4-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)-3,4-dihydropyrimidine-2(1H)-thione | 489399-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)-3,4-dihydropyrimidine-2(1H)-thione
• 英文别名: 4-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)-3,4-dihydro-1H-pyrimidine-2-thione
• CAS: 489399-30-6
• 化学式: C₁₉H₂₀N₂O₃S
• 分子量: 356.445
• InChiKey: UPNVCLGZCSJWTF-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200 °C(Solv: methanol (67-56-1))
• 沸点：
  508.7±60.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(3,4-dimethoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one 、 硫脲 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 以96%的产率得到4-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)-3,4-dihydropyrimidine-2(1H)-thione
  参考文献：
  名称：

  Synthesis and antiprotozoal activity of 1,2,3,4-tetrahydro-2-thioxopyrimidine analogs of combretastatin A-4

  摘要：

  Eighteen 1,2,3,4-tetrahydro-2-thioxopyrimidine analogs (5a-j, 6a-e, and 7a-c) of combretastatin A-4 were synthesized with the objective of discovering compounds capable of controlling the growth of Trypanosoma lewisii, Leishmania tarantole, Plasmodium falciparum, and Giardia lamblia. Even though the target compounds demonstrated differential cytotoxicity against mammalian cancer cells, with IC50 values ranging from 0.5 to > 100 mu M, the range of activity against Trypanosoma, Leishmania, and Plasmodium, and to a good extent for Giardia, was narrow. The IC50 values of "active" compounds against the parasites ranged from about 10 mu Ie to slightly greater than 50 mu M. Specifically, compounds 5a, 5g, 5h, 6c, 7a, and 7c were not cytotoxic against mammalian cancer cells (IC50 > 100 mu M) but showed good activity against the parasites, except Giardia (e.g., compounds 6c and 7a), suggesting that these compounds may act in a similar mechanism in parasites. Compounds 5f and 6b were previously shown to promote microtubule depolymerization in mammalian cells.

  DOI：

  10.1007/s00044-010-9334-1

文献信息

• Facile one-pot three-component synthesis of 4,6-diaryl-3,4-dihydropyrimidine-2(1<i>H</i>)-thiones under ultrasonic irradiation
  作者：Shymaa A. Abbass、Gamal A. I. Moustafa、Heba A. Hassan、Gamal El-Din A. Abuo-Rahma

  DOI：10.1080/00397911.2019.1652759

  日期：——

  Abstract We developed a facile one-pot procedure for the synthesis of 4,6-diaryl-3,4-dihydropyrimidine-2(1H)-thione under ultrasonic irradiation. The method is based on a three components reaction of aldehydes, ketones, and thiourea under basic conditions affording isolated yields of up to 95% within a reaction time of 30–90 min. Graphical Abstract

  摘要 我们开发了一种简便的一锅法，用于在超声波照射下合成 4,6-二芳基-3,4-二氢嘧啶-2(1H)-硫酮。该方法基于醛、酮和硫脲在碱性条件下的三组分反应，在 30-90 分钟的反应时间内提供高达 95% 的分离产率。图形概要