1-(4-bromophenylsulfonyl)-1H-indole

• 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: 1-(4-bromophenylsulfonyl)-1H-indole
• 英文别名: p-bromophenyl indol-1-yl sulfone；4-bromo-benzenesulfonylindole；1-[(4-bromophenyl)sulfonyl]-1H-indole；1-(4-bromophenyl)sulfonylindole
• 化学式: C₁₄H₁₀BrNO₂S
• 分子量: 336.209
• InChiKey: ZJXVKDOITQFQHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenylsulfonyl)-1H-indole 在 tin(II) chloride dihdyrate 、 palladium diacetate 、 sodium hydride 、 sodium carbonate 、 苯硫酚 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 0.08h， 生成 methyl 6-(4-(1H-indol-1-ylsulfonyl)phenyl)-1-hydroxy-1H-indole-2-carboxylate
  参考文献：
  名称：

  Synthesis of sulfonamide-containing N-hydroxyindole-2-carboxylates as inhibitors of human lactate dehydrogenase-isoform 5

  摘要：

  N-Hydroxyindole-2-carboxylates possessing sulfonamide-substituents at either position 5 or 6 were designed and synthesized. The inhibitory activities of these compounds against isoforms 1 and 5 of human lactate dehydrogenase were analysed, and K-i values of the most efficient inhibitors were determined by standard enzyme kinetic studies. Some of these compounds displayed state-of-the-art inhibitory potencies against isoform 5 (K-i values as low as 5.6 mu M) and behaved as competitive inhibitors versus both the substrate and the cofactor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.031
• 作为产物：
  描述：

  吲哚 、 4-溴苯磺酰氯 在 tetrabutylammonium hydrogensulfonate 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到1-(4-bromophenylsulfonyl)-1H-indole
  参考文献：
  名称：

  Novel Furanylarylene Arylsulfonylindolesulfonamides: Synthesis and Their Antibacterial Evaluation

  摘要：

  通过涉及溴化、链烷化、Stille 交叉偶联、还原、芳基磺酰化、氯磺酰化和缩合反应的多步合成方案，合成了一系列呋喃芳基芳基磺酰基吲哚磺酰胺。作为初步评估，我们采用两倍序列稀释法测试了这些类似物对一系列细菌菌株（如枯草杆菌、粪肠球菌、金黄色葡萄球菌、铜绿假单胞菌、大肠埃希菌和肺炎克雷伯菌）的抗菌活性。苯磺酰基苯环上未取代、溴取代或甲基取代的类似物活性较低，甲氧基和氯取代的类似物活性相对较高。研究发现，与标准链霉素相比，其中一些药物对选择性生物的活性更好。

  DOI：

  10.1248/cpb.57.591

文献信息

• Retinoid x receptor modulators
  申请人：——

  公开号：US20040167160A1

  公开（公告）日：2004-08-26

  The present invention is directed to compounds represented by Structural Formula (I) and pharmaceutically acceptable salts, solvates and hydrates thereof: (I). The invention is also directed to pharmaceutical compositions, methods of use and methods of making compounds represented by Structural Formula (I) and pharmaceutically acceptable salts, solvates and hydrates thereof.

  本发明涉及由结构式（I）表示的化合物及其药用可接受的盐、溶剂合物和水合物：（I）。该发明还涉及由结构式（I）表示的化合物及其药用可接受的盐、溶剂合物和水合物的药物组合物、使用方法和制备方法。
• New insights into the solubilization of Bodipy dyes
  作者：Song-Lin Niu、Gilles Ulrich、Pascal Retailleau、Jack Harrowfield、Raymond Ziessel

  DOI：10.1016/j.tetlet.2009.04.017

  日期：2009.7

  protection of sulfonate groups by pyrrole of indopyrrole appears efficient but the deprotection step does not offer viable routes. Conversion of the bromopyrene or iodo Bodipy compounds to sulfobetaine derivatives is feasible either by cross-coupling directly the ethynylsulfobetaine or by first cross-coupling 1-(N,N-dimethylamino)-prop-2-yne followed by quaternization of the dimethylamino residue with 1,3-propanesultone

  合成了具有各种取代基的几种Bodipy染料，这些取代基旨在改善水溶性。在不同的合成策略中，通过吲哚吡咯的吡咯保护磺酸盐基团似乎是有效的，但是脱保护步骤没有提供可行的途径。通过将乙炔基磺基甜菜碱直接交叉偶联或先将1-（N，N-二甲基氨基）-丙-2-炔进行交叉偶联，然后再将二甲基氨基残基季铵化，将溴化re或碘化的Bodipy化合物转化为磺基甜菜碱衍生物是可行的。 1,3-丙磺酸内酯。这些染料中的一些（Bodipy's和pyr）在水中可适当溶解，并且在极性溶剂和水中仍保持高荧光性。
• Triflic acid controlled successive annelation of aromatic sulfonamides: an efficient one-pot synthesis of N-sulfonyl pyrroles, indoles and carbazoles
  作者：Mohammed Abid、Liliana Teixeira、Béla Török

  DOI：10.1016/j.tetlet.2007.04.021

  日期：2007.6

  A novel one-pot synthesis of N-substituted heterocycles via successive cyclization/annelation starting from primary sulfonamides is described. This process leads directly to N-sulfonyl pyrroles, indoles and carbazoles. The selection of appropriate reactant/triflic acid ratio successfully controls the formation of the desired product.

  描述了一种从伯磺酰胺开始通过连续环化/退火来合成 N-取代杂环的新型一锅法。该过程直接生成N-磺酰基吡咯、吲哚和咔唑。选择适当的反应物/三氟甲磺酸比率成功地控制了所需产物的形成。
• Novel Furanylarylene Arylsulfonylindolesulfonamides: Synthesis and Their Antibacterial Evaluation
  作者：Chennan Ramalingan、In-Sook Lee、Young-Woo Kwak

  DOI：10.1248/cpb.57.591

  日期：——

  An array of furanylarylene arylsulfonylindolesulfonamides was synthesized through multi-step synthetic protocols involving bromination, stannylation, Stille cross coupling, reduction, arylsulfonylation, chlorosulfonylation, and condensation reactions. As a preliminary evaluation, these analogs were tested for antibacterial activity against a series of bacterial strains such as Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, and Klebsiella pneumoniae using a two-fold serial dilution assay. Whereas analogs possessing unsubstitution, bromosubstitution, or methyl substitution on the benzene ring of benzenesulfonyl group were less active/inactive, the methoxy and chloro substituted counterparts were demonstrated to be comparatively more active. A few of them were found to exhibit better activity than the standard, streptomycin against selective organisms.

  通过涉及溴化、链烷化、Stille 交叉偶联、还原、芳基磺酰化、氯磺酰化和缩合反应的多步合成方案，合成了一系列呋喃芳基芳基磺酰基吲哚磺酰胺。作为初步评估，我们采用两倍序列稀释法测试了这些类似物对一系列细菌菌株（如枯草杆菌、粪肠球菌、金黄色葡萄球菌、铜绿假单胞菌、大肠埃希菌和肺炎克雷伯菌）的抗菌活性。苯磺酰基苯环上未取代、溴取代或甲基取代的类似物活性较低，甲氧基和氯取代的类似物活性相对较高。研究发现，与标准链霉素相比，其中一些药物对选择性生物的活性更好。
• Tetrasulfonated diphosphine compounds and metal complexes thereof for
  申请人：Hoffmann-La Roche Inc.

  公开号：US05536858A1

  公开（公告）日：1996-07-16

  The invention is concerned with novel water-soluble racemic or optically active compounds of formulae ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently signify lower alkyl or lower alkoxy; m and n are 0, 1 or 2; and X signifies hydrogen, an alkali :metal, the equivalent of an earth alkali metal or an ammonium ion; with the provision that R.sup.3 is in position 4 or 5 and R.sup.4 is in position 4' or 5'. The invention is also concerned with complexes of such compounds with a metal of Group VIII. These complexes are, useful as catalysts for asymmetric hydrogenation and for enantioselective hydrogen displacement in prochiral allylic systems.

  本发明涉及公式##STR1##的新型水溶性外消旋或光学活性化合物，其中R.sup.1，R.sup.2，R.sup.3和R.sup.4独立地表示较低的烷基或较低的烷氧基；m和n为0、1或2；X表示氢，碱金属，地碱金属的当量或铵离子；但是R.sup.3在4或5位，R.sup.4在4'或5'位。本发明还涉及这些化合物与第VIII族金属的配合物。这些配合物可用作不对称氢化的催化剂以及在前手性烯丙基系统中进行对映选择性氢位移的催化剂。