[2-(4-Dimethylamino-naphthalen-1-yl)-4-oxo-thiazolidin-3-yl]-acetic acid | 793669-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [2-(4-Dimethylamino-naphthalen-1-yl)-4-oxo-thiazolidin-3-yl]-acetic acid
• CAS: 793669-14-4
• 化学式: C₁₇H₁₈N₂O₃S
• 分子量: 330.408
• InChiKey: NPQNJNLGWWLPJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  60.85
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  十八胺 、 [2-(4-Dimethylamino-naphthalen-1-yl)-4-oxo-thiazolidin-3-yl]-acetic acid 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-(2-(1-(dimethylamino) naphthalen-4-yl)-4-oxothiazolidin-3-yl)-N-octadecylacetamide
  参考文献：
  名称：

  Synthesis and antiproliferative activity of 2-aryl-4-oxo-thiazolidin-3-yl-amides for prostate cancer

  摘要：

  We have previously described serine amide phosphates (SAPs) as a novel class of cytotoxic agents for prostate cancer. Several of them showed potent cytotoxicity against human prostate cancer cell lines, but were not selective in non-tumor cells. To improve the selectivity and further enhance the potency, we designed a new series of 2-aryl-4-oxo-thiazolidin-3-yl amides. The current work describes synthesis, SAR, and biological evaluation of these compounds for their ability to inhibit the growth of prostate cancer cells. The antiproliferative effects of synthesized compounds were examined in five human prostate cancer cell lines (DU-145, PC-3, LNCaP, PPC-1, and TSU), and in RH7777 cells (negative controls). From this study, three potent compounds (8, 20, and 21) have been detected, which are effective in killing prostate cancer cells with improved selectivity compared to SAPs. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.08.029
• 作为产物：
  描述：

  methyl 2-[2-[4-(dimethylamino)naphthalen-1-yl]-4-oxo-1,3-thiazolidin-3-yl]acetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 [2-(4-Dimethylamino-naphthalen-1-yl)-4-oxo-thiazolidin-3-yl]-acetic acid
  参考文献：
  名称：

  Synthesis and antiproliferative activity of 2-aryl-4-oxo-thiazolidin-3-yl-amides for prostate cancer

  摘要：

  We have previously described serine amide phosphates (SAPs) as a novel class of cytotoxic agents for prostate cancer. Several of them showed potent cytotoxicity against human prostate cancer cell lines, but were not selective in non-tumor cells. To improve the selectivity and further enhance the potency, we designed a new series of 2-aryl-4-oxo-thiazolidin-3-yl amides. The current work describes synthesis, SAR, and biological evaluation of these compounds for their ability to inhibit the growth of prostate cancer cells. The antiproliferative effects of synthesized compounds were examined in five human prostate cancer cell lines (DU-145, PC-3, LNCaP, PPC-1, and TSU), and in RH7777 cells (negative controls). From this study, three potent compounds (8, 20, and 21) have been detected, which are effective in killing prostate cancer cells with improved selectivity compared to SAPs. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.08.029