4-bromo-1-methyl-1H-indole-2-carboxylic acid methyl ester | 167478-92-4

• 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: 4-bromo-1-methyl-1H-indole-2-carboxylic acid methyl ester
• 英文别名: methyl 4-bromo-1-methylindole-2-carboxylate；methyl 4-bromo-1-methyl-1H-indole-2-carboxylate；Methyl 4-bromo-1-methyl-2-indolecarboxylate
• CAS: 167478-92-4
• 化学式: C₁₁H₁₀BrNO₂
• 分子量: 268.11
• InChiKey: OIMNSVYNDCDFHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  83-84 °C
• 沸点：
  373.0±22.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-1-methyl-1H-indole-2-carboxylic acid methyl ester 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以95%的产率得到4-bromo-1-methyl-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Drug Design, in Vitro Pharmacology, and Structure−Activity Relationships of 3-Acylamino-2-aminopropionic Acid Derivatives, a Novel Class of Partial Agonists at the Glycine Site on the N-Methyl-d-aspartate (NMDA) Receptor Complex

  摘要：

  Retaining agonistic activity at the glycine coagonist site of the NMDA receptor in molecules derived from glycine or D-serine has proven to be difficult because in the vicinity of the alpha-amino acid group little substitution is tolerated. We have solved this problem by replacing the hydroxy group of D-serine with an amido group, thus keeping the hydrogen donor function and allowing For further substitution and exploration of the adjacent space. Heterocyclic substitutions resulted in a series of 3-acylamino-2-aminopropionic acid derivatives, with high affinities in a binding assay for the glycine site. In a functional assay assessing the activation of the glycine site, these compounds displayed a wide range of intrinsic efficacies, from antagonism to a high degree of partial agonism. Structure-activity relationships reveal that lipophilic substituents, presumably filling an additional hydrophobic pocket, are accepted by the glycine site, provided that they are separated from the alpha-amino acid group by a short linker.

  DOI：

  10.1021/jm900363q
• 作为产物：
  描述：

  methyl 2-azido-3-(2-bromophenyl)propenoate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 3.0h， 生成 4-bromo-1-methyl-1H-indole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  新型喹啉醌抗肿瘤药：使用NAD（P）H：醌氧化还原酶（NQO1）进行结构代谢研究。

  摘要：

  合成了一系列带有各种取代基的喹啉醌，研究了取代基对重组人NAD（P）H：醌氧化还原酶（hNQO1）代谢的影响。选择了一系列喹啉醌进行研究，并经过专门设计以探测C-2处芳基取代基的作用。使用三种常规策略制备了28种喹啉醌2-29，它们分别是：钯（0）催化的2-氯喹啉偶联，经典的弗里德兰德合成和对乙酰苯胺的双维尔斯迈尔反应。还制备了异喹啉醌30的一个实例，并通过循环伏安法测量了醌的还原电势。对于在喹啉2位的简单取代基R（2），对于R（2）= Cl>，由hNQO1引起的醌代谢速率降低 H大约Me> Ph。对于芳族取代基，对于R（2）＝ Ph> 1-萘基> 2-萘基> 4-联苯，还原速率显着降低。含有吡啶取代基的化合物是最好的底物，且比率随着R（2）= 4-吡啶基> 3-吡啶基> 2-吡啶基> 4-甲基-2-吡啶基> 5-甲基-2-吡啶基而降低。在代表醌中还研究了对人结肠癌细胞的毒性，该细胞既无可

  DOI：

  10.1016/j.bmc.2004.01.021

文献信息

• 4-Oxo-3,5-dihydro-4H-pyridazino[4,5-b]-indole-1-acetamide derivatives, their preparation and their application in therapy
  申请人：Sanofi-Synthelabo

  公开号：US06262045B1

  公开（公告）日：2001-07-17

  Compounds of general formula (I) in which X represents a hydrogen or halogen atom or a methyl, methoxy or phenylmethoxy group, Y represents a hydrogen atom, 1 or 2 halogen atoms or a hydroxyl, methoxy, nitro or methyl group, R1 represents a hydrogen atom or a (C1-C4)alkyl group, R2 and R3 each represent a hydrogen atom, a (C1-C4)alkyl group or a phenylmethyl group or else R2 and R3 form, with the nitrogen atom which carries them, an azetidinyl, pyrrolidinyl, 3-ethoxypyrrolidinyl, piperidinyl, morpholinyl, 4-methylpiperazinyl or 1,3-thiazolidinyl group. Application in therapeutics.

  通式（I）的化合物中，其中X代表氢或卤素原子或甲基、甲氧基或苯甲氧基基团，Y代表氢原子、1或2个卤素原子或羟基、甲氧基、硝基或甲基基团，R1代表氢原子或（C1-C4）烷基基团，R2和R3各自代表氢原子、（C1-C4）烷基基团或苯甲基基团，或者R2和R3与携带它们的氮原子形成氮杂环丙氧基环、吡咯环、3-乙氧基吡咯环、哌啶环、吗啉环、4-甲基哌嗪环或1,3-噻唑烷基团。在治疗学中的应用。
• Visible-Light-Induced Direct Photocatalytic Carboxylation of Indoles with CBr₄/MeOH
  作者：Qing-Qing Yang、Marianna Marchini、Wen-Jing Xiao、Paola Ceroni、Marco Bandini

  DOI：10.1002/chem.201503787

  日期：2015.12.7

  Photocatalysis enables the cascade reactions of indoles and CBr4 in MeOH through a C(sp2)H functionalization/methanolysis sequence. The title reaction provides an efficient access to indole 2‐ and 3‐carboxylates in a single operation (no preinstallation of protecting as well as directing groups was required) with good yields under mild reaction conditions.

  光催化通过C（sp 2）H官能化/甲烷分解序列实现吲哚和CBr 4在MeOH中的级联反应。标题反应可在温和的反应条件下以高收率在一次操作中高效获得吲哚2和3-羧酸酯（无需预先安装保护基团和导向基团）。
• Indole Compound and Use Thereof
  申请人：Takeuchi Jun

  公开号：US20080188532A1

  公开（公告）日：2008-08-07

  The present invention relates to a compound represented by the formula (I), wherein all symbols are as defined in the description, a salt thereof, a solvate thereof, or a prodrug thereof, which has a leukotriene receptor antagonistic activity which is expected to be more effective than those of the leukotriene receptor antagonists currently used in clinical trials. Therefore, it is useful as an agent for the prevention and/or treatment of a leukotriene-mediated disease such as a respiratory diseases such as bronchial asthma, chronic obstructive pulmonary disease, pulmonary emphysema, chronic bronchitis, pneumonia (e.g. interstitial pneumonia etc.), severe acute respiratory syndrome (SARS), acute respiratory distress syndrome (ARDS), allergic rhinitis, sinusitis (e.g. acute sinusitis, chronic sinusitis, etc.), or the like, or as an expectorant or an antiitussive.

  本发明涉及一种化合物，其表示为公式（I），其中所有符号如描述中所定义，其盐，溶剂化物或前药，具有期望比目前在临床试验中使用的白三烯受体拮抗剂更有效的白三烯受体拮抗作用。因此，它可用作预防和/或治疗白三烯介导的疾病，例如呼吸系统疾病，如支气管哮喘，慢性阻塞性肺疾病，肺气肿，慢性支气管炎，肺炎（例如间质性肺炎等），严重急性呼吸综合征（SARS），急性呼吸窘迫综合征（ARDS），过敏性鼻炎，鼻窦炎（例如急性鼻窦炎，慢性鼻窦炎等），或作为祛痰剂或止咳剂。
• INDOLE COMPOUND AND USE THEREOF
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1852420A1

  公开（公告）日：2007-11-07

  The present invention relates to a compound represented by the formula (I), wherein all symbols are as defined in the description, a salt thereof a solvate thereof, or a prodrug thereof, which has a leukotriene receptor antagonistic activity which is expected to be more effective than those of the leukotriene receptor antagonists currently used in clinical trials. Therefore, it is useful as an agent for the prevention and/or treatment of a leukotriene-mediated disease such as a respiratory diseases such as bronchial asthma, chronic obstructive pulmonary disease, pulmonary emphysema, chronic bronchitis, pneumonia (e.g. interstitial pneumonia etc.), severe acute respiratory syndrome (SARS), acute respiratory distress syndrome (ARDS), allergic rhinitis, sinusitis (e.g. acute sinusitis, chronic sinusitis, etc.), or the like, or as an expectorant or an antitussive.

  本发明涉及一种由式 (I) 代表的化合物、 本发明涉及一种由式（I）表示的化合物，其中所有符号如描述中所定义，它的盐，它的溶解物，或它的原药，它具有白三烯受体拮抗活性，预计比目前用于临床试验的白三烯受体拮抗剂更有效。因此，它可用作预防和/或治疗白三烯介导的疾病的药物，如支气管哮喘、慢性阻塞性肺病、肺气肿、慢性支气管炎、肺炎（如间质性肺炎等）等呼吸系统疾病。如间质性肺炎等）、严重急性呼吸系统综合征（SARS）、急性呼吸窘迫综合征（ARDS）、过敏性鼻炎、鼻窦炎（如急性鼻窦炎、慢性鼻窦炎等）等，或作为祛痰剂或抗鼻炎药。
• WO2008/57209
  申请人：——

  公开号：——

  公开（公告）日：——