(Z)-3-(benzofuran-2-yl)-2-(3,4-dimethoxyphenyl)acrylonitrile | 912288-40-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-3-(benzofuran-2-yl)-2-(3,4-dimethoxyphenyl)acrylonitrile
• 英文别名: α-(3,4-dimethoxyphenyl)-β-(benzofuran-2-yl)acrylonitrile；(Z)-3-benzofuran-2-yl-(3,4-dimethoxy-phenyl)-acrylonitrile；(Z)-3-(1-benzofuran-2-yl)-2-(3,4-dimethoxyphenyl)prop-2-enenitrile
• CAS: 912288-40-5
• 化学式: C₁₉H₁₅NO₃
• 分子量: 305.333
• InChiKey: FESOEGDQDRIKOC-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-3-(benzofuran-2-yl)-2-(3,4-dimethoxyphenyl)acrylonitrile 、 三正丁基叠氮化锡 以 邻二甲苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  新型高效的叠氮化三丁基锡介导的氰基苯甲酸酯合成1 H-四唑基苯甲酸酯

  摘要：

  建立了一种新颖且有效的路线来合成一系列（Z）-5-（2-（杂芳基-2-基）和（Z）-5-（3-（杂芳基-3-基）-1- （苯）乙烯基）-1 H-四唑（分别为3a - g和6a - f），它们来自氰基茂金属类似物，其中包含苯并[ b ]噻吩，苯并[ b ]呋喃和吲哚基团，使用三丁基叠氮化锡作为路易斯酸。叠氮化物的3，3-偶极[3 + 2]环加成到氰基茂金属前体分子的氰基上可提供相应四唑基茂金属类似物的良好产率，并且构成简单且成本有效的方法。

  DOI：

  10.1016/j.tetlet.2016.03.040
• 作为产物：
  描述：

  3,4-二甲氧基苯乙腈 、 苯并[b]呋喃-2-甲醛 在 sodium t-butanolate 作用下， 以 乙醇 为溶剂， 以66 %的产率得到(Z)-3-(benzofuran-2-yl)-2-(3,4-dimethoxyphenyl)acrylonitrile
  参考文献：
  名称：

  Tuning the Solid State Luminescence of Benzofuran‐Cyanostilbenes by Functionalization with Electron Donors or Acceptors

  摘要：

  摘要 已制备出三个系列的线性延伸苯并呋喃衍生物，这些衍生物的氰乙烯基单元与对氰基苯基（系列 1）和五氟苯基（系列 2）单元或电子供体 3,4-二甲氧基苯基（系列 3）分子等电子汲取系统相关联。通过在苯并呋喃的第 5 位和第 6 位添加电子供体甲氧基（化合物 BF2 和 BF3），或者通过增加与萘并呋喃单元（BF4）的共轭延伸，以及通过在苯并呋喃和氰乙烯键之间插入一个呋喃环（BF5），调整了苯并呋喃部分的供体特性。虽然大多数化合物在溶液中的发射率很低，但几乎所有化合物的微晶粉末在 350-400 纳米波长的激发下都显示出中等强度的发射，发射颜色从蓝绿到红色不等。研究表明，对于系列 1 和 2，发射颜色的变化主要是由于固体中分子的堆积类型造成的。对于系列 3，导致红移的首先是化合物共轭的扩展。

  DOI：

  10.1002/cplu.202300402

文献信息

• BCRP/ABCG2 INHIBITOR
  申请人：Yamazaki Ryuta

  公开号：US20090253656A1

  公开（公告）日：2009-10-08

  The present invention is directed to a breast cancer resistance protein (BCRP/ABCG2) inhibitor. The BCRP inhibitor contains, as an active ingredient, an acrylonitrile derivative represented by formula (1): wherein one of R 1 and R 2 represents a cyano group and the other represents a hydrogen atom; Ar 1 represents a group selected from among the groups represented by formulas (2) to (4): and Ar 2 represents an aromatic hydrocarbon group having a condensed ring which may be substituted by a halogen atom, or a group selected from among the groups represented by the following formulas (5) to (15): or a salt thereof.

  该发明涉及一种乳腺癌耐药蛋白（BCRP/ABCG2）抑制剂。该BCRP抑制剂包含以下化合物作为活性成分，其化学式为（1）：其中R1和R2中的一个代表氰基，另一个代表氢原子；Ar1代表从以下化学式（2）至（4）中选出的一种基团：Ar2代表一种含有可能被卤素原子取代的融合环的芳香烃基团，或者从以下化学式（5）至（15）中选出的一种基团：或其盐。
• BCRP/ABCG2 inhibitor
  申请人：Yamazaki Ryuta

  公开号：US08697742B2

  公开（公告）日：2014-04-15

  A breast cancer resistance protein (BCRP/ABCG2) inhibitor. The BCRP inhibitor contains, as an active ingredient, an acrylonitrile derivative or a salt thereof.

  一种乳腺癌抗性蛋白（BCRP/ABCG2）抑制剂。该BCRP抑制剂含有丙烯腈衍生物或其盐作为活性成分。
• STILBENE DERIVATIVE AND STILBENE ANALOG DERIVATIVE, AND USE THEREOF
  申请人：MORINAGA MILK INDUSTRY CO., LTD.

  公开号：EP0640586A1

  公开（公告）日：1995-03-01

  A compound with a 12-lipoxygenase inhibitor activity, represented by general formula (I), a precursor therefor, and a medicine containing the same, wherein R¹ represents hydrogen or hydroxy; one of R² and R³ represents hydrogen, while the other cyano; and Ar represents (a), (b) or (c), wherein R⁴ represents hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl or cyano.

  由通式（I）表示的具有 12-脂氧合酶抑制剂活性的化合物、其前体以及含有该化合物的药物，其中 R¹ 代表氢或羟基；R² 和 R³ 中的一个代表氢，另一个代表氰基；Ar 代表（a）、（b）或（c），其中 R⁴ 代表氢、低级烷基、低级烷氧基、卤素、三氟甲基或氰基。
• BCRP/ABCG3 Inhibitor
  申请人：Kabushiki Kaisha Yakult Honsha

  公开号：EP2332905A1

  公开（公告）日：2011-06-15

  A BCRP inhibitor comprising, as an active ingredient, an acrylonitrile derivative represented by formula (1): wherein one of R1 and R2 represents a cyano group and the other represents a hydrogen atom; Ar1 represents a group selected from among the groups represented by formulas (2) to (4): wherein R7 and R8, which are identical to or different from each other, each represent a hydrogen atom, a halogen atom, or a lower alkoxy group; A represents an oxygen atom, a sulfur atom, or NR9; and R9 represents a hydrogen atom or a lower alkyl group; Ar2 represents a group selected from among the groups represented by formulas (5) to (15): wherein R3 represents a hydrogen atom, an oxygen atom (as N-oxide), a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group, a methylsulfanyl group, a lower hydroxyalkyl group, an aromatic hydrocarbon group which may have a substituent, or NR5 (R6) R5 and R6, which are identical to or different from each other, each represent a hydrogen atom, a lower alkyl group which may have a substituent, a lower hydroxyalkyl group, or an aromatic hydrocarbon group which may have a substituent or heterocyclic group; R5 and R6 may form, with their adjacent nitrogen atom, a heterocyclic ring which may have a substituent; and the hydroxyl group of the lower hydroxyalkyl group or the heterocyclic ring substituted by a hydroxyl group or a lower hydroxyalkyl group may form an ester bond with a phosphoric acid group or a salt thereof or with an acyl group which may have a substituent; R4 represents a hydrogen atom, a lower alkyl group, a phenyl group which may have a substituent, or a benzyl group; X represents a carbon atom, CH, or a nitrogen atom, provided that when A is an oxygen atom, X is not a nitrogen atom; and A, R7, R8, and R9 have the same meanings as defined above; or a salt thereof.

  一种 BCRP 抑制剂，其活性成分包括由式（1）表示的丙烯腈衍生物： 其中 R1 和 R2 中的一个代表氰基，另一个代表氢原子； Ar1 代表选自式（2）至（4）所代表基团中的一个基团： 其中彼此相同或不同的 R7 和 R8 各自代表氢原子、卤素原子或低级烷氧基； A 代表氧原子、硫原子或 NR9；以及 R9 代表氢原子或低级烷基； Ar2 代表选自式 (5) 至 (15) 所代表基团中的一个基团： 其中 R3 代表氢原子、氧原子（作为 N-氧化物）、低级烷基、低级烷氧基、卤素原子、硝基、甲硫 基、低级羟烷基、可具有取代基的芳香烃基或 NR5 (R6) 彼此相同或不同的 R5 和 R6 分别代表一个氢原子、一个可带取代基的低级烷基、一个低级羟烷基或一个可带取代基或杂环基的芳香烃基；R5 和 R6 可与相邻的氮原子形成一个可带取代基的杂环；下羟烷基的羟基或被羟基或下羟烷基取代的杂环可与磷酸基团或其盐或可带有取代基的酰基形成酯键； R4 代表氢原子、低级烷基、可能具有取代基的苯基或苄基； X 代表碳原子、CH 或氮原子，但当 A 是氧原子时，X 不是氮原子；以及 A、R7、R8 和 R9 具有与上述定义相同的含义；或其盐。
• Synthesis, anticancer activity and molecular docking studies on a series of heterocyclic trans-cyanocombretastatin analogues as antitubulin agents
  作者：Narsimha Reddy Penthala、Hongliang Zong、Amit Ketkar、Nikhil Reddy Madadi、Venumadav Janganati、Robert L. Eoff、Monica L. Guzman、Peter A. Crooks

  DOI：10.1016/j.ejmech.2014.12.050

  日期：2015.3

  A series of heterocyclic combretastatin analogues have been synthesized and evaluated for their anti-cancer activity against a panel of 60 human cancer cell lines. The most potent compounds were two 3,4,5-trimethoxy phenyl analogues containing either an (Z)-indol-2-yl (8) or (Z)-benzo[b]furan-2-yl (12) moiety; these compounds exhibited GI(50) values of <10 nM against 74% and 70%, respectively, of the human cancer cell lines in the 60-cell panel. Compounds 8, and 12 and two previously reported compounds in the same structural class, i.e. 29 and 31, also showed potent anti-leukemic activity against leukemia MV4-11 cell lines with LD50 values = 44 nM, 47 nM, 18 nM, and 180 nM, respectively. From the NCI anti-cancer screening results and the data from the in vitro toxicity screening on cultured AML cells, seven compounds: 8, 12, 21, 23, 25, 29 and 31 were screened for their in vitro inhibitory activity on tubulin polymerization in MV4-11 AML cells; at 50 nM, 8 and 29 inhibited polymerization of tubulin by >50%. The binding modes of the three most active compounds (8, 12 and 29) to tubulin were also investigated utilizing molecular docking studies. All three molecules were observed to bind in the same hydrophobic pocket at the interface of alpha- and beta-tubulin that is occupied by colchicine, and were stabilized by van der Waals' interactions with surrounding tubulin residues. The results from the tubulin polymerization and molecular docking studies indicate that compounds 8 and 29 are the most potent anti-leukemic compounds in this structural class, and are considered lead compounds for further development as anti-leukemic drugs. (C) 2015 Elsevier Masson SAS. All rights reserved.