Sulforamate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 二硫代氨基甲酸及其衍生物
• 英文名称: Sulforamate
• 英文别名: 4-methylsulfinyl-1-(S-methyl-dithio-carbamyl)-butane；Sulforemate；methyl N-(4-methylsulfinylbutyl)carbamodithioate
• 化学式: C₇H₁₅NOS₃
• 分子量: 225.4
• InChiKey: SNJJPZNVUIICCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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， 反应 3.0h， 生成 Sulforamate
  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

• PROCESS FOR THE SYNTHESIS OF ISOTHIOCYANATES AND DERIVATIVES THEREOF AND USES OF SAME
  申请人：Dubois Jacques

  公开号：US20130142739A1

  公开（公告）日：2013-06-06

  A method for synthesizing an isothiocyanate of general formula (I) SCN—R 1 —R 4 —R 2 (I) wherein R 1 and R 2 represent independently of each other an alkyl-aryl or aryl group, R 4 represents a carbonyl, sulfinyl, sulfonyl group or a sulfide group and of its derivatives comprising a step for reacting an alkylalkylamine having the general formula (II) NH 2 —R 1 —R 4 —R 2 (II) wherein R 1 and R 2 represent independently of each other an alkyl, aryl or alkylaryl group, R 4 represents a carbonyl, sulfinyl, sulfonyl or sulfide group, in the presence of carbon sulfide and of di-tert-butyl dicarbonate with formation of the corresponding aforesaid isothiocyanate, compounds obtained by this method as well as their uses.

  一种合成一般式为（I）SCN-R1-R4-R2（I）的异硫氰酸酯的方法，其中R1和R2分别独立地表示烷基-芳基或芳基基团，R4表示羰基、亚磺酰基、磺酰基或硫醚基及其衍生物，包括通过在碳硫化物和双叔丁基二碳酸酯的存在下反应具有通式（II）NH2-R1-R4-R2（II）的烷基烷基胺，形成相应的上述异硫氰酸酯的步骤，以及通过该方法获得的化合物及其用途。
• 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.