(S)-6-(benzyloxy)-2-((R)-2-(4-fluorophenyl)-2-hydroxyethyl)hex-4-enoic acid | 1100155-27-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (S)-6-(benzyloxy)-2-((R)-2-(4-fluorophenyl)-2-hydroxyethyl)hex-4-enoic acid
• 英文别名: (2S)-2-[(2R)-2-(4-fluorophenyl)-2-hydroxyethyl]-6-phenylmethoxyhex-4-enoic acid
• CAS: 1100155-27-8
• 化学式: C₂₁H₂₃FO₄
• 分子量: 358.41
• InChiKey: ZCRAADZBMWGFOU-AZUAARDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-6-(benzyloxy)-2-((R)-2-(4-fluorophenyl)-2-hydroxyethyl)hex-4-enoic acid 在 硫酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 (S)-methyl 6-(benzyloxy)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)hex-4-enoate
  参考文献：
  名称：

  Antidotes to anthrax lethal factor intoxication. Part 2: Structural modifications leading to improved in vivo efficacy

  摘要：

  New anthrax lethal factor inhibitors (LFIs) were designed based upon previously identified potent inhibitors 1a and 2. Combining the new core structures with modifications to the C2-side chain yielded analogs with improved efficacy in the rat lethal toxin model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.010
• 作为产物：
  描述：

  4-(benzyloxy)-2-buten-1-ol 在 咪唑 、 碘 、 三苯基膦 、 potassium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 3.5h， 生成 (S)-6-(benzyloxy)-2-((R)-2-(4-fluorophenyl)-2-hydroxyethyl)hex-4-enoic acid
  参考文献：
  名称：

  Antidotes to anthrax lethal factor intoxication. Part 2: Structural modifications leading to improved in vivo efficacy

  摘要：

  New anthrax lethal factor inhibitors (LFIs) were designed based upon previously identified potent inhibitors 1a and 2. Combining the new core structures with modifications to the C2-side chain yielded analogs with improved efficacy in the rat lethal toxin model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.010

文献信息

• Hydroxamic acid derivatives of 4-phenyl 4-hydroxy, 4-phenyl 4-alkoxy and 4-phenyl 4-arylalkoxy butyric acid useful as therapeutic agents for treating anthrax poisoning
  申请人：Johnson Alan T.

  公开号：US20100286125A1

  公开（公告）日：2010-11-11

  Compounds having the formula wherein the symbols have the meaning described in the specification are hydroxamic acid derivatives of 4-phenyl-4-hydroxy-butyric acid and capable of inhibiting the lethal effects of infection by anthrax bacteria and are useful in the treatment of poisoning by anthrax.

  具有以下式的化合物是4-苯基-4-羟基丁酸的羟肟酸衍生物，能够抑制炭疽细菌感染的致命效应，并且在炭疽中毒的治疗中有用。
• Antidotes to anthrax lethal factor intoxication. Part 2: Structural modifications leading to improved in vivo efficacy
  作者：Seongjin Kim、Guan-Sheng Jiao、Mahtab Moayeri、Devorah Crown、Lynne Cregar-Hernandez、Linda McKasson、Stephen A. Margosiak、Stephen H. Leppla、Alan T. Johnson

  DOI：10.1016/j.bmcl.2011.02.010

  日期：2011.4

  New anthrax lethal factor inhibitors (LFIs) were designed based upon previously identified potent inhibitors 1a and 2. Combining the new core structures with modifications to the C2-side chain yielded analogs with improved efficacy in the rat lethal toxin model. (C) 2011 Elsevier Ltd. All rights reserved.