(2-(4-(aminomethyl)phenyl)thiazol-4-yl)(piperidin-1-yl)methanone | 1257216-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2-(4-(aminomethyl)phenyl)thiazol-4-yl)(piperidin-1-yl)methanone
• 英文别名: [2-[4-(Aminomethyl)phenyl]-1,3-thiazol-4-yl]-piperidin-1-ylmethanone
• CAS: 1257216-27-5
• 化学式: C₁₆H₁₉N₃OS
• 分子量: 301.412
• InChiKey: DPFYTUPOFSUSNS-UHFFFAOYSA-N

物化性质

• 熔点：
  145-150 °C
• 沸点：
  513.1±60.0 °C(predicted)
• 密度：
  1.242±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  87.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对氯苯乙酸 、 (2-(4-(aminomethyl)phenyl)thiazol-4-yl)(piperidin-1-yl)methanone 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙腈 为溶剂， 以81%的产率得到2-(4-chlorophenyl)-N-(4-(4-(piperidine-1-carbonyl)thiazol-2-yl)benzyl)acetamide
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-phenylthiazole-4-carboxamide derivatives as anticancer agents

  摘要：

  A series of substituted 2-phenylthiazole-4-carboxamide derivatives were synthesized as potential cytotoxic agents and evaluated against three human cancer cell lines including T47D (Breast cancer), Caco-2 (Colorectal cancer) and HT-29 (Colon cancer). The SAR of the arylacetamido pendent connected to the parts-position of 2-phenylthiazole were explored. It was found that substitution at the 4-position by a methoxy group led to improvement of activity against Caco-2 cells while 2-methoxy substituent could maintain the high activity against HT-29 and T47D cell lines. Also, 3-fluoro analog showed good cytotoxic activity profile against all cell lines with IC50 values less than 10 mu g/mL. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.063
• 作为产物：
  描述：

  2-(4-(4-(piperidine-1-carbonyl)thiazol-2-yl)benzyl)isoindoline-1,3-dione 在 乙醇 、 甲胺 作用下， 反应 6.0h， 以79%的产率得到(2-(4-(aminomethyl)phenyl)thiazol-4-yl)(piperidin-1-yl)methanone
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-phenylthiazole-4-carboxamide derivatives as anticancer agents

  摘要：

  A series of substituted 2-phenylthiazole-4-carboxamide derivatives were synthesized as potential cytotoxic agents and evaluated against three human cancer cell lines including T47D (Breast cancer), Caco-2 (Colorectal cancer) and HT-29 (Colon cancer). The SAR of the arylacetamido pendent connected to the parts-position of 2-phenylthiazole were explored. It was found that substitution at the 4-position by a methoxy group led to improvement of activity against Caco-2 cells while 2-methoxy substituent could maintain the high activity against HT-29 and T47D cell lines. Also, 3-fluoro analog showed good cytotoxic activity profile against all cell lines with IC50 values less than 10 mu g/mL. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.063

文献信息

• Synthesis and biological evaluation of 2-phenylthiazole-4-carboxamide derivatives as anticancer agents
  作者：Alireza Aliabadi、Fazel Shamsa、Seyed Nasser Ostad、Saeed Emami、Abbas Shafiee、Jamshid Davoodi、Alireza Foroumadi

  DOI：10.1016/j.ejmech.2010.08.063

  日期：2010.11

  A series of substituted 2-phenylthiazole-4-carboxamide derivatives were synthesized as potential cytotoxic agents and evaluated against three human cancer cell lines including T47D (Breast cancer), Caco-2 (Colorectal cancer) and HT-29 (Colon cancer). The SAR of the arylacetamido pendent connected to the parts-position of 2-phenylthiazole were explored. It was found that substitution at the 4-position by a methoxy group led to improvement of activity against Caco-2 cells while 2-methoxy substituent could maintain the high activity against HT-29 and T47D cell lines. Also, 3-fluoro analog showed good cytotoxic activity profile against all cell lines with IC50 values less than 10 mu g/mL. (C) 2010 Elsevier Masson SAS. All rights reserved.