N-(6-bromopyridin-2-yl)thiazol-2-amine | 439578-84-4

• 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
• 英文名称: N-(6-bromopyridin-2-yl)thiazol-2-amine
• 英文别名: 6-Bromo-N-(2-thiazolyl)pyridin-2-amine；N-(6-bromopyridin-2-yl)-1,3-thiazol-2-amine
• CAS: 439578-84-4
• 化学式: C₈H₆BrN₃S
• 分子量: 256.126
• InChiKey: QQRIRJHHZXAOIH-UHFFFAOYSA-N

物化性质

• 沸点：
  375.3±52.0 °C(Predicted)
• 密度：
  1.735±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(6-bromopyridin-2-yl)thiazol-2-amine 在 N-羟基-7-氮杂苯并三氮唑 、 溴 、 sodium methylate 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 N-(1-{5-[2-(6-Bromo-pyridin-2-ylamino)-thiazol-5-ylsulfanyl]-2-hydroxy-benzoyl}-piperidine-3-carbonyl)-methanesulfonamide
  参考文献：
  名称：

  Discovery and SAR of 2-amino-5-(thioaryl)thiazoles as potent and selective Itk inhibitors

  摘要：

  A series of structurally novel aminothiazole based small molecule inhibitors of Itk were prepared to elucidate their structure-activity relationships (SARs), selectivity, and cell activity in inhibiting IL-2 secretion in a Jurkat T-cell assay. Compound 3 is identified as a potent and selective Itk inhibitor which inhibits anti-TCR antibody induced IL-2 production in mice in vivo and was previously reported to reduce lung inflammation in a mouse model of ovalbumin induced allergy/asthma. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.060
• 作为产物：
  描述：

  2-氨基-6-溴吡啶 在 sodium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 N-(6-bromopyridin-2-yl)thiazol-2-amine
  参考文献：
  名称：

  Discovery and SAR of 2-amino-5-(thioaryl)thiazoles as potent and selective Itk inhibitors

  摘要：

  A series of structurally novel aminothiazole based small molecule inhibitors of Itk were prepared to elucidate their structure-activity relationships (SARs), selectivity, and cell activity in inhibiting IL-2 secretion in a Jurkat T-cell assay. Compound 3 is identified as a potent and selective Itk inhibitor which inhibits anti-TCR antibody induced IL-2 production in mice in vivo and was previously reported to reduce lung inflammation in a mouse model of ovalbumin induced allergy/asthma. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.060

文献信息

• Thiazolyl inhibitors of Tec family tyrosine kinases
  申请人：——

  公开号：US20030069238A1

  公开（公告）日：2003-04-10

  Novel thiazolyl compounds and salts thereof, pharmaceutical compositions containing such compounds, and methods of using such compounds in the treatment of Tec family tyrosine kinase-associated disorders such as cancer, immunologic disorders and allergic disorders.

  新型噻唑基化合物及其盐，含有这种化合物的药物组合物，以及在治疗 Tec 家族酪氨酸激酶相关疾病（如癌症、免疫性疾病和过敏性疾病）中使用这种化合物的方法。
• Encapsulation of Phosphorescent Pt(II) Complexes in Zn-Based Metal–Organic Frameworks toward Oxygen-Sensing Porous Materials
  作者：Tim-Oliver Knedel、Stefan Buss、Iván Maisuls、Constantin G. Daniliuc、Carsten Schlüsener、Philipp Brandt、Oliver Weingart、Annette Vollrath、Christoph Janiak、Cristian A. Strassert

  DOI：10.1021/acs.inorgchem.0c00678

  日期：2020.5.18

  In this work, we synthesized two tailored phosphorescent Pt(II) complexes bearing a cyclometalating tridentate thiazole-based C^N*N pincer luminophore (L) and exchangeable chlorido ([PtCl(L)]) or cyanido ([PtCN(L)]) coligands. While both complexes showed photoluminescence from metal-perturbed ligand-centered triplet states (3MP-LC), [PtCN(L)] reached the highest phosphorescence quantum yields and displayed

  在这项工作中，我们合成了两个定制的磷光Pt（II）配合物，它们带有一个基于环金属化三齿噻唑的C ^ N * N钳形发光体（L）和可交换氯基（[PtCl（L）]）或氰基（[PtCN（L） ]）大肠菌。两种配合物均显示出金属扰动的以配体为中心的三重态（3MP-LC）的光致发光，[PtCN（L）]达到了最高的磷光量子产率，并显示出对3O2猝灭的显着敏感性。我们将它们封装到两个基于Zn的金属有机框架中，即MOF-5和ZIF-8。有机金属化合物在所得复合物中的掺入[PtCl（L）] @ ZIF-8，[PtCN（L）] @ ZIF-8，[PtCl（L）] @ MOF-5和[PtCN（L）] @ MOF-5已通过粉末X射线衍射仪，扫描电子显微镜，时间分辨光致发光光谱和显微镜进行了验证，以及N2和Ar气体吸附研究。通过石墨炉原子吸收光谱法确定包封的配合物的量，显示出最大负载为3.7重量％。如果将其与固态形
• [EN] THIAZOLYL INHIBITORS OF TEC FAMILY TYROSINE KINASES<br/>[FR] INHIBITEURS THIAZOLYL DES TYROSINE KINASES DE LA FAMILLE TEC
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2002050071A1

  公开（公告）日：2002-06-27

  Novel thiazolyl compounds and salts thereof, pharmaceutical compositions containing such compounds, and methods of using such compounds in the treatment of Tec family tyrosine kinase-associated disorders such as cancer, immunologic disorders and allergic disorders.

  新型噻唑基化合物及其盐，含有这种化合物的药物组合物，以及使用这种化合物治疗Tec家族酪氨酸激酶相关疾病（如癌症、免疫性疾病和过敏性疾病）的方法。
• Thiazolyl inhibitors of tec family tyrosine kinases
  申请人：Bristol-Myers Squibb Company

  公开号：EP1671969A2

  公开（公告）日：2006-06-21

  Thiazolyl compounds and salts thereof, pharmaceutical compositions containing such compounds, and use of such compounds in the treatment of Tec family tyrosine kinase-associated disorders such as cancer, immunologic disorders and allergic disorders.

  噻唑基化合物及其盐类、含有此类化合物的药物组合物，以及此类化合物在治疗 Tec 家族酪氨酸激酶相关疾病（如癌症、免疫性疾病和过敏性疾病）中的用途。
• Identification of 2-amino-5-(thioaryl)thiazoles as inhibitors of nerve growth factor receptor TrkA
  作者：Soong-Hoon Kim、John S. Tokarski、Kenneth J. Leavitt、Brian E. Fink、Mark E. Salvati、Robert Moquin、Mary T. Obermeier、George L. Trainor、Gregory G. Vite、Linda K. Stadnick、Jonathan S. Lippy、Dan You、Matthew V. Lorenzi、Ping Chen

  DOI：10.1016/j.bmcl.2007.11.076

  日期：2008.1

  2-Amino-5-(thioaryl)thiazoles are potent inhibitors of TrkA (e.g., 20h, TrkA IC50 = 0.6 nM) that show anti-proliferative effect in cellular assays. A proposed inhibitor binding mode to TrkA active site is consistent with key SAR observations. (c) 2007 Elsevier Ltd. All rights reserved.