(1R,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-en-1-ol | 210162-78-0

• 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: (1R,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-en-1-ol
• 英文别名: (1R,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-enol；(1R,4R)-4-(6-chloropurin-9-yl)cyclopent-2-en-1-ol
• CAS: 210162-78-0
• 化学式: C₁₀H₉ClN₄O
• 分子量: 236.661
• InChiKey: KNHDEYXHYZZUNG-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-en-1-ol 在 甲醇 、 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 4.17h， 生成 (1S,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-en-1-ol
  参考文献：
  名称：

  CYCLOPENTENE-OXYMETHYLENE PHOSPHONAMIDATES AND RELATED COMPOUNDS AND THEIR USE IN TREATING MEDICAL CONDITIONS

  摘要：

  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.

  公开号：

  WO2024107859A1
• 作为产物：
  描述：

  (1R,3S)-(-)-1-乙酰氧基环戊烷-3-醇 在 四丁基氟化铵 、 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 10.0h， 生成 (1R,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-en-1-ol
  参考文献：
  名称：

  立体合成碳环2'，3'-二脱氧-2'，3'-二氢-5'-芥子苷的四个立体异构体二膦酰基膦酸酯

  摘要：

  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。

  DOI：

  10.1016/0040-4020(94)00986-5

文献信息

• Synthesis of the four possible stereoisomeric 5′-nor carbocyclic nucleosides from one common enantiomerically pure starting material
  作者：Natalja Dyatkina、Burkhard Costisella、Fritz Theil、Martin von Janta-Lipinski

  DOI：10.1016/s0040-4039(00)73022-x

  日期：1994.3

  A flexible synthesis of the four stereoisomeric enantiomerically pure 5′-nor carbocyclic nucleosides 2b, ent-2b, 3b, and ent-3b starting from the common enantiomerically pure allylic monoacetate 1 has been developed.

  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。
• Synthesis of 4′-modified noraristeromycins to clarify the effect of the 4′-hydroxyl groups for inhibitory activity against S-adenosyl-l-homocysteine hydrolase
  作者：Takayuki Ando、Kenji Kojima、Praveen Chahota、Atsushi Kozaki、Nikalje D. Milind、Yukio Kitade

  DOI：10.1016/j.bmcl.2008.03.029

  日期：2008.4

  4'-Modified noraristeromycin (NAM) analogs, 4'-sulfo-, 4'-sulfamoy, 4'-azido and 4'-amino-NAM, were systematically synthesized. The inhibitory activities of these analogs and related compounds against Plasmodium falciparum and human S-adenosyl-L-homocysteine hydrolase were investigated. (c) 2008 Elsevier Ltd. All rights reserved.
• Syntheses of novel hydroxylamine carbanucleosides
  作者：Mark J. Mulvihill、Marvin J. Miller

  DOI：10.1016/s0040-4020(98)00359-7

  日期：1998.6

  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.
• 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.