2-amino-9-[(1R*,3S*,4R*)-4-hydroxy-3-hydroxymethyl-2-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one | 188399-46-4

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: 2-amino-9-[(1R*,3S*,4R*)-4-hydroxy-3-hydroxymethyl-2-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one
• 英文别名: 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one；BMS-200475；(±)-entecavir；Entecavir；2-Amino-9-((1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-1H-purin-6(9H)-one；2-amino-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1H-purin-6-one
• CAS: 188399-46-4
• 化学式: C₁₂H₁₅N₅O₃
• 分子量: 277.283
• InChiKey: QDGZDCVAUDNJFG-BWZBUEFSSA-N

物化性质

• 熔点：
  >239°C (dec.)
• 密度：
  1.81
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1R,2S)-2-(苄氧甲基)-3-环戊烯-1-醇 在 盐酸 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 bis(acetylacetonate)oxovanadium 、 Nysted reagent 、 TEA 、 三氯化硼 、 四氯化钛 、 四丁基碘化铵 、 lithium hydride 、 sodium hydride 、 戴斯-马丁氧化剂 、 叔丁醇 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-amino-9-[(1R*,3S*,4R*)-4-hydroxy-3-hydroxymethyl-2-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one
  参考文献：
  名称：

  BMS-200475, a novel carbocyclic 2′-deoxyguanosine analog with potent and selective anti-hepatitis B virus activity in vitro

  摘要：

  BMS-200475, a novel carbocyclic analog of 2'-deoxyguanosine, is a potent inhibitor of hepatitis B virus in vitro (ED(50)=3 nM) with relatively low cytotoxicity (CC50=21-120 mu M). A practical 10-step asymmetric synthesis was developed affording BMS-200475 in 18% overall chemical yield and >99% optical purity. The enantiomer of EMS-200475 as well as the adenine, thymine, and iodouracil analogs are much less active. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(96)00594-x

文献信息

• Synthesis of racemic Entecavir
  作者：Nikolai S. Vostrikov、Ilya F. Lobko、Zuleikha R. Valiullina、Mansur S. Miftakhov

  DOI：10.1016/j.mencom.2017.01.002

  日期：2017.1

  Racemic Entecavir was prepared from Corey lactone diol benzylidene acetal in four steps in 24% overall yield.

  外消旋恩替卡韦由Corey内酯二醇亚苄基乙缩醛分四个步骤制备，总收率为24％。
• 10.1134/s1070428024030060
  作者：Valiullina、Ivanova、Miftakhov

  DOI：10.1134/s1070428024030060

  日期：——
• BMS-200475, a novel carbocyclic 2′-deoxyguanosine analog with potent and selective anti-hepatitis B virus activity in vitro
  作者：G.S. Bisacchi、S.T. Chao、C. Bachard、J.P. Daris、S. Innaimo、G.A. Jacobs、O. Kocy、P. Lapointe、A. Martel、Z. Merchant、W.A. Slusarchyk、J.E. Sundeen、M.G. Young、R. Colonno、R. Zahler

  DOI：10.1016/s0960-894x(96)00594-x

  日期：1997.1

  BMS-200475, a novel carbocyclic analog of 2'-deoxyguanosine, is a potent inhibitor of hepatitis B virus in vitro (ED(50)=3 nM) with relatively low cytotoxicity (CC50=21-120 mu M). A practical 10-step asymmetric synthesis was developed affording BMS-200475 in 18% overall chemical yield and >99% optical purity. The enantiomer of EMS-200475 as well as the adenine, thymine, and iodouracil analogs are much less active. (C) 1997, Elsevier Science Ltd.