ethyl 5-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-1H-pyrazole-3-carboxylate | 1402464-41-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 5-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-1H-pyrazole-3-carboxylate
• CAS: 1402464-41-8
• 化学式: C₁₇H₁₆N₄O₃S
• 分子量: 356.405
• InChiKey: XPEFZZGACIORHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 5-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-1H-pyrazole-3-carboxylate 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以75%的产率得到5-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-1H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  一种酯基吡唑联噻唑胺化合物及其制备方法和应用

  摘要：

  本发明公开了一种酯基吡唑联噻唑胺化合物及其制备方法和应用，其结构通式为：。该化合物是一种双五元氮杂环双官能团化合物，便于实现噻唑胺和吡唑的高通量合成和多样化衍生，可广泛应用于噻唑联吡唑类药物研发和生产中。

  公开号：

  CN111606902A
• 作为产物：
  描述：

  5-乙酰基-2-氨基-4-甲基噻唑 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-羰基二咪唑 、 lithium hexamethyldisilazane 、 肼 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.75h， 生成 ethyl 5-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  Efficient synthesis and cell migration inhibitory effect of substituted benzamidothiazolylpyrazole-capped AWD*I-NH2

  摘要：

  Substituted (2-benzamidothiazol-5-yl)pyrazole-capped AWD*I-NH2 were synthesized and their antimigration activity was studied. The improved efficiency and scalability of the analog synthesis was achieved via a late-stage diversification of the benzoyl group and a convergent route in which the bisazole capping agents and off-resin peptide AWD*I-NH2 were prepared in parallel and coupled together in solution at the last step. Bioassay results indicate that all the peptidomimetics can significantly inhibit the migration of breast cancer cells MDA-MB-231 but possess no apparent cytotoxicity. In general, the antimigration potency of the peptidomimetics is correlated to the electron-withdrawing capacity of the substituents on the terminal phenyl ring. The inhibitory effect shows dose-dependent and holds also against lung and cervical cancer cells. The level of f-actin was reduced dramatically in cells treated with the inhibitor, suggesting that the migration inhibitory effect is related to the disruption of cell locomotive protrusions.

  DOI：

  10.1016/j.bmcl.2019.126914

文献信息

• 一种酯基吡唑联噻唑胺化合物及其制备方法和应用
  申请人：武汉科技大学

  公开号：CN111606902A

  公开（公告）日：2020-09-01

  本发明公开了一种酯基吡唑联噻唑胺化合物及其制备方法和应用，其结构通式为：。该化合物是一种双五元氮杂环双官能团化合物，便于实现噻唑胺和吡唑的高通量合成和多样化衍生，可广泛应用于噻唑联吡唑类药物研发和生产中。
• Pyrazolylthiazole as ΔF508-Cystic Fibrosis Transmembrane Conductance Regulator Correctors with Improved Hydrophilicity Compared to Bithiazoles
  作者：Long Ye、John M. Knapp、Panjamaporn Sangwung、James C. Fettinger、A. S. Verkman、Mark J. Kurth

  DOI：10.1021/jm100235h

  日期：2010.5.13

  Deletion of phenylalanine residue 508 (Delta F508) in the cystic fibrosis (CF) transmembrane conductance regulator protein (CFTR) is a major cause of CF. Small molecule "correctors" of defective A Delta 508-CFTR cellular processing hold promise for CF therapy. We previously identified and characterized bithiazole CF corrector 1 and s-cis-locked bithiazole 2. Herein, we report the regiodivergent synthesis of N gamma and N beta isomers of thiazole-tethered pyrazoles with improved hydrophilicity compared to bithiazoles. We synthesized a focused library of 54 pyrazolylthiazoles 3, which included examples of both regioisomers 4 and 5. The thiazole-tethered pyrazoles allowed incorporation of property-modulating functionality on the pyrazole ring (ester, acid, and amide) while retaining Delta F508-CFTR corrector activity (EC50) of under 1 mu M. The most active pyrazolylthiazole (14h) has an experimentally determined log P of 4.1, which is 1.2 log units lower than bithiazole CF corrector 1.
• Efficient synthesis and cell migration inhibitory effect of substituted benzamidothiazolylpyrazole-capped AWD*I-NH2
  作者：Mian Yang、Jun Chen、Wancai Peng、Qiqi Li、Hui Shao、Guanping Tang、Tong-Cun Zhang、Yoshikazhu Takada、Long Ye、Xing-Hua Liao

  DOI：10.1016/j.bmcl.2019.126914

  日期：2020.2

  Substituted (2-benzamidothiazol-5-yl)pyrazole-capped AWD*I-NH2 were synthesized and their antimigration activity was studied. The improved efficiency and scalability of the analog synthesis was achieved via a late-stage diversification of the benzoyl group and a convergent route in which the bisazole capping agents and off-resin peptide AWD*I-NH2 were prepared in parallel and coupled together in solution at the last step. Bioassay results indicate that all the peptidomimetics can significantly inhibit the migration of breast cancer cells MDA-MB-231 but possess no apparent cytotoxicity. In general, the antimigration potency of the peptidomimetics is correlated to the electron-withdrawing capacity of the substituents on the terminal phenyl ring. The inhibitory effect shows dose-dependent and holds also against lung and cervical cancer cells. The level of f-actin was reduced dramatically in cells treated with the inhibitor, suggesting that the migration inhibitory effect is related to the disruption of cell locomotive protrusions.