(2E)-3-(3-fluorophenyl)-1-(4-methoxyphenyl)propenone

• 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: (2E)-3-(3-fluorophenyl)-1-(4-methoxyphenyl)propenone
• 英文别名: (2E)-3-(3-Fluorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one；(E)-3-(3-fluorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
• 化学式: C₁₆H₁₃FO₂
• 分子量: 256.276
• InChiKey: QLGKAFGARVTNOQ-BJMVGYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E)-3-(3-fluorophenyl)-1-(4-methoxyphenyl)propenone 在 1-羟基苯并三唑 、 一水合肼 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (2,3-dihydrobenzo[b][1,4]dioxin-6-yl)(5-(3-fluorophenyl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)methanone
  参考文献：
  名称：

  新型含2,3-二氢苯并[ b ] [1,4]二恶英的4,5-二氢-1 H-吡唑衍生物作为B-Raf激酶抑制剂的设计，修饰和3D QSAR研究

  摘要：

  合成了两个系列的新型含2,3-二氢苯并[ b ] [1,4]二恶英的4,5-二氢-1 H-吡唑衍生物C1 - C15和D1 - D15，并评估了它们对B-Raf的抑制作用和防扩散活动。化合物C14（（3-（4-溴苯基）-5-（2-氟苯基）-4,5-二氢-1 H-吡唑-1-基）（2,3-二氢苯并[ b ] [1,4]二恶英-6-yl）methanone）对B-Raf V600E（IC 50  = 0.11μM）和WM266.4人黑素瘤细胞系（GI 50 = 0.58μM），与阳性对照厄洛替尼相当，并且比我们以前最好的化合物更有效，而D10（（2,3-dihydrobenzo [ b ] [1,4] dioxin-2-yl）（5-（3-氟苯基）-3-苯基-4,5-二氢-1 H-吡唑-1-基）甲酮在D系列中表现最好（IC 50  = 1.70μM; GI 50  = 1.45μM）。进行了对接模

  DOI：

  10.1016/j.bmc.2012.08.043
• 作为产物：
  描述：

  对甲氧基苯乙酮 、 3-氟苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以82%的产率得到(2E)-3-(3-fluorophenyl)-1-(4-methoxyphenyl)propenone
  参考文献：
  名称：

  氟化甲氧基查耳酮作为选择性单胺氧化酶-B抑制剂的开发：合成，生物化学和分子对接研究

  摘要：

  合成了一系列具有氟和三氟甲基衍生物的甲氧基化查耳酮，并研究了它们抑制人单胺氧化酶A和B的能力。已通过其1 H NMR，13 C NMR，质谱数据对化合物的化学结构进行了表征。和元素分析。结果表明，这些化合物是具有竞争性抑制方式的可逆和选择性MAO-B抑制剂。最有效的化合物（2 ë）-1-（4-甲氧基苯基）-3- [4-（三氟甲基）苯基〕丙-2-烯-1-酮向显示hMAO-B具有最佳的活性和更高的选择性ķ我和SI值分别为0.22±0.01μM和0.05，与标准药物Selegiline K相当i和SI值分别为0.33±0.03μM和0.04。进行了分子对接研究，以进一步解释新化合物的体外结果，并确定hMAO-B抑制剂结合腔内化合物的假设结合模式。

  DOI：

  10.1016/j.bioorg.2015.07.001

文献信息

• Phosphate transport inhibitors
  申请人：GelTex Pharmaceuticals, Inc.

  公开号：US20040019113A1

  公开（公告）日：2004-01-29

  Disclosed are compounds which have been identified as inhibitors of phosphate transport. Many of the compounds are represented by Structural Formula (I): Ar 1 —W—X—Y—Ar 2 ; or a pharmaceutically acceptable salt thereof. Ar 1 and Ar 2 are independently a substituted or unsubstituted aryl group or an optionally substituted five membered or six membered non-aromatic heterocylic group fused to an optionally substituted monocylic aryl group. W and Y are independently a covalent bond or a C1-C3 substituted or unsubstituted alkylene group. X is a heteroatom-containing functional group, an aromatic heterocyclic group, substituted aromatic heterocyclic group, non-aromatic heterocyclic group, substituted non-aromatic heterocyclic group, an olefin group or a substituted olefin group. Also disclosed are methods of treating a subject with a disease associated with hyperphosphatemia, as well as a disease mediated by phosphate-transport function. The methods comprise the step of administering an effective amount of the one of the compounds described above.

  本文披露了被识别为磷酸盐转运抑制剂的化合物。许多化合物由结构式(I)表示：Ar1—W—X—Y—Ar2；或其药用可接受的盐。Ar1和Ar2独立地是取代或未取代的芳基或可取代的五元或六元非芳香杂环基与可取代的单环芳基融合。W和Y独立地是共价键或C1-C3取代或未取代的烷基基团。X是含杂原子的官能团、芳香杂环基、取代芳香杂环基、非芳香杂环基、取代非芳香杂环基、烯烃基或取代烯烃基。还披露了治疗与高磷血症相关疾病以及磷酸盐转运功能介导的疾病的方法。该方法包括给予上述化合物之一的有效量。
• ANTI-INVASIVE COMPOUNDS
  申请人：Universiteit Gent

  公开号：US20150011620A1

  公开（公告）日：2015-01-08

  The present invention relates to the field of anti-invasive compounds and methods for predicting the anti-invasive activity of said compounds, as well as their use in the prevention and/or treatment of diseases associated with undesired cell invasion; in particular, this invention relates to the field of anti-invasive chalcone-like compounds.

  本发明涉及抗侵袭化合物领域，以及预测该类化合物抗侵袭活性的方法，以及它们在预防和/或治疗与不受欢迎的细胞侵袭相关的疾病中的用途；特别是，本发明涉及抗侵袭的类似香豆素化合物领域。
• 4-Fluoro-3′,4′,5′-trimethoxychalcone as a new anti-invasive agent. From discovery to initial validation in an in vivo metastasis model
  作者：Bart I. Roman、Tine De Ryck、Atanas Patronov、Svetoslav H. Slavov、Barbara W.A. Vanhoecke、Alan R. Katritzky、Marc E. Bracke、Christian V. Stevens

  DOI：10.1016/j.ejmech.2015.06.029

  日期：2015.8

  Invasion and metastasis are responsible for 90% of cancer-related mortality. Herein, we report on our quest for novel, clinically relevant inhibitors of local invasion, based on a broad screen of natural products in a phenotypic assay. Starting from micromolar chalcone hits, a predictive QSAR model for diaryl propenones was developed, and synthetic analogues with a 100-fold increase in potency were obtained. Two nanomolar hits underwent efficacy validation and eADMET profiling; one compound was shown to increase the survival time in an artificial metastasis model in nude mice. Although the molecular mechanism(s) by which these substances mediate efficacy remain(s) unrevealed, we were able to eliminate the major targets commonly associated with antineoplastic chalcones. (C) 2015 Elsevier Masson SAS. All rights reserved.
• US9290427B2
  申请人：——

  公开号：US9290427B2

  公开（公告）日：2016-03-22
• [EN] ANTI-INVASIVE COMPOUNDS<br/>[FR] COMPOSÉS ANTI-INVASIFS
  申请人：UNIV GENT

  公开号：WO2013113722A1

  公开（公告）日：2013-08-08

  The present invention relates to the field of anti-invasive compounds and methods for predicting the anti-invasive activity of said compounds, as well as their use in the prevention and/or treatment of diseases associated with undesired cell invasion; in particular, this invention relates to the field of anti-invasive chalcone-like compounds.