(4-amino-2-phenylamino-thiazol-5-yl)-(3-nitrophenyl)-methanone | 223783-69-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-amino-2-phenylamino-thiazol-5-yl)-(3-nitrophenyl)-methanone
• 英文别名: (4-amino-2-phenylaminothiazol-5-yl)-(3-nitrophenyl)methanone；(4-amino-2-anilino-1,3-thiazol-5-yl)-(3-nitrophenyl)methanone
• CAS: 223783-69-5
• 化学式: C₁₆H₁₂N₄O₃S
• 分子量: 340.362
• InChiKey: ACIOMPFLDCPKIS-UHFFFAOYSA-N

物化性质

• 沸点：
  605.7±65.0 °C(Predicted)
• 密度：
  1.477±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4-amino-2-phenylamino-thiazol-5-yl)-(3-nitrophenyl)-methanone 在 钯 作用下， 以 四氢呋喃 为溶剂， 生成 (3-amino-phenyl)-(4-amino-2-phenylamino-thiazol-5-yl)-methanone
  参考文献：
  名称：

  Compounds, pharmaceutical compositions, and methods for inhibiting cyclin-dependent kinases

  摘要：

  含有以下公式中CDK抑制二氨基噻唑化合物的有效量的药物组合物（其中R1和R2如规范所定义）或其盐，或这些化合物或盐的前药或活性代谢物，可用于治疗癌症等疾病和疾病。在首选实施例中，R1和R2分别是未取代或取代的碳环或杂环芳香环结构。其中R2为邻位取代芳香族的化合物特别是CDKs如CDK4的有效抑制剂。

  公开号：

  US20030220326A1
• 作为产物：
  描述：

  氰胺 、 硫代异氰酸苯酯 、 2-溴-3'-硝基苯乙酮 在 sodium 作用下， 以 甲醇 为溶剂， 以52%的产率得到(4-amino-2-phenylamino-thiazol-5-yl)-(3-nitrophenyl)-methanone
  参考文献：
  名称：

  Substituted 4-amino-thiazol-2-yl compounds as cyclin-dependent kinase inhibitors

  摘要：

  含有以下式（其中R1和R2如规范中定义）的CDK抑制二氨基噻唑化合物或其盐、前药或这些化合物或盐的活性代谢物的有效量的药物组合物，对于治疗癌症等疾病和疾病是有用的： 在优选实施例中，R1和R2独立地是未取代或取代的碳环或杂环芳基环结构。其中R2为邻位取代芳基的化合物特别是CDK4的有效抑制剂。

  公开号：

  US06569878B1

文献信息

• Use of 2,4-diaminothiazole derivatives
  申请人：——

  公开号：US20010039275A1

  公开（公告）日：2001-11-08

  2,4-Diaminothiazole derivatives which inhibit GSK-3 (glycogen synthase kinase-3) and which are useful for the treatment and/or prevention disorders and diseases wherein an inhibition of GSK-3 is beneficial, especially especially Alzheimer's disease, bipolar disorder, IGT (impaired glucose tolerance), Type 1 diabetes, Type 2 diabetes and obesity.

  抑制GSK-3（糖原合成激酶-3）的2,4-二氨基噻唑衍生物，对治疗和/或预防GSK-3抑制有益的疾病和疾病特别有效，尤其是阿尔茨海默病、双相情感障碍、糖耐量受损（IGT）、1型糖尿病、2型糖尿病和肥胖症。
• [EN] 2,4-DIAMINOTHIAZOLE DERIVATIVES AND THEIR USE AS GLYCOGEN SYNTHASE KINASE-3 (GSK-3) INHIBITORS<br/>[FR] DERIVES DE 2,4-DIAMINOTHIAZOLE
  申请人：NOVO NORDISK AS

  公开号：WO2001056567A1

  公开（公告）日：2001-08-09

  2,4-Diaminothiazole derivatives which inhibit GSK-3 (glycogen synthase kinase-3) and which are useful for the treatment and/or prevention disorders and diseases wherein an inhibition of GSK-3 is beneficial, especially especially Alzheimer's disease, bipolar disorder, IGT (impaired glucose tolerance), Type 1 diabetes, Type 2 diabetes and obesity.

  2,4-二氨基噻唑衍生物抑制GSK-3（糖原合成酶激酶-3），对于治疗和/或预防抑制GSK-3有益的疾病和疾病特别是阿尔茨海默病、双相情感障碍、IGT（糖耐量受损）、1型糖尿病、2型糖尿病和肥胖症具有用处。
• Development of Highly Potent and Selective Diaminothiazole Inhibitors of Cyclin-Dependent Kinases
  作者：Ernst Schonbrunn、Stephane Betzi、Riazul Alam、Mathew P. Martin、Andreas Becker、Huijong Han、Rawle Francis、Ramappa Chakrasali、Sudhakar Jakkaraj、Aslamuzzaman Kazi、Said M. Sebti、Christopher L. Cubitt、Anthony W. Gebhard、Lori A. Hazlehurst、Joseph S. Tash、Gunda I. Georg

  DOI：10.1021/jm301234k

  日期：2013.5.23

  Cyclin-dependent kinases (CDKs) are serine/threonine protein kinases that act as key regulatory elements in cell cycle progression. We describe the development of highly potent diaminothiazole inhibitors of CDK2 (IC50 = 0.0009-0.0015 mu M) from a single hit compound with weak inhibitory activity (IC50 = 15 mu M), discovered by high-throughput screening. Structure-based design was performed using 35 cocrystal structures of CDK2 liganded with distinct analogues of the parent compound. The profiling of compound 51 against a panel of 339 kinases revealed high selectivity for CDKs, with preference for CDK2 and CDK5 over CDK9, CDK1, CDK4, and CDK6. Compound 51 inhibited the proliferation of 13 out of 15 cancer cell lines with IC50 values between 0.27 and 6.9 mu M, which correlated with the complete suppression of retinoblastoma phosphorylation and the onset of apoptosis. Combined, the results demonstrate the potential of this new inhibitors series for further development into CDK-specific chemical probes or therapeutics.
• 4-Aminothiazole derivatives, their preparation and their use as inhibitors of cyclin-dependent kinases
  申请人：AGOURON PHARMACEUTICALS, INC.

  公开号：EP1215208B1

  公开（公告）日：2006-07-12
• 4-AMINOTHIAZOLE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS INHIBITORS OF CYCLIN-DEPENDENT KINASES
  申请人：AGOURON PHARMACEUTICALS, INC.

  公开号：EP1056732A2

  公开（公告）日：2000-12-06