tert-butyl 6-bromo-2-iodo-1H-indole-1-carboxylate | 1305348-43-9

• 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: tert-butyl 6-bromo-2-iodo-1H-indole-1-carboxylate
• 英文别名: 6-bromo-1-(tert-butoxycarbonyl)-2-iodo-1H-indole；tert-butyl 6-bromo-2-iodoindole-1-carboxylate
• CAS: 1305348-43-9
• 化学式: C₁₃H₁₃BrINO₂
• 分子量: 422.06
• InChiKey: WKRLGDNGBQGERN-UHFFFAOYSA-N

物化性质

• 沸点：
  434.0±48.0 °C(Predicted)
• 密度：
  1.81±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  2
• 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：

  tert-butyl 6-bromo-2-iodo-1H-indole-1-carboxylate 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium hydride 、 sodium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 8.5h， 生成 (4R)-4-methyl-6-[1-methyl-6-(1-methylpyrazol-4-yl)indol-2-yl]-1,3,4,5-tetrahydro-1,5-benzodiazepin-2-one
  参考文献：
  名称：

  [EN] THERAPEUTIC COMPOUNDS AND USES THEREOF
  [FR] COMPOSÉS THÉRAPEUTIQUES ET LEURS UTILISATIONS

  摘要：

  本发明涉及式(I)的化合物及其盐，其中A具有规范中定义的任何值，以及其组合物和用途。这些化合物可用作CBP和/或EP300的抑制剂。还包括包含式(I)的化合物或其药学上可接受的盐的药物组合物，以及在治疗各种CBP和/或EP300介导的疾病中使用这些化合物和盐的方法。

  公开号：

  WO2016055028A1
• 作为产物：
  描述：

  tert-butyl 6-bromo-2-(trimethylstannyl)-1H-indole-1-carboxylate 在 碘 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以83%的产率得到tert-butyl 6-bromo-2-iodo-1H-indole-1-carboxylate
  参考文献：
  名称：

  Exploration of larger central ring linkers in furamidine analogues: Synthesis and evaluation of their DNA binding, antiparasitic and fluorescence properties

  摘要：

  The effects of replacing the central furan ring of furamidine with indole and benzimidazole on their DNA binding affinity, antiparasitic activity and fluorescence are reported. The bis-cyanophenylindoles required to make the corresponding amidines were prepared by sequential Stille and/or Suzuki coupling reactions. The bis-cyanophenylbenzimidazoles were obtained by coupling 4-cyanobenzaldehydes with the appropriate cyano substituted phenylenediamine. The bis-nitriles were converted to the diamidines by reaction with LiN[Si(CH3)(3)](2) or by Pinner methodology. Specifically, we have prepared new series of 2,6- and 2,5-diaryl indoles (6a, b, 12 and 17a-d) and the related benzimidazoles (24, 30 and 35). The new compounds bind in the DNA minor groove in DNA AT base pair sequences and eight of the ten new analogues exhibit Delta T-m values comparable to or higher than that of furamidine. Six of ten of the new compounds exhibit lower IC50 values against Trypanosoma brucei rhodesiense (T. b. r.) and eight of ten exhibit lower IC50 values against Plasmodium falciparum (P. f.) than furamidine. Four of the ten show greater efficacy than furamidine in the rigorous T. b. r. STIB900 mouse model for African trypanosomiasis. Generally, the fluorescence properties of the new analogues are similar to that of DAPI. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.045

文献信息

• Synthetic Studies on Chartelline C: Stereoselective Construction of the Core Skeleton
  作者：Kotaro Iwasaki、Rentaro Kanno、Toshiharu Morimoto、Tohru Yamashita、Satoshi Yokoshima、Tohru Fukuyama

  DOI：10.1002/anie.201204726

  日期：2012.9.3

  What a core‐ker! The title synthesis was achieved using a route featuring an intramolecular Mitsunobu reaction of a nosyl amide, stereoselective construction of the β‐lactam, and formation of an enamide moiety by selenoxide elimination. The stereochemistry of the alkylation for the formation of the β‐lactam was controlled by a secondary hydroxy group on the ten‐membered ring. SEM=2‐(trimethylsilyl)ethoxymethyl;

  什么是核心KER！标题合成使用配有通过氧化硒消除一个硝基苯磺酰酰胺中，β内酰胺的立体结构，和烯酰胺部分的形成的分子内Mitsunobu反应的路线来实现。烷基化的β内酰胺的形成的立体化学是由十元环上的仲羟基基团来控制。SEM = 2-（三甲基甲硅烷基）乙氧基甲基; TBS =叔丁基二甲基甲硅烷基。
• Therapeutic compounds and uses thereof
  申请人：GENENTECH, INC.

  公开号：US10206931B2

  公开（公告）日：2019-02-19

  The present invention relates to compounds of formula (I): and to salts thereof, wherein A has any of the values defined in the specification, and compositions and uses thereof. The compounds are useful as inhibitors of CBP and/or EP300. Also included are pharmaceutical compositions comprising a compound of formula (I) or a pharmaceutically acceptable salt thereof, and methods of using such compounds and salts in the treatment of various CBP and/or EP300-mediated disorders.

  本发明涉及式（I）化合物： 及其盐，其中 A 具有说明书中定义的任一值，以及其组合物和用途。这些化合物可用作 CBP 和/或 EP300 的抑制剂。还包括包含式（I）化合物或其药学上可接受的盐的药物组合物，以及使用此类化合物和盐治疗各种CBP和/或EP300介导的疾病的方法。
• [EN] ANTI-BACTERIAL PYRUVATE KINASE MODULATOR COMPOUNDS, COMPOSITIONS, USES AND METHODS<br/>[FR] COMPOSÉS ANTIBACTÉRIENS MODULATEURS DE LA PYRUVATE KINASE, COMPOSITIONS, UTILISATIONS ET PROCÉDÉS ASSOCIÉS
  申请人：UNIV FRASER SIMON

  公开号：WO2016004513A8

  公开（公告）日：2016-02-25
• THERAPEUTIC COMPOUNDS AND USES THEREOF
  申请人：Genentech, Inc.

  公开号：EP3204360A1

  公开（公告）日：2017-08-16
• COMPOUNDS THAT PARTICIPATE IN COOPERATIVE BINDING AND USES THEREOF
  申请人：Revolution Medicines, Inc.

  公开号：US20200197391A1

  公开（公告）日：2020-06-25

  The disclosure features macrocyclic compounds, alone and in combination with other therapeutic agents, as well as pharmaceutical compositions and protein complexes thereof, capable of modulating biological processes including RAS and RAS-RAF inhibition, and their uses in the treatment of cancers.