Ethyl 2-(3,4-dimethoxybenzoyl)-2-(dimethylaminomethylene)acetate | 128594-22-9

• 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: Ethyl 2-(3,4-dimethoxybenzoyl)-2-(dimethylaminomethylene)acetate
• 英文别名: ethyl 2-(3,4-dimethoxybenzoyl)-3-(dimethylamino)prop-2-enoate
• CAS: 128594-22-9
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: CAKKAZRJIFDQQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 2-(3,4-dimethoxybenzoyl)-2-(dimethylaminomethylene)acetate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 5-(3,4-Dimethoxy-phenyl)-1-(4-methanesulfonyl-phenyl)-1H-pyrazole-4-carboxylic acid
  参考文献：
  名称：

  4-Substituted 1,5-diarylpyrazole, analogues of celecoxib: synthesis and preliminary evaluation of biological properties

  摘要：

  A number of 5-aryl-1-[4-(methylsulfonyl)-phenyl]-1H-pyrazoles and 4-(5-aryl-1H-pyrazol-1-yl)benzenesulfonamides 3, 4, 5, 6, analogues of the COX-2 selective inhibitor celecoxib (celebrex), were synthesized. In order to verify the effects on the biological properties of certain substituents put on position 4 of the pyrazole nucleus, some of these compounds were screened in vivo for their anti-inflammatory and analgesic activities. Moreover, sodium salts of carboxylic acids 4 were tested in vitro for their platelet anti-aggregating properties. The results of these preliminary biological assays showed that new derivatives are not endowed with improved anti-inflammatory and analgesic properties, in comparison with celecoxib. In addition, docking studies were carried out on the most significative compounds to evaluate their interaction mode at the active site of both COX-1 and COX-2. Some remarks about the SAR of this class of COX-inhibitors are drown out.

  DOI：

  10.1016/s0014-827x(03)00136-8
• 作为产物：
  描述：

  3,4-二甲氧基苯甲酸乙酯 在 sodium hydride 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 Ethyl 2-(3,4-dimethoxybenzoyl)-2-(dimethylaminomethylene)acetate
  参考文献：
  名称：

  4-Substituted 1,5-diarylpyrazole, analogues of celecoxib: synthesis and preliminary evaluation of biological properties

  摘要：

  A number of 5-aryl-1-[4-(methylsulfonyl)-phenyl]-1H-pyrazoles and 4-(5-aryl-1H-pyrazol-1-yl)benzenesulfonamides 3, 4, 5, 6, analogues of the COX-2 selective inhibitor celecoxib (celebrex), were synthesized. In order to verify the effects on the biological properties of certain substituents put on position 4 of the pyrazole nucleus, some of these compounds were screened in vivo for their anti-inflammatory and analgesic activities. Moreover, sodium salts of carboxylic acids 4 were tested in vitro for their platelet anti-aggregating properties. The results of these preliminary biological assays showed that new derivatives are not endowed with improved anti-inflammatory and analgesic properties, in comparison with celecoxib. In addition, docking studies were carried out on the most significative compounds to evaluate their interaction mode at the active site of both COX-1 and COX-2. Some remarks about the SAR of this class of COX-inhibitors are drown out.

  DOI：

  10.1016/s0014-827x(03)00136-8

文献信息

• Pyrimidine derivatives and composition of the same
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04727073A1

  公开（公告）日：1988-02-23

  The invention relates to new pyrimidine derivatives, useful in the treatment of cerebrovascular disease, of the formula: ##STR1## wherein Ar, R.sup.1, R.sup.2 and R.sup.3 are defined in the specification.

  该发明涉及一种新的嘧啶衍生物，可用于治疗脑血管疾病，其化学式为：##STR1## 其中Ar、R.sup.1、R.sup.2和R.sup.3在说明书中有定义。
• 4-Substituted 1,5-diarylpyrazole, analogues of celecoxib: synthesis and preliminary evaluation of biological properties
  作者：Giulia Menozzi、Luisa Merello、Paola Fossa、Luisa Mosti、Antonietta Piana、Francesca Mattioli

  DOI：10.1016/s0014-827x(03)00136-8

  日期：2003.9

  A number of 5-aryl-1-[4-(methylsulfonyl)-phenyl]-1H-pyrazoles and 4-(5-aryl-1H-pyrazol-1-yl)benzenesulfonamides 3, 4, 5, 6, analogues of the COX-2 selective inhibitor celecoxib (celebrex), were synthesized. In order to verify the effects on the biological properties of certain substituents put on position 4 of the pyrazole nucleus, some of these compounds were screened in vivo for their anti-inflammatory and analgesic activities. Moreover, sodium salts of carboxylic acids 4 were tested in vitro for their platelet anti-aggregating properties. The results of these preliminary biological assays showed that new derivatives are not endowed with improved anti-inflammatory and analgesic properties, in comparison with celecoxib. In addition, docking studies were carried out on the most significative compounds to evaluate their interaction mode at the active site of both COX-1 and COX-2. Some remarks about the SAR of this class of COX-inhibitors are drown out.