1-(4-bromophenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine | 477872-36-9

• 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: 1-(4-bromophenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine
• 英文别名: 1-[(4-bromophenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine；1-(4-bromophenyl)sulfonylpyrrolo[2,3-b]pyridine
• CAS: 477872-36-9
• 化学式: C₁₃H₉BrN₂O₂S
• 分子量: 337.197
• InChiKey: YYSITIVBKPCOSW-UHFFFAOYSA-N

物化性质

• 沸点：
  500.9±56.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  60.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 palladium diacetate 、 碳酸氢钠 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Azaindolylsulfonamides, with a More Selective Inhibitory Effect on Histone Deacetylase 6 Activity, Exhibit Antitumor Activity in Colorectal Cancer HCT116 Cells

  摘要：

  A series of indolylsulfonylcinnamic hydroxamates has been synthesized. Compound 12, (E)-3-(3-((1H-pyrrolo[2,3-b]pyridin-1-yl)sulfonyl)phenyl)-N-hydroxyacrylamide, which has a 7-azaindole core cap, was shown to have antiproliferative activity against KB, H460, PC3, HSC-3, HONE-1, A549, MCF-7, TSGH, MKN45, HT29, and HCT116 human cancer cell lines. Pharmacological studies indicated that 12 functions as a potent HDAC inhibitor with an IC50 value of 0.1 mu M. It is highly selective for histone deacetylase 6 (HDAC6) and is 60-fold more active than against HDAC1 and 223-fold more active than against HDAC2. It has a good pharmacokinetic profile with oral bioavailability of 33%. In in vivo efficacy evaluations in colorectal HCT116 xenografts, compound 12 suppresses tumor growth more effectively than SAHA (1, N-hydroxy-N'-phenyloctanediamide) and is therefore seen as a suitable candidate for further investigation.

  DOI：

  10.1021/jm401899x
• 作为产物：
  描述：

  7-氮杂吲哚 、 4-溴苯磺酰氯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以69%的产率得到1-(4-bromophenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine
  参考文献：
  名称：

  1 H-吡咯并[2,3-b]吡啶（7-氮杂吲哚）的新磺酰胺和氨基甲酸酯衍生物的合成和生物活性评估

  摘要：

  摘要 报道了一系列新的7-氮杂吲哚磺酰胺和氨基甲酸酯衍生物的合成及其抗TMV和抗氧化活性的评估。通过IR，1 H和13 C NMR，质量和HRMS光谱分析对它们的化学结构进行了表征。生物测定表明，化合物4-硝基苯基1H-吡咯并[2,3-b]吡啶-1-羧酸（9g）和4-硝基苄基1H-吡咯并[2,3-b]吡啶-1-羧酸（9h）对烟草花叶病毒和自由基的提取具有很高的抑制作用。 图形概要

  DOI：

  10.1007/s11164-016-2547-2

文献信息

• Regioselective C–H sulfenylation of <i>N</i>-sulfonyl protected 7-azaindoles promoted by TBAI: a rapid synthesis of 3-thio-7-azaindoles
  作者：Jingyan Hu、Xiaoming Ji、Shuai Hao、Mingqin Zhao、Miao Lai、Tianbao Ren、Gaolei Xi、Erbin Wang、Juanjuan Wang、Zhiyong Wu

  DOI：10.1039/d0ra06635d

  日期：——

  This paper describes the regioselective C-3 sulfenylation of N-sulfonyl protected 7-azaindoles with sulfonyl chlorides. In this transformation, dual roles of TBAI serving as both promoter and desulfonylation reagent have been demonstrated. The reaction proceeded smoothly under simple conditions to afford 3-thio-7-azaindoles in moderate to good yields with broad substrate scopes. This protocol refrains

  本文描述了用磺酰氯对N-磺酰基保护的 7-氮杂吲哚进行区域选择性 C-3 亚磺酰化。在这种转化中，TBAI 作为促进剂和脱磺酰化试剂的双重作用已经得到证实。该反应在简单的条件下顺利进行，以中等至良好的收率得到具有广泛底物范围的3-硫代-7-氮杂吲哚。该协议避免使用过渡金属催化剂、强氧化剂或碱，并显示其在有机合成中的实用合成价值。
• Synthesis and evaluation of biological activities of new sulfonamide and carbamate derivatives of 1H-pyrrolo[2,3-b]pyridine (7-azaindole)
  作者：H. Sudhamani、S. K. Thaslim Basha、S. Muni Chandra Reddy、B. Sreedhar、S. Adam、C. Naga Raju

  DOI：10.1007/s11164-016-2547-2

  日期：2016.10

  Abstract Synthesis of a new series of sulfonamide and carbamate derivatives of 7-azaindole and evaluation of their anti-TMV and anti-oxidant activities are reported. Their chemical structures were characterized by IR, 1H and 13C NMR, mass and HRMS spectral analysis. The biological assay revealed that the compounds 4-nitrophenyl 1H-pyrrolo[2,3-b]pyridine-1-carboxylate (9g) and 4-nitrobenzyl 1H-pyrrolo[2

  摘要 报道了一系列新的7-氮杂吲哚磺酰胺和氨基甲酸酯衍生物的合成及其抗TMV和抗氧化活性的评估。通过IR，1 H和13 C NMR，质量和HRMS光谱分析对它们的化学结构进行了表征。生物测定表明，化合物4-硝基苯基1H-吡咯并[2,3-b]吡啶-1-羧酸（9g）和4-硝基苄基1H-吡咯并[2,3-b]吡啶-1-羧酸（9h）对烟草花叶病毒和自由基的提取具有很高的抑制作用。 图形概要
• Azaindolylsulfonamides, with a More Selective Inhibitory Effect on Histone Deacetylase 6 Activity, Exhibit Antitumor Activity in Colorectal Cancer HCT116 Cells
  作者：Hsueh-Yun Lee、An-Chi Tsai、Mei-Chuan Chen、Po-Jung Shen、Yun-Ching Cheng、Ching-Chuan Kuo、Shiow-Lin Pan、Yi-Min Liu、Jin-Fen Liu、Teng-Kuang Yeh、Jing-Chi Wang、Chi-Yen Chang、Jang-Yang Chang、Jing-Ping Liou

  DOI：10.1021/jm401899x

  日期：2014.5.22

  A series of indolylsulfonylcinnamic hydroxamates has been synthesized. Compound 12, (E)-3-(3-((1H-pyrrolo[2,3-b]pyridin-1-yl)sulfonyl)phenyl)-N-hydroxyacrylamide, which has a 7-azaindole core cap, was shown to have antiproliferative activity against KB, H460, PC3, HSC-3, HONE-1, A549, MCF-7, TSGH, MKN45, HT29, and HCT116 human cancer cell lines. Pharmacological studies indicated that 12 functions as a potent HDAC inhibitor with an IC50 value of 0.1 mu M. It is highly selective for histone deacetylase 6 (HDAC6) and is 60-fold more active than against HDAC1 and 223-fold more active than against HDAC2. It has a good pharmacokinetic profile with oral bioavailability of 33%. In in vivo efficacy evaluations in colorectal HCT116 xenografts, compound 12 suppresses tumor growth more effectively than SAHA (1, N-hydroxy-N'-phenyloctanediamide) and is therefore seen as a suitable candidate for further investigation.