(2S,3S)-2-(benzyloxy)-6-phenylhexan-3-ol | 201211-15-6

• 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: (2S,3S)-2-(benzyloxy)-6-phenylhexan-3-ol
• 英文别名: (2S,3S)-6-phenyl-2-phenylmethoxyhexan-3-ol
• CAS: 201211-15-6
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: CIIPAWNKMCDBTP-LPHOPBHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-(benzyloxy)-6-phenylhexan-3-ol 在 偶氮二甲酸二异丙酯 、 氨 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3R)-3-(6-aminopurin-9-yl)-2-(benzyloxy)-6-phenylhexane
  参考文献：
  名称：

  Adenosine Deaminase Inhibitors:  Synthesis and Biological Evaluation of Unsaturated, Aromatic, and Oxo Derivatives of (+)-erythro-9-(2‘S-Hydroxy-3‘R-nonyl)adenine [(+)-EHNA]

  摘要：

  The synthesis and biological evaluation of three classes of chain-modified derivatives of(+)EHNA are described. Among the 5',6'-unsaturated derivatives, the Z-isomer was the most potent inhibitor of adenosine deaminase (ADA) but 3-fold less active than (+)-EHNA. Several 9-aralkyladenines (ARADs) have been prepared, and their inhibitory activity was determined. A minimum of two carbon atoms separating the aromatic ring from the adenine-bearing carbon (C-3') was found to be essential for ADA activity equal to or slightly greater than that of (+)EHNA. Finally, replacement of the C-5' carbon with an oxygen resulted in reduced potency.

  DOI：

  10.1021/jm0002533
• 作为产物：
  描述：

  (2S,3S)-3-benzyloxy-1,2-epoxybutane 、 乙基溴苯 在 碘 、 magnesium 、 lithium chloride 、 copper dichloride 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 以82%的产率得到(2S,3S)-2-(benzyloxy)-6-phenylhexan-3-ol
  参考文献：
  名称：

  Adenosine Deaminase Inhibitors:  Synthesis and Biological Evaluation of Unsaturated, Aromatic, and Oxo Derivatives of (+)-erythro-9-(2‘S-Hydroxy-3‘R-nonyl)adenine [(+)-EHNA]

  摘要：

  The synthesis and biological evaluation of three classes of chain-modified derivatives of(+)EHNA are described. Among the 5',6'-unsaturated derivatives, the Z-isomer was the most potent inhibitor of adenosine deaminase (ADA) but 3-fold less active than (+)-EHNA. Several 9-aralkyladenines (ARADs) have been prepared, and their inhibitory activity was determined. A minimum of two carbon atoms separating the aromatic ring from the adenine-bearing carbon (C-3') was found to be essential for ADA activity equal to or slightly greater than that of (+)EHNA. Finally, replacement of the C-5' carbon with an oxygen resulted in reduced potency.

  DOI：

  10.1021/jm0002533

文献信息

• Adenosine deaminase inhibitors. Synthesis and biological evaluation of aralkyladenines (ARADS)
  作者：Mark A. Curtis、Vaibhav Varkhedkar、Palle V.P. Pragnacharyulu、Elie Abushanab

  DOI：10.1016/s0960-894x(98)00291-1

  日期：1998.7

  Several 9-aralkyladenines have been prepared and their ADA inhibitory activity was determined. A minimum of two carbon atoms separating the aromatic ring from the adenine-bearing carbon (C3') was found essential for potent activity. (C) 1998 Elsevier Science Ltd. All rights reserved.
• ADENOSINE DEAMINASE INHIBITORS
  申请人：THE BOARD OF GOVERNORS FOR HIGHER EDUCATION STATE OF RHODE ISLAND AND PROVIDENCE PLANTATIONS

  公开号：EP0936911A1

  公开（公告）日：1999-08-25
• EP0936911A4
  申请人：——

  公开号：EP0936911A4

  公开（公告）日：1999-10-06
• US5703084A
  申请人：——

  公开号：US5703084A

  公开（公告）日：1997-12-30
• [EN] ADENOSINE DEAMINASE INHIBITORS<br/>[FR] INHIBITEURS DE L'ADENOSINE DESAMINASE
  申请人：——

  公开号：WO1998002166A1

  公开（公告）日：1998-01-22

  [EN] This invention disclosed (2S,3R)-3(6-aminopurin-9-yl)aralkan-2-ols, a novel class of adenine derivatives (also called 9-aralkyladenines, ARADS), which have been shown to inhibit the enzyme adenosine deaminase at therapeutically useful levels. The relevant inhibitory constant (Ki) values are in the range of 10<-7> - 10<-10> M. These compounds with potencies in this range can reversibly inhibit ADA in an effective manner, without permanently deactivating the enzyme. ADA inhibitors that have similar biological profiles have been shown to be of therapeutic value when used to protect heart muscle against ischemic damage.
  [FR] L'invention concerne des (2S, 3R)-3(6-aminopurine-9-yl) aralcan-2-ols, une nouvelle classe de dérivés d'adénine (également appelée 9-aralkyladénines, ARADS) démontrant une capacité d'inhibition de l'ADA à des niveaux thérapeutiquement utiles. Les valeurs de la constante d'inhibition appropriée (Ki) sont comprises entre 10<-7> et 10<-10> M, et les composés dont le potentiel se situe dans cette fourchette peuvent inhiber l'ADA de manière réversible et efficace, sans désactivation permanente de l'enzyme. Les inhibiteurs de l'ADA ayant des profils biologiques similaires démontrent leur valeur thérapeutique dans les applications qui visent à protéger le myocarde contre une détérioration ischémique.