(E)-3-sec-butyl-2-hydroxy-5-(3-oxo-3-p-tolylprop-1-enyl)benzaldehyde | 1287262-18-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-sec-butyl-2-hydroxy-5-(3-oxo-3-p-tolylprop-1-enyl)benzaldehyde
• 英文别名: 3-sec-butyl-2-hydroxy-5-(3-oxo-3-p-tolyl-propenyl)-benzaldehyde；3-butan-2-yl-2-hydroxy-5-[(E)-3-(4-methylphenyl)-3-oxoprop-1-enyl]benzaldehyde
• CAS: 1287262-18-3
• 化学式: C₂₁H₂₂O₃
• 分子量: 322.404
• InChiKey: MXDKDMBEYREFPX-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-sec-butyl-2-hydroxy-5-(3-oxo-3-p-tolylprop-1-enyl)benzaldehyde 、 丙二酸二乙酯 在 哌啶 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到ethyl 8-sec-butyl-2-oxo-6-(3-oxo-3-p-tolylprop-1-enyl)-2H-chromene-3-carboxylate
  参考文献：
  名称：

  COUMARIN-CHALCONES AS ANTICANCER AGENTS

  摘要：

  本发明涉及某些香豆素/香草醛化合物或其药用盐。本发明特别涉及香豆素/香草醛化合物作为抗癌药物，用于治疗癌症。本发明还涉及所述化合物的制备过程。

  公开号：

  US20130210909A1
• 作为产物：
  描述：

  2-仲丁基苯酚 在 盐酸 、 三氟乙酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 (E)-3-sec-butyl-2-hydroxy-5-(3-oxo-3-p-tolylprop-1-enyl)benzaldehyde
  参考文献：
  名称：

  In vitro and in vivo antifilarial activity evaluation of 3,6-epoxy [1,5]dioxocines: A new class of antifilarial agents

  摘要：

  A series of 3,6-epoxy [1,5] dioxocines were synthesized and evaluated for their antifilarial activity against adult parasites of human lymphatic filarial parasite Brugia malayi (sub-periodic strain) in vitro. Out of these, six compounds (4a-f) possessed improved in vitro anti-filarial activity and examples 4d and 4f were also found to be active in the in vivo experiments. These results demonstrate that 3,6-epoxy [1,5] dioxocines exhibits potent antifilarial activity and might be developed into a new class of antifilarial drug. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.009
• 作为试剂：
  描述：

  5-tert-butyl-4-hydroxyisophthalaldehyde 、 对甲基苯乙酮 、 碘 、 1,4-二氧六环 在 disodium;dioxido-oxo-sulfanylidene-λ6-sulfane 、 氯仿 、 Sodium sulfate-III 、 silica gel 、 乙酸乙酯 、 正己烷 、 (E)-3-sec-butyl-2-hydroxy-5-(3-oxo-3-p-tolylprop-1-enyl)benzaldehyde 作用下， 反应 5.0h， 以provides (E)-3-tort-butyl-2-hydroxy-5-(3-oxo-3-p-tolylprop-1-enyl)benzaldehyde (General Formula III)的产率得到(E)-3-sec-butyl-2-hydroxy-5-(3-oxo-3-p-tolylprop-1-enyl)benzaldehyde
  参考文献：
  名称：

  COUMARIN-CHALCONES AS ANTICANCER AGENTS

  摘要：

  本发明涉及某些香豆素/查尔酮化合物或其药学上可接受的盐。本发明特别涉及香豆素/查尔酮化合物作为抗癌剂，用于治疗癌症。本发明还涉及制备所述化合物的方法。

  公开号：

  US20130210909A1

文献信息

• [EN] COUMARIN-CHALCONES AS ANTICANCER AGENTS<br/>[FR] COUMARINE-CHALCONES EN TANT QU'AGENTS ANTICANCÉREUX
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2012017454A1

  公开（公告）日：2012-02-09

  The present invention relates to certain coumarin/chalcone compounds or a pharmaceutically acceptable salt thereof. The present invention particularly relates to the coumarin/chalcone compounds as anticancer agents useful for the treatment of cancer. The present invention also relates to the process of preparation of the said compounds.

  本发明涉及某些香豆素/香根素化合物或其药用可接受的盐。本发明特别涉及香豆素/香根素化合物作为抗癌剂，用于治疗癌症。本发明还涉及所述化合物的制备过程。
• Coumarin-chalcones as anticancer agents
  申请人：Sashidhara Koneni Venkata

  公开号：US08815940B2

  公开（公告）日：2014-08-26

  The present invention relates to certain coumarin/chalcone compounds or a pharmaceutically acceptable salt thereof. The present invention particularly relates to the coumarin/chalcone compounds as anticancer agents useful for the treatment of cancer. The present invention also relates to the process of preparation of the said compounds.

  本发明涉及某些香豆素/查尔酮化合物或其药学上可接受的盐。本发明特别涉及香豆素/查尔酮化合物作为抗癌剂，用于治疗癌症。本发明还涉及所述化合物的制备方法。
• 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.
• Synthesis and in vitro evaluation of novel coumarin–chalcone hybrids as potential anticancer agents
  作者：Koneni V. Sashidhara、Abdhesh Kumar、Manoj Kumar、Jayanta Sarkar、Sudhir Sinha

  DOI：10.1016/j.bmcl.2010.10.116

  日期：2010.12

  A series of coumarin-chalcone hybrids have been synthesized and evaluated for their in vitro cytotoxicity against a panel of four human cancer cell lines and normal fibroblasts (NIH3T3). Among 21 compounds screened, three compounds (23, 25 and 26) showed IC50 range from 3.59 to 8.12 mu M. The most promising compound 26 showed around 30-fold more selectivity towards C33A (cervical carcinoma) cells over normal fibroblast NIH3T3 cells with an IC50 value of 3.59 mu M. (C) 2010 Elsevier Ltd. All rights reserved.
• US8815940B2
  申请人：——

  公开号：US8815940B2

  公开（公告）日：2014-08-26