[S-(E)]-3-[[[(2-羧基乙基)硫代][3-[2-(7-氯-2-喹啉基)乙烯基]苯基]甲基]硫代]丙酸1-甲酯 | 120385-98-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: [S-(E)]-3-[[[(2-羧基乙基)硫代][3-[2-(7-氯-2-喹啉基)乙烯基]苯基]甲基]硫代]丙酸1-甲酯
• 英文名称: (S)-3-(((3-(2-(7-chloroquinolin-2-yl)-(E)-ethenyl)phenyl)((3-methoxy-3-oxopropyl)thio)methyl)thio)propionic acid
• 英文别名: (S)-3-[({3-[2-(7-chloroquinolin-2-yl)-(E)-ethenyl]phenyl}[(3-methoxy-3-oxopropyl)thio]methyl)thio]propionic acid；(S,E)-3-((3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)(3-methoxy-3-oxopropylthio)methylthio)propanoic acid；3-[(S)-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-(3-methoxy-3-oxopropyl)sulfanylmethyl]sulfanylpropanoic acid
• CAS: 120385-98-0
• 化学式: C₂₅H₂₄ClNO₄S₂
• 分子量: 502.055
• InChiKey: FUNFCFISWSRFDG-KPPJJKTOSA-N

物化性质

• 沸点：
  684.2±55.0 °C(Predicted)
• 密度：
  1.354±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [S-(E)]-3-[[[(2-羧基乙基)硫代][3-[2-(7-氯-2-喹啉基)乙烯基]苯基]甲基]硫代]丙酸1-甲酯 生成 (S)-3-(((3-(2-(7-chloroquinolin-2-yl)-(E)-ethenyl)phenyl)((3-(dimethylamino)-3-oxopropyl)thio)methyl)thio)propionic acid methyl ester
  参考文献：
  名称：

  Synthesis of chiral dithioacetals: a chemoenzymic synthesis of a novel LTD4 antagonist

  摘要：

  DOI：

  10.1021/jo00269a007
• 作为产物：
  描述：

  3,3'-[[[3-[(1E)-2-(7-氯-2-喹啉基)乙烯基]苯基]亚甲基]二(硫代)]二-丙酸1,1'-二甲酯 在 Triton X-100 作用下， 生成 [S-(E)]-3-[[[(2-羧基乙基)硫代][3-[2-(7-氯-2-喹啉基)乙烯基]苯基]甲基]硫代]丙酸1-甲酯
  参考文献：
  名称：

  Shinkai, I; Bhupathy, M, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 1, p. 127 - 130

  摘要：

  DOI：

文献信息

• Stereospecific synthesis, assignment of absolute configuration, and biological activity of the enantiomers of 3-[[[3-[2-(7-chloroquinolin-2-yl)-(E)-ethenyl]phenyl][[3-(dimethylamino)-3-oxopropyl]thio]methyl]thio]propionic acid, a potent and specific leukotriene D4 receptor antagonist
  作者：J. Y. Gauthier、T. Jones、E. Champion、L. Charette、R. Dehaven、A. W. Ford-Hutchinson、K. Hoogsteen、A. Lord、P. Masson

  DOI：10.1021/jm00172a025

  日期：1990.10

  enantiomers of the leukotriene D4 antagonist 3-[[[3-[2-(7-chloroquinolin-2-yl)-(E)-ethenyl]phenyl] [[3-(dimethylamino)-3-oxopropyl]thio]methyl]thio]propionic acid (L-660,711)(MK-571) have been prepared, their absolute stereochemistry has been assigned as S for (+)-1 and R for (-)-1 by X-ray analysis of a synthetic intermediate (5), and the biological activity of the enantiomers has been explored. Unexpectedly

  白三烯D4拮抗剂3-[[[[3- [2-（7-氯喹啉-2-基）-（E）-乙烯基]苯基] [[3-（二甲基氨基）-3-氧丙基]硫代]甲基的对映异构体制备了]硫基]丙酸（L-660,711）（MK-571），通过合成中间体的X射线分析，其绝对立体化学被指定为（+）-1的S和（-）-1的R （5），并且已经探索了对映异构体的生物活性。出乎意料的是，在体外，对映异构体在生物学上均与LTD4受体的生物活性相当，而（+）-1的固有活性略高。
• A practical chemoenzymatic synthesis of an LTD4 antagonist
  作者：D.L. Hughes、Z. Song、G.B. Smith、J.J. Bergan、G.C. Dezeny、E.J.J. Grabowski、P.J. Reider

  DOI：10.1016/s0957-4166(00)80124-x

  日期：1993.5

  between the ester group and prochiral center is the cornerstone of a short and efficient synthesis of an LTD4 antagonist. The enzymatic hydrolysis occurs in a heterogeneous slurry, but a kinetic analysis shows that the reaction takes place in solution. Product inhibition of the enzyme is severe, requiring that a substantial amount of enzyme be used relative to substrate. To more efficiently use the expensive

  在酯基和前手性中心之间具有4个键的前手性二酯的酶促不对称化是LTD4拮抗剂的短而有效的合成的基础。酶促水解发生在异质淤浆中，但动力学分析表明该反应在溶液中发生。酶的产物抑制作用很严重，需要相对于底物使用大量的酶。为了更有效地使用昂贵的酶，将其固定在几种载体上，其中最有效的是带有交联酶的XAD 7。
• Lipase-catalyzed asymmetric hydrolysis of esters having remote chiral/prochiral centers
  作者：David L. Hughes、J. J. Bergan、J. S. Amato、M. Bhupathy、J. L. Leazer、J. M. McNamara、D. R. Sidler、P. J. Reider、E. J. J. Grabowski

  DOI：10.1021/jo00313a010

  日期：1990.12

  Enzymatic hydrolysis of prochiral and racemic dithioacetal esters having up to five bonds between the prochiral/chiral center and the ester carbonyl group proceeds with selectivities up to 98% enantiomeric excess when commercially available lipases are used. For lipase from Pseudomonas sp., chemical yields and ee's were better with the substrate having four bonds between the prochiral center and ester carbonyl than with the three-bond or five-bond analogues, demonstrating that selectivity does not necessarily diminish as the distance between the chiral center and the reaction site increases. These findings are the cornerstone of efficient chemoenzymatic syntheses of both enantiomers of a potent LTD4 antagonist.
• Kinetics of a heterogeneous enzymic hydrolysis of a prochiral diester
  作者：George B. Smith、Mahadevan Bhupathy、George C. Dezeny、Alan W. Douglas、Russel J. Lander

  DOI：10.1021/jo00042a040

  日期：1992.7
• Aluminum-Amine Complexes for the Conversion of Carboxylic Esters to Amides. Application to the Synthesis of LTD4 Antagonist MK-0679
  作者：Daniel R. Sidler、Thomas C. Lovelace、James M. McNamara、Paul J. Reider

  DOI：10.1021/jo00085a001

  日期：1994.3

  The preparation and characterization of N,N-dimethylammonium dialkylaluminum chloride and the use of these complexes in the synthesis of the LTD4 antagonist MK-0679 is described.