3-(S-allylmercapto)-1,2-propanediol | 400843-51-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(S-allylmercapto)-1,2-propanediol
• 英文别名: 3-(allylthio)propan-1,2-diol；3-Prop-2-enylsulfanylpropane-1,2-diol
• CAS: 400843-51-8
• 化学式: C₆H₁₂O₂S
• 分子量: 148.226
• InChiKey: ZULDIVHFCVYYBY-UHFFFAOYSA-N

物化性质

• 沸点：
  291.2±25.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  65.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(S-allylmercapto)-1,2-propanediol 在 sodium hydroxide 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 61.5h， 生成 S-[2-(S'-allyl-S'-dioxomercapto)-1-(hydroxymethyl)ethyl]glutathione
  参考文献：
  名称：

  Metabolism of the Chemoprotective Agent Diallyl Sulfide to Glutathione Conjugates in Rats

  摘要：

  The chemoprotective effects of diallyl sulfide (DAS), a flavor component of garlic, have been attributed to its inhibitory effects on CYP2E1-mediated bioactivation of certain carcinogenic chemicals. In addition to being a competitive inhibitor of CYP2E1 in vitro, DAS is known to cause irreversible inhibition of CYP2E1 in rats in vivo. The latter property is believed to be mediated by the DAS metabolite diallyl sulfone (DASO(2)), which is thought to be a mechanism-based inhibitor of CYP2E1, although the underlying mechanism remains unknown. In order to investigate the nature of the reactive intermediate(s) responsible for the inactivation of CY2BE1 by DAS and its immediate metabolites, the present studies were carried out to detect and identify potential glutathione (GSH) conjugates of DAS and its metabolites diallyl sulfoxide (DASO) and DASO(2). By means of ionspray LC-MS/MS, ten GSH conjugates were identified in bile collected from rats dosed with DAS, namely: S-[3-(S'-allyl-S'-oxomercapto)-2-hydroxypropyl]glutathione (M1, M2; diastereomers), S-[3-(S'-allyl-S'-dioxomercapto)-2-hydroxypropyl]-glutathione (M5), S-[2-(S'-allyl-S'-dioxomercapto)-1-(hydroxymethyl)ethyl]glutathione (M3, M4; diastereomers), S-[3-(S'-allylmercapto)-2-hydroxypropyl]glutathione(M6), S-(3-hydroxypropyl)-glutathione (M7), S-(2-carboxyethyl)glutathione (M8), allyl glutathionyl disulfide (M9), and S-allylglutathione (M10). With the exception of M6, all of the above GSH conjugates were detected in the bile of rats treated with DASO, while only M3, M4, M5, M8, and M10 were found in the bile of rats treated with DASO(2). Experiments conducted in vitro showed that GSH reacted spontaneously with DASO to form conjugates M9 and M10, and with DASO(2) to form M10. In the presence of NADPH and GSH, incubation of DAS with cDNA-expressed rat CYP2E1 resulted in the formation of metabolites M6, M9, and M10, while incubation with DASO led to the formation of M3, M4, M5, M9, and M10. When DASO(2) acted as substrate, CY2BE1 generated only conjugates M3, M4, M5, and M10. These results indicate that while DAS and DASO undergo extensive oxidation in vice at the sulfur atom, the allylic carbon, and the terminal double bonds, CY2BE1 preferentially catalyzes oxidation of the sulfur atom to form the sulfoxide and the sulfone (DASO and DASO(2)). However, it appears that the end product of this sequence, namely, DASO(2), undergoes further CYP2E1-mediated activation of the olefinic pi-bond, a reaction which transforms many terminal olefins to potent mechanism-based P450 inhibitors. We hypothesize, therefore, that it is this final metabolic event with DASO(2) which leads to autocatalytic destruction of CYP2E1 and which is mainly responsible for the chemoprotective effects of DAS in vivo.

  DOI：

  10.1021/tx9601768
• 作为产物：
  描述：

  烯丙硫醇 、 缩水甘油 在 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene on polystyrene.HL 作用下， 反应 0.02h， 以75%的产率得到3-(S-allylmercapto)-1,2-propanediol
  参考文献：
  名称：

  聚苯乙烯负载的 1,5,7-三氮杂双环 [4.4.0]dec-5-ene 作为一种高效且可重复使用的催化剂，用于在无溶剂条件下对 1,2-环氧化物进行硫解

  摘要：

  聚苯乙烯负载的 1,5,7-三氮杂双环 [4.4.0]dec-5-烯 (PS-TBD) 是一种有效的碱性催化剂，用于通过芳基-和烷基-硫解 1,2-环氧化物 1a-e在无溶剂条件下取代硫醇 2A-E，而其活性在 MeCN 中显着降低。这些反应是完全抗非对映选择性的，并且通常具有高度的 C-β 区域选择性。相应的羟基硫化物已以优异的产率分离出来，并且催化剂很容易回收和再利用，而不会降低工艺的效率和选择性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200500791

文献信息

• 3-Hydrocarbylthio-2-acyloxypropyl 2-trimethylammonioethyl phosphates, process for producing the same and pharmaceutical preparations containing the same
  申请人：A. Nattermann & Cie. GmbH

  公开号：EP0043472A1

  公开（公告）日：1982-01-13

  The present invention is directed to new 1-S-alkyl-2-O-acyl-3-phosphocholine-1-mercapto-2.3-propandiols of the general formula I process for producting the same and pharmaceutical preparations containing the same as active agent, in particular for the treatment of increased blood pressure and thromboembolic diseases.

  本发明涉及通式 I 的新 1-S-烷基-2-O-酰基-3-磷酸胆碱-1-巯基-2.3-丙二醇。 本发明涉及通式 I 的新的 1-S-烷基-2-O-酰基-3-磷酸胆碱-1-巯基-2.3-丙二醇，以及生产这种物质的工艺和含有这种物质作为活性剂的药物制剂，特别是用于治疗血压升高和血栓栓塞性疾病。
• Thiocationic lipids, pharmaceutical compositions and methods of use thereof
  申请人：GEN-PROBE INCORPORATED

  公开号：EP0747351A2

  公开（公告）日：1996-12-11

  Lipid molecules bearing a cationic charge are described. These cationic lipids are useful in the delivery of biomolecules, such as oligonucleotides, nucleic acids, peptides, diagnostic imaging agents, proteins and drug molecules. In the form of liposomes, they can effectively be used for the intracellular delivery of biomolecules for therapeutic or diagnostic purposes.

  本文描述了带有阳离子电荷的脂质分子。这些阳离子脂质可用于输送生物大分子，如寡核苷酸、核酸、肽、诊断成像剂、蛋白质和药物分子。以脂质体的形式，它们可有效地用于细胞内输送用于治疗或诊断目的的生物大分子。
• Functionally substituted sulfur-containing compounds. 9. Reactions of 2-[(organylthio)methyl]oxiranes with acetic anhydride and acetyl chloride
  作者：V. E. Kalugin、V. P. Litvinov

  DOI：10.1007/bf00961238

  日期：1991.7

  Reaction of 2-[(organylthio)methyl]oxiranes with acetic anhydride gives a mixture of 3-(organylthio)-1,2-diacetoxypropane and 2-(organylthio)-1,3-diacetoxypropane, and with acetyl chloride a mixture of 2-chloro-3-(organylthio)-1-acetoxypropane and 3-chloro-2-(organylthio)-1-acetoxypropane. In both cases, the ratio of the isomers depends on the nature of the organylthio group and on the nature of the electrophile.
• KALUGIN, V. E.;LITVINOV, V. P., IZV. AN CCCP. CEP. XIM.,(1991) N, S. 1574-1578
  作者：KALUGIN, V. E.、LITVINOV, V. P.

  DOI：——

  日期：——
• COMPOUNDS, COMPOSITIONS AND METHODS FOR THE TREATMENT OF POXVIRUS INFECTIONS
  申请人：Chimerix, Inc.

  公开号：EP1868628A2

  公开（公告）日：2007-12-26