7-bromo-1-(4-methoxysulfonyl)-6-azaindole | 1265023-89-9

• 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: 7-bromo-1-(4-methoxysulfonyl)-6-azaindole
• 英文别名: 7-bromo-1-(4-methoxybenzenesulfonyl)-1H-pyrrolo[2,3-c]pyridine；7-bromo-1-(4-methoxyphenylsulfonyl)-1H-pyrrolo[2,3-c]pyridine；7-bromo-1-(4-methoxyphenyl)sulfonylpyrrolo[2,3-c]pyridine
• CAS: 1265023-89-9
• 化学式: C₁₄H₁₁BrN₂O₃S
• 分子量: 367.223
• InChiKey: SOEWHZGOSNZBJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-bromo-1-(4-methoxysulfonyl)-6-azaindole 、 对氨基苯酚 在 吡啶 作用下， 以15%的产率得到7-(4-hydroxyanilino)-1-(4-methoxybenzenesulfonyl)-6-azaindole
  参考文献：
  名称：

  Furanylazaindoles: Potent Anticancer Agents in Vitro and in Vivo

  摘要：

  Preliminary biological data on 7-anilino-6-azaindoles (8-11) suggested that hydrophobic substituents at C7 contribute to enhancement of antiproliferative activity. A novel series of 7-aryl-6-azaindole-l-benzenesulfonamides (12-22) were developed and showed improved cytotoxicity compared to ABT7S1 (5). The conversion of C7 phenyl rings into C7 heterocycles led to a remarkable improvement of antiproliferative activity. Among all the synthetic products, 7-(2-furanyI)-1-(4methoxybenzenesulfonyl)-6-azaindole (21) exhibited the most potent anticancer activity against KB, HT29, MKN45, and H460 cancer cell lines with IC50 values of 21.1, 32.0, 27.5, and 40.0 nM, respectively. Bioassays indicated that 21 not only inhibits tubulin polymerization by binding to tubulin at the colchicine binding site but also arrests the cell cycle at the G2/M phase with slight arrest at the sub-G1 phase. Compound 21 also functions as a vascular disrupting agent and dose-dependently inhibits tumor growth without significant change of body weight in an HT29 xenograft mouse model. Taken together, compound 21 has potential for further development as a novel class of anticancer agents.

  DOI：

  10.1021/jm4011115
• 作为产物：
  描述：

  2-溴-3-硝基吡啶 在 四丁基硫酸氢铵 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 7-bromo-1-(4-methoxysulfonyl)-6-azaindole
  参考文献：
  名称：

  [EN] ARYL SUBSTITUTED SULFONAMIDE COMPOUNDS AND THEIR USE AS ANTICANCER AGENTS
  [FR] COMPOSÉS DE SULFONAMIDE SUBSTITUÉS PAR UN ARYLE ET LEUR UTILISATION EN TANT QU'AGENTS ANTICANCÉREUX

  摘要：

  公开号：

  WO2011019634A3

文献信息

• [EN] SYNTHESIS OF GLYCOLS VIA TRANSFER HYDROGENATION OF ALPHA-FUNCTIONAL ESTERS WITH ALCOHOLS<br/>[FR] SYNTHÈSE DE GLYCOLS AU MOYEN D'UNE HYDROGÉNATION PAR TRANSFERT D'ESTERS ALPHA-FONCTIONNELS AVEC DES ALCOOLS
  申请人：EASTMAN CHEM CO

  公开号：WO2019027948A1

  公开（公告）日：2019-02-07

  A transfer hydrogenation process for forming vicinal diols by hydrogenating 1,2-dioxygenated organic compounds using alcohols as the reducing agent instead of the traditional H2 gas. The transfer hydrogenation is carried out under milder conditions of temperature and pressure than is typical for ester hydrogenation with H2. The milder conditions of operation provide benefits, such as lower operating and capital costs for industrial scale production as well as savings in product purification due to the avoidance of by-products from exposure of reaction mixtures and products to high temperatures.

  一种通过使用醇作为还原剂而不是传统的氢气，在较温和的温度和压力条件下，通过氢化1,2-二氧化有机化合物形成邻二醇的转移加氢过程。操作的较温和条件提供了诸如工业规模生产的较低运营和资本成本以及由于避免将反应混合物和产物暴露在高温下而节省产品纯化成本的好处。
• [EN] LIPID ANALOGS AND LIPOSOMES COMPRISING SAME<br/>[FR] ANALOGUES LIPIDIQUES ET LIPOSOMES LES COMPRENANT
  申请人：YEDA RES & DEV

  公开号：WO2017109784A1

  公开（公告）日：2017-06-29

  A polymeric compound is disclosed herein, having the general formula I: wherein m, n, X, Y, Z and L are as defined herein. Further disclosed herein are lipid bilayers comprising at least one bilayer-forming lipid and the aforementioned polymeric compound, and liposomes comprising such a bilayer, as well as methods, uses and compositions utilizing such bilayers and/or liposomes for reducing a friction coefficient of a surface and/or for inhibiting biofilm formation.

  本公开揭示了一种具有一般公式I的聚合物化合物：其中m、n、X、Y、Z和L如本文所定义。本公开还揭示了包含至少一种形成双分子层的脂质和上述聚合物化合物的脂质双分子层，以及包含这种双分子层的脂质体，以及利用这种双分子层和/或脂质体来降低表面的摩擦系数和/或抑制生物膜形成的方法、用途和组合物。
• PROCESS FOR PREPARING 6-HYDROXYCAPROIC ESTERS
  申请人：Pinkos Rolf

  公开号：US20110015429A1

  公开（公告）日：2011-01-20

  The present application relates to an improved process for preparing 6-hydroxycaproic esters from the by-product mixtures which are obtained in the oxidation of cyclohexane to cyclohexanol and cyclohexanone with oxygen or oxygen-comprising gas mixtures.

  本申请涉及一种改进的工艺，用于从在将环己烷氧化为环己醇和环己酮时获得的副产物混合物中制备6-羟基己酸酯。
• HAFNIUM COMPLEXES OF HETEROCYCLIC ORGANIC LIGANDS
  申请人：Vosejpka Paul C.

  公开号：US20090069567A1

  公开（公告）日：2009-03-12

  Hafnium complexes of heterocyclic organic ligands having improved solubility in aliphatic hydrocarbon solvents and their use as components of olefin polymerization catalysts as well as novel syntheses of component parts thereof are disclosed.

  本发明揭示了具有改善的溶解性的杂环有机配体的铪配合物，在脂肪烃溶剂中的使用作为烯烃聚合催化剂的组分，以及其组分部分的新合成方法。
• Methods of Synthesizing Pharmaceutical Salts of a Factor Xa Inhibitor
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US20140046071A1

  公开（公告）日：2014-02-13

  Novel methods of preparing a compound of Formula I which is an inhibitor of Factor Xa and its maleate salt, are described herein.

  本文描述了制备化合物I及其马来酸盐的新方法，该化合物是因子Xa的抑制剂。