2-[1-(4-Chlorobenzoyl)-7-methoxy-2-methylindol-3-yl]acetic acid | 142653-11-0

• 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: 2-[1-(4-Chlorobenzoyl)-7-methoxy-2-methylindol-3-yl]acetic acid
• CAS: 142653-11-0
• 化学式: C₁₉H₁₆ClNO₄
• 分子量: 357.793
• InChiKey: IWQHEVHMLSWZRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-甲氧基-2-甲基-1H-吲哚 在 正丁基锂 、 10% Pd/C 、 potassium tert-butylate 、 氢气 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 乙酸乙酯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 2-[1-(4-Chlorobenzoyl)-7-methoxy-2-methylindol-3-yl]acetic acid
  参考文献：
  名称：

  Design and Synthesis of Indomethacin Analogues That Inhibit P-Glycoprotein and/or Multidrug Resistant Protein without Cox Inhibitory Activity

  摘要：

  We designed and synthesized conformationally restricted analogues and regioisomers of the nonsteroidal anti-inflammatory drug indomethacin. Evaluation of the inhibitory effects of these compounds on COX, P-glycoprotein, and multidrug resistance indicated that NSAIDS modulation of multidrug-resistant P-glycoprotein and multidrug-resistant protein-1 is not associated with COX-1 and COX-2 inhibitory activities.

  DOI：

  10.1021/jm301084z

文献信息

• Esters and amides of substituted pyrrole acetic acids
  申请人：FGN, INC.

  公开号：EP0485157A2

  公开（公告）日：1992-05-13

  Esters and amides of substituted pyrrole acetic acids of the formula : wherein n is 0 or 1, and X represents a condensed phenyl ring ; one of R1 and R2 is independently selected from hydrogen, halogen, lower alkyl ; and the other of R1 and R2 is independently selected from substituted or unsubstituted phenyl, benzyl, thienyl, napthyl, pyridyl, furyl, biphenyl, benzoyl, cinnamoyl, thienylcarbonyl, napthylcarbonyl, pyridylcarbonyl, furylcarbonyl or biphenylcarbonyl wherein said substituents are selected from amino, halogen, lower alkyl, lower alkylthio, lower alkoxy or lower haloalkyl ; m is an integer from 1 to 3 ; R3 is selected from hydrogen and lower alkyl, or one or more of hydrogen and lower alkyl when m is greater than 1 ; R4 is one or more of hydrogen, lower alkyl, alkoxy, haloalkyl, alkylthio, and halogen ; p is an integer of at least 2 ; Q is the deprotonated residue of a polymer or macromolecular structure having at least two primary and/or secondary amines and/or hydroxy groups ; and when n is 0, R5 is selected from hydrogen, halogen, lower alkyl, alkoxy, alkylthio, and halogen are useful in the treatment of colonic polyps.

  式中取代的吡咯乙酸的酯和酰胺： 其中 n 为 0 或 1，X 代表缩合苯基环； R1 和 R2 中的一个独立选自氢、卤素、低级烷基；R1 和 R2 中的另一个独立选自取代或未取代的苯基、苄基、噻吩基、萘基、吡啶基、呋喃基、联苯基、苯甲酰基、肉桂酰基、噻吩基羰基、萘基羰基、吡啶基羰基、呋喃基羰基或联苯基羰基，其中所述取代基选自氨基、卤素、低级烷基、低级烷硫基、低级烷氧基或低级卤代烷基； m 是 1 至 3 的整数； R3 选自氢和低级烷基，或当 m 大于 1 时，选自氢和低级烷基中的一个或多个； R4 是氢、低级烷基、烷氧基、卤代烷基、烷硫基和卤素中的一种或多种； p 是至少 2 的整数； Q 是聚合物或大分子结构的去质子化残基，至少有两个伯胺和/或仲胺和/或羟基；以及 当 n 为 0 时，R5 选自氢、卤素、低级烷基、烷氧基、烷硫基和卤素。
• US5721347A
  申请人：——

  公开号：US5721347A

  公开（公告）日：1998-02-24
• Design and Synthesis of Indomethacin Analogues That Inhibit P-Glycoprotein and/or Multidrug Resistant Protein without Cox Inhibitory Activity
  作者：Mitsuhiro Arisawa、Yayoi Kasaya、Tohru Obata、Takuma Sasaki、Tomonori Nakamura、Takuya Araki、Koujirou Yamamoto、Akito Sasaki、Akihito Yamano、Mika Ito、Hiroshi Abe、Yoshihiro Ito、Satoshi Shuto

  DOI：10.1021/jm301084z

  日期：2012.9.27

  We designed and synthesized conformationally restricted analogues and regioisomers of the nonsteroidal anti-inflammatory drug indomethacin. Evaluation of the inhibitory effects of these compounds on COX, P-glycoprotein, and multidrug resistance indicated that NSAIDS modulation of multidrug-resistant P-glycoprotein and multidrug-resistant protein-1 is not associated with COX-1 and COX-2 inhibitory activities.