(E)-6-(4-chlorophenyl)hex-5-enoic acid | 128577-56-0

• 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: (E)-6-(4-chlorophenyl)hex-5-enoic acid
• CAS: 128577-56-0
• 化学式: C₁₂H₁₃ClO₂
• 分子量: 224.687
• InChiKey: UGKLXPWOSHRBCH-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-6-(4-chlorophenyl)hex-5-enoic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 1.0h， 以84%的产率得到6-(4-chlorophenyl)hexanoic acid
  参考文献：
  名称：

  Benzophenone dicarboxylic acid antagonists of leukotriene B4. 2. Structure-activity relationships of the lipophilic side chain

  摘要：

  A series of lipophilic benzophenone dicarboxylic acid derivatives were found to inhibit the binding of the potent chemotaxin leukotriene B4 (LTB4) to its receptor on intact human neutrophils. Activity at the LTB4 receptor was determined by using a [3H]LTB4-binding assay. The structure-activity relationship for the lipophilic side chain was systematically investigated. Compounds with n-alkyl side chains of varying lengths were prepared and tested. Best inhibition of [3H]LTB4 binding was observed with the n-decyl derivative. Analogues with alkyl chains terminated with an aromatic ring showed improved activity. The 6-phenylhexyl side chain was optimal. Substitution on the terminal aromatic ring was also evaluated. Methoxyl, methylsulfinyl, and methyl substituents greatly enhanced the activity of the compound. For a given substituent, the para isomer had the best activity. Thus the nature of the lipophilic side chain can greatly influence the ability of the compounds to inhibit the binding of LTB4 to its receptor on intact human neutrophils. The most active compound from this series, 84 (LY223982), bound to the LTB4 receptor with an affinity approaching that of the agonist.

  DOI：

  10.1021/jm00172a020
• 作为产物：
  描述：

  环戊酮 在 三氟甲磺酸 、 对甲苯磺酸 作用下， 以 硝基甲烷 、 环己烷 为溶剂， 反应 1.5h， 生成 (E)-6-(4-chlorophenyl)hex-5-enoic acid
  参考文献：
  名称：

  通过环烷酮缩酮的位点特异性活化实现芳香羰基的烯化**

  摘要：

  简单的底物设计允许环酮的位点特异性活化，用于芳香族羰基化合物的烯化反应。

  DOI：

  10.1002/anie.202317003

文献信息

• Trisubstituted benzene leukotriene B4 receptor antagonists: Synthesis and structure-activity relationships
  作者：Mitoshi Konno、Takahiko Nakae、Shigeru Sakuyama、Yoshihiko Odagaki、Hisao Nakai、Nobuyuki Hamanaka

  DOI：10.1016/s0968-0896(97)00089-8

  日期：1997.8

  A series of trisubstituted benzenes which demonstrate leukotriene B4 (LTB4, 1) receptor affinity was prepared. Previous trisubstituted benzenes from our laboratory showed high affinity to the LTB4 receptor but demonstrated agonist activity in functional assays. Compound 3a, the initial lead compound of this new series, showed only modest affinity (IC50 = 0.20 microM). However, 3a was a receptor antagonist

  制备了一系列显示白三烯B4（LTB4，1）受体亲和力的三取代苯。我们实验室以前的三取代苯对LTB4受体显示出高亲和力，但在功能测定中显示出激动剂活性。该新系列的初始前导化合物化合物3a仅表现出适度的亲和力（IC50 = 0.20 microM）。但是，3a是一种受体拮抗剂，在高达30 microM时没有明显的激动剂活性。脂质尾部和芳基头部区域的进一步修饰导致3b（ONO-4057）的发现。该化合物无激动剂活性，对LTB4受体具有高亲和力（Ki = 3.7 +/- 0.9 nM）。
• Aralkanamidophenyl compounds
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0124791A1

  公开（公告）日：1984-11-14

  This disclosure describes novel substituted aralkanamidobenzoic acids and analogs thereof. These compounds are useful pharmaceutical agents for ameliorating atherosclerosis by inhibiting the formation and development of atherosclerotic lesions in the arterial wall of mammals.

  本公开介绍了新型取代的芳香酰胺基苯甲酸及其类似物。这些化合物可抑制哺乳动物动脉壁动脉粥样硬化病变的形成和发展，是改善动脉粥样硬化的有用药物。
• 2-Amino-5-hydroxy-4-methylpyrimidine derivatives
  申请人：PFIZER INC.

  公开号：EP0138464A2

  公开（公告）日：1985-04-24

  Novel 2-amino-5-hydroxy-4-methylpyrimidines and substituted amino derivatives thereof useful as inhibitors of leukotriene synthesis for the treatment of pulmonary, inflammatory and cardiovascular diseases, cancer and psoriasis. In addition these compounds are cytoprotective and therefore useful in the treatment of peptic ulcers. A process for the preparation of such active compounds by ring rearrangement of 2-amino-5-acetyloxazole, pharmaceutical compositions containing the novel active compounds and compositions containing these compounds in combination with other anti-inflammatory agents or gastric anti-secret- t ory agents.

  新型 2-氨基-5-羟基-4-甲基嘧啶及其取代氨基衍生物可作为白三烯合成抑制剂，用于治疗肺病、炎症性疾病、心血管疾病、癌症和牛皮癣。此外，这些化合物还具有细胞保护作用，因此可用于治疗消化性溃疡。通过 2-氨基-5-乙酰基恶唑的环重排制备此类活性化合物的工艺，含有新型活性化合物的药物组合物，以及含有这些化合物与其他消炎药或抗胃泌素药组合的组合物。
• GAPINSKI, D. MARK;MALLETT, BARBARA E.;FROELICH, LARRY L.;JACKSON, WILLIAM+, J. MED. CHEM., 33,(1990) N0, C. 2807-2813
  作者：GAPINSKI, D. MARK、MALLETT, BARBARA E.、FROELICH, LARRY L.、JACKSON, WILLIAM+

  DOI：——

  日期：——
• US4536346A
  申请人：——

  公开号：US4536346A

  公开（公告）日：1985-08-20