(Z)-1,3-dimethyl-5-(thiophen-3-yl)-9-(thiophen-3-ylmethylene)-8,9-dihydro-1H-pyrano[3',4':5,6]pyrido[2,3-d]pyrimidine-2,4(3H,6H)-dione | 1425937-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: (Z)-1,3-dimethyl-5-(thiophen-3-yl)-9-(thiophen-3-ylmethylene)-8,9-dihydro-1H-pyrano[3',4':5,6]pyrido[2,3-d]pyrimidine-2,4(3H,6H)-dione
• 英文别名: (14Z)-4,6-dimethyl-9-thiophen-3-yl-14-(thiophen-3-ylmethylidene)-12-oxa-2,4,6-triazatricyclo[8.4.0.03,8]tetradeca-1,3(8),9-triene-5,7-dione
• CAS: 1425937-00-3
• 化学式: C₂₁H₁₇N₃O₃S₂
• 分子量: 423.516
• InChiKey: MEDZPHIPBONSSB-VGOFMYFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,3-二甲基-6-氨基脲嘧啶 、 3,5-Bis(thiophen-3-ylmethylidene)oxan-4-one 在 苄基三甲基氢氧化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-1,3-dimethyl-5-(thiophen-3-yl)-9-(thiophen-3-ylmethylene)-8,9-dihydro-1H-pyrano[3',4':5,6]pyrido[2,3-d]pyrimidine-2,4(3H,6H)-dione
  参考文献：
  名称：

  The products of the reaction between 6-amine-1,3-dimethyl uracil and bis-chalcones induce cytotoxicity with massive vacuolation in HeLa cervical cancer cell line

  摘要：

  As a part of our research in the chemistry of chalcones we have prepared four pyrimidine monoadducts of bis-chalcones through the reaction with 6-amino-1,3-dimethyl uracil. These compounds displayed cytotoxicity with a massive vacuolation in different human cell lines in vitro. Compound 6 was the most cytotoxic inducer of vacuoles, this compound induced G1 phase cell cycle arrest, and their cytotoxicity went without morphological and biochemical evidence of apoptotic cell death in HeLa cells. In addition, our results showed that this vacuole formation does not require de novo protein synthesis and the content vacuolar is acidic. Compound 6 induce necrotic cell death with excessive vacuolation, similar to a process of autophagy. Spautin-1 an inhibitor of autophagy, decreased the transformation of microtubule-associated protein 1 light chain 3 (LC3B-I) to LC3B-II and the vacuolation induced by compound 6 in HeLa cells, both autophagy processes. These compounds could be of pivotal importance in the study of non-apoptotic cell death with vacuole formation and could be useful in research into new autophagy inhibitors agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.021

文献信息

• The products of the reaction between 6-amine-1,3-dimethyl uracil and bis-chalcones induce cytotoxicity with massive vacuolation in HeLa cervical cancer cell line
  作者：José D. Solano、Ignacio González-Sánchez、Marco A. Cerbón、Ángel Guzmán、Miguel A. Martínez-Urbina、Miguel A. Vilchis-Reyes、Eduardo C. Martínez-Zuñiga、Cuauhtémoc Alvarado、Angelina Quintero、Eduardo Díaz

  DOI：10.1016/j.ejmech.2012.12.021

  日期：2013.2

  As a part of our research in the chemistry of chalcones we have prepared four pyrimidine monoadducts of bis-chalcones through the reaction with 6-amino-1,3-dimethyl uracil. These compounds displayed cytotoxicity with a massive vacuolation in different human cell lines in vitro. Compound 6 was the most cytotoxic inducer of vacuoles, this compound induced G1 phase cell cycle arrest, and their cytotoxicity went without morphological and biochemical evidence of apoptotic cell death in HeLa cells. In addition, our results showed that this vacuole formation does not require de novo protein synthesis and the content vacuolar is acidic. Compound 6 induce necrotic cell death with excessive vacuolation, similar to a process of autophagy. Spautin-1 an inhibitor of autophagy, decreased the transformation of microtubule-associated protein 1 light chain 3 (LC3B-I) to LC3B-II and the vacuolation induced by compound 6 in HeLa cells, both autophagy processes. These compounds could be of pivotal importance in the study of non-apoptotic cell death with vacuole formation and could be useful in research into new autophagy inhibitors agents. (C) 2012 Elsevier Masson SAS. All rights reserved.