2-((2-bromoethyl)disulfanyl)ethanol | 113398-38-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 有机二硫化物
• 英文名称: 2-((2-bromoethyl)disulfanyl)ethanol
• 英文别名: 2-((2-bromoethyl)dithio)ethanol；Ethanol, 2-[(2-bromoethyl)dithio]-；2-(2-bromoethyldisulfanyl)ethanol
• CAS: 113398-38-2
• 化学式: C₄H₉BrOS₂
• 分子量: 217.151
• InChiKey: YQGQKJJGTYDWRN-UHFFFAOYSA-N

物化性质

• 沸点：
  291.0±25.0 °C(Predicted)
• 密度：
  1.630±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((2-bromoethyl)disulfanyl)ethanol 在 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 0.75h， 以74%的产率得到2-((2-hydroxyethyl)disulfanyl)ethyl nitrate
  参考文献：
  名称：

  Prodrugs containing novel bio-cleavable linkers

  摘要：

  本发明提供了公式(I)的化合物或其药用可接受的盐。本发明还提供了包含一个或多个公式I的化合物或其中间体以及一个或多个药用可接受的载体、车辆或稀释剂的药物组合物。本发明进一步提供了包括制备方法和使用方法在内的前药，包括释放一氧化氮的前药、双前药和相互前药，由公式I的化合物组成。

  公开号：

  US20060046967A1
• 作为产物：
  描述：

  2-羟乙基二硫化物 在 三苯基膦 、 四溴化碳 作用下， 以 二氯甲烷 为溶剂， 反应 10.75h， 以52%的产率得到2-((2-bromoethyl)disulfanyl)ethanol
  参考文献：
  名称：

  NO-NSAIDs: Gastric-sparing nitric oxide-releasable prodrugs of non-steroidal anti-inflammatory drugs

  摘要：

  Recently, a new class of nitric-oxide-releasing non-steroidal anti-inflammatory drugs (NO-NSAIDs) is being studied as 'Safe NSAIDs' because of their gastric-sparing properties. As an extension of our novel disulfide linker technology, we have designed, synthesized and evaluated novel NO-releasing NSAID prodrugs such as NO-Aspirin (1b-d) and NO-Diclofenac (2b-c). Although the amide-containing derivative 1d did not show any bioavailability, the remaining compounds have shown fair to excellent pharmacokinetic. anti-inflammatory and gastric-sparing properties. Among them, however, the NO-Diclofenac (2b) has shown the most promising pharmacokinetic, anti-inflammatory and NO-releasing properties and protected rats from NSAID-induced gastric damage which could be attributable to the beneficial effects of NO released from these prodrugs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.142

文献信息

• Nevalainen, Vesa; Pohjala, Esko, Journal of Chemical Research, Miniprint, 1988, # 6, p. 1401 - 1421
  作者：Nevalainen, Vesa、Pohjala, Esko

  DOI：——

  日期：——
• NEVALAINEN V.; POHJALA E., FINN. CHEM. LETT., 14,(1987) N 2, 71-78
  作者：NEVALAINEN V.、 POHJALA E.

  DOI：——

  日期：——
• Prodrugs containing novel bio-cleavable linkers
  申请人：Satyam Apparao

  公开号：US20060046967A1

  公开（公告）日：2006-03-02

  The invention provides the compounds of formula (I) or pharmaceutically acceptable salts thereof. The invention also provides pharmaceutical compositions comprising one or more compounds of formula I or intermediates thereof and one more of pharmaceutically acceptable carriers, vehicles or diluents. The invention further provides methods of preparation and methods of use of prodrugs including NO-releasing prodrugs, double prodrugs and mutual prodrugs comprising the compounds of formula I.

  本发明提供了公式(I)的化合物或其药用可接受的盐。本发明还提供了包含一个或多个公式I的化合物或其中间体以及一个或多个药用可接受的载体、车辆或稀释剂的药物组合物。本发明进一步提供了包括制备方法和使用方法在内的前药，包括释放一氧化氮的前药、双前药和相互前药，由公式I的化合物组成。
• NO-NSAIDs: Gastric-sparing nitric oxide-releasable prodrugs of non-steroidal anti-inflammatory drugs
  作者：Kumar V.S. Nemmani、Sunil V. Mali、Namdev Borhade、Asif R. Pathan、Manoj Karwa、Venu Pamidiboina、S.P. Senthilkumar、Machhindra Gund、Arun K. Jain、Naveen K. Mangu、Nauzer P. Dubash、Dattatraya C. Desai、Somesh Sharma、Apparao Satyam

  DOI：10.1016/j.bmcl.2009.07.142

  日期：2009.9

  Recently, a new class of nitric-oxide-releasing non-steroidal anti-inflammatory drugs (NO-NSAIDs) is being studied as 'Safe NSAIDs' because of their gastric-sparing properties. As an extension of our novel disulfide linker technology, we have designed, synthesized and evaluated novel NO-releasing NSAID prodrugs such as NO-Aspirin (1b-d) and NO-Diclofenac (2b-c). Although the amide-containing derivative 1d did not show any bioavailability, the remaining compounds have shown fair to excellent pharmacokinetic. anti-inflammatory and gastric-sparing properties. Among them, however, the NO-Diclofenac (2b) has shown the most promising pharmacokinetic, anti-inflammatory and NO-releasing properties and protected rats from NSAID-induced gastric damage which could be attributable to the beneficial effects of NO released from these prodrugs. (C) 2009 Elsevier Ltd. All rights reserved.