Ethyl N-(3,4-dichlorobenzyl)-4-nitroindole-2-carboxylate | 220677-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Ethyl N-(3,4-dichlorobenzyl)-4-nitroindole-2-carboxylate
• 英文别名: Ethyl 1-(3,4-dichlorobenzyl)-4-nitro-1H-indole-2-carboxylate；ethyl 1-[(3,4-dichlorophenyl)methyl]-4-nitroindole-2-carboxylate
• CAS: 220677-29-2
• 化学式: C₁₈H₁₄Cl₂N₂O₄
• 分子量: 393.226
• InChiKey: KTRMPRXXGFVIEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl N-(3,4-dichlorobenzyl)-4-nitroindole-2-carboxylate 在 三氯化钛 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以89%的产率得到Ethyl 4-amino-N-(3,4-dichlorobenzyl)indole-2-carboxylate
  参考文献：
  名称：

  ANTI-IMFLAMMATORY INDOLE DERIVATIVES

  摘要：

  公开号：

  EP1159269B1
• 作为产物：
  描述：

  4-硝基吲哚-2-羧酸乙酯 、 3,4-二氯氯苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Ethyl N-(3,4-dichlorobenzyl)-4-nitroindole-2-carboxylate
  参考文献：
  名称：

  N-Benzylindole-2-carboxylic acids: potent functional antagonists of the CCR2b chemokine receptor

  摘要：

  Screening of the corporate database led to the discovery of a novel series of N-benzylindole-2-carboxylic acid CCR2b chemokine receptor antagonists. These compounds demonstrate high affinity and functional inhibition of the CCR2b receptor. A discussion of the structure-activity relationships is presented, together with evidence for a highly selective receptor binding profile. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.049

文献信息

• Anti-inflammatory indole derivatives
  申请人：AstraZeneca AB

  公开号：US06569888B1

  公开（公告）日：2003-05-27

  Compounds of formula (I) or a pharmaceutically acceptable salt, in vivo hydrolysable ester, or an N—C1-6alkyl or N,N-di-(C1-6alkyl)amide thereof, where X is CH2 or SO2; R1 is an aryl optionally substituted by alkyl, alkenyl, alkynyl, halo, haloalkyl including perhaloalkyl such as trifluoromethyl, mercapto, alkoxy, haloalkoxy, alkenyloxy, alkynyloxy, hydroxyalkoxy, alkoxyalkoxy, alkanoyl, alkanoyloxy, cyano, nitro, amino, mono- or di-alkyl amino, oximino, sulphonamido, carbamoyl, mono or dialkylcarbamoyl or S(O)mR21 where m is defined above and R21 is hydrocarbyl; R4 is a group OR15 or S(O)qR15, where q is 0, 1 or 2 and R15 is a hydrogen-containing alkyl group substituted by at least one functional group as defined below, or an aryl group which is optionally substituted by one or more functional groups as defined below; and R2, R3, R5, R6 and R7 are specified organic groups. These compounds are useful in therapy, in particular of inflammatory disease, and methods of producing them as well as pharmaceutical compositions containing them are also described and claimed.

  化合物的结构式（I）或其药学上可接受的盐，在体内可水解的酯，或其N—C1-6烷基或N,N-二-(C1-6烷基)酰胺，其中X为CH2或SO2；R1为芳基，可选择地被烷基，烯基，炔基，卤素，卤代烷基（包括全氟烷基如三氟甲基），巯基，烷氧基，卤代烷氧基，烯氧基，炔氧基，羟基烷氧基，烷氧基烷氧基，烷酰基，烷酰氧基，氰基，硝基，氨基，单烷基或双烷基氨基，肟基，磺胺基，氨基甲酰基，单烷基或双烷基氨基甲酰基或S(O)mR21（其中m如上所定义，R21为烃基）取代的芳基；R4为OR15或S(O)qR15基团，其中q为0，1或2，R15为含氢烷基，取代至少一个如下所定义的功能基团的烷基，或者是可选择地被一个或多个如下所定义的功能基团取代的芳基；而R2、R3、R5、R6和R7为特定的有机基团。这些化合物在治疗中特别有用，尤其是在炎症性疾病中，同时还描述和声明了生产它们的方法以及含有它们的药物组合物。
• Monocyte chemoattractant protein-1 inhibitor compounds
  申请人：ZENECA LIMITED

  公开号：US20030119830A1

  公开（公告）日：2003-06-26

  The invention concerns the use of a compound of formula (I), in which Z, X, T, A, R 1 , R 2 , p and q have any of the meanings defined herein, and their pharmaceutically acceptable salts or in vivo hydrolysable esters, in the treatment of a disease or condition mediated by monocyte chemoattractant protein-1 (MCP-1). Certain of the components of formula (I) are novel and are provided, together with pharmaceutical compositions thereof, as further features of the invention.

  本发明涉及使用式（I）的化合物，其中Z，X，T，A，R1，R2，p和q具有本文所定义的任何含义，以及其药学上可接受的盐或体内水解酯，在治疗由单核细胞趋化蛋白-1（MCP-1）介导的疾病或状况中的应用。式（I）的某些组分是新颖的，并且作为本发明的进一步特征提供其制药组合物。
• INDOLE DERIVATIVES AND THEIR USE AS MCP-1 ANTAGONISTS
  申请人：AstraZeneca AB

  公开号：EP1003504B1

  公开（公告）日：2003-07-02
• US6441004B1
  申请人：——

  公开号：US6441004B1

  公开（公告）日：2002-08-27
• US6569888B1
  申请人：——

  公开号：US6569888B1

  公开（公告）日：2003-05-27