4-amino-5-benzoyl-2-(1-piperidinyl)-1,3-thiazole | 72100-52-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-amino-5-benzoyl-2-(1-piperidinyl)-1,3-thiazole
• 英文别名: 4-Amino-5-benzoyl-2-piperidinothiazole；(4-Amino-2-piperidin-1-yl-1,3-thiazol-5-yl)-phenylmethanone
• CAS: 72100-52-8
• 化学式: C₁₅H₁₇N₃OS
• 分子量: 287.385
• InChiKey: ZVOLWCBOPRGSJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-5-benzoyl-2-(1-piperidinyl)-1,3-thiazole 在 亚硝酸特丁酯 、 copper dichloride 作用下， 以 乙腈 为溶剂， 以59%的产率得到(4-chloro-2-(piperidin-1-yl)-1,3-thiazol-5-yl)(phenyl)methanone
  参考文献：
  名称：

  4-Bromo-2-(piperidin-1-yl)thiazol-5-yl-phenyl methanone (12b) inhibits Na+/K+-ATPase and Ras oncogene activity in cancer cells

  摘要：

  The in vitro growth inhibitory activity of 26 thiazoles (including 4-halogeno-2,5-disubtituted-1,3-thiazoles) and 5 thienothiazoles was assessed on a panel of 6 human cancer cell lines, including glioma cell lines. (4-Chloro-2-(piperidin-1-yl)thiazol-5-yl)(phenyl)methanone (12a) and (4-bromo-2-(piperidin-1-yl)thiazol-5-yl)(phenyl)methanone (12b) displayed similar to 10 times greater in vitro growth inhibitory activity than perillyl alcohol (POH), which therapeutically benefits glioma patients through the inhibition of both alpha-1 Na+/K+-ATPase (NAK) and Ras oncogene activity. The in vitro cytostatic activities (as revealed by quantitative videomicroscopy) displayed by 12a and 12b were independent of the intrinsic resistance to pro-apoptotic stimuli associated with cancer cells. Compounds 12a and 12b displayed relatively similar inhibitory activities on purified guinea pig brain preparations that mainly express NAK alpha-2 and alpha-3 subunits, whereas only compound 12b was efficacious against purified guinea pig kidney preparations that mainly express the NAK alpha-1 subunit, which is also expressed in gliomas, melanomas and non-small-cell lung cancers NSCLCs. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.046
• 作为产物：
  描述：

  氰胺 、 5-Phenyl-2-piperidino-1,3-oxathiolium perchlorate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.25h， 以76%的产率得到4-amino-5-benzoyl-2-(1-piperidinyl)-1,3-thiazole
  参考文献：
  名称：

  Heterocyclic cation systems. 14. Synthesis of thieno[3,2-e][1,4]diazepine, thiazolo[4,5-e][1,4]diazepine, and s-triazolo[3,4-c]thiazolo[4,5-e][1,4]diazepine derivatives

  摘要：

  DOI：

  10.1021/jo01290a010

文献信息

• One-pot synthesis of new 2,4,5-trisubstituted 1,3-thiazoles and 1,3-selenazoles
  作者：David Thomae、Enrico Perspicace、Zhanjie Xu、Dorothée Henryon、Serge Schneider、Stéphanie Hesse、Gilbert Kirsch、Pierre Seck

  DOI：10.1016/j.tet.2009.01.104

  日期：2009.4

  In this work, we describe the synthesis of new 2,4,5-trisubstituted-1,3-thiazoles and 1,3-selenazole achieved by an easy one-pot four-step procedure. Expected compounds were obtained in good yield from dimethyl cyanodithioimidocarbonate, which was the common starting material for the preparation of all 1,3-thiazoles and 1,3-selenazoles. Chemical diversity was introduced on thiazole and selenazole rings

  在这项工作中，我们描述了通过简单的一锅四步法实现的新2,4,5-三取代-1,3-噻唑和1,3-硒唑的合成。从氰基二硫代亚氨基碳酸二甲酯中可以以高收率获得预期的化合物，后者是制备所有1,3-噻唑和1,3-硒唑的常用原料。通过改变所用的胺和活化的卤化物，在噻唑和硒唑环上引入了化学多样性。
• HIRARI K.; SUGIMOTO H.; ISHIBA T., J. ORG. CHEM., 1980, 45, NO 2, 253-260
  作者：HIRARI K.、 SUGIMOTO H.、 ISHIBA T.

  DOI：——

  日期：——
• Heterocyclic cation systems. 14. Synthesis of thieno[3,2-e][1,4]diazepine, thiazolo[4,5-e][1,4]diazepine, and s-triazolo[3,4-c]thiazolo[4,5-e][1,4]diazepine derivatives
  作者：Kentaro Hirai、Hirohiko Sugimoto、Teruyuki Ishiba

  DOI：10.1021/jo01290a010

  日期：1980.1
• 4-Bromo-2-(piperidin-1-yl)thiazol-5-yl-phenyl methanone (12b) inhibits Na+/K+-ATPase and Ras oncogene activity in cancer cells
  作者：Florence Lefranc、Zhanjie Xu、Patricia Burth、Véronique Mathieu、Germain Revelant、Mauro Velho de Castro Faria、Caroline Noyon、Diogo Gomes Garcia、Damien Dufour、Céline Bruyère、Cassiano Felippe Gonçalves-de-Albuquerque、Pierre Van Antwerpen、Bernard Rogister、Stéphanie Hesse、Gilbert Kirsch、Robert Kiss

  DOI：10.1016/j.ejmech.2013.01.046

  日期：2013.5

  The in vitro growth inhibitory activity of 26 thiazoles (including 4-halogeno-2,5-disubtituted-1,3-thiazoles) and 5 thienothiazoles was assessed on a panel of 6 human cancer cell lines, including glioma cell lines. (4-Chloro-2-(piperidin-1-yl)thiazol-5-yl)(phenyl)methanone (12a) and (4-bromo-2-(piperidin-1-yl)thiazol-5-yl)(phenyl)methanone (12b) displayed similar to 10 times greater in vitro growth inhibitory activity than perillyl alcohol (POH), which therapeutically benefits glioma patients through the inhibition of both alpha-1 Na+/K+-ATPase (NAK) and Ras oncogene activity. The in vitro cytostatic activities (as revealed by quantitative videomicroscopy) displayed by 12a and 12b were independent of the intrinsic resistance to pro-apoptotic stimuli associated with cancer cells. Compounds 12a and 12b displayed relatively similar inhibitory activities on purified guinea pig brain preparations that mainly express NAK alpha-2 and alpha-3 subunits, whereas only compound 12b was efficacious against purified guinea pig kidney preparations that mainly express the NAK alpha-1 subunit, which is also expressed in gliomas, melanomas and non-small-cell lung cancers NSCLCs. (C) 2013 Elsevier Masson SAS. All rights reserved.