6-methoxy-2-methyl-1H-indole-5-carboxylic acid | 672293-78-6

• 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: 6-methoxy-2-methyl-1H-indole-5-carboxylic acid
• 英文别名: 2-Methyl-6-methoxyindole-5-carboxylic acid
• CAS: 672293-78-6
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: LJUAQFUHMMWPBX-UHFFFAOYSA-N

物化性质

• 沸点：
  433.4±40.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-methoxy-2-methyl-1H-indole-5-carboxylic acid methyl ester 在 氢氧化钾 、 水 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以100%的产率得到6-methoxy-2-methyl-1H-indole-5-carboxylic acid
  参考文献：
  名称：

  Indole-type derivatives as inhibitors of p38 kinase

  摘要：

  该发明涉及使用含有苯基或噻吩基通过哌啶或哌嗪核与吲哚残基相连的化合物来抑制p38-α激酶的方法，其中吲哚残基上强制地具有环氮上的氨基或取代氨基基团。

  公开号：

  US20040142940A1

文献信息

• Indole-type inhibitors of p38 kinase
  申请人：——

  公开号：US20030100588A1

  公开（公告）日：2003-05-29

  The invention is directed to inhibition of p38-a kinase using compounds of the formula 1 and the pharmaceutically acceptable salts thereof, or a pharmaceutical composition thereof, wherein Ar is an aryl group substituted with 0-5 non-interfering substituents, wherein two adjacent noninterfering substituents can form a fused aromatic or nonaromatic ring; L 1 and L 2 are linkers; X is an aliphatic monocyclic or aliphatic polycyclic moiety optionally comprising one or more hetero ring atoms wherein the cyclic moiety may be optionally substituted with one or more noninterfering substituents and where said optional substituents may constitute a ring fused to X; n is 0-3; each R 1 is hydrogen or a noninterfering substituent; 2 represents a single or double bond; one Z 2 is CA or CR 2 A; the other Z 2 is CR 3 , CR 3 2 , NR 4 or N; and each R 2 , R 3 and R 4 is independently hydrogen or a noninterfering substituent; Z 3 is NR 5 or O; where R 5 is hydrogen or a noninterfering substituent; A is —W i —COX j Y, where Y is COR 6 or an isostere thereof, each of W and X is a spacer of 2-6 Å; each of i and j is independently 0 or 1; and R 6 is a noninterfering substituent; and wherein the smallest number of covalent bonds in the compound separating the atom of Ar linked to L 2 and the atom of the &agr; ring linked to L 1 is at least 5, each said bond having a bond length of 1.2 to 2.0 angstroms; and/or the distance in space between the atom of Ar linked to L 2 and the atom of the &agr; ring linked to L 1 is 4.5-24 angstroms; and with the proviso that the portion of the compound represented by L 2 —X—L 1 is not: 3 where L 2 and L 1 are linkers; Z 1 is CR or N wherein R is hydrogen or a non-interfering substituent; each R 1 is independently a non-interfering substituent; and each of l and k is 0-3; and m is 0-4.

  该发明涉及使用式1中的化合物及其药学上可接受的盐来抑制p38-a激酶，或者其药物组合物，其中Ar是带有0-5个非干扰取代基的芳基，其中两个相邻的非干扰取代基可以形成融合的芳香环或非芳香环；L1和L2是连接物；X是一种脂肪单环或脂肪多环基团，可选地包含一个或多个杂环原子，其中环基团可以选择地被一个或多个非干扰取代基取代，这些可选取代基可以构成与X融合的环；n为0-3；每个R1是氢或一个非干扰取代基；2表示单键或双键；一个Z2是CA或CR2A；另一个Z2是CR3、CR32、NR4或N；每个R2、R3和R4独立地是氢或一个非干扰取代基；Z3是NR5或O；其中R5是氢或非干扰取代基；A是—Wi—COXjY，其中Y是COR6或其同分异构体，W和X各自是2-6埃的间隔；i和j各自独立地为0或1；R6是一个非干扰取代基；并且化合物中连接到L2的Ar原子与连接到L1的α环原子之间的共价键的最小数量至少为5，每个所述键的键长为1.2到2.0埃；和/或连接到L2的Ar原子与连接到L1的α环原子之间的空间距离为4.5-24埃；但化合物中由L2—X—L1表示的部分不是：3，其中L2和L1是连接物；Z1是CR或N，其中R是氢或非干扰取代基；每个R1独立地是一个非干扰取代基；l和k分别为0-3；m为0-4。
• Inhibitors of p38 kinase
  申请人：——

  公开号：US20030092717A1

  公开（公告）日：2003-05-15

  The invention is directed to methods to inhibit p38-&agr; kinase using compounds of the formula 1 and the pharmaceutically acceptable salts thereof, or a pharmaceutical composition thereof, wherein represents a single or double bond; B is —W i —COX j Y wherein Y is COR 2 or an isostere thereof and R 2 is hydrogen or a noninterfering substituent, each of W and X is a spacer of 2-6 Å, and each of i and j is independently 0 or 1; each R 3 is independently a noninterfering substituent, where n is 0-3; Z 3 is NR 7 or O; wherein R 7 is H or a noninterfering substituent; one Z 2 is CA or CR 8 A and the other is CR 1 , CR 1 2 , NR 6 or N wherein each R 1 , R 6 and R 8 is independently hydrogen or noninterfering substituent; wherein A is: 2 such that Z 1 is CR 5 or N wherein R 5 is hydrogen or a noninterfering substituent; each of 1 and k is an integer from 0-2 wherein the sum of 1 and k is 0-3; Ar is an aryl group substituted with 0-5 noninterfering substituents, wherein two noninterfering substituents can form a fused ring; each R 4 is independently a noninterfering substituent where m is 0-4; each of L 1 and L 2 is a linker; and the distance between the atom of Ar linked to L 2 and the center of the &bgr; ring is 4.5-24 Å.

  该发明涉及使用式1化合物及其药用盐来抑制p38-α激酶的方法，或者其药物组合物，其中表示单键或双键；B为—Wi—COXjY，其中Y为COR2或其同分异构体，R2为氢或非干扰基，W和X各自为2-6埃的间隔物，i和j各自独立为0或1；每个R3各自为非干扰基，其中n为0-3；Z3为NR7或O；其中R7为H或非干扰基；一个Z2为CA或CR8A，另一个为CR1、CR12、NR6或N，其中每个R1、R6和R8各自独立为氢或非干扰基；其中A为:2，使得Z1为CR5或N，其中R5为氢或非干扰基；每个1和k为0-2的整数，其中1和k的和为0-3；Ar为带有0-5个非干扰基的芳基，其中两个非干扰基可形成融合环；每个R4各自为非干扰基，其中m为0-4；每个L1和L2为连接物；以及与L2连接的Ar原子与β环中心之间的距离为4.5-24埃。
• [EN] INDOLE-TYPE DERIVATIVES AS INHIBITORS OF p38 KINASE<br/>[FR] DERIVES DE TYPE INDOLE EN TANT QU'INHIBITEURS DE p38 KINASE
  申请人：SCIOS INC

  公开号：WO2000071535A1

  公开（公告）日：2000-11-30

  The invention is directed to methods to inhibit p38-α kinase using compounds of formula (1), and the pharmaceutically acceptable salts thereof, or a pharmaceutical composition thereof, wherein (a) represents a single or double bond; one Z2 is CA or CR8A and the other is CR1, CR12, NR6 or N wherein each R?1, R6 and R8¿ is independently hydrogen or noninterfering substituent; A is -W¿i?-COXjY wherein Y is COR?2¿ or an isostere thereof and R2 is hydrogen or a noninterfering substituent, each of W and X is a spacer of 2-6Å, and each of i and j is independently 0 or 1; Z?3 is NR7¿ or O; each R3 is independently a noninterfering substituent; n is 0-3; each of L?1 and L2¿ is a linker; each R4 is independently a noninterfering substituent; m is 0-4; Z?1 is CR5¿ or N wherein R5 is hydrogen or a noninterfering substituent; each of l and k is an integer from 0-2 wherein the sum of l and k is 0-3; Ar is an aryl group substituted with 0-5 noninterfering substituents, wherein two noninterfering substituents can form a fused ring; and the distance between the atom of Ar linked to L2 and the center of the α ring is 4.5-24Å.

  该发明涉及使用式（1）的化合物及其药学上可接受的盐或药物组合物来抑制p38-α激酶的方法，其中（a）表示单个或双键；Z2中的一个为CA或CR8A，另一个为CR1、CR12、NR6或N，其中每个R?1、R6和R8¿都独立地表示氢或非干扰取代基；A为-W¿i?-COXjY，其中Y为COR?2¿或其同分异构体，R2为氢或非干扰取代基，W和X各自为2-6Å的间隔，i和j各自独立地为0或1；Z?3为NR7¿或O；每个R3都独立地表示非干扰取代基；n为0-3；每个L?1和L2¿都是一个连接基；每个R4都独立地表示非干扰取代基；m为0-4；Z?1为CR5¿或N，其中R5为氢或非干扰取代基；每个l和k都是0-2的整数，其中l和k的和为0-3；Ar是一个芳基基团，其被0-5个非干扰取代基取代，其中两个非干扰取代基可以形成融合环；并且与L2连接的Ar原子与α环中心的距离为4.5-24Å。
• Benzofuran derivatives as inhibitors of p38-alpha kinase
  申请人：——

  公开号：US20030158417A1

  公开（公告）日：2003-08-21

  The invention is directed to methods to inhibit p38-&agr; kinase using compounds of the formula 1 and the pharmaceutically acceptable salts thereof, or a pharmaceutical composition thereof, wherein represents a single or double bond; one Z 2 is CA or CR 8 A and the other is CR 1 , CR 1 2 , NR 6 or N wherein each R 1 , R 6 and R 8 is independently hydrogen or noninterfering substituent; A is —W i —COX j Y wherein Y is COR 2 or an isostere thereof and R 2 is hydrogen or a noninterfering substituent, each of W and X is a spacer of 2-6 Å, and each of i and j is independently 0 or 1; Z 3 is NR 7 or O; each R 3 is independently a noninterfering substituent; n is 0-3; each of L 1 and L 2 is a linker; each R 4 is independently a noninterfering substituent; m is 0-4; Z 1 is CR 5 or N wherein R 5 is hydrogen or a noninterfering substituent; each of l and k is an integer from 0-2 wherein the sum of l and k is 0-3; Ar is an aryl group substituted with 0-5 noninterfering substituents, wherein two noninterfering substituents can form a fused ring; and the distance between the atom of Ar linked to L 2 and the center of the &agr; ring is 4.5-24 Å.

  本发明涉及使用式1化合物及其药学上可接受的盐或制剂的方法，以抑制p38-α激酶，其中： - 表示单个或双键； - 其中一个Z2是CA或CR8A，另一个是CR1、CR12、NR6或N，其中每个R1、R6和R8独立地表示氢或非干扰取代基； - A是-Wi-COXjY，其中Y是COR2或其异构体，R2是氢或非干扰取代基，W和X分别是2-6埃的间隔基，i和j各自独立地为0或1； - Z3是NR7或O； - 每个R3独立地表示非干扰取代基； - n为0-3； - 每个L1和L2是连接基； - 每个R4独立地表示非干扰取代基； - m为0-4； - Z1是CR5或N，其中R5是氢或非干扰取代基； - 每个l和k是0-2的整数，其中l和k的和为0-3； - Ar是芳基基团，其上取代0-5个非干扰基团，其中两个非干扰基团可以形成融合环； - Ar与L2连接的原子与α环中心之间的距离为4.5-24埃。
• INDOLE-TYPE DERIVATIVES AS INHIBITORS OF P38 KINASE
  申请人：Chakravarty Sarvajit

  公开号：US20070232617A1

  公开（公告）日：2007-10-04

  The invention is directed to methods to inhibit p38-α kinase using compounds comprising a phenyl or thienyl coupled through a piperidine or piperazine nucleus to an indole residue wherein the indole residue mandatorily has a substituent on the ring nitrogen which is an amino or substituted amino group.

  该发明涉及使用含有苯基或噻吩基的化合物来抑制p38-α激酶的方法，其中所述化合物通过哌啶或哌嗪核与吲哚残基耦合，所述吲哚残基上的环氮原子强制具有氨基或取代氨基基团。