(E)-2-hydroxy-3-methyl-5-(3-oxo-3-(thiophen-2-yl)prop-1-enyl)benzaldehyde | 1373497-79-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-2-hydroxy-3-methyl-5-(3-oxo-3-(thiophen-2-yl)prop-1-enyl)benzaldehyde
• 英文别名: 2-hydroxy-3-methyl-5-[(E)-3-oxo-3-thiophen-2-ylprop-1-enyl]benzaldehyde
• CAS: 1373497-79-0
• 化学式: C₁₅H₁₂O₃S
• 分子量: 272.324
• InChiKey: KWSZYMHXARZNRT-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  82.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氨基噻唑 、 (E)-2-hydroxy-3-methyl-5-(3-oxo-3-(thiophen-2-yl)prop-1-enyl)benzaldehyde 以 乙醇 为溶剂， 反应 3.0h， 以74%的产率得到(E)-1-(furan-2-yl)-3-(4-hydroxy-3-methyl-5-((E)-(thiazol-2-ylimino)methyl)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and antifilarial activity of chalcone–thiazole derivatives against a human lymphatic filarial parasite, Brugia malayi

  摘要：

  Here we report the synthesis of novel chalcone thiazole compounds and their antifilarial activity. The antifilarial properties of these hybrids were assessed against microfilariae as well as adult worms of Brugia malayi. Among all the synthesized compounds, only two compounds, namely 4g and 4n were identified to be promising in vitro. These active compounds were tested in B. malayi-jird (Meriones unguiculatus) and B. malayi-Mastomys coucha models. Compound 4n showed 100% embryostatic effect and 49% macrofilaricidal in jirds and M. coucha models, respectively. This study provides a new structural clue for the development of novel antifilarial lead molecules. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.029
• 作为产物：
  描述：

  邻甲酚 在 盐酸 、 三氟乙酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 生成 (E)-2-hydroxy-3-methyl-5-(3-oxo-3-(thiophen-2-yl)prop-1-enyl)benzaldehyde
  参考文献：
  名称：

  吲哚-查尔酮基苯并吡喃类化合物的合成及生物评价作为有望的抗连接酶和抗增殖剂

  摘要：

  DNA复制和修复是复杂的过程，通过酶和蛋白质网络的协同作用来完成。DNA连接酶通过催化DNA链之间的缺口连接，在这些过程中起着至关重要的作用。与正常细胞相比，据报道在某些癌症中人类DNA连接酶I（hLigI）的水平升高。我们研究了抑制hLigI介导的DNA切口封闭活性，然后研究了基于吲哚-查尔酮的新型苯并吡喃化合物对癌细胞的抗增殖活性。与其他连接酶相比，一种称为化合物27的分子表现出对hLigI抑制的显着偏好，与正常细胞相比，对结肠癌（DLD-1）细胞的细胞毒性增强。机理研究表明，化合物27在连接过程中直接与hLigI相互作用，而与DNA底物不相互作用。这种新型有效的hLigI抑制剂对模拟实体瘤的DLD-1细胞的单层培养和3D培养均显示出显着抑制作用。它还影响了DLD-1细胞的迁移，表明其潜在的抗转移活性。因此，这种新颖的hLigI抑制剂可以作为抗癌药物开发的有希望的先导。

  DOI：

  10.1016/j.ejmech.2017.11.015

文献信息

• Highly Efficient Synthesis of Chalcones from Poly Carbonyl Aromatic Compounds Using BF<sub>3</sub>–Et<sub>2</sub>O <i>via</i> a Regioselective Condensation Reaction
  作者：Satyanarayana Reddy Julakanti、Manimala Patel、Venkateswarlu Ponneri

  DOI：10.1248/cpb.c15-00939

  日期：——

  A new, simple, highly efficient method for the synthesis of different types of carbonyl chalcones through a regioselective condensation reaction of appropriate 5-acetyl-2-hydroxybenzaldehyde with various substituted acetophenones and 4-hydroxyisothalaldehyde with various substituted aldehydes using BF3-Et2O as a reagent is described.

  一种新的，简单，高效的方法，通过使用BF3-Et2O作为试剂，通过适当的5-乙酰基-2-羟基苯甲醛与各种取代的苯乙酮和4-羟基异乙醛与各种取代的醛的区域选择性缩合反应，合成不同类型的羰基查耳酮描述。
• Efficient and General Synthesis of 3-Aryl Coumarins Using Cyanuric Chloride¹
  作者：Koneni Sashidhara、Gopala Palnati、Srinivasa Avula、Abdhesh Kumar

  DOI：10.1055/s-0031-1290344

  日期：2012.3

  protocol for a rapid synthesis of different substituted 3-aryl coumarins is reported. A series of different substituted phenyl acetic acids have been successfully reacted with different substituted 2-hydroxy benzaldehydes in the presence of cyanuric chloride (2,4,6-trichloro-1,3,5-triazine) and N-methyl morpholine to afford 3-aryl coumarins in good to excellent yields. synthesis - 3-aryl coumarins -

  报道了快速合成不同取代的3-芳基香豆素的有效且通用的方案。在氰尿酰氯（2,4,6-三氯-1,3,5-三嗪）和N-甲基吗啉的存在下，一系列不同的取代苯基乙酸已成功与不同的取代的2-羟基苯甲醛反应，得到3芳基香豆素的收率高至优异。 合成-3-芳基香豆素-氰尿酰氯-2-羟基苯甲醛 系列“新型合成方法论研究”的第八部分。
• Antiplasmodial activity of novel keto-enamine chalcone-chloroquine based hybrid pharmacophores
  作者：Koneni V. Sashidhara、Manoj Kumar、Ram K. Modukuri、Rajeev Kumar Srivastava、Awakash Soni、Kumkum Srivastava、Shiv Vardan Singh、J.K. Saxena、Harsh M. Gauniyal、Sunil K. Puri

  DOI：10.1016/j.bmc.2012.03.011

  日期：2012.5

  A series of novel keto-enamine chalcone-chloroquine based hybrids were synthesized following new methodology developed in our laboratory. The synthesized compounds were screened against chloroquine sensitive strain (3D7) of Plasmodium falciparum in an in vitro model. Some of the compounds were showing comparable antimalarial activity at par with chloroquine. Compounds with significant in vitro antimalarial activity were then evaluated for their in vivo efficacy in Swiss mice against Plasmodium yoelii (chloroquine resistant N-67 strain), wherein compounds 25 and 27 each showed an in vivo suppression of 99.9% parasitaemia on day 4. Biochemical studies reveal that inhibition of hemozoin formation is the primary mechanism of action of these analogues. (C) 2012 Elsevier Ltd. All rights reserved.