2-[4-[(2,4-dioxothiazolidin-5-ylidene)methyl]phenoxy]-N-(5-nitrothiazol-2-yl)acetamide | 1228763-97-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[4-[(2,4-dioxothiazolidin-5-ylidene)methyl]phenoxy]-N-(5-nitrothiazol-2-yl)acetamide
• 英文别名: (Z)-2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)-N-(5-nitrothiazol-2-yl)acetamide；2-[4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-N-(5-nitro-1,3-thiazol-2-yl)acetamide
• CAS: 1228763-97-0
• 化学式: C₁₅H₁₀N₄O₆S₂
• 分子量: 406.4
• InChiKey: VKDSUFMTXWDFQR-YHYXMXQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  197
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (Z)-5-(4-hydroxyphenylmethylene)-2,4-thiazolidinedione 、 2-氯-N-(5-硝基-2-噻唑基)乙酰胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到2-[4-[(2,4-dioxothiazolidin-5-ylidene)methyl]phenoxy]-N-(5-nitrothiazol-2-yl)acetamide
  参考文献：
  名称：

  Synthesis and primary cytotoxicity evaluation of new 5-benzylidene-2,4-thiazolidinedione derivatives

  摘要：

  In the present work, ten novel derivatives (3a-3j) of 5-benzylidene-2,4-thiazolidinediones were synthesized and their structures were determined by analytical and spectral (FTIR, (1)H NMR, (13)C NMR) methods. The newly synthesized compounds were evaluated for their antiproliferative activity at Tata Memorial's Advanced Center for Treatment. Research and Education in Cancer (ACTREC), India, in a panel of 7 cancer cell lines using four concentrations at 10-fold dilutions. Sulforhodamine B (SRB) protein assay was used to estimate cell stability or growth. Though the compounds showed varying degrees of cytotoxicity in the tested cell lines, most marked effect was observed by compound 3e in MCF7 (breast cancer), K562 (leukemia) and GURAV (nasopharyngeal cancer) cell lines with logo GI(50) values of -6 7. -6.72 and -6.73 respectively. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.014

文献信息

• Synthesis and evaluation of the hypoglycemic and hypolipidemic activity of novel 5-benzylidene-2,4-thiazolidinedione analogs in a type-2 diabetes model
  作者：Sonali Mehendale-Munj、Rumi Ghosh、C. S. Ramaa

  DOI：10.1007/s00044-010-9359-5

  日期：2011.6

  This article reports synthesis and evaluation of two novel thiazolidinedione ring containing molecules namely (Z)-5-(2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)acetyl)-2-hydroxybenzamide (4) and (Z)-2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)-N-(5-nitrothiazol-2-yl)acetamide (7). The new chemical entities were tested for hypoglycemic activity and for their total cholesterol (CHL)

  本文报道了两个新颖的含噻唑烷二酮环的分子的合成和评价，即（Z）-5-（2-（4-（（2,4-二氧噻唑并偶氮-5-亚甲基）甲基）苯氧基）乙酰基）-2-羟基苯甲酰胺（4）和（Z）-2-（4-（（2,4-二氧噻唑啉基-5-亚甲基）甲基）苯氧基）-N-（5-硝基噻唑-2-基）乙酰胺（7）。在喂养高脂饮食（HFD）的Sprague–Dawley大鼠中，测试了新的化学实体的降血糖活性以及总胆固醇（CHL）和甘油三酸酯（TG）的降低作用。治疗14天后，合成的分子显示出血糖，CHL和TG水平的显着降低。
• Synthesis and primary cytotoxicity evaluation of new 5-benzylidene-2,4-thiazolidinedione derivatives
  作者：Vijay Patil、Kalpana Tilekar、Sonali Mehendale-Munj、Rhea Mohan、C.S. Ramaa

  DOI：10.1016/j.ejmech.2010.07.014

  日期：2010.10

  In the present work, ten novel derivatives (3a-3j) of 5-benzylidene-2,4-thiazolidinediones were synthesized and their structures were determined by analytical and spectral (FTIR, (1)H NMR, (13)C NMR) methods. The newly synthesized compounds were evaluated for their antiproliferative activity at Tata Memorial's Advanced Center for Treatment. Research and Education in Cancer (ACTREC), India, in a panel of 7 cancer cell lines using four concentrations at 10-fold dilutions. Sulforhodamine B (SRB) protein assay was used to estimate cell stability or growth. Though the compounds showed varying degrees of cytotoxicity in the tested cell lines, most marked effect was observed by compound 3e in MCF7 (breast cancer), K562 (leukemia) and GURAV (nasopharyngeal cancer) cell lines with logo GI(50) values of -6 7. -6.72 and -6.73 respectively. (C) 2010 Elsevier Masson SAS. All rights reserved.