(4-amino-2-propylaminothiazol-5-yl)phenylmethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-amino-2-propylaminothiazol-5-yl)phenylmethanone
• 英文别名: [4-Amino-2-(propylamino)-1,3-thiazol-5-yl]-phenylmethanone
• 化学式: C₁₃H₁₅N₃OS
• 分子量: 261.348
• InChiKey: HJFCSWBVMGVXBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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 、 1-(N-nitroamidino)-3-n-propylthiourea 在 三乙胺 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以88%的产率得到(4-amino-2-propylaminothiazol-5-yl)phenylmethanone
  参考文献：
  名称：

  SYNTHESIS AND CYCLIZATION OF 1-(N-NITROAMIDINO)THIOUREAS TO 2,4-DIAMINOTHIAZOLES

  摘要：

  DOI：

  10.1080/00304949809355265

文献信息

• Traceless Solid-Phase Synthesis of 2,4,5-Trisubstituted Thiazoles
  作者：Ill Young Lee、Young-Dae Gong、Jin Young Lee、Hye Jin Lee

  DOI：10.1055/s-2005-872687

  日期：——

  The solid-phase synthesis of trisubstituted thiazoles is described. The synthetic strategy involves the formation of a polymer-bound thiazole by reacting resin-bound cyanodithioimidocarbonic acid and α-bromoketone. The resin-bound thiazole was reacted with acyl chlorides or isocyanates. After oxidation-activation of a thioether linker to a sulfone linker, traceless cleavage was achieved with nucleophiles

  描述了三取代噻唑的固相合成。合成策略涉及通过树脂结合的氰基二硫亚氨基碳酸和α-溴酮反应形成聚合物结合的噻唑。树脂结合的噻唑与酰氯或异氰酸酯反应。硫醚接头氧化活化为砜接头后，用亲核试剂实现无痕切割，得到三取代的噻唑。
• 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.
• SYNTHESIS AND CYCLIZATION OF 1-(<i>N</i>-NITROAMIDINO)THIOUREAS TO 2,4-DIAMINOTHIAZOLES
  作者：R. Binu、K. K. Thomas、G. C. Jenardanan、K. N. Rajasekharan

  DOI：10.1080/00304949809355265

  日期：1998.2