methyl 2,2-dimethyl-6-mercaptohexanoate | 83009-41-0

• 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 2,2-dimethyl-6-mercaptohexanoate
• 英文别名: methyl 2,2-dimethyl-6-sulfanylhexanoate
• CAS: 83009-41-0
• 化学式: C₉H₁₈O₂S
• 分子量: 190.307
• InChiKey: YXLUASOUIRKCEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  methyl 2,2-dimethyl-6-mercaptohexanoate 在 氢氟酸 、 叔丁基锂 、 苯硫酚铜(I) 、 三乙胺 、 三(二甲胺基)膦 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 6-[(1S,2R,3S)-2-((E)-(S)-3-Cyclohexyl-3-hydroxy-propenyl)-3-hydroxy-5-oxo-cyclopentylsulfanyl]-2,2-dimethyl-hexanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of 7-thiaprostaglandin E1 congeners: Potent inhibitors of platelet aggregation.

  摘要：

  合成了一系列新型的7-硫前列腺素E1衍生物和同系物，采用一步法的三组分耦合过程，该过程涉及向(R)-4-叔丁基二甲基硅氧基-2-环戊烯酮引入α侧链（硫醇）和β侧链（有机铜试剂）。还通过酶法或化学方法制备了几种7-硫前列腺素E1的酸衍生物。这些产物的立体化学基于对手性保护的环戊烯酮和手性ω侧链的结果进行分配。发现某些7-硫前列腺素E1同系物的血小板聚集抑制活性比PGE1更强。文中讨论了这些同系物的结构-活性关系。

  DOI：

  10.1248/cpb.33.2359

文献信息

• Substituted bicyclic bis-aryl compounds exhibiting selective leukotriene
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05366982A1

  公开（公告）日：1994-11-22

  This invention relates to compounds having selective LTB.sub.4 antagonist properties, compositions comprising said compounds and methods for the treatment of disorders involving LTB.sub.4 agonist-mediated activity utilizing said compositions wherein the compounds are described by the general formula ##STR1## and pharmaceutically acceptable salts thereof.

  本发明涉及具有选择性LTB.sub.4拮抗性的化合物，包括所述化合物的组合物以及利用所述组合物治疗涉及LTB.sub.4激动剂介导活性的疾病的方法，其中所述化合物由一般公式##STR1##和其药用可接受的盐描述。
• Thiaprostaglandin E.sub.1 derivatives, process for production thereof,
  申请人：Teijin Limited

  公开号：US04466980A1

  公开（公告）日：1984-08-21

  A novel compound selected from the group consisting of 7-(or 6- or 4-)thiaprostaglandin E.sub.1 derivatives of the formula (I). ##STR1## wherein A represents --CH.sub.2 -- or ##STR2## in which n is 0, 1 or 2, provided that only one A cut of three is ##STR3## R.sup.1 -R.sup.7 and G are as defined in the specification, the 15-epimers of said thiaprostaglandin E.sub.1 derivatives, the enatiomers of said thiaprostaglandin E.sub.1 derivatives or their 15-epimers, and mixtures of these compounds. A 7-thiaprostaglandin E.sub.1 derivative and/or its optical isomer may be prepared by reacting a 2-organo-2-cyclopentenone (II) with an organic copper-lithium compound (III) to effect conjugation reaction. A 6-thiaprostaglandin E.sub.1 derivative and/or its optical isomer may be prepared by subjecting an .alpha.,.beta.-unsaturated ketone (IV) and a thiol (V) to the Michael addition reaction. And, 4-thiaprostaglandin derivative and/or its optical isomer may also be prepared by the Michael addition reaction from a 2-allyl substituted cyclopentanone (VI) and a thiol (VIII). Some compounds ((I)-1) amongst the compounds of the formula (I) and/or their optical isomer are useful for controlling vascular actions such as angina pectoris, vasodilation etc.

  从以下化合物组中选择一种新的化合物，该组化合物包括公式（I）的7-（或6-或4-）硫代前列腺素E.sub.1衍生物。其中，A表示--CH.sub.2--或##STR2##其中n为0、1或2，前提是只有一个A切口为三个##STR3##R.sup.1-R.sup.7和G如规范中所定义，所述硫代前列腺素E.sub.1衍生物的15-表异构体，所述硫代前列腺素E.sub.1衍生物的对映异构体或其15-表异构体，以及这些化合物的混合物。可以通过将2-有机-2-环戊酮（II）与有机铜锂化合物（III）反应以进行共轭反应来制备7-硫代前列腺素E.sub.1衍生物和/或其光学异构体。可以通过将α，β-不饱和酮（IV）和硫醇（V）进行Michael加成反应来制备6-硫代前列腺素E.sub.1衍生物和/或其光学异构体。此外，也可以通过从2-烯丙基取代的环戊酮（VI）和硫醇（VIII）进行Michael加成反应来制备4-硫代前列腺素衍生物和/或其光学异构体。公式（I）的化合物（（I）-1）中的某些化合物和/或其光学异构体对于控制血管作用，如心绞痛、血管扩张等非常有用。
• Substituted quinolyl compounds exhibiting selective leukotriene B.sub.4
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05492915A1

  公开（公告）日：1996-02-20

  This invention relates to compounds having selective LTB.sub.4 antagonist properties. Therapeutic compositions comprising said compounds and methods for the treatment of disorders involving LTB.sub.4 agonist-mediated activity utilizing said compositions wherein the compounds are described by the formula ##STR1## wherein R.sub.4, X, R, Y, R', Q, m and n are herein defined, and pharmaceutically acceptable salts thereof.

  本发明涉及具有选择性LTB.sub.4拮抗剂特性的化合物。包括该化合物的治疗组合物和使用该组合物治疗涉及LTB.sub.4激动剂介导的活性的疾病的方法，其中该化合物由以下式子描述：##STR1## 其中R.sub.4、X、R、Y、R'、Q、m和n在此定义，并且其药学上可接受的盐。
• Novel thiaprostaglandin E1 derivatives, process for production thereof, and pharmaceuticals containing these compounds
  申请人：TEIJIN LIMITED

  公开号：EP0051284A1

  公开（公告）日：1982-05-12

  A novel compound selected from the group consisting of 7-(or 6- or 4-) thiaprostaglandin E1 derivatives of the formula wherein A represents - in which n is 0,1 or 2, provided that only one A cut of three is (O)n ; R1- R7 and G are defined in claim 1, the 15-epimers of said thiaprostaglandin E1 derivatives, the enatiomers of said thiaprostaglandin E1 derivatives or their 15-epimers, and mixtures of these compounds, A 7-thiaprostagiandin E, derivatives and/or its optical isomer may be prepared by reacting a 2-organo-2-cyclopentenone (II) with an organic copper-lithium compound (III) to effect conjugation reaction. A 6-thiaprostaglandin E1 derivative and/or its optical isomer may be prepared by subjecting an α-β-unsaturated ketone (IV) and a thiol (V) to the Michael addition reaction. And 4-thiaprostaglandin derivative and/or its optical isomer may also be prepared by the Michael addition reaction from a 2-allyl substituted cyclopentanone (VI) and a thiol (VIII). Some compounds ((I)-1) amongst the compounds of the formula (I) and/or their optical isomer are useful for controlling vascularactions such as angina pectoris, vasodilation etc.

  选自由式 7-（或 6-或 4-）硫前列腺素 E1 衍生物组成的组的新型化合物 其中 A 代表 - 其中 n 为 0、1 或 2，条件是三个 A 中只有一个是 (O)n ;R1- R7和G在权利要求1中定义，所述硫前列腺素E1衍生物的15-表聚体，所述硫前列腺素E1衍生物的对映体或它们的15-表聚体，以及这些化合物的混合物、 7-硫前列腺素 E 衍生物和/或其光学异构体可通过 2-有机-2-环戊烯酮 (II) 与有机铜锂化合物 (III) 发生共轭反应来制备。6- 硫前列腺素 E1 衍生物和/或其光学异构体可通过使 α-β- 不饱和酮（IV）和硫醇（V）发生迈克尔加成反应来制备。4-硫代前列腺素衍生物和/或其光学异构体也可以由 2-烯丙基取代的环戊酮（VI）和硫醇（VIII）通过迈克尔加成反应制备。 式（I）化合物中的某些化合物（(I)-1）和/或其光学异构体可用于控制血管反应，如心绞痛、血管扩张等。
• .omega.-[(4-Phenyl-2-quinolyl)oxy]alkanoic acid derivatives: a new family of potent LTB4 antagonists
  作者：Richard Labaudiniere、Wolfram Hendel、Bernard Terlain、Francoise Cavy、Olivier Marquis、Norbert Dereu

  DOI：10.1021/jm00101a007

  日期：1992.11

  A series of omega-[(4-phenyl-2-quinolyl)oxy]alkanoic acid derivatives was prepared which inhibited the binding of the leukotriene B4 to its receptors on guinea pig spleen membranes and on human polymorphonuclear leukocytes. A structure-activity relationship was investigated. The length of the carboxylic acid side chain was important for potent binding activity. The replacement of the oxygen atom at the beginning of the chain with other polar or nonpolar linking groups led to considerable loss of potency, indicating that the oxygen linking atom might be involved in the receptor recognition. Alpha-Substitution on the carboxylic acid side chain led to substantially more potent compounds. Substitution on the phenyl ring and on the quinoline ring was also evaluated.