benzyl (4-(methylsulfinyl)butyl)carbamodithioate

• 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: benzyl (4-(methylsulfinyl)butyl)carbamodithioate
• 英文别名: benzyl N-(4-methylsulfinylbutyl)carbamodithioate
• 化学式: C₁₃H₁₉NOS₃
• 分子量: 301.498
• InChiKey: SHILGOYVXPZMTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(3-(甲亚磺酰基)丁基)异吲哚啉-1,3-二酮 在 咪唑 、 肼 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl (4-(methylsulfinyl)butyl)carbamodithioate
  参考文献：
  名称：

  Cancer chemopreventive activity of sulforamate derivatives

  摘要：

  Chemoprevention can be defined as air intervention in the carcinogenic process by use of natural or synthetic substances. Induction of Phase 11 enzyme is an important mechanism of chemoprevention. In the present studies we have synthesized several derivatives of (+)(-) 4-methylsulfinyl-1-(S-methyldithiocarbamyl)-butane (sulforamate) and evaluated their effectiveness as monofunctional inducer of the NAD(P)H Quinone oxidoreductase [quinone reductase (QR)] a phase II enzyme in cultured Hepa1c1c7 murine hepatoma cells. The cytotoxicity of some of the derivatives was strongly reduced in comparison to [(-)-1-isothiocyanato-4(R)-(methylsulfinyl)butane] (sulforaphane). However, the induction potential of these compounds was comparable to sulforaphane. On the basis of these results sulforamate derivatives can be regarded as simple, inexpensive and readily available chemopreventive agents. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.10.002

文献信息

• Design, synthesis and biological evaluation of novel carbamodithioates as anti-proliferative agents against human cancer cells
  作者：Xia Liu、Zhijun Wang、Rui Xie、Pingwah Tang、Qipeng Yuan

  DOI：10.1016/j.ejmech.2018.07.038

  日期：2018.9

  number of carbamodithioate derivatives with benzenethiols (substituted or unsubstituted) (1l, 1m, 1n, 1o, 1q, 1s, 2l, 2n, 2p, 2q, 2r and 2s) were investigated for in vitro anti-proliferative activities against five cancer cell lines: SMMC-7721, A549, A375, HCT 116 and Hela. The carbamodithioate compounds (1l, 1m, 1n, 1o, 1q and 1s) derived from SFE and the carbamodithioate compounds (2l, 2n, 2p, 2q, 2r and

  已成功合成了一系列新的氨基硫代氨基甲酸酯化合物。通常，SFE和SFA与苯硫酚（取代或未取代的）的所有氨基乙二硫醚衍生物均比其母体化合物SFE和SFA表现出更高的抑制百分比。研究了许多具有苯硫酚（取代或未取代）的氨基甲酰胺基氨基甲酸酯衍生物（1l，1m，1n，1o，1q，1s，2l，2n，2p，2q，2r和2s）对五个癌细胞的体外抗增殖活性。线路：SMMC-7721，A549，A375，HCT 116和Hela。衍生自SFE的氨基脲二甲酸酯化合物（1l，1m，1n，1o，1q和1s）和氨基硫脲二甲酸酯化合物（2l，2n，2p，2q，2r和2s源自SFA的）对SMMC-7721和A549癌细胞比对其他癌细胞更敏感，因为它们的IC 50值明显较低。此外，它们显示出比其母体化合物SFE和SFE更强的抑制活性。进一步的研究表明，这些硫代氨基甲酰胺衍生物抑制了SMMC-7721的集落形成，并显着诱导了SMMC-7721癌细胞的G2
• Cancer chemopreventive activity of sulforamate derivatives
  作者：R MORIARTY、R NAITHANI、J KOSMEDER、O PRAKASH

  DOI：10.1016/j.ejmech.2005.10.002

  日期：2006.1

  Chemoprevention can be defined as air intervention in the carcinogenic process by use of natural or synthetic substances. Induction of Phase 11 enzyme is an important mechanism of chemoprevention. In the present studies we have synthesized several derivatives of (+)(-) 4-methylsulfinyl-1-(S-methyldithiocarbamyl)-butane (sulforamate) and evaluated their effectiveness as monofunctional inducer of the NAD(P)H Quinone oxidoreductase [quinone reductase (QR)] a phase II enzyme in cultured Hepa1c1c7 murine hepatoma cells. The cytotoxicity of some of the derivatives was strongly reduced in comparison to [(-)-1-isothiocyanato-4(R)-(methylsulfinyl)butane] (sulforaphane). However, the induction potential of these compounds was comparable to sulforaphane. On the basis of these results sulforamate derivatives can be regarded as simple, inexpensive and readily available chemopreventive agents. (c) 2005 Elsevier SAS. All rights reserved.