1-[2-羟基-4-(3-甲基丁-2-烯氧基)苯基]-3-苯基丙-2-烯-1-酮 | 38965-74-1

• 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
• 中文名称: 1-[2-羟基-4-(3-甲基丁-2-烯氧基)苯基]-3-苯基丙-2-烯-1-酮
• 英文名称: Cordoin
• 英文别名: (E)-1-(2-hydroxy-4-((3-methylbut-2-en-1-yl)oxy)phenyl)-3-phenylprop-2-en-1-one；(E)-1-(2-hydroxy-4-(3-methylbut-2-enyloxy)phenyl)-3-phenylprop-2-en-1-one；(E)-1-[2-hydroxy-4-(3-methylbut-2-enyloxy)phenyl]-3-phenylprop-2-en-1-one；derricidine；derricidin；(E)-1-[2-hydroxy-4-(3-methylbut-2-enoxy)phenyl]-3-phenylprop-2-en-1-one
• CAS: 38965-74-1
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: DGUGLZYULGVSIZ-DHZHZOJOSA-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：

  1-[2-羟基-4-(3-甲基丁-2-烯氧基)苯基]-3-苯基丙-2-烯-1-酮 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 7-acetoxy-5-(α,α-dimethylallyl)flavanone
  参考文献：
  名称：

  Islam, Azizul; Krishnamurti, M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 12, p. 1037 - 1038

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 18.0h， 生成 1-[2-羟基-4-(3-甲基丁-2-烯氧基)苯基]-3-苯基丙-2-烯-1-酮
  参考文献：
  名称：

  确定查尔酮为基础的抗疟疾药物靶向锥虫硫磷还原酶。

  摘要：

  当前所有用于治疗利什曼病的一线和二线药物均表现出若干缺点，包括毒性，高成本和给药途径。此外，一些药物与耐药性的出现有关。因此，开发新的利什曼病治疗方法是被忽视的热带病领域的优先事项。本工作着重介绍了使用天然来源的产品（即查耳酮）作为抗疟剂的潜在来源。已经合成了三十一种新的查耳酮化合物，并且已经评估了它们对利什曼原虫的前鞭毛体的活性。16种化合物在3.0至21.5μM范围内对多诺氏乳杆菌有活性，对哺乳动物细胞毒性低。在这些分子中，图6和16显示对前鞭毛体和胞内变形虫均具有良好的抑制活性，并具有高选择性指数。此外，化合物6和16抑制了其他利什曼原虫物种的前鞭毛体生长，包括热带麻疯树，大乳杆菌和婴儿乳杆菌。最后，6和16与Trypanothione还原酶（TR）具有高亲和力相互作用，TR是利什曼原虫的必不可少的酶，化合物6以亚微摩尔浓度抑制TR。因此，针对利什曼原虫的有效抑制活性，对哺乳动物细胞

  DOI：

  10.1016/j.ejmech.2018.04.057

文献信息

• [EN] SKIN PIGMENTATION MODIFIERS TO DARKEN OR LIGHTEN THE SKIN<br/>[FR] AGENTS DE MODIFICATION DE LA PIGMENTATION DE LA PEAU EN VUE DE L'ASSOMBRIR OU DE L'ÉCLAIRCIR
  申请人：AFFICHEM

  公开号：WO2016193220A1

  公开（公告）日：2016-12-08

  The present invention relates to a method for changing the pigmentation of a skin, a mucous membrane or hair with a compound of general formula (I), a cosmetic use of said compound of general formula (I), to cosmetic compositions comprising said compound of general formula (I), and to new depigmenting agents.

  本发明涉及一种改变皮肤、粘膜或头发色素的方法，使用一般式(I)的化合物，以及所述一般式(I)的化合物的化妆用途，包括所述一般式(I)的化合物的化妆组合物，以及新的脱色剂。
• DEPIGMENTING AGENTS TO LIGHTEN THE SKIN
  申请人：Affichem

  公开号：EP3097904A1

  公开（公告）日：2016-11-30

  The present invention relates to a method for lightening a skin or a mucous membrane with a depigmenting agent, a cosmetic use of said depigmenting agent, to cosmetic compositions comprising said agent, and to new depigmenting agents.

  本发明涉及一种使用脱色剂淡化皮肤或粘膜的方法、所述脱色剂的化妆品用途、包含所述脱色剂的化妆品组合物以及新型脱色剂。
• Effects of Flavonoids on Cell Proliferation and Caspase Activation in a Human Colonic Cell Line HT29:  An SAR Study
  作者：Jean-Baptiste Daskiewicz、Flore Depeint、Lionel Viornery、Christine Bayet、Geraldine Comte-Sarrazin、Gilles Comte、Jennifer M. Gee、Ian T. Johnson、Karine Ndjoko、Kurt Hostettmann、Denis Barron

  DOI：10.1021/jm040770b

  日期：2005.4.1

  A library of 42 natural and synthetic flavonoids has been screened for their effect on cell proliferation and apoptosis in a human colonic cell line (HT-29). Examples of different classes of flavonoids have been screened, and the effects of hydroxylation, methoxylation and/or C-alkylation at various positions in the A- and B-rings have been assessed. Flavones and flavonols possess greater antiproliferative activity than chalcones and flavanones. With respect to structural modification of flavonoids, C-isoprenylation was by far the most effective, with substitution at the 8-position and longer chains, such as geranyl giving the best results. Finally, most compounds that significantly reduced cell survival also increased caspase activity, suggesting that at least part of their antiproliferative activity might be attributable to an apoptotic response.
• Chalcones: A Valid Scaffold for Monoamine Oxidases Inhibitors
  作者：Franco Chimenti、Rossella Fioravanti、Adriana Bolasco、Paola Chimenti、Daniela Secci、Francesca Rossi、Matilde Yáñez、Francisco Orallo、Francesco Ortuso、Stefano Alcaro

  DOI：10.1021/jm801590u

  日期：2009.5.14

  A large series of substituted chalcones have been synthesized and tested in vitro for their ability to inhibit human monoamine oxidases A and B (hMAO-A and hMAO-B). While all the compounds showed hMAO-B selective activity in the micro- and nanomolar ranges, the best results were obtained in the presence of chlorine and hydroxyl or methoxyl substituents. To better understand the enzyme-inhibitor interaction and to explain the selectivity of the most active compounds toward hMAO-B, molecular modeling studies were carried out on new, high resolution, hMAO-B crystallographic structures. For the only compound that also showed activity against hMAO-A as well as low selectivity, the molecular modeling study was also performed on the hMAO-A crystallographic structure. The docking technique provided new insight on the inhibition mechanism and the rational drug design of more potent/selective hMAO inhibitors based on the chalcone scaffold.
• Structure–activity relationships of chalcone analogs as potential inhibitors of ADP- and collagen-induced platelet aggregation
  作者：M. Vijaya Bhaskar Reddy、Wei-Jern Tsai、Keduo Qian、Kuo-Hsiung Lee、Tian-Shung Wu

  DOI：10.1016/j.bmc.2011.08.004

  日期：2011.12

  In an effort to develop potent antiplatelet agents, 12 O-prenylated (2-13) and 10 O-allylated (14-23) chalcones were synthesized and screened for in vitro inhibitory effects on aggregation of washed rabbit platelets induced by ADP (20 mu M) and collagen (10 mu g/mL). In addition, the platelet aggregation activity of previously synthesized Mannich bases of heterocyclic chalcones (MBHC) (24-62) was evaluated. The preliminary structure-activity relationships suggested that the antiplatelet activity was governed to a great extent by the presence of a pyridyl ring-B and a hydroxy group at position C-3' in ring-A of the MBHC templates. (C) 2011 Published by Elsevier Ltd.