2-mercapto-1,3-propanediol | 59129-78-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 英文名称: 2-mercapto-1,3-propanediol
• 英文别名: 2-thioglycerol；1,3-Propanediol, 2-mercapto-；2-sulfanylpropane-1,3-diol
• CAS: 59129-78-1
• 化学式: C₃H₈O₂S
• 分子量: 108.161
• InChiKey: NBUVVXNTRSKQSQ-UHFFFAOYSA-N

物化性质

• 沸点：
  287.7±30.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  41.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  花生四烯酰氯 、 2-mercapto-1,3-propanediol 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80 mg的产率得到S-arachidonoyl 2-thioglycerol
  参考文献：
  名称：

  S-Arachidonoyl-2-thioglycerol synthesis and use for fluorimetric and colorimetric assays of monoacylglycerol lipase

  摘要：

  We report the first synthesis of 2-thioglycerol and S-arachidonoyl-2-thioglycerol (the thioester analog of the endocannabinoid 2-arachidonoylglycerol) in an eight or nine step procedure with a yield of similar to 25% and establish the use of this substrate for maleimide-based fluorescent and dithiobis(2-nitrobenzoic acid)-based colorimetric assays of human recombinant monoacylglycerol (MAG) lipase (hMAGL) and human brain membrane MAG hydrolase activity. Inhibitor structure-activity relationships observed here for hMAGL and 2-ATG correlate well (r(2) = 0.93, n = 9) with earlier findings for mouse brain MAG hydrolase with non-thiol substrates. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.034
• 作为产物：
  描述：

  S-arachidonoyl 2-thioglycerol 在 human recombinant monoacylglycerol lipase 作用下， 以 aq. Tris buffer 为溶剂， 生成 2-mercapto-1,3-propanediol
  参考文献：
  名称：

  S-Arachidonoyl-2-thioglycerol synthesis and use for fluorimetric and colorimetric assays of monoacylglycerol lipase

  摘要：

  We report the first synthesis of 2-thioglycerol and S-arachidonoyl-2-thioglycerol (the thioester analog of the endocannabinoid 2-arachidonoylglycerol) in an eight or nine step procedure with a yield of similar to 25% and establish the use of this substrate for maleimide-based fluorescent and dithiobis(2-nitrobenzoic acid)-based colorimetric assays of human recombinant monoacylglycerol (MAG) lipase (hMAGL) and human brain membrane MAG hydrolase activity. Inhibitor structure-activity relationships observed here for hMAGL and 2-ATG correlate well (r(2) = 0.93, n = 9) with earlier findings for mouse brain MAG hydrolase with non-thiol substrates. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.034

文献信息

• A ring opening reaction of benzisothiazolones. A new route to unsymmetrical disulfides
  作者：Joseph P. Sanchez

  DOI：10.1002/jhet.5570340515

  日期：1997.9

  A series of unsymmetrical disulfides has been prepared by employing a reaction involving a ring opening, nucleophilic attack of a thiol on a 1,2-benzisothiazol-3-one. The benzisothiazolones were in turn prepared by an intramolecular ring closure of an amide on a sulfenyl thiocarbonate. The sulfenyl esters were synthesized as intermediates for preparing mixed-disulfides, but the benzisothiazolone ring

  通过采用涉及开环的反应制备了一系列不对称的二硫键，硫醇对1，2-苯并噻唑-3-酮进行了亲核攻击。苯并异噻唑酮依次通过亚硫基硫代碳酸酯上的酰胺的分子内闭环来制备。合成了亚砜基酯作为制备混合二硫化物的中间体，但苯并异噻唑酮的开环是自发发生的。最初认为混合二硫化物是由亚硫基酯形成的，但苯并异噻唑酮的分离和逐步反应为反应机理提供了证据。
• GLYCEROL DERIVATIVE, PREPARATION METHOD THEREFOR, AND IMMUNOMODULATOR COMPRISING SAME AS EFFECTIVE INGREDIENT
  申请人：ENZYCHEM LIFESCIENCES CORPORATION

  公开号：US20210198183A1

  公开（公告）日：2021-07-01

  Disclosed are a glycerol derivative that is useful for improving, preventing or treating inflammation-related diseases by inhibiting overexpression of various inflammatory cytokines such as IL-4, IL-6 and so on, or chemokine CXCL8 and reducing migration of HL-60 cell lines, preparation method therefor, and an immunomodulator containing the same as active ingredient. It includes a glycerol derivative represented by Chemical formula 2 or 3 in the specification.

  本发明揭示了一种甘油衍生物，通过抑制IL-4、IL-6等多种炎症细胞因子的过度表达，或CXCL8趋化因子，减少HL-60细胞系的迁移，有助于改善、预防或治疗与炎症相关的疾病。还包括一种以化学式2或3所代表的甘油衍生物，以及其制备方法和含有该甘油衍生物作为活性成分的免疫调节剂。