3,4-dimethoxy-8-(4'-chlorothiophenoxy)propiophenone | 169210-73-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dimethoxy-8-(4'-chlorothiophenoxy)propiophenone
• 英文别名: 1-Propanone, 2-[(4-chlorophenyl)thio]-1-(3,4-dimethoxyphenyl)-；2-(4-chlorophenyl)sulfanyl-1-(3,4-dimethoxyphenyl)propan-1-one
• CAS: 169210-73-5
• 化学式: C₁₇H₁₇ClO₃S
• 分子量: 336.839
• InChiKey: WRGMEHJRTPYLAW-UHFFFAOYSA-N

物化性质

• 沸点：
  470.5±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-dimethoxy-8-(4'-chlorothiophenoxy)propiophenone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以96%的产率得到threo-2-[(4-chlorophenyl)thio]-1-(3,4-dimethoxyphenyl)propan-1-ol
  参考文献：
  名称：

  Structure–activity relationship of antileishmanials neolignan analogues

  摘要：

  Twenty-two synthetic analogues of neolignans comprising beta-ketoethers and beta-ketosulfides were obtained from condensation reactions among beta-bromoketones and phenols or thiophenols, respectively, in basic solutions, and assayed in vitro for activity against intracellular Leishmania amazonensis and Leishmania donovani amastigotes, the causative agents of cutaneous and visceral leishmaniasis. The highest selective activity was found for compounds with sulfur bridges, whereas beta-ketosulphoxides and beta-ketosulphones had significantly less growth inhibitory activity. Compounds 2-[(4-chlorophenyl)thio]propan-1-one and 1-(3,4-dimethoxy)2-[(4-methylphenyl)thio]propan-1-one were the most potent, inhibiting the growth parasite species by over 90% at microgram/mL, but only compound 1-(3,4-dimethoxy)-2-[(4-methylphenyl)thio]propan-1-one was selectively toxic to the parasites. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.016
• 作为产物：
  描述：

  2-溴-3-4-二甲氧基苯丙酮 、 4-氯苯硫酚 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 8.17h， 以81.7%的产率得到3,4-dimethoxy-8-(4'-chlorothiophenoxy)propiophenone
  参考文献：
  名称：

  Synthesis, X-ray crystal structure and theoretical calculations of antileishmanial neolignan analogues

  摘要：

  本文介绍了两种新木质素类似物 2-(4-氯苯基)-1-苯基乙酮（20）和 2-[(4-氯苯基)硫]-1-(3,4-二甲氧基苯基)丙-1-酮（12）的合成和 X 射线晶体衍射结构。化合物 12 对引起皮肤和内脏利什曼病的细胞内唐氏利什曼原虫和亚马逊利什曼原虫具有活性。此外，还采用 B3LYP 混合函数的密度泛函理论（DFT）计算了 19 种具有抗利什曼病活性的新木质素合成类似物的分子描述符。随后，进行了逐步判别分析，以研究分子描述符与生物活性之间可能存在的关系。通过这种分析，根据生物活性的程度将化合物分为活性和非活性两类，而更重要的性质是一些关键原子上的电荷、电子亲和力和 ClogP。

  DOI：

  10.1590/s0103-50532010001000006

文献信息

• Anti-leishmanial activity of neolignans from Virola species and synthetic analogues
  作者：Lauro E.S Barata、Lourivaldo S Santos、Pedro H Ferri、J.David Phillipson、Angela Paine、Simon L Croft

  DOI：10.1016/s0031-9422(00)00240-5

  日期：2000.11

  Surinamensin, a neolignan isolated from Virola surinamensis, 3,4,5-trimethoxy-8-[2',6'-dimethoxy-4'-(E)-propenylphenoxy]-phenylpropane, a neolignan isolated from Virola pavonis, and 25 of its synthetic analogues or correlated substances with ether linkages and their corresponding C-8 sulphur and nitrogen analogues, were tested for activity against Leishmania donovani amastigotes and promastigotes in

  Surinamensin，一种从 Virola surinamensis 中分离的新木脂素，3,4,5-trimethoxy-8-[2',6'-dimethoxy-4'-(E)-propenylphenoxy]-phenylpropane，一种从 Virola pavonis 中分离的新木脂素，以及 25在体外测试了其合成类似物或具有醚键的相关物质及其相应的 C-8 硫和氮类似物对多诺瓦利什曼原虫无鞭毛体和前鞭毛体的活性。有些在 30 microM 时对 L. donovani 前鞭毛体有活性，但对细胞内无鞭毛体无活性。来自 V.pavonis 的天然新木脂素对 100 microM 的前鞭毛体有活性。在具有硫桥的那些化合物中发现了最高的选择性活性。β-酮硫化物 (3,4-二甲氧基)-8-(4'-甲基噻吩氧基)-苯丙酮对 L. 产生了 42% 的抑制作用。
• Structure–activity relationship of antileishmanials neolignan analogues
  作者：Mário Aveniente、Eduardo F. Pinto、Lourivaldo S. Santos、Bartira Rossi-Bergmann、Lauro E.S. Barata

  DOI：10.1016/j.bmc.2007.08.016

  日期：2007.12

  Twenty-two synthetic analogues of neolignans comprising beta-ketoethers and beta-ketosulfides were obtained from condensation reactions among beta-bromoketones and phenols or thiophenols, respectively, in basic solutions, and assayed in vitro for activity against intracellular Leishmania amazonensis and Leishmania donovani amastigotes, the causative agents of cutaneous and visceral leishmaniasis. The highest selective activity was found for compounds with sulfur bridges, whereas beta-ketosulphoxides and beta-ketosulphones had significantly less growth inhibitory activity. Compounds 2-[(4-chlorophenyl)thio]propan-1-one and 1-(3,4-dimethoxy)2-[(4-methylphenyl)thio]propan-1-one were the most potent, inhibiting the growth parasite species by over 90% at microgram/mL, but only compound 1-(3,4-dimethoxy)-2-[(4-methylphenyl)thio]propan-1-one was selectively toxic to the parasites. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis, X-ray crystal structure and theoretical calculations of antileishmanial neolignan analogues
  作者：Josenaide P. do Nascimento、Lourivaldo S. Santos、Regina Helena A. Santos、Érica Tozzo、Janaina G. Ferreira、Maria Carolina L. do Carmo、Davi S. B. Brasil、Cláudio N. Alves

  DOI：10.1590/s0103-50532010001000006

  日期：——

  The synthesis and X-ray crystal diffraction structure of two analogues of neolignans, 2-(4-chlorophenyl)-1-phenylethanone (20) and 2-[(4-chlorophenyl)thio]-1-(3,4-dimethoxyphenyl)propan-1-one (12) is described. The compound 12 presents activity against intracellular Leishmania donovani and Leishmania amazonensis amastigotes that cause cutaneous and visceral leishmaniasis. In addition, the density functional theory (DFT) with the B3LYP hybrid functional was employed to calculate a set of molecular descriptors for nineteen synthetic analogues of neolignans with antileishmanial activities. Afterwards, the stepwise discriminant analysis was performed to investigate possible relationship between the molecular descriptors and biological activities. Through this analysis the compounds were classified into two groups active and inactive according to their degree of biological activities, and the more important properties were charges on some key atoms, electronic affinity and ClogP.

  本文介绍了两种新木质素类似物 2-(4-氯苯基)-1-苯基乙酮（20）和 2-[(4-氯苯基)硫]-1-(3,4-二甲氧基苯基)丙-1-酮（12）的合成和 X 射线晶体衍射结构。化合物 12 对引起皮肤和内脏利什曼病的细胞内唐氏利什曼原虫和亚马逊利什曼原虫具有活性。此外，还采用 B3LYP 混合函数的密度泛函理论（DFT）计算了 19 种具有抗利什曼病活性的新木质素合成类似物的分子描述符。随后，进行了逐步判别分析，以研究分子描述符与生物活性之间可能存在的关系。通过这种分析，根据生物活性的程度将化合物分为活性和非活性两类，而更重要的性质是一些关键原子上的电荷、电子亲和力和 ClogP。