5-苄氧基-7-甲基-吲哚 | 4792-65-8

• 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: 5-苄氧基-7-甲基-吲哚
• 英文名称: 5-(benzyloxy)-7-methyl-1H-indole
• 英文别名: 7-methyl-5-phenylmethoxy-1H-indole
• CAS: 4792-65-8
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: BQXGEFUVJSBEIY-UHFFFAOYSA-N

物化性质

• 熔点：
  71-72 °C
• 沸点：
  422.1±30.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5-苄氧基-7-甲基-吲哚 在 草酰氯 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Discovery of a small molecule RXFP3/4 agonist that increases food intake in rats upon acute central administration

  摘要：

  The relaxin family peptide receptors have been implicated in numerous physiological processes including energy homeostasis, cardiac function, wound healing, and reproductive function. Two family members, RXFP3 and RXFP4, are class A GPCRs with endogenous peptide ligands (relaxin-3 and insulin-like peptide 5 (INSL5), respectively). Polymorphisms in relaxin-3 and RXFP3 have been associated with obesity, diabetes, and hyper-cholesterolemia. Moreover, central administration of relaxin-3 in rats has been shown to increase food intake, leading to body weight gain. Reported RXFP3 and RXFP4 ligands have been restricted to peptides (both endogenous and synthetic) as well as a low molecular weight positive allosteric modulator requiring a non-endogenous orthosteric ligand. Described here is the discovery of the first potent low molecular weight dual agonists of RXFP3/4. The scaffold identified is competitive with a chimeric relaxin-3/INSL5 peptide for RXFP3 binding, elicits similar downstream signaling as relaxin-3, and increases food intake in rats following acute central administration. This is the first report of small molecule RXFP3/4 agonism.

  DOI：

  10.1016/j.bmcl.2019.02.013
• 作为产物：
  描述：

  3,5-二甲基-4-硝基苯酚 在 四氢吡咯 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0~90.0 ℃ 、101.33 kPa 条件下， 反应 20.67h， 生成 5-苄氧基-7-甲基-吲哚
  参考文献：
  名称：

  [EN] CHEMICAL PROCESS FOR PREPARING PHENYLPIPERIDINYL INDOLE DERIVATIVES
  [FR] PROCÉDÉ CHIMIQUE POUR LA PRÉPARATION DE DÉRIVÉS DE PHÉNYLPIPÉRIDINYL INDOLE

  摘要：

  公开号：

  WO2020016749A3

文献信息

• HETEROARYLAMIDE LOWER CARBOXYLIC ACID DERIVATIVE
  申请人：Machinaga Nobuo

  公开号：US20090324581A1

  公开（公告）日：2009-12-31

  To provide a novel compound which has S1P receptor agonistic activity, exhibits excellent immunosuppressing effect, gives less adverse side effects, and can be orally administered. The invention provides a compound represented by general formula (I) (wherein A is a single bond, —O—, or —CH 2 —; R 1 represents a hydrogen atom or a C 1 -C 6 alkyl group, and V represents any one group selected from among the following groups (1) to (3): (1) -G 1 -, (2) -G 2 -N(R 2 )-G 3 -, and (3) a group represented by formula 2, wherein each of Z 1 and Z 2 represents a hydrogen atom or a C 1 -C 6 alkyl group, Z 3 represents a hydrogen or the like, Q represents —CH 2 —O— or the like, and Y represents a group represented by formula 3, a salt thereof, or a solvate thereof.

  提供一种新型化合物，具有S1P受体激动活性，表现出优异的免疫抑制效果，产生较少的不良副作用，并可口服。本发明提供一种由通式（I）表示的化合物（其中A是单键，-O-或-CH2-；R1表示氢原子或C1-C6烷基基团，V表示从以下组（1）至（3）中选择的任一组：（1）-G1-，（2）-G2-N（R2）-G3-，以及（3）由式2表示的组，其中Z1和Z2分别表示氢原子或C1-C6烷基基团，Z3表示氢或类似物，Q表示-CH2-O-或类似物，Y表示由式3表示的基团，其盐或溶剂化物。
• Chemical process for preparing phenylpiperidinyl indole derivatives
  申请人：NOVARTIS AG

  公开号：US11208398B2

  公开（公告）日：2021-12-28

  The present invention relates to a method of synthesizing a compound of formula (I) also referred to as 4-((2S,4S)-(4-ethoxy-1-((5-methoxy-7-methyl-1H-indol-4-yl)methyl)piperidin-2-yl))benzoic acid, or a pharmaceutically acceptable salt thereof, and/or intermediates thereof, their use as pharmaceuticals and pharmaceutical compositions and the use of intermediates for preparing a compound of formula (I), or a pharmaceutically acceptable salt thereof.

  本发明涉及一种合成也称为 4-((2S,4S)-(4-乙氧基-1-((5-甲氧基-7-甲基-1H-吲哚-4-基)甲基)哌啶-2-基))苯甲酸或其药学上可接受的盐和/或其中间体的式 (I) 化合物的方法、它们作为药物和药物组合物的用途以及制备式 (I) 化合物或其药学上可接受的盐的中间体的用途。
• CHEMICAL PROCESS FOR PREPARING PHENYLPIPERIDINYL INDOLE DERIVATIVES
  申请人：NOVARTIS AG

  公开号：US20220169630A1

  公开（公告）日：2022-06-02

  The present invention relates to a method of synthesizing a compound of formula (I) also referred to as 4-(((2S,4S)-(4-ethoxy-1-(((5-methoxy-7-methyl-1H-indol-4-yl)methyl)piperidin-2-yl))benzoic acid, or a pharmaceutically acceptable salt thereof, and/or intermediates thereof, their use as pharmaceuticals and pharmaceutical compositions and the use of intermediates for preparing a compound of formula (I), or a pharmaceutically acceptable salt thereof.
• [EN] CHEMICAL PROCESS FOR PREPARING PHENYLPIPERIDINYL INDOLE DERIVATIVES<br/>[FR] PROCÉDÉ CHIMIQUE POUR LA PRÉPARATION DE DÉRIVÉS DE PHÉNYLPIPÉRIDINYL INDOLE
  申请人：NOVARTIS AG

  公开号：WO2020016749A3

  公开（公告）日：2020-03-05
• Discovery of a small molecule RXFP3/4 agonist that increases food intake in rats upon acute central administration
  作者：Brian DeChristopher、Soo-Hee Park、Linh Vong、Derek Bamford、Hyun-Hee Cho、Rohit Duvadie、Allison Fedolak、Christopher Hogan、Toshiyuki Honda、Pramod Pandey、Olga Rozhitskaya、Liansheng Su、Elizabeth Tomlinson、Iain Wallace

  DOI：10.1016/j.bmcl.2019.02.013

  日期：2019.4

  The relaxin family peptide receptors have been implicated in numerous physiological processes including energy homeostasis, cardiac function, wound healing, and reproductive function. Two family members, RXFP3 and RXFP4, are class A GPCRs with endogenous peptide ligands (relaxin-3 and insulin-like peptide 5 (INSL5), respectively). Polymorphisms in relaxin-3 and RXFP3 have been associated with obesity, diabetes, and hyper-cholesterolemia. Moreover, central administration of relaxin-3 in rats has been shown to increase food intake, leading to body weight gain. Reported RXFP3 and RXFP4 ligands have been restricted to peptides (both endogenous and synthetic) as well as a low molecular weight positive allosteric modulator requiring a non-endogenous orthosteric ligand. Described here is the discovery of the first potent low molecular weight dual agonists of RXFP3/4. The scaffold identified is competitive with a chimeric relaxin-3/INSL5 peptide for RXFP3 binding, elicits similar downstream signaling as relaxin-3, and increases food intake in rats following acute central administration. This is the first report of small molecule RXFP3/4 agonism.