5-溴-2-硝基噻唑 | 182692-69-9

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-溴-2-硝基噻唑
• 英文名称: 5-bromo-2-nitrothiazole
• 英文别名: 5-bromo-2-nitro-1,3-thiazole
• CAS: 182692-69-9
• 化学式: C₃HBrN₂O₂S
• 分子量: 209.023
• InChiKey: RTBUHHOZDGNXDE-UHFFFAOYSA-N

物化性质

• 熔点：
  82 °C
• 沸点：
  343.6±34.0 °C(Predicted)
• 密度：
  2.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  5-溴-2-硝基噻唑 在 吡啶 作用下， 生成 2-硝基噻唑
  参考文献：
  名称：

  有关硝噻唑化合物的知识III

  摘要：

  合成了2-硝基-5-溴噻唑，并将该体的性质和响应与异构体2-溴5-硝基噻唑进行了比较。此外，制备2-甲基-5-硝基噻唑，另一方面，通过降解2-甲基-噻唑-5-羧酸获得2-甲基-5-乙酰基氨基噻唑。

  DOI：

  10.1002/hlca.19500330214
• 作为产物：
  描述：

  2-氨基-5-溴噻唑 生成 5-溴-2-硝基噻唑
  参考文献：
  名称：

  Thiazole derivatives and their use as cdk inhibitors

  摘要：

  公开号：

  EP1256578B1

文献信息

• Unexpected rearrangement products from animations of 5-bromo-2-nitrothiazole
  作者：Ho H. Lee、Brian D. Palmer、Maruta Boyd、William A. Denny

  DOI：10.1002/jhet.5570330431

  日期：1996.7

  2-bromo-5-nitrothiazole (2) with weakly basic secondary aliphatic amines gives the expected 2-amino products from nucleophilic displacement of the bromine, reaction of the isomeric 5-bromo-2-nitrothiazole (3) with such amines gives mixtures of the expected 5-amino products together with 2-aminated 5-nitrothiazole rearrangement products. The identity of the latter were detemined by alternative synthesis, and by X-ray

  虽然2-溴-5-硝基噻唑（2）与弱碱性仲脂肪胺反应可从溴的亲核取代反应获得预期的2-氨基产物，但异构5-溴-2-硝基噻唑（3）与此类胺反应得到预期的5-氨基产物与2-胺化的5-硝基噻唑重排产物的混合物。后者的身份通过替代合成和X射线晶体学测定衍生物确定。提出的机理是将5-溴-2-硝基噻唑（3）缓慢热异构化为反应性更高的2-溴-5-硝基异构体2 在较弱的胺亲核试剂的情况下，其与5-溴基团的直接（但缓慢）亲核取代竞争，形成正常的取代产物。
• [EN] KINASE INHIBITOR COMPOUNDS AND COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSÉS INHIBITEURS DE KINASE, COMPOSITIONS ET MÉTHODES D'UTILISATION
  申请人：ICAHN SCHOOL MED MOUNT SINAI

  公开号：WO2021263129A1

  公开（公告）日：2021-12-30

  Disclosed herein are kinase inhibitor compounds having the structure (I) or a stereoisomer, pharmaceutically acceptable salt, oxide, or solvate thereof, where R1, R2, X, L, Q, and Y are as defined herein. Also disclosed are compositions containing the kinase inhibitor compounds, methods of inhibiting activity of a kinase in a cell, methods of increasing cell proliferation in a population of pancreatic beta cells, methods of treating a subject for a condition associated with insufficient insulin secretion, and methods of treating a subject for a neurological disorder.

  本文披露了具有结构（I）或其立体异构体、药学上可接受的盐、氧化物或溶剂的激酶抑制剂化合物，其中R1、R2、X、L、Q和Y如本文所定义。还披露了含有激酶抑制剂化合物的组合物，抑制细胞中激酶活性的方法，增加胰岛β细胞群体中细胞增殖的方法，治疗因胰岛素分泌不足引起的疾病的方法，以及治疗神经系统疾病的方法。
• Thiazole derivatives
  申请人：Pfizer Inc.

  公开号：US20030078252A1

  公开（公告）日：2003-04-24

  The invention provides compounds of formula 1 1 wherein R 1 , R 3 , and R 4 are as defined, and their pharmaceutically acceptable salts. Compounds of formula 1 are indicated to have activity inhibiting cdk5, cdk2, and GSK-3. Pharmaceutical compositions and methods comprising compounds of formula 1 for treating diseases and conditions comprising abnormal cell growth, such as cancer, and neurodegenerative diseases and conditions and those affected by dopamine neurotransmission are described. Also described are pharmaceutical compositions and methods comprising compounds of formula 1 for treating male fertility and sperm motility; diabetes mellitus; impaired glucose tolerance; metabolic syndrome or syndrome X; polycystic ovary syndrome; adipogenesis and obesity; myogenesis and frailty, for example age-related decline in physical performance; acute sarcopenia, for example muscle atrophy and/or cachexia associated with burns, bed rest, limb immobilization, or major thoracic, abdominal, and/or orthopedic surgery; sepsis; hair loss, hair thinning, and balding; and immunodeficiency.

  本发明提供了公式11中的化合物，其中R1、R3和R4如定义所述，并且它们的药学上可接受的盐。公式1的化合物被指示具有抑制cdk5、cdk2和GSK-3的活性。本发明描述了包括治疗异常细胞生长的疾病和病况，如癌症和神经退行性疾病和病况以及受多巴胺神经递质影响的疾病和病况的公式1化合物的制药组合物和方法。还描述了包括治疗男性生育能力和精子运动能力；糖尿病；糖耐量受损；代谢综合征或综合征X；多囊卵巢综合征；脂肪生成和肥胖症；肌生成和衰弱，例如与年龄相关的身体表现下降；急性肌肉萎缩，例如与烧伤、卧床、肢体固定或重大胸腹和/或骨科手术相关的肌肉萎缩和/或消瘦；脓毒症；脱发、头发变薄和秃发；以及免疫缺陷的公式1化合物的制药组合物和方法。
• Discovery and SAR of 2-aminothiazole inhibitors of cyclin-dependent kinase 5/p25 as a potential treatment for Alzheimer’s disease
  作者：Christopher J. Helal、Mark A. Sanner、Christopher B. Cooper、Thomas Gant、Mavis Adam、John C. Lucas、Zhijun Kang、Stanley Kupchinsky、Michael K. Ahlijanian、Bonnie Tate、Frank S. Menniti、Kristin Kelly、Marcia Peterson

  DOI：10.1016/j.bmcl.2004.09.006

  日期：2004.11

  High-throughput screening with cyclin-dependent kinase 5 (cdk5)/p25 led to the discovery of N-(5-isopropyl-thiazol-2-yl)isobutyramide (1). This compound is an equipotent inhibitor of cdk5 and cyclin-dependent kinase 2 (cdk2)/cyclin E (IC50 = ca. 320nM). Parallel and directed synthesis techniques were utilized to explore the SAR of this series. Up to 60-fold improvements in potency at cdk5 and 12-fold selectivity over cdk2 were achieved. (C) 2004 Elsevier Ltd. All rights reserved.