(4-amino-2-ethylaminothiazol-5-yl)phenylmethanone | 107401-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-amino-2-ethylaminothiazol-5-yl)phenylmethanone
• 英文别名: (4-Amino-2-ethylamino-thiazol-5-yl)-phenyl-methanone；[4-amino-2-(ethylamino)-1,3-thiazol-5-yl]-phenylmethanone
• CAS: 107401-75-2
• 化学式: C₁₂H₁₃N₃OS
• 分子量: 247.321
• InChiKey: DOPTXFSKHKVWMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  96.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-溴苯乙酮 在 三乙胺 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 2.0h， 生成 (4-amino-2-ethylaminothiazol-5-yl)phenylmethanone
  参考文献：
  名称：

  Studies on the Synthesis of 5-Acyl-2,4-diaminothiazoles from Amidinothioureas

  摘要：

  1-烷基或芳基-3-脒基硫脲与δ-卤酮反应或不反应，生成 5-酰基-2,4-二氨基噻唑。

  DOI：

  10.1055/s-1986-31634

文献信息

• Inhibitors of glycogen synthase kinase-3 (gsk-3) for treating glaucoma
  申请人：——

  公开号：US20040186159A1

  公开（公告）日：2004-09-23

  The use of inhibitors of GSK-3 useful for treating glaucoma is disclosed.

  抑制GSK-3用于治疗青光眼的方法被揭示。
• 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。
• Inhibitors of glycogen synthase kinase-3 (GSK-3) for treating glaucomatous optic neuropathy
  申请人：Alcon, Inc.

  公开号：EP2281560A1

  公开（公告）日：2011-02-09

  The use of inhibitors of GSK-3 useful for treating, preventing or inhibiting glaucoma, including treating glaucomatous optic neuropathy, is disclosed.

  本研究公开了用于治疗、预防或抑制青光眼（包括治疗青光眼性视神经病变）的 GSK-3 抑制剂的用途。
• 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.