2-(ethylthio)ethyl-acetylacetate | 75090-79-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2-(ethylthio)ethyl-acetylacetate
• 英文别名: acetoacetic acid-(2-ethylthioethyl) ester；2-Ethylsulfanylethyl 3-oxobutanoate
• CAS: 75090-79-8
• 化学式: C₈H₁₄O₃S
• 分子量: 190.263
• InChiKey: WPAKOPHMWHYSDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  7
• 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：

  2-(ethylthio)ethyl-acetylacetate 在 哌啶 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 3-O-ethyl 5-O-(2-ethylsulfanylethyl) 4-(2-cyanophenyl)-2-(diethoxymethyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Studies on Nilvadipine. II. Synthesis and Structure-Activity Relationships of 2-Hydroxymethyl- and 2-Cyano-1,4-dihydropyridines Containing Heteroatom-Substituted Ester at the 5-Position.

  摘要：

  描述了新型2-羟甲基-和2-氰基-1, 4-二氢吡啶的合成，这些化合物在其核的5位上具有杂原子取代的烷基酯基团。酯的引入是通过以下方法之一进行的：经过改进的Hantzsch方法（方法A）、通过方法A获得的氯乙酸酯的水解（方法B）或用各种氨基取代氯原子（方法C）。2位的羟甲基和氰基团的制备与之前的文献相似。1）本文中制备的化合物的降压活性与之前报告的在5位的相应烷基酯进行了比较。发现N-苄基甲基氨基乙酯，特别是N-(4-氯苄基)-和N-(3, 4-二氯苄基)-N-甲基氨基乙酯，是1, 4-二氢吡啶核5位上合适的取代基，并且在一系列2-羟甲基-1, 4-二氢吡啶衍生物中，这些取代基的降压活性比简单的烷基酯略强。然而，在一系列2-氰基-1, 4-二氢吡啶衍生物中，效果则相反。两者均被发现不如已经在临床上用于治疗高血压的nilvadipine (1c)。

  DOI：

  10.1248/cpb.40.912
• 作为产物：
  描述：

  乙基2-羟乙基硫醚 、 2,2,6-三甲基-4H-1,3-二英-4-酮 以 xylene 为溶剂， 反应 1.0h， 以92%的产率得到2-(ethylthio)ethyl-acetylacetate
  参考文献：
  名称：

  4-Alkyl-1,4-dihydropyridine derivatives as specific PAF-acether antagonists

  摘要：

  A new series of 4-alkyl-1,4-dihydropyridines (1,4-DHP) were synthesized and evaluated for their ability to inhibit washed rabbit platelet aggregation induced by PAF-acether (1-O-hexadecyl/octadecyl-2-O-acetyl-sn-glycero-3-phosphorylcholine) and to reverse PAF-induced hypotension in anesthetized rats. Additionally, compounds were evaluated for their ability to inhibit the binding of radiolabeled PAF to its receptor on rabbit platelets. Among these compounds, 6I and 6L were the most potent and specific antagonists. At concentrations up to 100 microM, neither compound 6I nor compound 6L caused platelet aggregation nor did they inhibit platelet aggregation induced by collagen or adenosine diphosphate. Compound 6L did not show in vitro calcium channel blocker activity measured on vascular smooth muscle preparations of rabbit aorta and on [3H]nitrendipine binding assays. The compound did not show any cardiovascular effects in anesthetized rat at iv doses up to 1000 micrograms/kg, and the Ki value was 568.62 nmol. These results indicate that compound 6L is a potent and specific PAF antagonist with 1,4-dihydropyridine structure but devoid of a significant cardiovascular activity related to calcium-antagonist properties.

  DOI：

  10.1021/jm00174a017

文献信息

• 4-alkyl-1,4-dihydropyridines with PAF-antagonist activity
  申请人：Alter, S.A.

  公开号：US05177211A1

  公开（公告）日：1993-01-05

  4-alkyl-1,4-dihyropyridines, with PAF-antagonist activity, of formula (I) wherein R is saturated C.sub.1 -C.sub.4, R' is saturated C.sub.1 -C.sub.6 alkyl which may be interrupted by an oxygen atom, or 2-tetrahydrofurfuryl and R.sup.2 is saturated C.sub.1 -C.sub.4 or phenyl, the compound wherein R is methyl, R' is ethyl and R.sup.2 is phenyl remain excluded, are described. The compounds (I) are prepared by: (a) reaction of (II) with (III); (b) reaction of (IV) with (V); (c) reaction of (VI) with (III) and with (VII); (d) reaction of (VIII) with (V) and with (VII); or (e) reaction of (VIII) with (VI) and with (VII) in the presence of ammonia. The compounds (I) are useful due to their antagonist activity of the platelet activating factor. ##STR1##

  4-烷基-1,4-二氢吡啶，具有PAF拮抗活性，其化学式为（I），其中R为饱和的C.sub.1-C.sub.4，R'为饱和的C.sub.1-C.sub.6烷基，可以被氧原子中断，或2-四氢呋喃基，R.sup.2为饱和的C.sub.1-C.sub.4或苯基，其中化合物中R为甲基，R'为乙基，R.sup.2为苯基除外。化合物（I）通过以下方法制备：（a）将（II）与（III）反应；（b）将（IV）与（V）反应；（c）将（VI）与（III）和（VII）反应；（d）将（VIII）与（V）和（VII）反应；或（e）将（VIII）与（VI）和（VII）在氨的存在下反应。由于其拮抗血小板活化因子的活性，化合物（I）具有实用价值。
• METHOD OF LABELING SULFENIC ACID-CONTAINING PROTEINS AND PEPTIDES
  申请人：Wake Forest University Health Sciences

  公开号：US20150346209A1

  公开（公告）日：2015-12-03

  A method of labeling a sulfenic acid (—SOH) group of a cysteine residue in a protein or peptide, comprises contacting said protein or peptide with a beta-ketoester to covalently couple said beta-ketoester to said cysteine residue and form a beta-ketoester-labeled cysteine residue in said protein or peptide.

  一种标记蛋白质或肽中半胱氨酸残基的磺酰基（—SOH）的方法，包括将所述蛋白质或肽与β-酮酸酯接触，使β-酮酸酯共价耦合到所述半胱氨酸残基上，并在所述蛋白质或肽中形成一个β-酮酸酯标记的半胱氨酸残基。
• 4-alkyl-1, 4-dihydropyridines with PAF-antagonist activity
  申请人：ALTER, S.A.

  公开号：EP0325187A1

  公开（公告）日：1989-07-26

  4-alkyl-1,4-dihyropyridines, with PAF-antagonist activity, of formula (I) wherein R is saturated C₁-C₄, R′ is saturated C₁-C₆ alkyl which may be interrupted by an oxygen atom, or 2-tetrahydrofurfuryl and R² is saturated C₁-C₄ or phenyl, the compound wherein R is methyl, R′ is ethyl and R² is phenyl remain excluded, are described. The compounds (I) are prepared by: (a) reaction of (II) with (III); (b) reaction of (IV) with (V); (c) reaction of (VI) with (III) and with (VII); (d) reaction of (VIII) with (V) and with (VII); or (e) reaction of (VIII) with (VI) and with (VII) in the presence of ammonia. The compounds (I) are useful due to their antagonist activity of the platelet activating factor.

  具有 PAF-拮抗剂活性的式 (I) 的 4-烷基-1,4-二氢吡啶类化合物 其中 R 是饱和 C₁-C₄，R′是饱和 C₁-C₆烷基，可被氧原子打断、或 2-四氢糠基且 R² 为饱和 C₁-C₄ 或苯基的化合物，不包括 R 为甲基、R′ 为乙基且 R² 为苯基的化合物。 化合物 (I) 的制备方法如下(a) (II) 与 (III) 反应；(b) (IV) 与 (V) 反应；(c) (VI) 与 (III) 和 (VII) 反应；(d) (VIII) 与 (V) 和 (VII) 反应；或 (e) (VIII) 与 (VI) 和 (VII) 在氨存在下反应。化合物(I)具有拮抗血小板活化因子的活性，因此非常有用。
• SUNKEL, CARLOS E.;DE, CASA-JUANA MIGUEL FAU;SANTOS, LUIS;GOMEZ, M. MAR;VI+, J. MED. CHEM., 33,(1990) N2, C. 3205-3210
  作者：SUNKEL, CARLOS E.、DE, CASA-JUANA MIGUEL FAU、SANTOS, LUIS、GOMEZ, M. MAR、VI+

  DOI：——

  日期：——
• US4214088A
  申请人：——

  公开号：US4214088A

  公开（公告）日：1980-07-22