2-bromo-1-(1-methyl-1H-indol-3-yl)ethanone | 433335-72-9

• 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: 2-bromo-1-(1-methyl-1H-indol-3-yl)ethanone
• 英文别名: 2-bromo-1-(1-methyl-1H-indole-3-yl)ethan-1-one；3-bromoacetyl-1-methylindole；1-methylindole-3-glyoxylyl bromide；2-bromo-1-(1-methyl-1H-indol-3-yl)ethan-1-one；2-bromo-1-(1-methylindol-3-yl)ethanone
• CAS: 433335-72-9
• 化学式: C₁₁H₁₀BrNO
• 分子量: 252.11
• InChiKey: CDJRALKVAHFNMJ-UHFFFAOYSA-N

物化性质

• 熔点：
  205-206 °C
• 沸点：
  366.3±17.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 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：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-1-(1-methyl-1H-indol-3-yl)ethanone 在 盐酸 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 丙酮 为溶剂， 反应 22.75h， 生成 cyclobutanecarboxylic acid [2-(1-methyl-1H-indol-3-yl)-2-oxoethyl]amide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel β-substituted indol-3-yl ethylamido melatoninergic analogues

  摘要：

  摘要：已合成一系列新的褪黑激素类似物。有趣的是，其中两种新化合物，11c和11e，虽然未显示出对褪黑激素受体的明显亲和力，但被发现是大鼠肝微粒体中脂质过氧化的强效抑制剂。特别是类似物11c比褪黑激素更好地具有抗氧化剂作用。

  DOI：

  10.1211/0022357021771869
• 作为产物：
  描述：

  1-(1-甲基-1H-吲哚-3-基)-1-乙酮 在 溴 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以70%的产率得到2-bromo-1-(1-methyl-1H-indol-3-yl)ethanone
  参考文献：
  名称：

  3-[4-(1H-Indol-3-yl)-1,3-thiazol-2-yl]-1H-pyrrolo[2,3-b]pyridines, Nortopsentin Analogues with Antiproliferative Activity

  摘要：

  我们高效合成了一系列新的去甲斑蝥素类似物，其中天然产物的咪唑环被噻唑取代，噻唑环第2位上的吲哚单元被一个7-氮杂吲哚分子取代。其中两种新的去甲斑蝥素类似物对 NCI 全部人类肿瘤细胞系（约 60 种）具有良好的抗增殖作用，其 GI50 值从低微摩尔到纳摩尔水平不等。在对人类肝癌 HepG2 细胞的研究中，这些衍生物的抗增殖作用机制是促进细胞凋亡，与质膜磷脂酰丝氨酸外化和线粒体功能障碍有关。此外，这些化合物还诱导细胞在亚 G0/G1 期进行浓度依赖性积累，同时将有活力的细胞限制在 G2/M 期。

  DOI：

  10.3390/md13041901

文献信息

• Process for the preparation of 2-substituted and 2,3-disubstituted
  申请人：Hoffmann-La Roche Inc.

  公开号：US05399712A1

  公开（公告）日：1995-03-21

  The invention relates to a process for the manufacture of substituted maleimides of the formula ##STR1## wherein R.sup.1 is alkyl, aryl or heteroaryl and R.sup.2 is hydrogen, alkyl, alkoxycarbonyl, aryl or heteroaryl, by reacting an activated glyoxylate of the formula ##STR2## wherein R.sup.1 has the above significance and X is a leaving atom or group, with an imidate of the formula ##STR3## wherein R.sup.2 has the above significance, R.sup.3 is alkyl, aryl or trialkylsilyl and Y is oxygen or sulfur, in the presence of a base and, after treating the resulting reaction product obtained in which R.sup.2 is hydrogen or alkyl with a strong base, hydrolyzing and dehydrating the resulting hydroxy-pyrrolinone of the formula ##STR4## wherein R.sup.1, R.sup.2, R.sup.3 and Y have the above significance. The substituted maleimides of formula I are pharmacologically active, for example as protein kinase C inhibitors and which a useful, for example, in the treatment and prophylaxis of inflammatory, immunological, bronchopulmonary and cardiovascular disorders, or as antiproliferative agents useful, for example, in the treatment of immune diseases and allergic disorders.

  该发明涉及一种制备式为##STR1##的取代马来酰亚胺的方法，其中R.sup.1是烷基、芳基或杂环芳基，R.sup.2是氢、烷基、烷氧羰基、芳基或杂环芳基，通过将式为##STR2##的活化的甘醇酸酯与式为##STR3##的亚胺在碱存在下反应，其中R.sup.1具有上述含义，X是一个脱离原子或基团，然后处理所得的反应产物，其中R.sup.2是氢或烷基，用强碱处理后，水解和脱水所得的式为##STR4##的羟基吡咯烷酮，其中R.sup.1、R.sup.2、R.sup.3和Y具有上述含义。式I的取代马来酰亚胺在药理学上具有活性，例如作为蛋白激酶C抑制剂，可用于治疗和预防炎症、免疫、支气管肺部和心血管疾病，或作为抗增殖剂，例如用于治疗免疫性疾病和过敏性疾病。
• Synthesis and Antitumor Activity of New Thiazole Nortopsentin Analogs
  作者：Virginia Spanò、Alessandro Attanzio、Stella Cascioferro、Anna Carbone、Alessandra Montalbano、Paola Barraja、Luisa Tesoriere、Girolamo Cirrincione、Patrizia Diana、Barbara Parrino

  DOI：10.3390/md14120226

  日期：——

  New thiazole nortopsentin analogs in which one of the two indole units was replaced by a naphthyl and/or 7-azaindolyl portion, were conveniently synthesized. Among these, three derivatives showed good antiproliferative activity, in particular against MCF7 cell line, with GI50 values in the micromolar range. Their cytotoxic effect on MCF7 cells was further investigated in order to elucidate their mode

  方便地合成了新的噻唑降冰片素类似物，其中两个吲哚单元之一被萘基和/或7-氮杂吲哚基部分取代。其中，三种衍生物显示出良好的抗增殖活性，尤其是针对MCF7细胞系，其GI50值在微摩尔范围内。为了阐明它们的作用方式，进一步研究了它们对MCF7细胞的细胞毒性作用。结果表明，这三种化合物可作为促凋亡剂，诱导活细胞向早期凋亡的明显转移，而不会发挥坏死作用。它们还引起细胞周期扰动，G0 / G1和S期细胞百分比显着下降，同时G2 / M期细胞百分比增加，并出现subG1细胞群。
• A New Methodology for Functionalization at the 3-Position of Indoles by a Combination of Boron Lewis Acid with Nitriles
  作者：Kenta Mizoi、Yu Mashima、Yuya Kawashima、Masato Takahashi、Seisuke Mimori、Masakiyo Hosokawa、Yasuoki Murakami、Hiroshi Hamana

  DOI：10.1248/cpb.c15-00157

  日期：——

  We discovered that a reagent comprising a combination of PhBCl2 and nitriles was useful for syntheses of both 3-acylindoles and 1-(1H-indol-3-yl)alkylamine from indoles. The reaction proceeded selectively at the 3-position of indoles providing 3-acylindoles in moderate to high yields on treatment with the above reagent. Furthermore, the reaction provided the corresponding amine products in moderate

  我们发现包含PhBCl 2和腈的组合的试剂可用于从吲哚合成3-酰基环吲哚和1-（1H-吲哚-3-基）烷基胺。在用上述试剂处理后，该反应在吲哚的3-位选择性地进行，从而以中等至高产率提供3-酰基环吲哚。此外，在中间体亚胺被NaBH 3 CN还原后，该反应以中等至高产率提供了相应的胺产物。这些反应在温和的条件下进行，适用于在3-位官能化的吲哚的形成。
• Synthesis and Antitumor Activity of 3-(2-Phenyl-1,3-thiazol-4-yl)-1H-indoles and 3-(2-Phenyl-1,3-thiazol-4-yl)-1H-7-azaindoles
  作者：Patrizia Diana、Anna Carbone、Paola Barraja、Alessandra Montalbano、Barbara Parrino、Alessia Lopergolo、Marzia Pennati、Nadia Zaffaroni、Girolamo Cirrincione

  DOI：10.1002/cmdc.201100078

  日期：2011.7.4

  AbstractGiven the potent antimicrobial, antiviral, and antitumor activities of many natural products, there is an increasing interest in the synthesis of new molecules based on natural compound scaffolds. Based on a 2,4‐bis(3′‐indolyl)imidazole skeleton, two new series of phenylthiazolylindoles and phenylthiazolyl‐7‐azaindoles were obtained by Hantzsch reaction between substituted phenylthioamides and the α‐bromoacetyl derivatives. Some azaindole derivatives, tested at the National Cancer Institute against a panel of ∼60 tumor cell lines derived from nine human cancer cell types, showed inhibitory effects against all cell lines investigated at micromolar to nanomolar concentrations. Two of them exhibited a high affinity for CDK1, with IC50 values of 0.41 and 0.85 μM. These promising results will set the foundation for future investigations into the development of anticancer therapies.
• [EN] P300/CBP HAT INHIBITORS<br/>[FR] INHIBITEURS DE HAT P300/CBP
  申请人：CONSTELLATION PHARMCEUTICALS INC

  公开号：WO2019161157A1

  公开（公告）日：2019-08-22

  Provided are compounds of Formula (I): and pharmaceutically acceptable salts and compositions thereof, which are useful for treating a variety of conditions associated with histone acetyltransferase (HAT).