<1S-(1α,2β,3α,4β)>-2-fluoro-4-(phenylmethoxy)-3-<(phenylmethoxy)methyl>-1-cyclopentanamine | 110567-26-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: <1S-(1α,2β,3α,4β)>-2-fluoro-4-(phenylmethoxy)-3-<(phenylmethoxy)methyl>-1-cyclopentanamine
• 英文别名: (1S-(1α,2β,3α,4β))-2-fluoro-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-1-cyclopentanamine；(1S,2S,3R,4S)-2-fluoro-4-phenylmethoxy-3-(phenylmethoxymethyl)cyclopentan-1-amine
• CAS: 110567-26-5
• 化学式: C₂₀H₂₄FNO₂
• 分子量: 329.414
• InChiKey: GBKPEAMLRIOZEL-FYQPLNBISA-N

物化性质

• 沸点：
  436.9±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  <1S-(1α,2β,3α,4β)>-2-fluoro-4-(phenylmethoxy)-3-<(phenylmethoxy)methyl>-1-cyclopentanamine 在 palladium on activated charcoal 硫酸 、 氢气 、 碘 、 硝酸 作用下， 以 氯仿 为溶剂， 生成 carbocyclic 1-(2'-deoxy-6'-α-fluororibofuranosyl)-5-iodouracil
  参考文献：
  名称：

  氟化碳环核苷的合成：碳环1-（2'-脱氧-6'-氟核呋喃呋喃糖基）-5-碘喹啉的制备

  摘要：

  用叠氮化物离子和氟离子区域选择性地打开环氧化物（4），分别得到醇（5）和（13）作为主要产物。叠氮基醇（5）被转化为抗病毒碳环的2'-脱氧-6'-氟尿苷（11）和（16）[获得了化合物（15）的晶体数据]。

  DOI：

  10.1039/c39870000255
• 作为产物：
  描述：

  [(1S,2R,3R,5R)-3-azido-2-fluoro-5-phenylmethoxycyclopentyl]methoxymethylbenzene 在 Lindlar's catalyst 氢气 作用下， 反应 3.5h， 生成 <1S-(1α,2β,3α,4β)>-2-fluoro-4-(phenylmethoxy)-3-<(phenylmethoxy)methyl>-1-cyclopentanamine
  参考文献：
  名称：

  氟碳环核苷：2'-和6'-氟碳环嘧啶核苷的合成和抗病毒活性，包括碳环1-（2-脱氧-2-氟-β-D-阿拉伯呋喃糖基）-5-甲基尿嘧啶和碳环1-（2-脱氧-2-氟-β-D-阿拉伯呋喃糖基）-5-碘尿嘧啶

  摘要：

  外消旋碳环的2'-氟阿拉伯糖基嘧啶核苷8、9（C-FIAU），12和13（C-FMAU）和2'-氟核糖基嘧啶核苷17、20和21是由它们各自的受保护的2'-氟代氨基二醇5和14。碳环2'-2'-二氟胸苷类似物27是从被保护的二氟氨基二醇24获得的，该二氟氨基二醇24是由酮23和（二乙基氨基）三氟化硫（DAST）制备的。由受保护的6'-氟氨基二醇30和36合成手性碳环2'-脱氧-6'-氟尿苷33、34、38和39，它们是通过还原叠氮化物28和35制备的。C-FMAU （13）和C-FIAU（9）在体外对HSV-1有活性，ID50值分别为4.4和11微克/ mL，但对HSV-2无活性。

  DOI：

  10.1021/jm00163a030

文献信息

• 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：——