3-(4-methylpiperazin-1-yl)-N-(4-phenylthiazol-2-yl)propanamide | 20496-05-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(4-methylpiperazin-1-yl)-N-(4-phenylthiazol-2-yl)propanamide
• 英文别名: 4-Phenyl-2-<β-(N'-methyl-piperazino)-propionylamino>-thiazol；3-(4-methyl-piperazin-1-yl)-N-(4-phenyl-thiazol-2-yl)-propionamide；3-(4-methylpiperazin-1-yl)-N-(4-phenyl-1,3-thiazol-2-yl)propanamide
• CAS: 20496-05-3
• 化学式: C₁₇H₂₂N₄OS
• 分子量: 330.454
• InChiKey: AOFSIOSFGDVTHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基-4-苯基噻唑 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 生成 3-(4-methylpiperazin-1-yl)-N-(4-phenylthiazol-2-yl)propanamide
  参考文献：
  名称：

  取代的噻唑VI。新的2-乙酰氨基和2或3-丙酰胺基噻唑类似物的合成及其抗肿瘤活性

  摘要：

  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。

  DOI：

  10.1016/j.ejmech.2012.06.013

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。
• Selim,M. et al., Bulletin de la Societe Chimique de France, 1968, p. 2117 - 2120
  作者：Selim,M. et al.

  DOI：——

  日期：——
• Development of 2-amino-4-phenylthiazole analogues to disrupt myeloid differentiation factor 88 and prevent inflammatory responses in acute lung injury
  作者：Lingfeng Chen、Hongjin Chen、Pengqin Chen、Wenxin Zhang、Chao Wu、Chuchu Sun、Wu Luo、Lulu Zheng、Zhiguo Liu、Guang Liang

  DOI：10.1016/j.ejmech.2018.09.068

  日期：2019.1

  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.