cordoin | 51619-65-9

• 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: cordoin
• 英文别名: Derricidin；2'-Hydroxy-4'-prenyloxychalcone；1-[2-hydroxy-4-(3-methylbut-2-enoxy)phenyl]-3-phenylprop-2-en-1-one
• CAS: 51619-65-9
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: DGUGLZYULGVSIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cordoin 、 溶剂黄146 在 一水合肼 作用下， 生成 1-[5-[2-Hydroxy-4-(3-methylbut-2-enoxy)phenyl]-3-phenyl-3,4-dihydropyrazol-2-yl]ethanone
  参考文献：
  名称：

  Synthesis and molecular modelling studies of prenylated pyrazolines as MAO-B inhibitors

  摘要：

  A series of N-substituted-3-[(2'-hydroxy-40-prenyloxy)-phenyl]-5-phenyl-4,5-dihydro-(1H)-pyrazolines were synthesized and tested on human monoamine oxidase-A and -B isoforms. Structure-activity relationships and molecular modelling showed that some substitutions, such as benzyloxy or chlorine atom, improve the best interaction with active site of hMAO-B. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.061
• 作为产物：
  描述：

  1-[2-羟基-4-(3-甲基-2-丁烯氧基)-苯基]-乙酮 、 苯甲醛 在 barium hydroxide octahydrate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 cordoin
  参考文献：
  名称：

  Synthesis and molecular modelling studies of prenylated pyrazolines as MAO-B inhibitors

  摘要：

  A series of N-substituted-3-[(2'-hydroxy-40-prenyloxy)-phenyl]-5-phenyl-4,5-dihydro-(1H)-pyrazolines were synthesized and tested on human monoamine oxidase-A and -B isoforms. Structure-activity relationships and molecular modelling showed that some substitutions, such as benzyloxy or chlorine atom, improve the best interaction with active site of hMAO-B. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.061

文献信息

• Ultrasound assisted synthesis and cytotoxicity evaluation of known 2′,4′-dihydroxychalcone derivatives against cancer cell lines
  作者：Joan Villena、Iván Montenegro、Bastian Said、Enrique Werner、Susana Flores、Alejandro Madrid

  DOI：10.1016/j.fct.2021.111969

  日期：2021.2

  This work reports on the development of an efficient and ecofriendly ultrasound assisted method for the high yield synthesis (70.0-94.0%) of eighteen oxyalkylated derivatives of 2',4'-dihydroxychalcone. Synthesized compounds were subjected to in vitro biological assays against HT-29 (colorectal), MCF-7 (breast), and PC-3 (prostate) human tumor cell lines, these cell lines are among the ten most aggressive

  这项工作报告了一种高效，环保的超声辅助方法的开发，该方法可以高产率地合成18种2'，4'-二羟基查耳酮的烷氧基化衍生物（70.0-94.0％）。对合成的化合物进行了针对HT-29（结肠直肠），MCF-7（乳腺癌）和PC-3（前列腺）人类肿瘤细胞系的体外生物学分析，这些细胞系是世界上诊断出的十种最具侵袭性的恶性肿瘤之一。细胞毒性评估表明，四种合成的化合物对MCF-7（IC 50 = 8.4–34.3μM）和PC-3（IC 50 = 9.3-29.4μM）表现出中等至非常高的毒性，与5-氟尿嘧啶（IC 5016.4–22.3μM）。相同的化合物仅对HT-29（IC 50 15.3-36.3μM）具有中等活性，接近柔红霉素（IC 50 15.1μM ）。接着，尽管化合物的选择性指数（SI）较弱，但化合物18对癌细胞显示出显着的选择性细胞毒性活性（5.8-10.57）。除此以外，大多数化合物显着降
• Synthesis and molecular modelling studies of prenylated pyrazolines as MAO-B inhibitors
  作者：Rossella Fioravanti、Adriana Bolasco、Fedele Manna、Francesca Rossi、Francisco Orallo、Matilde Yáñez、Alberto Vitali、Francesco Ortuso、Stefano Alcaro

  DOI：10.1016/j.bmcl.2010.09.061

  日期：2010.11

  A series of N-substituted-3-[(2'-hydroxy-40-prenyloxy)-phenyl]-5-phenyl-4,5-dihydro-(1H)-pyrazolines were synthesized and tested on human monoamine oxidase-A and -B isoforms. Structure-activity relationships and molecular modelling showed that some substitutions, such as benzyloxy or chlorine atom, improve the best interaction with active site of hMAO-B. (C) 2010 Elsevier Ltd. All rights reserved.