3-[1-(4-chlorobenzyl)-3-methyl-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid | 103253-35-6

• 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: 3-[1-(4-chlorobenzyl)-3-methyl-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid
• 英文别名: 3-[1-[(4-chlorophenyl)methyl]-5-methoxy-3-methylindol-2-yl]-2,2-dimethylpropanoic acid
• CAS: 103253-35-6
• 化学式: C₂₂H₂₄ClNO₃
• 分子量: 385.89
• InChiKey: VXBFXUXEJMLIGE-UHFFFAOYSA-N

物化性质

• 沸点：
  574.4±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[1-(4-chlorobenzyl)-3-methyl-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 lithium hydroxide 、 三溴化硼 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-(5-(biphenyl-4-yl)-1-(4-chlorobenzyl)-3-methyl-1H-indol-2-yl)-2,2-dimethylpropanoic acid
  参考文献：
  名称：

  Inhibitors of the inducible microsomal prostaglandin E2 synthase (mPGES-1) derived from MK-886

  摘要：

  A series of potent and selective inhibitors of the inducible microsomal PGE(2) synthase (mPGES-1) has been developed based on the indole FLAP inhibitor MK-886. Compounds 23 and 30 inhibit mPGES-1 with potencies in the low nanomolar range and with selectivities of at least 100-fold compared to their inhibition of mPGES-2, thromboxane synthase and binding affinity to FLAP. They also block the production of PGE(2) in cell based assays but with a decreased potency and more limited selectivity compared to the enzyme assays. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.027
• 作为产物：
  描述：

  4-氯氯苄 在 三乙胺 作用下， 以 甲苯 、 叔丁醇 为溶剂， 反应 30.0h， 生成 3-[1-(4-chlorobenzyl)-3-methyl-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid
  参考文献：
  名称：

  Inhibitors of the inducible microsomal prostaglandin E2 synthase (mPGES-1) derived from MK-886

  摘要：

  A series of potent and selective inhibitors of the inducible microsomal PGE(2) synthase (mPGES-1) has been developed based on the indole FLAP inhibitor MK-886. Compounds 23 and 30 inhibit mPGES-1 with potencies in the low nanomolar range and with selectivities of at least 100-fold compared to their inhibition of mPGES-2, thromboxane synthase and binding affinity to FLAP. They also block the production of PGE(2) in cell based assays but with a decreased potency and more limited selectivity compared to the enzyme assays. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.027

文献信息

• Indole-2-alkanoic acids compositions of and anti allergic use thereof
  申请人：Merck Frosst Canada, Inc.

  公开号：US05081145A1

  公开（公告）日：1992-01-14

  Indole-2-alkanoic acids are disclosed. The compounds act as prostaglandin and thromboxane antagonists and are useful in treating asthma, inflammation, diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion and dismenorrhea and as cytoprotective agents.

  本文介绍了吲哚-2-烷基酸。这些化合物作为前列腺素和血栓素拮抗剂，可用于治疗哮喘、炎症、腹泻、高血压、心绞痛、血小板聚集、脑痉挛、早产、自然流产和痛经，并可作为细胞保护剂。
• (Azaarylmethoxy)indoles as inhibitors of leukotriene biosynthesis
  申请人：Merck Frosst Canada, Inc.

  公开号：US05389650A1

  公开（公告）日：1995-02-14

  Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion, dysmenorrhea, and migraine.

  具有公式I的化合物：##STR1##是白三烯生物合成的抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。它们还可用于治疗腹泻、高血压、心绞痛、血小板聚集、脑痉挛、早产、自然流产、痛经和偏头痛。
• (Polycyclic-arylmethoxy) indoles as inhibitors of leukotriene
  申请人：Merck Frosst Canada, Inc.

  公开号：US05190968A1

  公开（公告）日：1993-03-02

  Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion, dysmenorrhea, and migraine.

  具有公式I的化合物：##STR1##是白三烯生物合成的抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。它们还可用于治疗腹泻、高血压、心绞痛、血小板聚集、脑痉挛、早产、自然流产、痛经和偏头痛。
• Bicyclic-azaarylmethoxy) indoles as inhibitors of leukotriene
  申请人：Merck Frosst Canada Inc.

  公开号：US05273980A1

  公开（公告）日：1993-12-28

  Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion, dysmenorrhea, and migraine.

  化合物I的化学式为：##STR1##，它们是白三烯生物合成的抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。它们还可用于治疗腹泻、高血压、心绞痛、血小板聚集、脑痉挛、早产、自发流产、痛经和偏头痛。
• (Bicyclic-hetero-arylmethoxy)indoles as inhibitors of leukotriene
  申请人：Merck Frosst Canada, Inc.

  公开号：US05308850A1

  公开（公告）日：1994-05-03

  Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion, dysmenorrhea, and migraine.

  具有公式I的化合物：##STR1## 是白三烯生物合成的抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。它们还可用于治疗腹泻、高血压、心绞痛、血小板聚集、脑痉挛、早产、自然流产、痛经和偏头痛。