ethyl 3-(acetyl-thio)-2-methylpropanoate | 142148-04-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: ethyl 3-(acetyl-thio)-2-methylpropanoate
• 英文别名: ethyl 3-acetylsulfanyl-2-methylpropanoate
• CAS: 142148-04-7
• 化学式: C₈H₁₄O₃S
• 分子量: 190.263
• InChiKey: SIHZGXAHFFTEBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-(acetyl-thio)-2-methylpropanoate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 3-巯基-2-甲基丙酸乙酯
  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：

  甲基丙烯酸乙酯 、 硫代乙酸 生成 ethyl 3-(acetyl-thio)-2-methylpropanoate
  参考文献：
  名称：

  Unsaturated hydroxyalkylquinoline acids as leukotriene antagonists

  摘要：

  具有以下化学式I的化合物是白三烯拮抗剂和白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。它们还可用于治疗心绞痛、脑痉挛、肾小球肾炎、肝炎、内毒素血症、葡萄膜炎和移植排斥反应。

  公开号：

  US05565473A1

文献信息

• Fluorinated hydroxyalkylquinoline acids as leukotriene antagonists
  申请人：Merck Frosst Canada, Inc.

  公开号：US05270324A1

  公开（公告）日：1993-12-14

  Compounds having the formula I: ##STR1## are leukotriene antagonists and 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, uveitis, and allograft rejection.

  具有以下化学式的化合物 I: ##STR1## 是白三烯拮抗剂，也是白三烯生物合成的抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎症和细胞保护剂。它们还可用于治疗心绞痛、脑痉挛、肾小球肾炎、肝炎、内毒素血症、葡萄膜炎和移植排斥反应。
• Unsaturated hydroxyalkylquinoline acids as leukotriene antagonists
  申请人：Merck Frosst Canada, Inc.

  公开号：US05565473A1

  公开（公告）日：1996-10-15

  Compounds having the formula I: ##STR1## are leukotriene antagonists and 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, uveitis, and allograft rejection.

  具有以下化学式I的化合物是白三烯拮抗剂和白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。它们还可用于治疗心绞痛、脑痉挛、肾小球肾炎、肝炎、内毒素血症、葡萄膜炎和移植排斥反应。
• THIOL-CONTAINING FRAGRANCE AND FLAVOR MATERIALS
  申请人：Blandino Maureen

  公开号：US20110256071A1

  公开（公告）日：2011-10-20

  One aspect of the present invention provides a compound represented by formula (I), wherein, R 1 is hydrogen or an acetyl group and R 2 is a C 1-3 straight chain or branched alkyl group. Another aspect of the present invention provides flavor or fragrance compositions comprising at least one compound of formula (I).

  本发明的一个方面提供了一种由式(I)表示的化合物，其中，R1是氢或乙酰基，R2是C1-3直链或支链烷基。本发明的另一个方面提供了至少含有一种式(I)化合物的香味或香料组合物。
• METHOD FOR PRODUCING SULFUR-CONTAINING CARBOXYLIC ACID ESTERS
  申请人：Inaba Teruhiko

  公开号：US20110282089A1

  公开（公告）日：2011-11-17

  The present invention provides a method for producing sulfur-containing carboxylic acid esters that are useful for aromatizing and flavoring purpose and can cater to the needs for diversified aromatized and/or flavored products, and to further provide a fragrance and/or flavor composition comprising the ester producible by the method and an aromatized and/or flavored product comprising the same. The sulfur-containing carboxylic acid ester is represented by the following formula (3): wherein R 1 represents an alkyl group having 1 to 10 carbon atoms or an optionally substituted phenyl group (wherein the substituent thereof is an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms), R 2 and R 3 independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, or R 2 and R 3 together form an alkylene group, and R 4 represents an alkyl group having 1 to 4 carbon atoms.

  本发明提供了一种用于生产含硫羧酸酯的方法，这些酯对于芳香和调味目的非常有用，并且可以满足多样化芳香和/或调味产品的需求，进一步提供了一种香味和/或味道组合物，该组合物由通过该方法可制备的酯和包含该酯的芳香和/或调味产品组成。含硫羧酸酯由以下式子（3）表示：其中，R1表示具有1至10个碳原子的烷基或可选择取代的苯基（其取代基为具有1至4个碳原子的烷基或1至4个碳原子的烷氧基），R2和R3独立地表示氢原子、具有1至10个碳原子的烷基或具有2至10个碳原子的烯基，或R2和R3一起形成烷基。R4表示具有1至4个碳原子的烷基。
• Saturated hydroxyalkylquinoline acids as leukotriene antagonists
  申请人：Merck Frosst Canada, Inc.

  公开号：US05428033A1

  公开（公告）日：1995-06-27

  Compounds having the formula I: ##STR1## are leukotriene antagonists and 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, uveitis, and allograft rejection.

  化学式为I：##STR1##的化合物是白三烯拮抗剂和白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。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、葡萄膜炎和同种异体移植排斥反应。