Aceton-(m-chlor-phenylhydrazon) | 67175-12-6

• 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: Aceton-(m-chlor-phenylhydrazon)
• 英文别名: 3-chloro-N-(propan-2-ylideneamino)aniline
• CAS: 67175-12-6
• 化学式: C₉H₁₁ClN₂
• mdl: MFCD21606408
• 分子量: 182.653
• InChiKey: QPTZUWYLUJDDFN-UHFFFAOYSA-N

物化性质

• 沸点：
  257.0±42.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Aceton-(m-chlor-phenylhydrazon) 在 正丁基锂 、 sodium hydride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 methyl 4-[[2-[4-chloro-(1-diphenylmethyl)-2-methyl-1H-indol-3-yl]ethyl]sulfonyl]benzoate
  参考文献：
  名称：

  Inhibition of Cytosolic Phospholipase A₂α: Hit to Lead Optimization

  摘要：

  Compound I was previously reported to be a potent inhibitor of cPLA,(x in both artificial monomeric substrate and cell-based assays. However, I was inactive in whole blood assays previously used to characterize cyclooxygenase and lipoxygenase inhibitors. The IC(50) of 1 increased dramatically with cell number or lipid/detergent concentration. In an attempt to insert an electrophilic ketone between the indole and benzoic acid moieties, we discovered that increasing the distance between the two moieties gave a compound with activity in the GLU (7-hydroxycoumarinyl-gamma-linolenate) micelle assay, which contains lipid and detergent. Extensive structure-activity relationship work around this lead identified a potent pharmacophore for cPLA a inhibition. The IC(50)s between the GLU micelle and rat whole blood assays correlated highly. No correlation was found for other parameters, including lipophilicity or acidity of the required acid functionality. Compounds 25, 39, and 94 emerged as potent, selective inhibitors of cPLA(2)alpha and represent well-validated starting points for further optimization.

  DOI：

  10.1021/jm0507882
• 作为产物：
  描述：

  丙酮 、 间氯苯肼 以 水 为溶剂， 反应 2.0h， 以100%的产率得到Aceton-(m-chlor-phenylhydrazon)
  参考文献：
  名称：

  Heterocyclic sodium/proton exchange inhibitors and method

  摘要：

  提供了杂环化合物，这些化合物是钠/质子交换（NHE）抑制剂，其结构如下： 其中n为1至5；X为N或C—R5，其中R5为H、卤素、烯基、炔基、烷氧基、烷基、芳基或杂芳基；Z为杂芳基团，R1、R2、R3和R4如本文所定义，且其中X为N。R1最好为芳基或杂芳基，并且可用作抗心绞痛和心脏保护剂。此外，提供了一种方法，用于预防或治疗心绞痛、心脏功能障碍、心肌坏死和心律失常，采用上述杂环衍生物。

  公开号：

  US06887870B1

文献信息

• Kilany, Yeldez El; Mousaad, Ahmed; Hamid, Hamida Abdel, Gazzetta Chimica Italiana, 1988, vol. 118, # 9, p. 617 - 622
  作者：Kilany, Yeldez El、Mousaad, Ahmed、Hamid, Hamida Abdel、Ashry, El Sayed H. El

  DOI：——

  日期：——
• Piper,J.R.; Stevens,F.J., Journal of Heterocyclic Chemistry, 1966, vol. 3, p. 95 - 97
  作者：Piper,J.R.、Stevens,F.J.

  DOI：——

  日期：——
• EL, KILANY YELDEZ;MOUSAAD, AHMED;HAMID, HAMIDA ABDEL;EL, ASHRY EL SAYED H+, GAZZ. CHIM. ITAL., 118,(1988) N 9, C. 617-621
  作者：EL, KILANY YELDEZ、MOUSAAD, AHMED、HAMID, HAMIDA ABDEL、EL, ASHRY EL SAYED H+

  DOI：——

  日期：——
• Heterocyclic sodium/proton exchange inhibitors and method
  申请人：Ahmad Saleem

  公开号：US06887870B1

  公开（公告）日：2005-05-03

  Heterocyclic are provided which are sodium/proton exchange (NHE) inhibitors which have the structure wherein n is 1 to 5; X is N or C—R 5 wherein R 5 is H, halo, alkenyl, alkynyl, alkoxy, alkyl, aryl or heteroaryl; Z is a heteroaryl gorup, R 1 , R 2 , R 3 and R 4 are as defined herein, and where X is N. R 1 is preferably aryl or heteroaryl, and are useful as antianginal and cardioprotective agents. In addition, a method is provided for preventing or treating angina pectoris, cardiac dysfunction, myocardial necrosis, and arrhythmia employing the above heterocyclic derivatives.

  提供了杂环化合物，这些化合物是钠/质子交换（NHE）抑制剂，其结构如下： 其中n为1至5；X为N或C—R5，其中R5为H、卤素、烯基、炔基、烷氧基、烷基、芳基或杂芳基；Z为杂芳基团，R1、R2、R3和R4如本文所定义，且其中X为N。R1最好为芳基或杂芳基，并且可用作抗心绞痛和心脏保护剂。此外，提供了一种方法，用于预防或治疗心绞痛、心脏功能障碍、心肌坏死和心律失常，采用上述杂环衍生物。
• Inhibition of Cytosolic Phospholipase A₂α: Hit to Lead Optimization
  作者：John C. McKew、Megan A. Foley、Paresh Thakker、Mark L. Behnke、Frank E. Lovering、Fuk-Wah Sum、Steve Tam、Kun Wu、Marina W. H. Shen、Wen Zhang、Mario Gonzalez、Shanghao Liu、Anu Mahadevan、Howard Sard、Soo Peang Khor、James D. Clark

  DOI：10.1021/jm0507882

  日期：2006.1.1

  Compound I was previously reported to be a potent inhibitor of cPLA,(x in both artificial monomeric substrate and cell-based assays. However, I was inactive in whole blood assays previously used to characterize cyclooxygenase and lipoxygenase inhibitors. The IC(50) of 1 increased dramatically with cell number or lipid/detergent concentration. In an attempt to insert an electrophilic ketone between the indole and benzoic acid moieties, we discovered that increasing the distance between the two moieties gave a compound with activity in the GLU (7-hydroxycoumarinyl-gamma-linolenate) micelle assay, which contains lipid and detergent. Extensive structure-activity relationship work around this lead identified a potent pharmacophore for cPLA a inhibition. The IC(50)s between the GLU micelle and rat whole blood assays correlated highly. No correlation was found for other parameters, including lipophilicity or acidity of the required acid functionality. Compounds 25, 39, and 94 emerged as potent, selective inhibitors of cPLA(2)alpha and represent well-validated starting points for further optimization.