7-甲氧基-2-甲基-1H-吲哚 | 53512-46-2

• 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
• 中文名称: 7-甲氧基-2-甲基-1H-吲哚
• 英文名称: 2-methyl-7-methoxy indole
• 英文别名: 2-methyl-7-methoxyindole；7-methoxy-2-methylindole；7-methoxy-2-methyl-indole；7-Methoxy-2-methyl-indol；2-methyl-7-(methyloxy)-1H-indole；7-methoxy-2-methyl-1H-indole
• CAS: 53512-46-2
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: PKSVZXMZMGPDDG-UHFFFAOYSA-N

物化性质

• 熔点：
  83-84℃
• 沸点：
  309℃
• 密度：
  1.134
• 闪点：
  113℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P264,P280,P302+P352,P305+P351+P338,P332+P313,P337+P313,P362
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  7-甲氧基-2-甲基-1H-吲哚 在 2,3,5-三甲基吡啶 、 氢氧化钾 作用下， 以 乙腈 为溶剂， 生成 7-甲氧基-2-甲基-1H-吲哚-3-羧酸甲酯
  参考文献：
  名称：

  C-3 Amido-Indole cannabinoid receptor modulators

  摘要：

  C-3 Amido-indoles were found to selectively bind to the CB2 receptor. SAR studies led to optimized compounds with excellent in vivo potency against LPS induced TNF-alpha release in murine models of cytokine production. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00466-3
• 作为产物：
  描述：

  7-甲氧基吲哚-2-羧酸 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 21.0h， 以56%的产率得到7-甲氧基-2-甲基-1H-吲哚
  参考文献：
  名称：

  [EN] FAAH INHIBITORS
  [FR] INHIBITEURS DE FAAH

  摘要：

  本公开涉及作为脂肪酰胺水解酶（FAAH）抑制剂有用的化合物。该公开还提供包括本公开化合物的药学上可接受的组合物，以及使用这些组合物在治疗或预防各种疾病中的方法。发明的化合物在表1中描述。

  公开号：

  WO2012088469A1

文献信息

• [EN] PIPERIDINYLHYDROXYETHYLPIPERIDINES AS MODULATORS OF CHEMOKINE RECEPTORS<br/>[FR] PIPÉRIDINYLHYDROXYÉTHYLPIPÉRIDINES UTILISABLES EN TANT QUE MODULATEURS DES RÉCEPTEURS AUX CHIMIOKINES
  申请人：GLAXO GROUP LTD

  公开号：WO2009049113A1

  公开（公告）日：2009-04-16

  The present invention relates to a compound of the formula (I), or a pharmaceutically acceptable salt thereof, wherein R1-R8 and X, m, and n are defined. Compounds and compositions of the present invention are useful the treatment of atherosclerosis.

  本发明涉及公式（I）的化合物或其药学上可接受的盐，其中R1-R8和X、m和n已定义。本发明的化合物和组合物对动脉粥样硬化的治疗是有用的。
• 3-ACYLINDOLE DERIVATIVES, PREPARATION AND THERAPEUTIC USE THEREOF
  申请人：BARTH Francis

  公开号：US20080275102A1

  公开（公告）日：2008-11-06

  The invention relates to compounds of formula (I), wherein X, R 1 , R 2 , R 3 , R 4 and R 5 are as described herein. The invention also includes preparative methods for the preparation of compounds of formula (I). A method for the therapeutic use of the inventive compounds is also disclosed and claimed.

  这项发明涉及式(I)的化合物，其中X，R1，R2，R3，R4和R5如本文所述。 该发明还包括制备式(I)化合物的制备方法。还公开并声明了一种利用这些创新化合物的治疗方法。
• CB.sub.2 Receptor agonist compounds
  申请人：Sanofi

  公开号：US06013648A1

  公开（公告）日：2000-01-11

  The use of human CB.sub.2 receptor-specific agonists of formula (I) or (I') for preparing immunomodulating drugs is disclosed. In formulae (I) and (I'), R.sub.1 is a group selected from --CH.sub.2 CHR.sub.10 NR.sub.6 R.sub.11, --(CH.sub.2).sub.2 NR'.sub.6 R'.sub.11, --CHR.sub.9 CH.sub.2 NR'.sub.6 R'.sub.11, --(CH.sub.2).sub.n Z and --COR.sub.8 ; R'.sub.1 is a --CH.sub.2 CHR.sub.10 NR.sub.6 R.sub.11 or --(CH.sub.2).sub.2 NR'.sub.6 R'.sub.11 group; R.sub.2 and R'.sub.2 are hydrogen, halogen or C.sub.1-4 alkyl; R.sub.3 is hydrogen, C.sub.1-4 alkyl or a group selected from --CH.sub.2 CHR.sub.10 NR.sub.6 R.sub.11, --(CH.sub.2).sub.2 NR'.sub.6 R'.sub.11 and --COR.sub.8 ; R'.sub.3 is a .dbd.CR.sub.6 R.sub.8 group; R.sub.4 has one of the meanings given for R.sub.5 or is a --COR.sub.8 group; R.sub.5 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, a halogen atom, a CF.sub.3 group, an OCF.sub.3 group or C.sub.1-4 alkylthio; R'.sub.5 has one of the meanings given for R.sub.5 and is in the 5 or 6 position of the indene ring; R.sub.6 is hydrogen or C.sub.1-4 alkyl; R'.sub.6 is C.sub.1-4 alkyl; R.sub.7 has one of the meanings given for R.sub.5 or R.sub.7 and R.sub.9 together form a --Y--CH.sub.2 -- group attached to the indole ring in the 7 position by a group Y; R.sub.8 is phenyl substituted one to four times by a substituent selected from halogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy; a polycyclic ring selected from naphth-1-yl, naphth-2-yl, 1,2,3,4-tetrahydronaphth-1-yl, 1,2,3,4-tetrahydronaphth-5-yl, anthryl, benzofuryl, benzothien-2-yl, benzothien-3-yl, 2-, 3-, 4- or 8-quinolyl, said polycyclic rings optionally being substituted once or twice by a substituent selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, halogen, cyano, hydroxyl, trifluoromethyl and imidazol-1-yl; R.sub.10 and R.sub.11 together are a group selected from --CH.sub.2 --O--CH.sub.2 --CR.sub.12 R.sub.13 -- and --(CH.sub.2).sub.p --CR.sub.12 R.sub.13 --, wherein the carbon atom substituted by R.sub.12 and R.sub.13 is attached to the nitrogen atom; R'.sub.11 is C.sub.1-4 alkyl; or R'.sub.11 and R'.sub.6, taken together with the nitrogen atom to which they are attached, form a group selected from morpholin-4-yl, thiomorpholin-4-yl, piperidin-1-yl and pyrrolidin-1-yl; each of R.sub.12 and R.sub.13 is independently hydrogen or C.sub.1-4 alkyl; n is 2, 3, 4 or 5; p is 2 or 3; Z is a methyl group or a halogen atom; and Y is a methylene group or an oxygen atom.

  公开了使用公式（I）或（I'）的人类CB.sub.2受体特异性激动剂制备免疫调节药物。在公式（I）和（I'）中，R.sub.1是从--CH.sub.2 CHR.sub.10 NR.sub.6 R.sub.11，--(CH.sub.2).sub.2 NR'.sub.6 R'.sub.11，--CHR.sub.9 CH.sub.2 NR'.sub.6 R'.sub.11，--(CH.sub.2).sub.n Z和--COR.sub.8中选择的一个基团；R'.sub.1是一个--CH.sub.2 CHR.sub.10 NR.sub.6 R.sub.11或--(CH.sub.2).sub.2 NR'.sub.6 R'.sub.11基团；R.sub.2和R'.sub.2是氢，卤素或C.sub.1-4烷基；R.sub.3是氢，C.sub.1-4烷基或从--CH.sub.2 CHR.sub.10 NR.sub.6 R.sub.11，--(CH.sub.2).sub.2 NR'.sub.6 R'.sub.11和--COR.sub.8中选择的一个基团；R'.sub.3是一个.dbd.CR.sub.6 R.sub.8基团；R.sub.4具有给出的R.sub.5的含义之一或是一个--COR.sub.8基团；R.sub.5是氢，C.sub.1-4烷基，C.sub.1-4烷氧基，卤素原子，CF.sub.3基团，OCF.sub.3基团或C.sub.1-4烷基硫基；R'.sub.5具有给出的R.sub.5的含义之一，并且位于茚环的第5或第6位置；R.sub.6是氢或C.sub.1-4烷基；R'.sub.6是C.sub.1-4烷基；R.sub.7具有给出的R.sub.5或R.sub.7的含义之一，且R.sub.9和R.sub.7一起形成一个通过Y连接到茚环的7位置的--Y--CH.sub.2--基团；R.sub.8是苯基，通过卤素，C.sub.1-4烷基或C.sub.1-4烷氧基取代一到四次；从萘-1-基，萘-2-基，1,2,3,4-四氢萘-1-基，1,2,3,4-四氢萘-5-基，蒽基，苯并呋喃基，苯并噻吩-2-基，苯并噻吩-3-基，2-, 3-, 4-或8-喹啉基中选择的多环环，所述多环环可以选择地被C.sub.1-4烷基，C.sub.1-4烷氧基，C.sub.1-4烷硫基，卤素，氰基，羟基，三氟甲基和咪唑-1-基取代一次或两次；R.sub.10和R.sub.11一起是从--CH.sub.2--O--CH.sub.2--CR.sub.12 R.sub.13--和--(CH.sub.2).sub.p--CR.sub.12 R.sub.13--中选择的一个基团，其中由R.sub.12和R.sub.13取代的碳原子连接到氮原子；R'.sub.11是C.sub.1-4烷基；或R'.sub.11和R'.sub.6，与它们连接的氮原子一起形成从吗啉-4-基，硫代吗啉-4-基，哌啶-1-基和吡咯啉-1-基中选择的一个基团；R.sub.12和R.sub.13中的每一个独立地是氢或C.sub.1-4烷基；n为2、3、4或5；p为2或3；Z为甲基基团或卤素原子；Y为亚甲基基团或氧原子。
• Synthesis and biological evaluation of isomeric methoxy substitutions on anti-cancer indolyl-pyridinyl-propenones: Effects on potency and mode of activity
  作者：Christopher J. Trabbic、Sage M. George、Evan M. Alexander、Shengnan Du、Jennifer M. Offenbacher、Emily J. Crissman、Jean H. Overmeyer、William A. Maltese、Paul W. Erhardt

  DOI：10.1016/j.ejmech.2016.06.016

  日期：2016.10

  isomeric methoxy substitutions on the indole ring. Additionally, analogues containing a trimethoxyphenyl group in place of the pyridinyl moiety were evaluated for anticancer activity. The results demonstrate that the location of the methoxy group can alter both the potency and the mechanism of cell death. Remarkably, changing the methoxy from the 5-position to the 6-position switched the biological activity

  某些吲哚基-吡啶基-丙烯酮类似物杀死已经对常规治疗药物产生抗性的胶质母细胞瘤细胞。这些类似物中的一些诱导了一种新形式的非凋亡性细胞死亡，称为变态，而其他类似物则主要引起微管破坏。当存在一个简单的甲氧基时，对5-吲哚取代的容易获得对这两种类型的机理都至关重要。现在，我们报告吲哚环上异构甲氧基取代的合成和生物学效应。另外，评估了含有三甲氧基苯基代替吡啶基部分的类似物的抗癌活性。结果表明，甲氧基的位置可以改变效力和细胞死亡的机制。值得注意的是 将甲氧基从5位更改为6位可将生物学活性从诱导变色转变为破坏微管。后者可以代表具有潜在治疗用途的新型有丝分裂抑制剂的原型。
• [EN] SELECTIVE D3 DOPAMINE RECEPTOR AGONISTS AND METHODS OF THEIR USE<br/>[FR] AGONISTES SÉLECTIFS DU RÉCEPTEUR DE LA DOPAMINE D3 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：US HEALTH

  公开号：WO2017181004A1

  公开（公告）日：2017-10-19

  The disclosure of a compound of Formula (I) or a pharmaceutically acceptable salt thereof (I) The variables W, R1, R2, R3, and R4 are defined in the disclosure. The disclosure provides a compound or salt of Formula (I) together with a pharmaceutically acceptable carrier. The disclosure also provides methods of treating a patient for Parkinson's disease and related syndromes, dyskinesia, especially dyskinesias secondary to treating Parkinson's disease with L-DOPA, neurodegenerative disorders such as Alzheimer's disease and dementia, Huntington's disease, restless legs syndrome, bipolar disorder and depression, schizophrenia, cognitive dysfunction, or substance use disorders, the methods comprising administering a compound of Formula I or salt thereof to the patient. The disclosure provides combination methods of treatment in which the compound of Formula (I) is administered to the patient together with one or more additional active agents.

  公式(I)的化合物或其药用可接受的盐的披露。变量W、R1、R2、R3和R4在披露中有定义。该披露提供了公式(I)的化合物或盐，以及药用可接受的载体。该披露还提供了治疗帕金森病和相关综合征、特别是因治疗帕金森病使用L-DOPA而引起的运动障碍、神经退行性疾病如阿尔茨海默病和痴呆症、亨廷顿病、不安腿综合征、躁郁症和抑郁症、精神分裂症、认知功能障碍或物质使用障碍的方法，包括向患者施用公式I的化合物或其盐。该披露提供了联合治疗方法，其中将公式(I)的化合物与一个或多个额外活性剂一起施用给患者。