3-(2-溴乙基)-2-甲基-1H-吲哚 | 56365-56-1

• 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: 3-(2-溴乙基)-2-甲基-1H-吲哚
• 英文名称: 2-Methyl-tryptophyl-bromid
• 英文别名: α-methyl-β-(β-bromoethyl)indole；3-(2-bromo-ethyl)-2-methyl-indole；3-(2-Brom-aethyl)-2-methyl-indol；3-(2-Bromoethyl)-2-methyl-1H-indole
• CAS: 56365-56-1
• 化学式: C₁₁H₁₂BrN
• 分子量: 238.127
• InChiKey: GKDOBWORFYLTIL-UHFFFAOYSA-N

物化性质

• 熔点：
  58 °C
• 沸点：
  355.0±27.0 °C(Predicted)
• 密度：
  1.450±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-(2-溴乙基)-2-甲基-1H-吲哚 在 potassium phtalimide 、 肼 作用下， 生成 1H-2-甲基-3-氨乙基吲哚
  参考文献：
  名称：

  Discovery of (2E)-3-{2-Butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5-yl}-N-hydroxyacrylamide (SB939), an Orally Active Histone Deacetylase Inhibitor with a Superior Preclinical Profile

  摘要：

  A series of 3-(1,2-disubstituted-1H-benzimidazol-5-yl)-N-hydroxyacrylamides (1) were designed and synthesized as HDAC inhibitors. Extensive SARs have been established for in vitro potency (HDAC I enzyme and COLO 205 cellular IC50), liver microsomal stability (t(1/2)), cytochrome P450 inhibitory (3A4 IC50), and clogP, among others. These parameters were fine-tuned by carefully adjusting the substituents at positions 1 and 2 of the benzimidazole ring. After comprehensive in vitro and in vivo profiling of the selected compounds, SB939 (3) was identified as a preclinical development candidate. 3 is a potent pan-HDAC inhibitor with excellent druglike properties, is highly efficacious in in vivo tumor models (HCT-116, PC-3, A2780, MV4-11, Ramos), and has high and dos-proportional oral exposures and very good ADME, safety, and pharmaceutical properties. When orally dosed to tumor-bearing mice, 3 is enriched in tumor tissue which may contribute to its potent antitumor activity and prolonged duration of action. 3 is currently being tested in phase I and phase II clinical trials.

  DOI：

  10.1021/jm2003552
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醚 、 三溴化磷 作用下， 生成 3-(2-溴乙基)-2-甲基-1H-吲哚
  参考文献：
  名称：

  Grandberg et al., Zhurnal Obshchei Khimii, 1957, vol. 27, p. 3342; engl. Ausg. S. 3378

  摘要：

  DOI：

文献信息

• Enantioselective Synthesis of Spiroindolines via Cascade Isomerization/Spirocyclization/Dearomatization Reaction
  作者：Zhiqiang Pan、Yuchang Liu、Fengchi Hu、Qinglong Liu、Wenbin Shang、Xu Ji、Chengfeng Xia

  DOI：10.1021/acs.orglett.0c00181

  日期：2020.2.21

  with 2,7-diazaspiro[4.4]nonane exists in various structurally intricate and biologically active monoterpene indole alkaloids. A catalytic asymmetric cascade enamine isomerization/spirocyclization/dearomatization succession to construct the spiroindoline was developed, which employed the indolyl dihydropyridine as a substrate under catalysis of the chiral phosphoric acid. This cascade reaction provided

  具有2,7-二氮杂螺[4.4]壬烷的螺二氢吲哚骨架存在于各种结构复杂且具有生物活性的单萜吲哚生物碱中。开发了一种催化不对称的级联烯胺异构化/螺环化/脱芳香化序列以构建螺二氢吲哚，该化合物在手性磷酸的催化下，以吲哚基二氢吡啶为底物。该级联反应以非对映选择性和对映体选择性的方式提供了各种螺二氢吲哚。
• 4-Oxospiro[benzopyran-2,4′-piperidines] as selective α1a-adrenergic receptor antagonists
  作者：Jennie B. Nerenberg、Jill M. Erb、Jeffrey M. Bergman、Stacey O'Malley、Raymond S.L. Chang、Ann L. Scott、Theodore P. Broten、Mark G. Bock

  DOI：10.1016/s0960-894x(98)00732-x

  日期：1999.1

  The 4-oxospiro[benzopyran-2,4'-piperidine] ring system is contained within potent class III antiarrhythmic agents. We highlight how these agents can be chemically transformed into a new class of potent (< 1 nM) and selective (> 25-fold) alpha 1a-receptor subtype adrenergic antagonists.

  有效的III类抗心律不齐药物包含4-氧代螺并[苯并吡喃-2,4'-哌啶]环系统。我们重点介绍如何将这些药物化学转化为一类新的有效（<1 nM）和选择性（> 25倍）α1a受体亚型肾上腺素能拮抗剂。
• Benzoylpiperidylalkylindoles
  申请人：American Hoechst Corporation

  公开号：US04046900A1

  公开（公告）日：1977-09-06

  New benzoylpiperidylalkylindoles and related compounds possessing tranquilizing, anti-hypertensive and analgesic properties and a process for the preparation thereof are described.

  本文描述了具有镇静、降压和镇痛特性的新苯甲酰哌啶基烷基吲哚和相关化合物，以及其制备过程。
• Benzoylpiperidylalkylindoles in alleviating pain
  申请人：American Hoechst Corporation

  公开号：US04110459A1

  公开（公告）日：1978-08-29

  New benzoylpiperidylalkylindoles and related compounds possessing tranquilizing, anti-hypertensive and analgesic properties and a process for the preparation thereof are described.

  本文描述了一种具有镇静、降压和镇痛性质的新苯甲酰哌啶烷基吲哚类化合物及其相关化合物，以及制备方法。
• 9-(2-(3-Indolyl)ethyl)-1-oxa-4,9-diazaspiro(5.5)undecan-3-ones
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0061333A1

  公开（公告）日：1982-09-29

  Compounds useful in the prevention and/or treatment of hypertension, congestive heart failure, arrhythmia, migraine, vasospastic disorders, and asthma are represented by the formula wherein: R, R1, R2, R3, and R4 are independently hydrogen or lower alkyl of one to four carbon atoms; and R5 and R6 are independently hydrogen, lower alkyl of one to four carbon atoms or lower alkoxy of one to four carbon atoms; and the pharmaceutically acceptable acid addition salts thereof.

  用于预防和/或治疗高血压、充血性心力衰竭、心律失常、偏头痛、血管痉挛性疾病和哮喘的化合物由式表示 其中 R、R1、R2、R3 和 R4 独立地为氢或一至四个碳原子的低级烷基；以及 R5 和 R6 独立地是氢、一至四个碳原子的低级烷基或一至四个碳原子的低级烷氧基；以及 其药学上可接受的酸加成盐。