ethyl 2-(mercaptomethyl)butanoate | 133772-53-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-(mercaptomethyl)butanoate
• 英文别名: ethyl 2-ethyl-3-mercaptopropanoate；ethyl 2-(sulfanylmethyl)butanoate
• CAS: 133772-53-9
• 化学式: C₇H₁₄O₂S
• 分子量: 162.253
• InChiKey: RUWINAYFAKVVDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  27.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(mercaptomethyl)butanoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 72.0h， 生成 丁酸,2-(巯基甲基)-
  参考文献：
  名称：

  Thiopyrano[2,3,4-cd]indoles as 5-Lipoxygenase Inhibitors: Synthesis, Biological Profile, and Resolution of 2-[2-[1-(4-Chlorobenzyl)-4-methyl-6-[(5-phenylpyridin-2-yl)methoxy]-4,5-dihydro-1H-thiopyrano[2,3,4-cd]indol-2-yl]ethoxy]butanoic Acid

  摘要：

  Leukotriene biosynthesis inhibitors have potential as new therapies for asthma and inflammatory diseases. The recently disclosed thiopyrano[2,3,4-cd] indole class of 5-lipoxygenase (5-LO) inhibitors has been investigated with particular emphasis on the side chain bearing the acidic functionality. The SAR studies have shown that the inclusion of a heteroatom (O or S) in conjunction with an alpha-ethyl substituted acid leads to inhibitors of improved potency. The most potent inhibitor prepared contains a 2-ethoxybutanoic acid side chain. This compound, 14d (2-[2-[1-(4-chlorobenzyl)-4-methyl-6-[ (5-phenylpyridin-2-yl)methoxy]-4,5-dihydro-1H-thiopyrano[2,3,4-cd]indol-2-yl]ethoxy]-butanoic acid, L-699,333), inhibits 5-HPETE production by human 5-LO and LTB(4) biosynthesis by human PMN leukocytes and human whole blood (IC(50)s Of 22 nM, 7 nM and 3.8 mu M, respectively). The racemic acid 14d has been shown to be functionally active in a rat pleurisy model (inhibition of LTB(4), ED(50) = 0.65 mg/kg, 6 h pretreatment) and in the hyperreactive rat model of antigen-induced dyspnea(50% inhibition at 2 and 4 h pretreatment; 0.5 mg/kg po). In addition, 14d shows excellent functional activity against antigen-induced bronchoconstriction in the conscious squirrel monkey [89% inhibition of the increase in R(L) and 68% inhibition in the decrease in C-dyn (0.1 mg/kg, n = 3)] and in the conscious sheep models of asthma (iv infusion at 2.5 mu g/kg/min). Acid 14d is highly selective as an inhibitor of 5-LO activity when compared to the inhibition of human 15-LO, porcine 12-LO and ram seminal vesicle cyclooxygenase (IC50 > 5 mu M) Or competition in a FLAP binding assay (IC5O > 10 mu M). Resolution of 14d affords 14g, the most potent diastereomer, which inhibits the 5-HPETE production of human 5-LO and LTB(4) biosynthesis of human PMN leukocytes and human whole blood with IC(50)s Of 8 nM, 4 nM, and 1 mu M respectively. The in vitro and in vivo profile of 14d is comparable to that of MK-0591, which has showed biochemical efficacy in inhibiting ex vivo LTB(4) biosynthesis and urinary LTE(4) excretion in clinical trials.

  DOI：

  10.1021/jm00034a013
• 作为产物：
  描述：

  2-乙基丙烯酸乙酯 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 36.5h， 生成 ethyl 2-(mercaptomethyl)butanoate
  参考文献：
  名称：

  Thiopyrano[2,3,4-cd]indoles as 5-Lipoxygenase Inhibitors: Synthesis, Biological Profile, and Resolution of 2-[2-[1-(4-Chlorobenzyl)-4-methyl-6-[(5-phenylpyridin-2-yl)methoxy]-4,5-dihydro-1H-thiopyrano[2,3,4-cd]indol-2-yl]ethoxy]butanoic Acid

  摘要：

  Leukotriene biosynthesis inhibitors have potential as new therapies for asthma and inflammatory diseases. The recently disclosed thiopyrano[2,3,4-cd] indole class of 5-lipoxygenase (5-LO) inhibitors has been investigated with particular emphasis on the side chain bearing the acidic functionality. The SAR studies have shown that the inclusion of a heteroatom (O or S) in conjunction with an alpha-ethyl substituted acid leads to inhibitors of improved potency. The most potent inhibitor prepared contains a 2-ethoxybutanoic acid side chain. This compound, 14d (2-[2-[1-(4-chlorobenzyl)-4-methyl-6-[ (5-phenylpyridin-2-yl)methoxy]-4,5-dihydro-1H-thiopyrano[2,3,4-cd]indol-2-yl]ethoxy]-butanoic acid, L-699,333), inhibits 5-HPETE production by human 5-LO and LTB(4) biosynthesis by human PMN leukocytes and human whole blood (IC(50)s Of 22 nM, 7 nM and 3.8 mu M, respectively). The racemic acid 14d has been shown to be functionally active in a rat pleurisy model (inhibition of LTB(4), ED(50) = 0.65 mg/kg, 6 h pretreatment) and in the hyperreactive rat model of antigen-induced dyspnea(50% inhibition at 2 and 4 h pretreatment; 0.5 mg/kg po). In addition, 14d shows excellent functional activity against antigen-induced bronchoconstriction in the conscious squirrel monkey [89% inhibition of the increase in R(L) and 68% inhibition in the decrease in C-dyn (0.1 mg/kg, n = 3)] and in the conscious sheep models of asthma (iv infusion at 2.5 mu g/kg/min). Acid 14d is highly selective as an inhibitor of 5-LO activity when compared to the inhibition of human 15-LO, porcine 12-LO and ram seminal vesicle cyclooxygenase (IC50 > 5 mu M) Or competition in a FLAP binding assay (IC5O > 10 mu M). Resolution of 14d affords 14g, the most potent diastereomer, which inhibits the 5-HPETE production of human 5-LO and LTB(4) biosynthesis of human PMN leukocytes and human whole blood with IC(50)s Of 8 nM, 4 nM, and 1 mu M respectively. The in vitro and in vivo profile of 14d is comparable to that of MK-0591, which has showed biochemical efficacy in inhibiting ex vivo LTB(4) biosynthesis and urinary LTE(4) excretion in clinical trials.

  DOI：

  10.1021/jm00034a013

文献信息

• Diarylstrylquinoline diacids and pharmaceutical compositions thereof
  申请人：Merck Frosst Canada, Inc.

  公开号：US05104882A1

  公开（公告）日：1992-04-14

  Compounds having the formula: ##STR1## are leukotriene antagonists and inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents.

  具有以下公式的化合物：##STR1## 是白三烯拮抗剂和白细胞三烯生物合成抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。
• 3-Arylisothiazoles and their use as herbicides
  申请人：——

  公开号：US20040023807A1

  公开（公告）日：2004-02-05

  3-Arylisothiazoles of the formula I 1 in which the variables X, Q, R 1 , R 2 , R 3 , R 4 , R 5 are as defined in claim 1, and salts thereof, and their use for controlling harmful plants, are described.

  描述了具有以下公式I1的3-芳基异噻唑，其中变量X、Q、R1、R2、R3、R4、R5如权利要求1中定义的，并且其盐及其用于控制有害植物的用途。
• 2-Aryl-5-trifluoromethylpyridines
  申请人：——

  公开号：US20040043903A1

  公开（公告）日：2004-03-04

  The present invention relates to 2-aryl-5-trifluoromethylpyridines of the formula I 1 in which the variables m, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and X have the meanings given in claim 1, and their agriculturally tolerated salts. Moreover, the invention relates to the use of compounds I and their salts as herbicides and/or for the desiccation and/or defoliation of plants, to herbicidal compositions and compositions for the desiccation and/or defoliation of plants comprising the compounds I and/or their salts as active substances.

  本发明涉及具有以下通式I中给定的变量m、R1、R2、R3、R4、R5、R6和X含义的2-芳基-5-三氟甲基吡啶，以及它们在农业中可容忍的盐。此外，本发明涉及化合物I及其盐作为除草剂和/或用于植物干燥和/或落叶的用途，以及包含化合物I和/或其盐作为活性物质的除草剂组合物和用于植物干燥和/或落叶的组合物。
• 1-aryl-4-alkyl halide-2(1h)-pyridones and their use as herbicides
  申请人：——

  公开号：US20030216257A1

  公开（公告）日：2003-11-20

  The use of 1-aryl-4-haloalkyl-2-[1H]-pyridones of the formula I 1 in which the variables are as defined in claim 1, and their use as herbicides, is described.

  本文描述了以公式I1表示的1-芳基-4-卤代烷基-2-[1H]-吡啶酮的使用，其中变量如权利要求1所定义的，并且它们的用途是作为除草剂。
• Thiopyrano[2,3,4-c,d]indoles as inhibitors of leukotriene biosynthesis
  申请人：Merck Frosst Canada, Inc.

  公开号：US05202321A1

  公开（公告）日：1993-04-13

  Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, psoriasis, uveitis and allograft rejection and in preventing the formation of atherosclerotic plaques.

  化学式为I的化合物：##STR1## 是白三烯生物合成的抑制剂。这些化合物可作为抗哮喘、抗过敏、抗炎和细胞保护剂使用。它们还可用于治疗心绞痛、脑血管痉挛、肾小球肾炎、肝炎、内毒素血症、银屑病、葡萄膜炎和移植排斥，并可预防动脉粥样硬化斑块的形成。