(+/-)-(1α,2β,3α,4α)-4-<(2-amino-6-chloro-9H-purin-9-yl)amino>-3-fluoro-2-hydroxycyclopentanemethanol | 110289-21-9

• 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: (+/-)-(1α,2β,3α,4α)-4-<(2-amino-6-chloro-9H-purin-9-yl)amino>-3-fluoro-2-hydroxycyclopentanemethanol
• 英文别名: (1R,2R,3R,5R)-3-(2-amino-6-chloropurin-9-yl)-2-fluoro-5-(hydroxymethyl)cyclopentan-1-ol
• CAS: 110289-21-9
• 化学式: C₁₁H₁₃ClFN₅O₂
• 分子量: 301.708
• InChiKey: QXDVQRYUNAJJKE-UAKXSSHOSA-N

物化性质

• 沸点：
  630.5±65.0 °C(Predicted)
• 密度：
  1.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+/-)-(1α,2β,3α,4α)-4-<(2-amino-6-chloro-9H-purin-9-yl)amino>-3-fluoro-2-hydroxycyclopentanemethanol 在 盐酸 作用下， 以76%的产率得到2-氨基-9-[(2S,3S,4S)-2-氟-3-羟基-4-(羟基甲基)环戊基]-3H-嘌呤-6-酮
  参考文献：
  名称：

  合成与碳2'的酶法拆分ARA -氟鸟苷：一种有效的新抗疱疹剂

  摘要：

  合成了（±）-碳环-9-（2'-脱氧-2'-β-氟阿拉伯呋喃糖基）鸟嘌呤（8）和相应的呋喃糖化合物（12）；前一种化合物[通过形成单磷酸酯（20）和使用5'-核苷酸酶进行对映选择性水解而拆分]是一种非常有效的1型和2型单纯疱疹病毒抑制剂。

  DOI：

  10.1039/c39880000656
• 作为产物：
  描述：

  (+/-)-(1α,2β,3α,4α)-4-[(2,5-diamino-6-chloro-4-pyrimidinyl)amino]-3-fluoro-2-hydroxycyclopentanemethanol 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (+/-)-(1α,2β,3α,4α)-4-<(2-amino-6-chloro-9H-purin-9-yl)amino>-3-fluoro-2-hydroxycyclopentanemethanol
  参考文献：
  名称：

  合成与碳2'的酶法拆分ARA -氟鸟苷：一种有效的新抗疱疹剂

  摘要：

  合成了（±）-碳环-9-（2'-脱氧-2'-β-氟阿拉伯呋喃糖基）鸟嘌呤（8）和相应的呋喃糖化合物（12）；前一种化合物[通过形成单磷酸酯（20）和使用5'-核苷酸酶进行对映选择性水解而拆分]是一种非常有效的1型和2型单纯疱疹病毒抑制剂。

  DOI：

  10.1039/c39880000656

文献信息

• 4′-Modification of carbocyclic nucleosides: synthesis of 4′-α-fluoro, 4′α-hydroxy and 4′,6′-unsaturated derivatives of the antiviral agent 2′-ara-fluoro carbocyclic guanosine
  作者：Keith Biggadike、Alan D. Borthwick

  DOI：10.1039/c39900001380

  日期：——

  4′-α-Fluoro 13, 4′-α-hydroxy 11, and 4′,6′-unsaturated 15 derivatives of (±) 2′-ara-fluoro carbocylci guanosine 1 are prepared via the 4′,5′-alkene 8.

  4'-α氟13，4'-α羟基11，和4'，6'-不饱和15个（±）-2'-的衍生物ARA氟carbocylci鸟苷1制备通过，5'-烯烃的4' 8。
• Cyclopentane derivatives
  申请人：GLAXO GROUP LIMITED

  公开号：EP0345076A1

  公开（公告）日：1989-12-06

  The present invention provides the compounds of formula (I) and salts and solvates thereof wherein R1 represents a hydrogen or fluorine atom or a hydroxy group, R2 represents a fluorine atom or a hydroxyl or C1-6alkoxy group and B represents a purine base, and describes processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of viral infections, particularly those caused by the Herpetoviridae.

  本发明提供了式(I)化合物及其盐和溶液 及其盐和溶剂，其中 R1 代表氢原子或氟原子或羟基，R2 代表氟原子或羟基或 C1-6 烷氧基，B 代表嘌呤碱；本发明还描述了制备它们的工艺、含有它们的药物组合物以及它们在治疗病毒感染（尤其是由赫氏病毒科引起的病毒感染）中的用途。
• Novel carbocyclic analogs of certain nucleosides
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0468866A1

  公开（公告）日：1992-01-29

  This invention relates to novel carbocyclic analogs of certain nucleosides, to the process for their preparation and to their use as anti-viral agents.

  本发明涉及某些核苷的新型碳环类似物、其制备工艺及其作为抗病毒剂的用途。
• Fluorocarbocyclic nucleosides: synthesis and antiviral activity of 2'- and 6'-fluorocarbocyclic 2'-deoxyguanosines
  作者：Alan D. Borthwick、Barrie E. Kirk、Keith Biggadike、Anne M. Exall、Suzanne Butt、Stanley M. Roberts、David J. Knight、Jonathan A. V. Coates、D. Michael Ryan

  DOI：10.1021/jm00107a006

  日期：1991.3

  A series of four isomeric 2'- and 6'-fluorocarbocyclic guanosine analogues have been prepared and evaluated as potential anti-herpes agents. The racemic 2'-beta-fluoro isomer 2-amino-1,9-dihydro-9-[(1-alpha, 2-alpha, 3-beta, 4-alpha)-2-fluoro-3-hydroxy-4-(hydroxymethyl)cyclopenty]-6H-purin-6-one (11a, C-AFG) and its 2'-alpha-fluoro epimer 11b plus the chiral 6'-beta-fluoro isomer 2-amino-1,9-dihydro-9-[[1S-(1-alpha, 2-alpha, 3-alpha, 4-beta)]-2-fluoro-4-hydroxy-3-(hydroxymethyl)cyclopentyl]-6H-purin-6-one (11c) and its 6'-alpha-fluoro epimer 11d were prepared from their respective fluoro amino diol hydrochlorides (6a,d). For comparison, the furanosyl compound 9-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)guanine (17, AFG) was prepared by coupling 2-amino-6-chloropurine with 2-deoxy-2-fluoro-3,5-di-O-benzoyl-alpha-D-arabinofuranosyl bromide followed by base hydrolysis. The 6'-alpha-fluoro derivative 11d exhibited comparable activity to that of acyclovir (ACV) against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in vitro but was > 30-fold more active than ACV against HSV-1 and HSV-2 in vivo in the mouse systemic model. The 2'-beta-fluoro derivative (11a, C-AFG) was extremely potent in vitro against HSV-1 and HSV-2 (ID50 0.006 and 0.05-mu-g/mL) and in vivo it was greater than 2 orders of magnitude more potent than ACV against HSV-1 and 70-fold more potent against HSV-2. The 2'-alpha-fluoro 11b and 6'-beta-fluoro 11c isomers were much less active.
• BORTWICK, A. D.;KIRK, B. E.;BIGGADIKE, KEITH;EXALL, ANNE M.;BUTT, SUZANNE+, J. MED. CHEM., 34,(1991) N, C. 1834
  作者：BORTWICK, A. D.、KIRK, B. E.、BIGGADIKE, KEITH、EXALL, ANNE M.、BUTT, SUZANNE+

  DOI：——

  日期：——