, synthesis, and anti-HIV activity of 4′-modified carbocyclic nucleoside phosphonate reverse transcriptase inhibitors
  作者：Constantine G. Boojamra、Jay P. Parrish、David Sperandio、Ying Gao、Oleg V. Petrakovsky、Sharon K. Lee、David Y. Markevitch、Jennifer E. Vela、Genevieve Laflamme、James M. Chen、Adrian S. Ray、Abraham C. Barron、Mark L. Sparacino、Manoj C. Desai、Choung U. Kim、Tomas Cihlar、Richard L. Mackman

  DOI：10.1016/j.bmc.2008.12.028

  日期：2009.2

  A diphosphate of a novel cyclopentyl based nucleoside phosphonate with potent inhibition of HIV reverse transcriptase (RT) (20, IC(50) = 0.13 mu M) has been discovered. In cell culture the parent phosphonate diacid 9 demonstrated antiviral activity EC(50) = 16 mu M, within two-fold of GS-9148, a prodrug of which is currently under clinical investigation, and within 5-fold of tenofovir (PMPA). In vitro cellular metabolism studies using 9 confirmed that the active diphosphate metabolite is produced albeit at a lower efficiency relative to GS-9148. (C) 2009 Elsevier Ltd. All rights reserved.
• CYCLOPENTENE-OXYMETHYLENE PHOSPHONAMIDATES AND RELATED COMPOUNDS AND THEIR USE IN TREATING MEDICAL CONDITIONS
  申请人：[en]ROME THERAPEUTICS, INC.

  公开号：WO2024107859A1

  公开（公告）日：2024-05-23

  Substituted cyclopentene-oxymethylene phosphonamidates and related compounds, pharmaceutical compositions, their use for inhibiting LINE1 reverse transcriptase and/or HERV- K reverse transcriptase activity, and their use in the treatment of medical disorders, such as cancer, are disclosed herein.