1-(N,N'-di(4-chlorophenyl)amidino)-3-(4-methoxyphenyl)thiourea | 1196787-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(N,N'-di(4-chlorophenyl)amidino)-3-(4-methoxyphenyl)thiourea
• 英文别名: 1-[N,N'-di(4-chorophenyl)amidino]-3-(4-methoxyphenyl)thiourea
• CAS: 1196787-67-3
• 化学式: C₂₁H₁₈Cl₂N₄OS
• 分子量: 445.372
• InChiKey: XHRXCCLHEYEPAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  57.68
• 氢给体数：
  3.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-溴-1-(1H-吲哚-3-基)乙酮 、 1-(N,N'-di(4-chlorophenyl)amidino)-3-(4-methoxyphenyl)thiourea 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以91%的产率得到4-(4-chlorophenylamino)-2-(4-methoxyphenylamino)-5-(indol-3-oyl)thiazole
  参考文献：
  名称：

  4-Amino-2-arylamino-5-indoloyl/cinnamoythiazoles, analogs of topsentin-class of marine alkaloids, induce apoptosis in HeLa cells

  摘要：

  Marine organisms provide several biologically active compounds that include alkaloids with high cytotoxic activity but only a few of them have so far reached clinical stage, due partly to their limited supply and complex structural features. In an attempt to develop novel anticancer compounds, we have now synthesized diaminoindoloylthiazoles (4a-c; DIT1-3) and diaminocinnamoylthiazoles (5a,b; DCT1-2) as analogs based on a topsentin scaffold and investigated the cytotoxic and apoptotic activities of these compounds in HeLa cells. The results suggest that diaminoindoloylthiazoles (DIT1-3) inhibit cell growth and among these, DIT3 is the most cytotoxic against HeLa cells (IC50 1 mu M). The diaminocinnamoylthiazoles DCT1 and DCT2, which can be viewed as curcumin-diaminothiazole hybrids, also inhibited cell growth but at relatively higher concentrations with IC50 values of 60 and 30 mu M, respectively. These compounds induced apoptosis through the intrinsic pathway by reducing the mitochondrial membrane potential and activating caspases, 9 and 3, but not caspase 8. Among the marine alkaloid analogs tested in this study, DIT1-3 are very effective in inducing apoptosis of HeLa cells followed by DCT2 and DCT1. The treated cells were arrested in G(2)/M phase followed by accumulation of the cells in the Sub G(0) phase. The curcumin-diaminothiazole hybrid DCT1 had the maximum effect in downregulating TNF-induced NF-kappa B activation among the compounds tested in this study. Thus, we demonstrate that diaminoindoloylthiazoles and diaminocinnamoylthiazoles induce apoptosis, regulate cell cycle and NF-kappa B signaling and thus show promising anticancer effects that warrant further investigation. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.032

文献信息

• Synthesis of [2,4-bis(arylamino)thiazol-5-yl](1-methyl-1<i>H</i>-benzimidazol-2-yl)methanones
  作者：T. F. Abbs Fen Reji、Kallikat N. Rajasekharan

  DOI：10.1002/jhet.162

  日期：2009.9

  [2,4-Bis(arylamino)thiazol-5-yl]-(1-methyl-1H-benzimidazol-2-yl)methanones, as the analogs of the cytotoxic marine alkaloid dendrodoine, are synthesized and characterized by elemental analysis, IR, NMR, and Mass spectral data. The thiourea derivatives provide four ring atoms for the thiazole ring construction and thus act as [CNCS] synthons. The remaining carbon of the thiazole is sourced from 2-(

  合成了[2,4-双（芳基氨基）噻唑-5-基]-（1-甲基-1 H-苯并咪唑-2-基）甲酮，作为细胞毒性海洋生物碱树突藤碱的类似物，并通过元素分析对其进行了表征， IR，NMR和质谱数据。硫脲衍生物为噻唑环的结构提供了四个环原子，因此可作为[C N C S]合成子。噻唑的剩余碳源于2-（2-溴乙酰基）-1-甲基-1 H-苯并咪唑。该[4 + 1]杂环化反应被用于合成新型的1-甲基-1 H-苯并咪唑衍生物。J.杂环化​​学，（2009）。
• Abbs Fen Reji; Manju; Rajasekharan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 3, p. 323 - 326
  作者：Abbs Fen Reji、Manju、Rajasekharan

  DOI：——

  日期：——