[4-氨基-2-(甲基氨基)-1,3-噻唑-5-基](苯基)甲酮 | 107401-74-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: [4-氨基-2-(甲基氨基)-1,3-噻唑-5-基](苯基)甲酮
• 英文名称: (4-Amino-2-methylamino-thiazol-5-yl)-phenyl-methanone
• 英文别名: [4-Amino-2-(methylamino)-1,3-thiazol-5-yl](phenyl)methanone；[4-amino-2-(methylamino)-1,3-thiazol-5-yl]-phenylmethanone
• CAS: 107401-74-1
• 化学式: C₁₁H₁₁N₃OS
• mdl: MFCD04060946
• 分子量: 233.294
• InChiKey: SQWPGESDJHLLBD-UHFFFAOYSA-N

物化性质

• 熔点：
  195 °C
• 沸点：
  454.7±55.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  在 三乙胺 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 [4-氨基-2-(甲基氨基)-1,3-噻唑-5-基](苯基)甲酮
  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

• 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.
• RAJASEKHARAN, K. N.;NAIR, K. P.;JENARDANAN, G. C., SYNTHESIS, BRD, 1986, N 5, 353-355
  作者：RAJASEKHARAN, K. N.、NAIR, K. P.、JENARDANAN, G. C.

  DOI：——

  日期：——