2-(phenylthio)ethyl-acetylacetate | 100303-72-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(phenylthio)ethyl-acetylacetate
• 英文别名: 2-phenylsulfanylethyl 3-oxobutanoate
• CAS: 100303-72-8
• 化学式: C₁₂H₁₄O₃S
• 分子量: 238.307
• InChiKey: NJEMODZFRVCPHU-UHFFFAOYSA-N

物化性质

• 沸点：
  361.2±22.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-(phenylthio)ethyl-acetylacetate 在 哌啶 、 溶剂黄146 作用下， 以 叔丁醇 、 苯 为溶剂， 反应 48.0h， 生成 3-Cyclopentyl-1,6-dimethyl-4-(2-nitro-phenyl)-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid 2-phenylsulfanyl-ethyl ester; hydrochloride
  参考文献：
  名称：

  Studies on dihydropyridines. II. Synthesis of 4,7-dihydropyrazolo(3,4-b)pyridines with vasodilating and antihypertensive activities.

  摘要：

  合成了一系列4-芳基-4, 7-二氢吡唑[3, 4-b]吡啶-5-羧酸酯衍生物（72-149），并对这些化合物进行了在分离的豚鼠门静脉中的钙通道阻滞活性、自发性高血压大鼠中的抗高血压活性以及在分离的豚鼠心脏中的冠状血管扩张作用的测试。多种衍生物具有强效的抗高血压和冠状血管扩张活性。该系列的结构-活性关系表明，3-环戊基或3-环己基取代基以及具有适度体积的疏水性5-酯基团对于提高药理活性是有效的。

  DOI：

  10.1248/cpb.35.3235
• 作为产物：
  描述：

  2-苯硫基乙醇 、 2,2,6-三甲基-4H-1,3-二英-4-酮 以 xylene 为溶剂， 反应 1.0h， 以88%的产率得到2-(phenylthio)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。
• 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.
  作者：Yoshinari SATOH、Masaharu ICHIHASHI、Kazuo OKUMURA

  DOI：10.1248/cpb.40.912

  日期：——

  The synthesis of new 2-hydroxymethyl- and 2-cyano-1, 4-dihydropyridines possessing a heteroatom-substituted alkyl ester group at the 5-position of the nucleus in described. The esters were introduced via a suitable method selected from the modified Hantzsch method (method A), the hydrolysis of a chloroethyl ester obtained by method A (method B) or the replacement of the chlorine atom with various kinds of amino groups (method C). Hydroxymethyl and cyano groups at the 2-position were prepared in a similar manner to that described in a previous papare.1)The hypotensive activities of the compounds prepared in this paper were compared with the corresponding alkyl ester at the 5-position reported previously. It was found that N-benzylmethylaminoethyl esters, especially N-(4-chlorobenzyl)-and N-(3, 4-dichlorobenzyl)-N-methylaminoethyl esters, were suitable substituents at the 5-position of the 1, 4-dihydropyridine nucleus and that these substituents were somewhat more effective for hypotensive activity than simple alkyl esters in a series of 2-hydroxymethyl-1, 4-dihydropyridine derivatives. But it was found that the effect was reversed in a series of 2-cyano-1, 4-dihydropyridine derivatives. Both of them were found to be inferior to nilvadipine (1c), accepted in clinical use for the treatment of hypertension.

  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)。
• 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：——
• ADACHI, IKUO;YAMAMORI, TERUO;UEDA, MOTOHIKO;SATO, HATSUO
  作者：ADACHI, IKUO、YAMAMORI, TERUO、UEDA, MOTOHIKO、SATO, HATSUO

  DOI：——

  日期：——
• ADACHI, IKUO;YAMAMORI, TERUO;HIRAMATSU, YOSHIHARU;SAKAI, KATSUNORI;SATO, +, CHEM. AND PHARM. BULL., 35,(1987) N 8, 3235-3252
  作者：ADACHI, IKUO、YAMAMORI, TERUO、HIRAMATSU, YOSHIHARU、SAKAI, KATSUNORI、SATO, +

  DOI：——

  日期：——