4-Phenyl-2-<β-chlor-propionylamino>-thiazol | 20495-98-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-Phenyl-2-<β-chlor-propionylamino>-thiazol
• 英文别名: 3-chloro-N-(4-phenyl-1,3-thiazol-2-yl)propanamide
• CAS: 20495-98-1
• 化学式: C₁₂H₁₁ClN₂OS
• mdl: MFCD01834743
• 分子量: 266.751
• InChiKey: HLHXOPNLYVGAHN-UHFFFAOYSA-N

物化性质

• 熔点：
  171 °C
• 密度：
  1.344±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Phenyl-2-<β-chlor-propionylamino>-thiazol 在 三乙胺 作用下， 以 苯 为溶剂， 反应 0.08h， 以69%的产率得到4-phenyl-thiazol-2-acrylamide
  参考文献：
  名称：

  酰胺基连接的恶唑基/噻唑基/咪唑基吡唑和异恶唑的合成

  摘要：

  酰胺基连接的恶唑基/噻唑基/咪唑基吡唑和异恶唑是由合成中间体恶唑基/噻唑基/咪唑基丙烯酰胺与1,3-偶极环加成腈亚胺和氧化腈制备的。

  DOI：

  10.1002/jhet.2185
• 作为产物：
  描述：

  苯乙酮 在 碘 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 4-Phenyl-2-<β-chlor-propionylamino>-thiazol
  参考文献：
  名称：

  Development of 2-amino-4-phenylthiazole analogues to disrupt myeloid differentiation factor 88 and prevent inflammatory responses in acute lung injury

  摘要：

  Myeloid differentiation primary response protein 88 (MyD88), an essential adapter protein used by toll like receptors (TLR), is a promising target molecule for the treatment of respiratory inflammatory diseases. Previous studies explored the activities of novel 2-amino-4-phenylthiazole analogue (6) in inflammation-induced cancer, and identified the analogue as an inhibitor of MyD88 toll/interleukin-1 receptor (TIR) homology domain dimerization. Here, we describe the synthesis of 47 new analogues by modifying different sites on this lead compound and assessed their anti-inflammatory activities in lipopolysaccharide-induced mouse primary peritoneal macrophages (MPMs). The most promising compound, 15d, was found to effectively interact with MyD88 protein and prevented formation of the MyD88 homodimeric complex. Furthermore, 15d showed in vivo anti-inflammatory activity in LPS-caused model of acute lung injury. This work provides new candidates as MyD88 inhibitors to combat inflammation diseases. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.09.068

文献信息

• Substituted thiazoles VI. Synthesis and antitumor activity of new 2-acetamido- and 2 or 3-propanamido-thiazole analogs
  作者：Shahenda M. El-Messery、Ghada S. Hassan、Fatmah A.M. Al-Omary、Hussein I. El-Subbagh

  DOI：10.1016/j.ejmech.2012.06.013

  日期：2012.8

  A novel series of 2-acetamido and 2 or 3-propanamido derivatives of 4- or 5-substituted-thiazoles was designed and synthesized. Structure elucidation of the new synthesized compounds was attained by the use of 1H & 13C NMR, and Mass spectrometry. Compounds were subjected to NCI in vitro assessment for their antitumor activity, at a single dose of 10 μM of test compounds. Compounds bearing straight

  设计并合成了一系列新的2-乙酰氨基和4-或5-取代的噻唑的2-或3-丙酰胺基衍生物。通过使用1 H和13 C NMR和质谱分析，可以阐明新合成的化合物的结构。以单剂量10μM的测试化合物对化合物的抗肿瘤活性进行NCI体外评估。具有直链取代基或4-苯基功能的化合物被证明比其支链或4-甲基同类物更具活性。化合物37，41和42显示出广谱抗肿瘤活性。化合物23和27被证明具有致命性，而化合物18，21，32和37显示出75.5，69.3，96.2和92.7％至白血病CCRF-CEM细胞系显着的GI值。
• Synthesis and Biological Evaluation of New 4,5-Disubstituted-Thiazolyl Amides, Derivatives of 4-Hydroxy-Piperidine or of 4-N-Methyl Piperazine
  作者：A. Geronikaki、D. Hadjipavlou-Litina、C. Chatziopoulos、G. Soloupis

  DOI：10.3390/80600472

  日期：——

  4,5-disubstituted-thizolyl amides, derivatives of 4-hydroxy-piperidine and of 4-N-methyl piperazine, were synthesized and tested as anti-inflammatory agents. Log P values were theoretically calculated and experimentally determined. These compounds were tested for antioxidant activity, as hydroxyl radical scavengers and for their ability to interact with stable 1,1-diphenyl-2-picryl hydrazyl free radical

  4,5-二取代-噻唑基酰胺、4-羟基-哌啶和4-N-甲基哌嗪的衍生物被合成并作为抗炎剂进行测试。Log P 值是通过理论计算和实验确定的。测试了这些化合物的抗氧化活性、羟基清除剂以及它们与稳定的 1,1-二苯基-2-苦基肼自由基 (DPPH) 相互作用的能力。使用角叉菜胶诱导的小鼠爪水肿模型研究了合成化合物对炎症的影响。抗炎和抗氧化活性取决于合成化合物的一些结构特征。
• Selim,M. et al., Bulletin de la Societe Chimique de France, 1968, p. 2117 - 2120
  作者：Selim,M. et al.

  DOI：——

  日期：——
• Novel schistosomicides. S-2-{[2-(2-Thiazolylcarbamoyl)ethyl]amino}ethyl hydrogen thiosulfate and related compounds
  作者：Roger D. Westland、Leslie M. Werbel、John R. Dice、Joyce L. Holmes、Barbara G. Zahm

  DOI：10.1021/jm00292a006

  日期：1971.10
• Aminothiazole derivatives with antidegenerative activity on cartilage
  作者：Anna Maria Panico、Athina Geronikaki、Remi Mgonzo、Venera Cardile、Barbara Gentile、Irini Doytchinova

  DOI：10.1016/s0968-0896(03)00149-4

  日期：2003.7

  A series of 2-dialkylamino-N-(4-substituted thiazolyl-2)acetamides and 3-dialkylamino-N-(4-substituted thiazolyl-2)propionamides were synthesized and evaluated for their anti-inflammatory activity. Encouraging results led us to investigate the effect of these compounds on NO production and GAGs release. Their effects were evaluated in vitro on the metabolism of pig cartilage, treated with IL-1beta. The amount of glycosaminoglycans (GAGs) and the production of nitric oxide (NO) in the culture medium were determined. The results, obtained, showed that all compounds, in the presence of IL-1beta, blocked the cartilage breakdown, with different behavior. A quantitative structure-activity relationship (QSAR) study was performed. (C) 2003 Elsevier Science Ltd. All rights reserved.