(Z)-3-(3,4-dimethoxy-phenyl)-2-pyridin-2-yl-acrylonitrile | 912288-15-4

• 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-(3,4-dimethoxy-phenyl)-2-pyridin-2-yl-acrylonitrile
• 英文别名: 2-(2-pyridyl)-3-(3,4-dimethoxy-phenyl)-2-propenenitrile；3-(3,4-Dimethoxyphenyl)-2-(2-pyridinyl)acrylonitrile；(Z)-3-(3,4-dimethoxyphenyl)-2-pyridin-2-ylprop-2-enenitrile
• CAS: 912288-15-4
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: QXSRLZYSIFQJJS-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-3-(3,4-dimethoxy-phenyl)-2-pyridin-2-yl-acrylonitrile 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以99%的产率得到(Z)-3-(3,4-dimethoxy-phenyl)-2-pyridin-2-yl-acrylonitrile hydrochloride
  参考文献：
  名称：

  EP1864972

  摘要：

  公开号：
• 作为产物：
  描述：

  3-吡啶乙腈 、 3,4-二甲氧基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 (Z)-3-(3,4-dimethoxy-phenyl)-2-pyridin-2-yl-acrylonitrile
  参考文献：
  名称：

  Structural Studies on Bioactive Compounds. 32. Oxidation of Tyrphostin Protein Tyrosine Kinase Inhibitors with Hypervalent Iodine Reagents

  摘要：

  Hydroxylated styrenes (tyrphostins) undergo oxidation by hypervalent iodine oxidants such as [(diacetoxy)iodo]benzene (DAIB) to give a range of products depending on the structure of the phenolic substrate, the solvent, the oxidant stoichiometry, and the purification strategy. Conditions have been developed to modify the phenolic component of the tyrphostin without affecting the appended substituted-vinyl moiety. Novel products include: unstable 2-acyloxy-2-methoxy-4-(substituted-vinyl)cyclohexadienones and their rearrangement products 2-acyloxy-4-hydroxy-3 -methoxy-1-(substituted-vinyl)benzenes; phenyliodoniophenolates and their rearrangement products iodophenoxytyrphostins; and 3,3'-dialkoxy-2,2'-dihydroxy-5,5'-di(substituted-vinyl)biphenyls. None of these oxidation products displayed enhanced activity in vitro in the NCI 60-cell line panel or in a panel of human breast cancer cell lines, compared to their tyrphostin precursors. The inhibitory activity of three representative tyrphostins (3e,n, 28) was not modulated by aerobic/anaerobic conditions in MCF-7 and MDA 468 cells and was independent of EGFR status in clones of ZR75B cells transfected with this receptor. Basal growth of MCF-7 cells was unaffected by co-administration of the growth factors EGF, TGF-alpha, IGF-I, and IGF-II, and the new agents did not inhibit EGFR and c-erbB2 autaphosphorylation in cell lysates from MDA 468 or SkBr3 cells, respectively, suggesting that receptor tyrosine kinases are not targets for these compounds. Growth stimulation by the tyrphostin 3n in the ER+ breast cell lines MCF-7, T47D, and ZR75-1 was abolished by 1 mu M tamoxifen, suggesting that this compound has estrogen agonist activity.

  DOI：

  10.1021/jm990947f

文献信息

• Styryl-substituted pyridyl compounds which inhibit EGF receptor tyrosine
  申请人：Rhone-Poulenc Rorer Pharmaceuticals Inc.

  公开号：US05302606A1

  公开（公告）日：1994-04-12

  Methods of inhibiting cell proliferation in a patient suffering from such disorder comprising the use of a styryl-substituted heteroaryl compound wherein the heteroaryl group is a monocyclic ring with 1 or 2 heteroatoms, or a bicyclic ring with 1 to about 4 heteroatoms, said compound optionally substituted or polysubstituted, with the proviso that when said ring is polysubstituted, the substituents do not have a common point of attachment to said ring, and those compounds wherein no substituent on the heteroaryl group is a carboxy group or an ester group, and pharmaceutical compositions comprising such compounds.

  抑制患有细胞增殖障碍的患者细胞增殖的方法，包括使用一种取代了苯乙烯的杂环化合物，其中杂环基是具有1或2个杂原子的单环或具有1到约4个杂原子的双环，该化合物可以取代或多取代，但前提是当该环多取代时，取代基不具有该环的共同连接点，并且该杂环基上没有取代基是羧基或酯基，以及包含这种化合物的制药组合物。
• 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。
• Regioselective Synthesis of 1‐Cyano‐3‐arylindolizines: Construction of Pyrroles via DDQ‐Mediated Ring Closure of Cyclopropyl Pyridines
  作者：Dirgha Raj Joshi、Ikyon Kim

  DOI：10.1002/adsc.202200590

  日期：2022.9.6

  A modular approach to a wide range of 1-cyano-3-(hetero)arylindolizines through aldol-cyclopropanation-oxidative cycloisomerization is described where DDQ was utilized for the regioselective synthesis of the pyrrole units from cyclopropyl pyridines for the first time. A key to success is regioselective oxidation of benzylic position by DDQ, which enabled us to access to one regioisomer out of two possible

  描述了一种通过醛醇-环丙烷化-氧化环异构化制备各种 1-氰基-3-(杂)芳基吲哚嗪的模块化方法，其中 DDQ 首次用于从环丙基吡啶中区域选择性合成吡咯单元。成功的关键是 DDQ 对苄基位置的区域选择性氧化，这使我们能够从两种可能的区域异构体中获得一种。在 DDQ 存在下，中氮茚 C2、C5 或 C7 位点的同源二聚化也首次被发现。
• 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。