methyl 3(S)-(acetylthio)butanoate | 79473-56-6

• 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: methyl 3(S)-(acetylthio)butanoate
• 英文别名: methyl 3-acetylsulfanylbutyrate；methyl 3-(acetylthio)butanoate；Methyl 3-acetylsulfanylbutanoate
• CAS: 79473-56-6
• 化学式: C₇H₁₂O₃S
• 分子量: 176.236
• InChiKey: JWJRIOOXTVVAGA-UHFFFAOYSA-N

物化性质

• 沸点：
  232.0±23.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  methyl 3(S)-(acetylthio)butanoate 在 sodium hydride 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  含青霉素G亚结构的新型单环β-内酰胺的设计与合成研究

  摘要：

  Sang Hyup Lee 药学院，Duksung 女子大学，首尔 132-714，韩国。E-mail: [e-mail] 2014年5月16日接收, 2014年6月15日接受 新型单环β-内酰胺酯4(R/S)-(1'-methoxycarbonylpropyl-2'(R)的设计与合成研究/S)-硫代)-3(R)-苯基乙酰氨基氮杂环丁烷-2-酮 (3a) 和 4(R/S)-(1'-甲氧基羰基-2'-甲基-丙基-2'-硫代)-3(R )-phenylacetamidoazetidin-2-one (3b) 进行了描述。化合物 3a 和 3b 专门设计用于保留除双环系统外的所有青霉素亚结构，双环系统将通过裂解青霉素 G 的 C(3)-N(4) 键来构想。化合物 3a 和 3b 在结构阐明的背景下特别感兴趣来自青霉素的单环β-内酰胺。关键中间体，β-巯基酯 6a 和 6b，

  DOI：

  10.5012/bkcs.2014.35.10.2990
• 作为产物：
  描述：

  巴豆酸甲酯 、 硫代乙酸 反应 24.0h， 以76%的产率得到methyl 3(S)-(acetylthio)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

• Effect of the α-Methyl Substituent on Chemoselectivity in Esterase-Catalyzed Hydrolysis of <i>S</i>-Acetyl Sulfanylalkanoates
  作者：Ish Kumar、Ravinder S. Jolly

  DOI：10.1021/ol990544+

  日期：1999.7.1

  The isomeric compounds 1 and 3, which differ only in the position of a methyl substituent, give opposite chemoselectivities in an esterase-catalyzed hydrolysis reaction. The esterase was chemoselective for the oxoester in 1, but for the thiol ester group in 3. A high enantioselectivity was observed for both 1 and 3.

  仅在甲基取代基的位置上不同的异构体化合物1和3在酯酶催化的水解反应中具有相反的化学选择性。酯酶对1中的氧代酯具有化学选择性，但对3中的硫醇酯基具有化学选择性。对1和3均观察到高对映选择性。
• Diarylstyrylquinoline diacids
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0399818A1

  公开（公告）日：1990-11-28

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

  具有以下式子的化合物 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。
• Saturated hydroxyalkylquinoline acids as leukotriene antagonists
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0480716A1

  公开（公告）日：1992-04-15

  Compounds having the formula I: 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、葡萄膜炎和异体移植排斥反应。
• A Thioesterase for Chemoselective Hydrolysis of <i>S</i>-Acyl Sulfanylalkanoates
  作者：Ish Kumar、Ravinder S. Jolly

  DOI：10.1021/ol0069195

  日期：2001.1.1

  [GRAPHICS]A thioesterase, isolated from a strain of Alcallgenes sp. ISH108, chemoselectively hydrolyzes thiol esters. The application of the enzyme has been demonstrated in the preparation of the antihypertensive agent captopril.
• Unsaturated hydroxyalkylquinoline acids as leukotriene antagonists
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0480717B1

  公开（公告）日：1998-04-15