3-溴-5-异氰酰基吡啶 | 167951-51-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 3-溴-5-异氰酰基吡啶
• 中文别名: 3-溴-5-异氰酸根合吡啶
• 英文名称: 5-bromo-3-pyridyl isocyanate
• 英文别名: 3-Bromo-5-isocyanatopyridine
• CAS: 167951-51-1
• 化学式: C₆H₃BrN₂O
• 分子量: 199.007
• InChiKey: PNEYUZGELZQGCX-UHFFFAOYSA-N

物化性质

• 沸点：
  247.9±25.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 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：
  42.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-溴-5-异氰酰基吡啶 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 20.0h， 生成 N-(5-cyanopyridin-3-yl)-4-{4-[(3-fluorobenzyl)oxy]phenoxy}piperidine-1-carboxamide
  参考文献：
  名称：

  EP2065369

  摘要：

  公开号：
• 作为产物：
  描述：

  (5-bromo-3-pyridyl)carbonyl azide 以 甲苯 为溶剂， 反应 1.0h， 生成 3-溴-5-异氰酰基吡啶
  参考文献：
  名称：

  Biarylcarbamoylindolines Are Novel and Selective 5-HT_2C Receptor Inverse Agonists:  Identification of 5-Methyl-1-[[2-[(2-methyl-3-pyridyl)oxy]- 5-pyridyl]carbamoyl]-6-trifluoromethylindoline (SB-243213) as a Potential Antidepressant/Anxiolytic Agent

  摘要：

  The evolution, synthesis, and biological activity of a novel series of 5-HT2C receptor inverse agonists are reported. Biarylcarbamoylindolines have been identified with excellent 5-HT2C affinity and selectivity over 5-HT2A receptors. In addition, (pyridyloxypyridyl)carbamoylindolines have been discovered with additional selectivity over the closely related 5-HT2B receptor. Compounds from this series are inverse agonists at the human cloned 5-HT2C receptor, completely abolishing basal activity in a functional assay. The new series have reduced P450 inhibitory liability compared to a previously described series of 1-(3-pyridylcarbamoyl)indolines (Bromidge et al. J. Med. Chem. 1998, 41, 1598) from which they evolved. Compounds from this series showed excellent oral activity in a rat mCPP hypolocomotion model and in animal models of anxiety. On the basis of their favorable biological profile, 32 (SB-228357) and 40 (SB-243213) have been selected for further evaluation to determine their therapeutic potential for the treatment of CNS disorders such as depression and anxiety.

  DOI：

  10.1021/jm990388c

文献信息

• Synthesis and biological evaluation of novel thienopyrimidine derivatives as diacylglycerol acyltransferase 1 (DGAT-1) inhibitors
  作者：Dong Jin Hong、Seung Hyun Jung、Jisook Kim、Danbee Jung、Young Gil Ahn、Kwee Hyun Suh、Kyung Hoon Min

  DOI：10.1080/14756366.2019.1693555

  日期：2020.1.1

  A novel series of thieno[3,2-d]pyrimidine derivatives were synthesised and their inhibitory effects against diacylglycerol acyltransferase 1 (DGAT-1) were assessed. cis-Isomer 17a showed potent and selective inhibitory activity against DGAT-1 in SF9 cells. In addition, 17a had an acceptable pharmacokinetic profile and accumulated mainly in the small intestine and liver. Oral administration of 17a led

  合成了一系列新的噻吩并[3,2-d]嘧啶衍生物，并评估了其对二酰基甘油酰基转移酶1（DGAT-1）的抑制作用。顺式异构体17a在SF9细胞中显示了对DGAT-1的有效和选择性抑制活性。另外，17a具有可接受的药代动力学特征，并且主要在小肠和肝脏中积累。在鼠和犬模型中进行口服脂质耐受性测试（OLTT）期间，口服17a导致血浆三酰甘油水平显着降低。两者合计，17a是一个高质量的候选对象，值得进一步研究。
• 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.
• THIADIAZOLE DERIVATIVES FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES
  申请人：GRIFFIOEN Gerard

  公开号：US20090054410A1

  公开（公告）日：2009-02-26

  This invention provides specifically substituted 1,2,4-thiadiazole derivatives for use in the treatment of an α-synucleopathy such as Parkinson's disease, diffuse Lewy body disease, traumatic brain injury, amyotrophic lateral sclerosis, Niemann-Pick disease, Hallervorden-Spatz syndrome, Down syndrome, neuroaxonal dystrophy, multiple system atrophy and Alzheimer's disease. This invention also provides various methods for producing such substituted 1,2,4-thiadiazole derivatives.
• US8541406B2
  申请人：——

  公开号：US8541406B2

  公开（公告）日：2013-09-24