(+/-)-2-ethyl-2-(methanesulfonyloxymethyl)hexanal | 178678-55-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (+/-)-2-ethyl-2-(methanesulfonyloxymethyl)hexanal
• 英文别名: 2-ethyl-2-(mesyloxymethyl)hexanal；(2-ethyl-2-formylhexyl) methanesulfonate
• CAS: 178678-55-2
• 化学式: C₁₀H₂₀O₄S
• 分子量: 236.332
• InChiKey: GDVUGFJXFFCXMX-UHFFFAOYSA-N

物化性质

• 沸点：
  359.4±25.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-2-ethyl-2-(methanesulfonyloxymethyl)hexanal 在 palladium on activated charcoal 氢气 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、482.63 kPa 条件下， 反应 102.0h， 生成 2-((2-phenylmethylphenylsulfonyl)methyl)-2-ethylhexanal
  参考文献：
  名称：

  Discovery of Potent, Nonsystemic Apical Sodium-Codependent Bile Acid Transporter Inhibitors (Part 1)

  摘要：

  Elevated plasma levels of low-density lipoprotein (LDL) cholesterol are a major risk factor for atherosclerosis leading to coronary artery disease (CAD), which remains the main cause of mortality in Western society. We believe that by preventing the reabsorption of bile acids, a minimally absorbed apical sodium-codependent bile acid transporter (ASBT) inhibitor would lower the serum cholesterol without the potential systemic side effects of an absorbed drug. A series of novel benzothiepines (3R,3R'-2,3,4,5-tetrahydro-5-aryl-l-benzothiepin-4-ol 1,1-dioxides) were synthesized and tested for their ability to inhibit the apical sodium dependent bile acid transport (ASBT)-mediated uptake of [C-14]taurocholate (TC) in H14 cells. A 3R,4.R,5R13S,4S,5S racemate was found to have greater potency than the other three possible racemates. Addition of electron-donating groups such as a dimethylamino substituent at the 7 position greatly enhanced potency, and incorporation of a long-chain quaternary ammonium substituent on the 5-phenyl ring was useful in minimizing systemic exposure of this locally active ASBT inhibitor while also increasing water solubility and maintaining potency. The reported results describe the synthesis and SAR development of this benzothiepine class of ASBT inhibitors resulting in an 6000-fold improvement in ASBT inhibition with desired minimal systemic exposure of this locally acting drug candidate.

  DOI：

  10.1021/jm040215+
• 作为产物：
  描述：

  2-乙基-2-(羟甲基)-己醛 、 甲基磺酰氯 在 盐酸 、 二氯甲烷 、 magnesium sulfate 作用下， 反应 18.0h， 以to give 24.4 g of brown oil的产率得到(+/-)-2-ethyl-2-(methanesulfonyloxymethyl)hexanal
  参考文献：
  名称：

  Combination therapy employing ileal bile acid transport inhibiting benzothiepines and HMG Co-A reductase inhibitors

  摘要：

  提供了新型苯并噻吩及其衍生物和类似物；含有它们的药物组合物；以及在医学中使用这些化合物和组合物的方法，特别是在哺乳动物中预防和治疗与动脉粥样硬化或高胆固醇血症相关的高脂血症状况。还提供了组合疗法的组合物和方法，采用回肠胆酸转运抑制剂和HMG Co-A还原酶抑制剂治疗高脂血症状况。

  公开号：

  US06420417B1
• 作为试剂：
  描述：

  二乙二醇二甲醚 、 甲酮,(2-巯基苯基)苯基- 在 三乙胺 作用下， 以 (+/-)-2-ethyl-2-(methanesulfonyloxymethyl)hexanal 为溶剂， 以20.5 g (58%)的产率得到2-((2-benzoylphenylthio)methyl)-2-ethylhexanal
  参考文献：
  名称：

  Benzothiepines having activity as inhibitors of ileal bile acid

  摘要：

  提供了新颖的苯硫杂环丙烯类化合物及其衍生物和类似物；含有它们的药物组合物；以及在医学中使用这些化合物和组合物的方法，特别是在哺乳动物中预防和治疗与动脉粥样硬化或高胆固醇血症相关的高脂血症状。

  公开号：

  US05994391A1

文献信息

• Novel benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake
  申请人：G.D. Searle & Co.

  公开号：US20020013476A1

  公开（公告）日：2002-01-31

  Provided are novel benzothiepines, derivatives, and analogs thereof; pharmaceutical compositions containing them; and methods of using these compounds and compositions in medicine, particularly in the prophylaxis and treatment of hyperlipidemic conditions such as those associated with atherosclerosis or hypercholesterolemia, in mammals.

  提供了新型苯并噻吩类化合物及其衍生物和类似物；含有它们的药物组合物；以及在医学中使用这些化合物和组合物的方法，特别是在哺乳动物中预防和治疗高脂血症状，如与动脉粥样硬化或高胆固醇血症相关的情况。
• Substituted 5-aryl-benzothiepines having activity as inhibitors of ileal
  申请人：G.D. Searle and Company

  公开号：US06107494A1

  公开（公告）日：2000-08-22

  Provided are novel benzothiepines, derivatives, and analogs thereof; pharmaceutical compositions containing them; and methods of using these compounds and compositions in medicine, particularly in the prophylaxis and treatment of hyperlipidemic conditions such as those associated with atherosclerosis or hypercholesterolemia, in mammals.

  提供了新型苯硫杂吲哚类化合物及其衍生物和类似物；包含它们的药物组合物；以及在医学中使用这些化合物和组合物的方法，特别是在哺乳动物中预防和治疗高脂血症状，如与动脉粥样硬化或高胆固醇血症相关的情况。
• Novel benzothiepines having activity as inhibitors of lleal bile acid transport and taurocholate uptake
  申请人：G.D. Searle & Co.

  公开号：US20040014803A1

  公开（公告）日：2004-01-22

  Provided are novel benzothiepines, derivatives, and analogs thereof; pharmaceutical compositions containing them; and methods of using these compounds and compositions in medicine, particularly in the prophylaxis and treatment of hyperlipidemic conditions such as those associated with atherosclerosis or hypercholesterolemia, in mammals.

  提供了新型苯硫杂吲哚类化合物及其衍生物和类似物；含有它们的药物组合物；以及在医学中使用这些化合物和组合物的方法，特别是在哺乳动物中预防和治疗高脂血症状，如与动脉粥样硬化或高胆固醇血症相关的情况。
• Benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake
  申请人：G.D. Searle & Co.

  公开号：US06387924B2

  公开（公告）日：2002-05-14

  Provided are novel benzothiepines, derivatives, and analogs thereof; pharmaceutical compositions containing them; and methods of using these compounds and compositions in medicine, particularly in the prophylaxis and treatment of hyperlipidemic conditions such as those associated with atherosclerosis or hypercholesterolemia, in mammals.

  提供了新颖的苯硫杂环丙烷类化合物及其衍生物和类似物；含有它们的药物组合物；以及在医学中使用这些化合物和组合物的方法，特别是在哺乳动物中预防和治疗与动脉粥样硬化或高胆固醇血症相关的高脂血症条件。
• Combination therapy employing ileal bile acid transport inhibiting benzothiepines and HMG Co-A reductase inhibitors
  申请人：G. D. Searle & Co.

  公开号：US06268392B1

  公开（公告）日：2001-07-31

  Provided are novel benzothiepines, derivatives, and analogs thereof; pharmaceutical compositions containing them; and methods of using these compounds and compositions in medicine, particularly in the prophylaxis and treatment of hyperlipidemic conditions such as those associated with atherosclerosis or hypercholesterolemia, in mammals. Also provided are compositions and methods for combination therapy employing ileal bile acid transport inhibitors and EG Co-A reductase inhibitors for the treatment of hyperlipidemic conditions.

  提供了新型苯硫氮杂环化合物，其衍生物和类似物；含有它们的药物组合物；以及在医学中使用这些化合物和组合物的方法，特别是在哺乳动物中用于预防和治疗高脂血症状，如与动脉粥样硬化或高胆固醇血症相关的情况。还提供了使用回肠胆酸转运抑制剂和EG Co-A还原酶抑制剂联合治疗高脂血症状的组合疗法的组合物和方法。