4-bromo-2-(5-chlorothiophen-2-yl)pyridine | 1233720-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 4-bromo-2-(5-chlorothiophen-2-yl)pyridine
• 英文别名: 4-bromo-2-(5-chloro-2-thienyl)pyridine；4-Bromo-2-(5-chlorothiophen-2-yl)pyridine
• CAS: 1233720-89-2
• 化学式: C₉H₅BrClNS
• 分子量: 274.568
• InChiKey: KYWRHYNGWLBXCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-2-(5-chlorothiophen-2-yl)pyridine 、 3-羟基苯硼酸 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.0h， 以90%的产率得到4-(3-hydroxyphenyl)-2-(5-chlorothiophen-2-yl)pyridine
  参考文献：
  名称：

  Palladium-catalyzed highly regioselective 2-arylation of 2,x-dibromopyridines and its application in the efficient synthesis of a 17β-HSD1 inhibitor

  摘要：

  2,3- and 2,5-Dibromopyridines reacted with arylboronic acids, catalyzed by Pd(OAc)(2)/PPh3 in the presence of K2CO3 in CH3CN/MeOH (2:1) at 50 degrees C for 24 h, to afford 2-aiylpyridines in good to high yields, while 2,4-dibromopyridine reacted with arylboronic acid pinacol esters, catalyzed by Pd(OAc)(2)/PPh3 in the presence of KOH in CH3CN at 70 degrees C for 24 h, to afford 2-arylpyridines in good to high yields. To expand this methodology, a 170-HSD1 inhibitor was synthesized in good yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.065
• 作为产物：
  描述：

  2,4-二溴吡啶 、 5-氯噻吩-2-硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 18.0h， 以24%的产率得到4-bromo-2-(5-chlorothiophen-2-yl)pyridine
  参考文献：
  名称：

  Novel estrone mimetics with high 17β-HSD1 inhibitory activity

  摘要：

  17 beta-Hydroxysteroid dehydrogenase type 1 (17 beta-HSD1) catalyzes the reduction of estrone into estradiol, which is the most potent estrogen in humans. Lowering intracellular estradiol concentration by inhibition of this enzyme is a promising new option for the treatment of estrogen-dependent diseases like breast cancer and endometriosis. Combination of ligand- and structure-based design resulted in heterocyclic substituted biphenylols and their aza-analogs as new 17 beta-HSD1 inhibitors. The design was based on mimicking estrone, especially focusing on the imitation of the D-ring keto group with (substituted) heterocycles. Molecular docking provided insights into plausible protein-ligand interactions for this class of compounds. The most promising compound 12 showed an inhibitory activity in the high nanomolar range and very low affinity for the estrogen receptors alpha and beta. Thus, compound 12 is a novel tool for the elucidation of the pharmacological relevance of 17 beta-HSD1 and might be a lead for the treatment of estrogen-dependent diseases. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.065

文献信息

• Palladium-catalyzed highly regioselective 2-arylation of 2,x-dibromopyridines and its application in the efficient synthesis of a 17β-HSD1 inhibitor
  作者：Qizhong Zhou、Bin Zhang、Liangjun Su、Tiansheng Jiang、Rener Chen、Tieqi Du、Yuyuan Ye、Jianfen Shen、Guoliang Dai、Deman Han、Huajiang Jiang

  DOI：10.1016/j.tet.2013.10.065

  日期：2013.12

  2,3- and 2,5-Dibromopyridines reacted with arylboronic acids, catalyzed by Pd(OAc)(2)/PPh3 in the presence of K2CO3 in CH3CN/MeOH (2:1) at 50 degrees C for 24 h, to afford 2-aiylpyridines in good to high yields, while 2,4-dibromopyridine reacted with arylboronic acid pinacol esters, catalyzed by Pd(OAc)(2)/PPh3 in the presence of KOH in CH3CN at 70 degrees C for 24 h, to afford 2-arylpyridines in good to high yields. To expand this methodology, a 170-HSD1 inhibitor was synthesized in good yield. (C) 2013 Elsevier Ltd. All rights reserved.
• Novel estrone mimetics with high 17β-HSD1 inhibitory activity
  作者：Alexander Oster、Tobias Klein、Ruth Werth、Patricia Kruchten、Emmanuel Bey、Matthias Negri、Sandrine Marchais-Oberwinkler、Martin Frotscher、Rolf W. Hartmann

  DOI：10.1016/j.bmc.2010.03.065

  日期：2010.5

  17 beta-Hydroxysteroid dehydrogenase type 1 (17 beta-HSD1) catalyzes the reduction of estrone into estradiol, which is the most potent estrogen in humans. Lowering intracellular estradiol concentration by inhibition of this enzyme is a promising new option for the treatment of estrogen-dependent diseases like breast cancer and endometriosis. Combination of ligand- and structure-based design resulted in heterocyclic substituted biphenylols and their aza-analogs as new 17 beta-HSD1 inhibitors. The design was based on mimicking estrone, especially focusing on the imitation of the D-ring keto group with (substituted) heterocycles. Molecular docking provided insights into plausible protein-ligand interactions for this class of compounds. The most promising compound 12 showed an inhibitory activity in the high nanomolar range and very low affinity for the estrogen receptors alpha and beta. Thus, compound 12 is a novel tool for the elucidation of the pharmacological relevance of 17 beta-HSD1 and might be a lead for the treatment of estrogen-dependent diseases. (C) 2010 Elsevier Ltd. All rights reserved.