glycidyl N-tosyl-4-indolyl ether | 113854-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: glycidyl N-tosyl-4-indolyl ether
• 英文别名: 1-[1-(p-toluenesulfonyl)indol-4-yloxy]-2,3-epoxypropane；1-(p-toluenesulphonyl)-4-oxiranylmethoxyindole；1-(4-methylphenyl)sulfonyl-4-(oxiran-2-ylmethoxy)indole
• CAS: 113854-62-9
• 化学式: C₁₈H₁₇NO₄S
• 分子量: 343.403
• InChiKey: ZWBIMGPLFRADGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  551.4±56.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  69.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  glycidyl N-tosyl-4-indolyl ether 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 62.0h， 生成 [3-([1'-(Adamantane-1-carbonyl)-[4,4']bipiperidinyl-1-carbonyl]-{2-hydroxy-3-[1-(toluene-4-sulfonyl)-1H-indol-4-yloxy]-propyl}-amino)-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  A Wrench-Shaped Synthetic Molecule that Modulates a Transcription Factor−Coactivator Interaction

  摘要：

  Development of synthetic molecules that provide external control over the transcription of a given gene represents a challenge in medicinal and bioorganic chemistry. Here we report design and analysis of wrenchnolol, a wrench-shaped synthetic molecule that impairs the transcription of the Her2 oncogene by disrupting association of transcription factor ESX with its coactivator Sur-2. The "jaw" part of the compound mimics the alpha-helical interface of the activation domain of ESX, and the "handle" region accepts chemical modifications for a range of analysis. A water-soluble handle permitted NMR study in aqueous solution; a biotinylated handle verified the selectivity of the interaction, and a fluorescent handle confirmed the cell permeability of the compound. The case study of wrenchnolol foreshadows the promise and the challenge of targeting protein-protein interactions in the nucleus and may lead to the development of unique synthetic modulators of gene transcription.

  DOI：

  10.1021/ja038855+
• 作为产物：
  描述：

  4-羟基吲哚 在 氢氧化钾 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 glycidyl N-tosyl-4-indolyl ether
  参考文献：
  名称：

  A Wrench-Shaped Synthetic Molecule that Modulates a Transcription Factor−Coactivator Interaction

  摘要：

  Development of synthetic molecules that provide external control over the transcription of a given gene represents a challenge in medicinal and bioorganic chemistry. Here we report design and analysis of wrenchnolol, a wrench-shaped synthetic molecule that impairs the transcription of the Her2 oncogene by disrupting association of transcription factor ESX with its coactivator Sur-2. The "jaw" part of the compound mimics the alpha-helical interface of the activation domain of ESX, and the "handle" region accepts chemical modifications for a range of analysis. A water-soluble handle permitted NMR study in aqueous solution; a biotinylated handle verified the selectivity of the interaction, and a fluorescent handle confirmed the cell permeability of the compound. The case study of wrenchnolol foreshadows the promise and the challenge of targeting protein-protein interactions in the nucleus and may lead to the development of unique synthetic modulators of gene transcription.

  DOI：

  10.1021/ja038855+
• 作为试剂：
  描述：

  4-(2,3-环氧丙氧基)吲哚 、 sodium;hydride 、 、 对甲苯磺酰氯 在 氯仿 、 Sodium sulfate-III 、 silica gel 、 Aceton-Benzol-Komplex 、 glycidyl N-tosyl-4-indolyl ether 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以to give the glycidyl N-tosyl-4-indolyl ether (compound 1b) (1.5 g, 82%) as a white solid的产率得到glycidyl N-tosyl-4-indolyl ether
  参考文献：
  名称：

  Small molecule inhibitors of HER2 expression

  摘要：

  提供了一种具有一般公式的Sur-2肽类模拟小分子抑制剂：

  公开号：

  US20050283007A1

文献信息

• Aryloxypropanolaminotetralins, a process for their preparation and
  申请人：Elf Sanofi

  公开号：US05254595A1

  公开（公告）日：1993-10-19

  Aryloxypropanolaminotetralins with beta-antagonist activity of the formula ##STR1## wherein R is hydrogen, hydroxy or methoxy and Ar is an optionally substituted aromatic or heteroaromatic group, in optically active or inactive form as well as their acid addition salts are described. A process for their preparation and pharmaceutical compositions containing the compounds of formula (i) or their pharmaceutically acceptable acid addition salts, are also described.

  具有β-阻断活性的芳氧基丙醇胺四氢萘，其通式为##STR1##，其中R为氢、羟基或甲氧基，Ar为可选择性取代的芳香或杂芳香基团，以光学活性或非活性形式及其酸加成盐被描述。它们的制备方法以及含有通式(i)化合物或其药学上可接受的酸加成盐的药物组合物也被描述。
• 4-hydroxyindole derivatives, the process for preparation thereof and
  申请人：Sanofi

  公开号：US04977274A1

  公开（公告）日：1990-12-11

  The invention relates to new 4-hydroxyindole derivatives of general formula: ##STR1## in which R represents a labile protective group and R.sub.1 can represent hydrogen, a C.sub.1 -C.sub.6 alkyl radical, a C.sub.3 -C.sub.6 cycloalkyl radical, a lower alkoxy radical, a lower hydroxyalkyl radical, a lower (lower alkoxy) alkyl radical, a phenyl radical optionally substituted with a halogen atom or a lower alkyl or lower alkoxy radical, a cyano radical, a radical of formula ##STR2## in which R.sub.2 and R.sub.3, which may be identical or different, each represent hydrogen or a lower alkyl radical, R.sub.4 represents a hydroxy group, a lower alkyl or lower alkoxy radical or a radical ##STR3## in which R.sub.2 and R.sub.3 have the same meaning as above, R.sub.5 represents a lower alkyl radical and Alk represents a single bond or a straight- or branched-chain alkylene radical having from 1 to 4 carbon atoms. The invention also relates to a process for preparing 4-(3-amino-2-hydroxypropoxy)indole derivatives from the said 4-hydroxyindole derivatives.

  该发明涉及一般式为新的4-羟基吲哚衍生物：##STR1##其中R代表一个不稳定的保护基团，R.sub.1可以代表氢，C.sub.1 -C.sub.6烷基基团，C.sub.3 -C.sub.6环烷基基团，较低的烷氧基团，较低的羟基烷基基团，较低的(较低的烷氧基)烷基基团，苯基基团，可选择地取代卤素原子或较低的烷基或较低的烷氧基团，氰基团，式中R.sub.2和R.sub.3，可以相同也可以不同，每个代表氢或较低的烷基基团，R.sub.4代表一个羟基，较低的烷基或较低的烷氧基团或一个基团##STR3##其中R.sub.2和R.sub.3的含义与上述相同，R.sub.5代表较低的烷基基团，Alk代表一个单键或具有1到4个碳原子的直链或支链烷基基团。该发明还涉及一种从所述4-羟基吲哚衍生物制备4-(3-氨基-2-羟基丙氧基)吲哚衍生物的方法。
• DESCAMPS, MARCEL;VERSTRAETEN, WALTER
  作者：DESCAMPS, MARCEL、VERSTRAETEN, WALTER

  DOI：——

  日期：——
• Nouveaux dérivés d'hydroxy-4 indole, leur procédé de préparation et leur utilisation
  申请人：SANOFI S.A.

  公开号：EP0228356B1

  公开（公告）日：1989-08-02
• Aryloxypropanolaminotétralines, un procédé pour leur préparation et composés pharmaceutiques les contenant
  申请人：ELF SANOFI

  公开号：EP0375560B1

  公开（公告）日：1993-05-12