4-(3,4-Dimethoxyphenyl)benzoyl chloride | 193153-27-4

• 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: 4-(3,4-Dimethoxyphenyl)benzoyl chloride
• CAS: 193153-27-4
• 化学式: C₁₅H₁₃ClO₃
• 分子量: 276.719
• InChiKey: JKWFLWPLTRBETO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3,4-Dimethoxyphenyl)benzoyl chloride 在 4-二甲氨基吡啶 、 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (E,2R,3R)-2-[(3-cyanophenyl)methyl]-3-[[4-(3,4-dimethoxyphenyl)benzoyl]amino]-5-phenylpent-4-enoic acid
  参考文献：
  名称：

  Identification and Initial Structure−Activity Relationships of a Novel Class of Nonpeptide Inhibitors of Blood Coagulation Factor Xa

  摘要：

  The discovery and some of the basic structure-activity relationships of a series of novel nonpeptide inhibitors of blood coagulation Factor Xa is described. These inhibitors are functionalized p-alanines, exemplified by 2a. Docking experiments placing 2a in the active site of Factor Xa implied that the Most expeditious route to enhancing in vitro potency was to modify the group occupying the S3 site of the enzyme. Increasing the hydrophobic contacts between the inhibitor and the enzyme in this region led to 8, which has served as the prototype for this series. In addition, an enantioselective synthesis of these substituted p-alanines was also developed.

  DOI：

  10.1021/jm970482y
• 作为产物：
  描述：

  4-溴黎芦醚 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 正丁基锂 、 草酰氯 、 二异丁基氢化铝 、 N,N-二甲基甲酰胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-(3,4-Dimethoxyphenyl)benzoyl chloride
  参考文献：
  名称：

  Identification and Initial Structure−Activity Relationships of a Novel Class of Nonpeptide Inhibitors of Blood Coagulation Factor Xa

  摘要：

  The discovery and some of the basic structure-activity relationships of a series of novel nonpeptide inhibitors of blood coagulation Factor Xa is described. These inhibitors are functionalized p-alanines, exemplified by 2a. Docking experiments placing 2a in the active site of Factor Xa implied that the Most expeditious route to enhancing in vitro potency was to modify the group occupying the S3 site of the enzyme. Increasing the hydrophobic contacts between the inhibitor and the enzyme in this region led to 8, which has served as the prototype for this series. In addition, an enantioselective synthesis of these substituted p-alanines was also developed.

  DOI：

  10.1021/jm970482y

文献信息

• Biphenylcarboxamide derivatives as antagonists of platelet-activating factor
  作者：Jefferson W. Tilley、John W. Clader、Sonja Zawoiski、Maria Wirkus、Ronald A. LeMahieu、Margaret O'Donnell、Herman Crowley、Ann F. Welton

  DOI：10.1021/jm00128a025

  日期：1989.8

  A series of N-[4-(3-pyridinyl)butyl]-1,1'-biphenyl-4-carboxamides was prepared, and the compounds were evaluated for platelet-activating factor (PAF) antagonist activity in a binding assay employing washed, whole dog platelets and in vivo for their ability to inhibit PAF-induced bronchoconstriction in the guinea pig. The inclusion of a methyl group in the R configuration on the side-chain carbon adjacent to the carboxamide nitrogen atom of these derivatives resulted in a marked enhancement of potency in the binding assay for compounds unsubstituted in the biphenyl 2-position and, more importantly, in improved oral bioavailability. Previous work with related pyrido[2,1-b]-quinazoline-8-carboxamides suggests that the presence of such an alkyl group improves bioavailability by rendering the resulting compounds resistant to degradation by liver amidases. The most interesting compounds to emerge from this work are (R)-2-bromo-3',4'-dimethoxy-N-[1-methyl-4-(3-pyridinyl)butyl]-1,1'-bi phe nyl- 4-carboxamide (33) and (R)-2-butyl-3',4'-dimethoxy-N-[1-methyl-4-(3-pyridinyl)butyl]- 1,1'-biphenyl-4-carboxamide (40) each of which inhibits PAF-induced bronchoconstriction in the guinea pig by greater than 55%. 6 h after an oral dose of 50 mg/kg.
• (2-Amino-phenyl)-amides of ω-substituted alkanoic acids as new histone deacetylase inhibitors
  作者：Arkadii Vaisburg、Naomy Bernstein、Sylvie Frechette、Martin Allan、Elie Abou-Khalil、Silvana Leit、Oscar Moradei、Giliane Bouchain、James Wang、Soon Hyung Woo、Marielle Fournel、Pu T. Yan、Marie-Claude Trachy-Bourget、Ann Kalita、Carole Beaulieu、Zuomei Li、A.Robert MacLeod、Jeffrey M. Besterman、Daniel Delorme

  DOI：10.1016/j.bmcl.2003.08.083

  日期：2004.1

  A variety of omega-substituted alkanoic acid (2-amino-phenyl)-amides were designed and synthesized. These compounds were shown to inhibit recombinant human histone deacetylases (HDACs) with IC50 values in the low micromolar range and induce hyperacetylation of histones in whole cells. They induced expression of p21WAFl/Cip1 and caused cell-cycle arrest in human cancer cells. Compounds in this class showed efficacy in human tumor xenograft models. (C) 2003 Elsevier Ltd. All rights reserved.
• US6080767A
  申请人：——

  公开号：US6080767A

  公开（公告）日：2000-06-27
• US6140504A
  申请人：——

  公开号：US6140504A

  公开（公告）日：2000-10-31
• US6323227B1
  申请人：——

  公开号：US6323227B1

  公开（公告）日：2001-11-27