5-bromothiophen-2-yl isocyanate | 76537-03-6

• 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: 5-bromothiophen-2-yl isocyanate
• 英文别名: 5-bromo-2-thienyl isocyanate；5-bromo-thien-2-yl isocyanate；2-Bromo-5-isocyanatothiophene
• CAS: 76537-03-6
• 化学式: C₅H₂BrNOS
• mdl: MFCD09931425
• 分子量: 204.047
• InChiKey: FQQKFLOQZBJWAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromothiophen-2-yl isocyanate 、 1-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)piperidin-4-amine 以 二氯甲烷 为溶剂， 以78%的产率得到1-(5-bromothiophen-2-yl)-3-(1-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)piperidin-4-yl)urea
  参考文献：
  名称：

  Identification and structure–activity relationships of 1-aryl-3-piperidin-4-yl-urea derivatives as CXCR3 receptor antagonists

  摘要：

  The synthesis and biological evaluation of a series of 1-aryl-3-piperidin-4-yl-urea derivatives as small-molecule CXCR3 antagonists is described. SAR studies resulted in significant improvement of potency and physicochernical properties and established the key pharmacophore of the series, and led to the identification of 9t, which exhibits an IC50 of 16 nM in the GTP gamma S-35 functional assay. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.088
• 作为产物：
  描述：

  5-Bromothiophene-2-carbonyl azide 以 甲苯 为溶剂， 生成 5-bromothiophen-2-yl isocyanate
  参考文献：
  名称：

  Identification and structure–activity relationships of 1-aryl-3-piperidin-4-yl-urea derivatives as CXCR3 receptor antagonists

  摘要：

  The synthesis and biological evaluation of a series of 1-aryl-3-piperidin-4-yl-urea derivatives as small-molecule CXCR3 antagonists is described. SAR studies resulted in significant improvement of potency and physicochernical properties and established the key pharmacophore of the series, and led to the identification of 9t, which exhibits an IC50 of 16 nM in the GTP gamma S-35 functional assay. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.088

文献信息

• Heterocyclic tetrahydro-1-alkyl-4-oxo-1H-imidazol-2-ylidene urea and
  申请人：ICI Americas Inc.

  公开号：US04230713A1

  公开（公告）日：1980-10-28

  Heterocyclic tetrahydro-1-alkyl-4-oxo-1H-imidazol-2-ylidene urea and compounds which are useful as anxiolytic agents in living animals and also some of which act to block acid secretions.

  杂环四氢-1-烷基-4-氧代-1H-咪唑-2-基脲和其它一些化合物可用作镇静剂，对活体动物有益，并且其中一些化合物可用于阻断酸分泌。
• 4β-[4′-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA topoisomerase I and IIα inhibitors and apoptosis inducing agents
  作者：Ahmed Kamal、Paidakula Suresh、M. Janaki Ramaiah、T. Srinivasa Reddy、Ravi Kumar Kapavarapu、Bolla Narasimha Rao、Syed Imthiajali、T. Lakshminarayan Reddy、S.N.C.V.L. Pushpavalli、Nagula Shankaraiah、Manika Pal-Bhadra

  DOI：10.1016/j.bmc.2013.06.033

  日期：2013.9

  A series of 4 beta-[4'-(1-(aryl)ureido)benzamide]podophyllotoxin congeners (11a-1) were synthesized and evaluated for their cytotoxic activity against six human cancer cell lines. Some of the compounds like 11a, 11h, 11k and 11I showed significant anti-proliferative activity in Colo-205 cells and were superior to etoposide. The flow-cytometric analysis studies indicated that these compounds show strong G1 cell cycle arrest, as well exhibited improved inhibitory activities on DNA topoisomerase I and Ha enzymes. These compounds induce apoptosis by up regulating caspase-3 protein as observed by ELISA and Western blotting analysis. In addition, a brief structure-activity relationship studies within the series along with docking results of representative compounds 11a, 11h, 11k, 11I were presented. (C) 2013 Elsevier Ltd. All rights reserved.
• Identification and structure–activity relationships of 1-aryl-3-piperidin-4-yl-urea derivatives as CXCR3 receptor antagonists
  作者：Daniel R. Allen、Amanda Bolt、Gayle A. Chapman、Roland L. Knight、Johannes W.G. Meissner、David A. Owen、Robert J. Watson

  DOI：10.1016/j.bmcl.2006.10.088

  日期：2007.2

  The synthesis and biological evaluation of a series of 1-aryl-3-piperidin-4-yl-urea derivatives as small-molecule CXCR3 antagonists is described. SAR studies resulted in significant improvement of potency and physicochernical properties and established the key pharmacophore of the series, and led to the identification of 9t, which exhibits an IC50 of 16 nM in the GTP gamma S-35 functional assay. (c) 2006 Elsevier Ltd. All rights reserved.