methyl 3-(5-bromo-1-methyl-1H-indol-3-yl)propanoate | 1403228-94-3

• 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: methyl 3-(5-bromo-1-methyl-1H-indol-3-yl)propanoate
• 英文别名: Methyl 3-(5-bromo-1-methylindol-3-yl)propanoate；methyl 3-(5-bromo-1-methylindol-3-yl)propanoate
• CAS: 1403228-94-3
• 化学式: C₁₃H₁₄BrNO₂
• 分子量: 296.164
• InChiKey: BVACTTKPSNCDBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  methyl 3-(5-bromo-1-methyl-1H-indol-3-yl)propanoate 在 甲醇 、 sodium tetrahydroborate 、 正丁基锂 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 lithium hydroxide 、 dysprosium(III) trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 63.67h， 生成 2-bromo-12-((3-chlorophenyl)amino)-5-methyl-5,6,7,9,10,11-hexahydro-8H-6,9-methanocycloocta[b]indol-8-one
  参考文献：
  名称：

  阳离子触发的Domino Aza-Piancatelli重排/ Friedel-Crafts吲哚系呋喃基醇的烷基化反应，从而获得环辛基[ b ]吲哚生物碱核心

  摘要：

  开发了一种通过aza-Piancatelli重排/ Friedel-Crafts烷基化级联反应桥接多环[ b ]吲哚酮的多米诺方法。这种转化是通过在路易斯酸存在下使吲哚链连接的2-呋喃基甲醇与取代的苯胺反应以引发aza-Piancatelli重排，然后进行原位分子内Friedel-Crafts烷基化反应以在一个罐中获得桥联的四环骨架而实现的。

  DOI：

  10.1021/acs.orglett.0c03155
• 作为产物：
  描述：

  5-溴吲哚 在 氯化锆(IV) 、 potassium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 methyl 3-(5-bromo-1-methyl-1H-indol-3-yl)propanoate
  参考文献：
  名称：

  Indole-Derived Psammaplin A Analogues as Epigenetic Modulators with Multiple Inhibitory Activities

  摘要：

  A SAR study has been carried out around a modified scaffold of the natural product psammaplin A obtained by replacing the o-bromophenol unit by an indole ring. A series of indole psammaplin A constructs were generated in a short synthetic sequence that starts with the functionalization of the C3 indole position with in situ generated nitrosoacrylate, and this is followed by protection of the beta-indole-alpha-oximinoesters, saponification, condensation with symmetrical diamines, and deprotection. Biochemical and cellular characterization using U937 and MCF-7 cells confirmed that many of these analogues displayed more potent actitivies than the parent natural product. Moreover, in addition to the reported HDAC and DNMT dual epigenetic inhibitory profile of the parent compound, some analogues, notably 4a (UVI5008), also inhibited the NAD(+)-dependent SIRT deacetylase enzymes. The SAR study provides structural insights into the mechanism of action of these multiple epigenetic ligands and paves the way for additional structural exploration to optimize their pharmacological profiles. Because of their multi(epi)target features and their action in ex vivo samples, the indole-based psammaplin A derivatives are attractive molecules for the modulation of epigenetic disorders.

  DOI：

  10.1021/jm300618u

文献信息

• Cation Triggered Domino Aza-Piancatelli Rearrangement/Friedel–Crafts Alkylation of Indole-Tethered Furfuyl Alcohols to Access Cycloocta[<i>b</i>]indole Core of Alkaloids
  作者：Nagarjuna Reddy Vonteddu、Pooja R. Solanke、Kiranmai Nayani、Srivari Chandrasekhar

  DOI：10.1021/acs.orglett.0c03155

  日期：2020.11.6

  A domino approach to bridged cycloocta[b]indolone through a cascade of aza-Piancatelli rearrangement/Friedel–Crafts alkylation is developed. This transformation has been realized by reaction of an indole-tethered 2-furylcarbinol and substituted aniline in the presence of a Lewis acid to initiate aza-Piancatelli rearrangement followed by an in situ intramolecular Friedel–Crafts alkylation to access bridged

  开发了一种通过aza-Piancatelli重排/ Friedel-Crafts烷基化级联反应桥接多环[ b ]吲哚酮的多米诺方法。这种转化是通过在路易斯酸存在下使吲哚链连接的2-呋喃基甲醇与取代的苯胺反应以引发aza-Piancatelli重排，然后进行原位分子内Friedel-Crafts烷基化反应以在一个罐中获得桥联的四环骨架而实现的。
• Indole-Derived Psammaplin A Analogues as Epigenetic Modulators with Multiple Inhibitory Activities
  作者：Raquel Pereira、Rosaria Benedetti、Santiago Pérez-Rodríguez、Angela Nebbioso、José García-Rodríguez、Vincenzo Carafa、Mayra Stuhldreier、Mariarosaria Conte、Fátima Rodríguez-Barrios、Hendrik G. Stunnenberg、Hinrich Gronemeyer、Lucia Altucci、Ángel R. de Lera

  DOI：10.1021/jm300618u

  日期：2012.11.26

  A SAR study has been carried out around a modified scaffold of the natural product psammaplin A obtained by replacing the o-bromophenol unit by an indole ring. A series of indole psammaplin A constructs were generated in a short synthetic sequence that starts with the functionalization of the C3 indole position with in situ generated nitrosoacrylate, and this is followed by protection of the beta-indole-alpha-oximinoesters, saponification, condensation with symmetrical diamines, and deprotection. Biochemical and cellular characterization using U937 and MCF-7 cells confirmed that many of these analogues displayed more potent actitivies than the parent natural product. Moreover, in addition to the reported HDAC and DNMT dual epigenetic inhibitory profile of the parent compound, some analogues, notably 4a (UVI5008), also inhibited the NAD(+)-dependent SIRT deacetylase enzymes. The SAR study provides structural insights into the mechanism of action of these multiple epigenetic ligands and paves the way for additional structural exploration to optimize their pharmacological profiles. Because of their multi(epi)target features and their action in ex vivo samples, the indole-based psammaplin A derivatives are attractive molecules for the modulation of epigenetic disorders.