2-((2-amino-4-methylthiazol-5-yl)selanyl)acetonitrile

• 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-((2-amino-4-methylthiazol-5-yl)selanyl)acetonitrile
• 英文别名: 2-[(2-Amino-4-methyl-1,3-thiazol-5-yl)selanyl]acetonitrile；2-[(2-amino-4-methyl-1,3-thiazol-5-yl)selanyl]acetonitrile
• 化学式: C₆H₇N₃SSe
• 分子量: 232.168
• InChiKey: DKDJDMAPZFILJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.31
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-methyl-5-selenocyanatothiazol-2-amine 、 氯乙腈 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以43%的产率得到2-((2-amino-4-methylthiazol-5-yl)selanyl)acetonitrile
  参考文献：
  名称：

  Synthesis and biochemical studies of novel organic selenides with increased selectivity for hepatocellular carcinoma and breast adenocarcinoma

  摘要：

  Nineteen organoselenides were synthesized and tested for their intrinsic cytotoxicity in hepatocellular carcinoma (HepG2) and breast adenocarcinoma (MCF-7) cell lines and their corresponding selective cytotoxicity (SI) was estimated using normal lung fibroblast (Wl-38) cells. Most of the organic selenides exhibited good anticancer activity, and this was more pronounced in HepG2 cells. Interestingly, the naphthoquinone- (5), thiazol- (12), and the azo-based (13) organic selenides demonstrated promising SI (up to 76). Furthermore, the amine 4c, naphthoquinone 5, and azo-based 13 and 15 organic selenides were able to down-regulate the expression of Bcl-2 and up-regulate the expression levels of IL-2, IL-6 and CD40 in HepG2 cells compared to untreated cells. Moreover, most of the synthesized candidates manifested good free radical-scavenging and GPx-like activities comparable to vitamin C and ebselen. The obtained results suggested that some of the presented organoselenium candidates have promising antiHepG2 and antioxidant activities. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.06.075

文献信息

• Synthesis and biochemical studies of novel organic selenides with increased selectivity for hepatocellular carcinoma and breast adenocarcinoma
  作者：Saad Shaaban、Abeer M. Ashmawy、Amr Negm、Ludger A. Wessjohann

  DOI：10.1016/j.ejmech.2019.06.075

  日期：2019.10

  Nineteen organoselenides were synthesized and tested for their intrinsic cytotoxicity in hepatocellular carcinoma (HepG2) and breast adenocarcinoma (MCF-7) cell lines and their corresponding selective cytotoxicity (SI) was estimated using normal lung fibroblast (Wl-38) cells. Most of the organic selenides exhibited good anticancer activity, and this was more pronounced in HepG2 cells. Interestingly, the naphthoquinone- (5), thiazol- (12), and the azo-based (13) organic selenides demonstrated promising SI (up to 76). Furthermore, the amine 4c, naphthoquinone 5, and azo-based 13 and 15 organic selenides were able to down-regulate the expression of Bcl-2 and up-regulate the expression levels of IL-2, IL-6 and CD40 in HepG2 cells compared to untreated cells. Moreover, most of the synthesized candidates manifested good free radical-scavenging and GPx-like activities comparable to vitamin C and ebselen. The obtained results suggested that some of the presented organoselenium candidates have promising antiHepG2 and antioxidant activities. (C) 2019 Elsevier Masson SAS. All rights reserved.