(1S,2R,5S)-5-(6-aminopurine-9-yl)-4-fluoro-3-(2-hydroxyethyl)-cyclopent-3(4)-en-1,2-diol | 1373314-02-3

• 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: (1S,2R,5S)-5-(6-aminopurine-9-yl)-4-fluoro-3-(2-hydroxyethyl)-cyclopent-3(4)-en-1,2-diol
• 英文别名: (1S,2R,5S)-5-(6-aminopurin-9-yl)-4-fluoro-3-(2-hydroxyethyl)cyclopent-3(4)ene-1,2-diol；(1S,2R,5S)-5-(6-aminopurine-9-yl)-4-fluoro-3-hydroxyethylcyclopent-3(4)-en-1,2-diol；6'-fluoro-homoneplanocin A；fluoro-homoneplanocin A；fluorohomoneplanocin A；FHNA；(1S,2R,5S)-5-(6-aminopurin-9-yl)-4-fluoro-3-(2-hydroxyethyl)cyclopent-3-ene-1,2-diol
• CAS: 1373314-02-3
• 化学式: C₁₂H₁₄FN₅O₃
• 分子量: 295.273
• InChiKey: QEXZQCBJBLNADX-BBBLOLIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (R)-1-((4R,5S)-5-((S)-1-hydroxyallyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol 在 吡啶 、 Grubbs catalyst first generation 、 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 正丁基锂 、 potassium hydrogen bifluoride 、 cerium(III) chloride heptahydrate 、 偶氮二甲酸二异丙酯 、 sodium perborate tetrahydrate 、 四丁基氟化铵 、 氨 、 水 、 sodium methylate 、 tetrabutylammonium bifluoride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 三苯基膦 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 叔丁醇 、 苯 为溶剂， 反应 286.75h， 生成 (1S,2R,5S)-5-(6-aminopurine-9-yl)-4-fluoro-3-(2-hydroxyethyl)-cyclopent-3(4)-en-1,2-diol
  参考文献：
  名称：

  立体选择性合成氟代人单胞菌素A作为潜在的抗病毒药

  摘要：

  氟homoneplanocin A（4）由合成d -核糖，经由的烯炔闭环复分解9，环氧化物的立体选择性开口23a中被氟，和一个同时氧化消除反应。关键中间体8有望用作合成核苷的通用中间体。

  DOI：

  10.1021/ol300667q

文献信息

• Fluoro-homoneplanocin A and nucleoside derivatives, method for the synthesis thereof, and the pharmaceutical compositions comprising the same as an active component for treatment of cancer
  申请人：COLLABORATION FOUNDATION EWHA UNIVERSITY - INDUSTRY

  公开号：US20130310403A1

  公开（公告）日：2013-11-21

  The present invention relates to a fluoro-homoneplanocin A, its nucleoside derivative, and synthetic methods. The novel fluoro-homoneplanocin A and its nucleoside derivative in the present invention have an effect on cancer prevention or treatment, and therefore can be used as anticancer drugs.

  本发明涉及一种氟代-homoneplanocin A、其核苷衍生物及其合成方法。本发明中的新型氟代-homoneplanocin A及其核苷衍生物具有预防或治疗癌症的效果，因此可用作抗癌药物。
• Structure–Activity Relationships of Neplanocin A Analogues as <i>S</i>-Adenosylhomocysteine Hydrolase Inhibitors and Their Antiviral and Antitumor Activities
  作者：Girish Chandra、Yang Won Moon、Yoonji Lee、Ji Yong Jang、Jayoung Song、Akshata Nayak、Kawon Oh、Varughese A. Mulamoottil、Pramod K. Sahu、Gyudong Kim、Tong-Shin Chang、Minsoo Noh、Sang Kook Lee、Sun Choi、Lak Shin Jeong

  DOI：10.1021/acs.jmedchem.5b00553

  日期：2015.6.25

  On the basis of the potent inhibitory activity of neplanocin A (1) against S-adenosylhomocysteine (AdoHcy) hydrolase, we analyzed the comprehensive structure-activity relationships by modifying the adenine and carbasugar moiety of 1 to find the pharmacophore in the active site of the enzyme. The introduction of 7-deazaadenine instead of adenine eliminated the inhibitory activity against the AdoHcy hydrolase, while 3-deazaadenine maintained the inhibitory activity of the enzyme, indicating that N-7 is essential for its role as a hydrogen bonding acceptor. The substitution of hydrogen at the 6'-position with fluorine increased the inhibitory activity Of the enzyme. The one-carbon homologation at the 5'-position generally decreased the inhibitory activity of the enzyme, indicating that steric repulsion exists. A molecular docking study also supported these experimental data. In this study, 6'-fluoroneplanocin A (2) was the most potent inhibitor of AdoHcy hydrolase (IC50 = 0.24 mu M). It showed a potent anti-VSV activity (EC50 = 0.43 mu M) and potent anticancer activity in all the human tumor cell lines tested.
• US9120760B2
  申请人：——

  公开号：US9120760B2

  公开（公告）日：2015-09-01
• Stereoselective Synthesis of Fluoro-homoneplanocin A as a Potential Antiviral Agent
  作者：Girish Chandra、Mahesh S. Majik、Ji Yee Lee、Lak Shin Jeong

  DOI：10.1021/ol300667q

  日期：2012.4.20

  Fluoro-homoneplanocin A (4) was synthesized from d-ribose, via the enyne ring-closing metathesis of 9, the stereoselective opening of epoxide 23a with fluoride, and a simultaneous oxidation–elimination reaction. The key intermediate 8 is expected to serve as a versatile intermediate for the synthesis of carbanucleosides.

  氟homoneplanocin A（4）由合成d -核糖，经由的烯炔闭环复分解9，环氧化物的立体选择性开口23a中被氟，和一个同时氧化消除反应。关键中间体8有望用作合成核苷的通用中间体。