(E)-5-(4-hydroxy-3-methoxyphenyl)-1-phenylpent-4-ene-1,3-dione | 1001203-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-5-(4-hydroxy-3-methoxyphenyl)-1-phenylpent-4-ene-1,3-dione
• 英文别名: (4E)-5-(4-hydroxy-3-methoxyphenyl)-1-phenyl-4-pentene-1,3-dione
• CAS: 1001203-56-0
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: LRYKCNRJNJXIFZ-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-5-(4-hydroxy-3-methoxyphenyl)-1-phenylpent-4-ene-1,3-dione 在 溶剂黄146 、 肼 作用下， 以 乙醇 为溶剂， 以10%的产率得到2-methoxy-4-((E)-2-(5-phenyl-1H-pyrazol-3-yl)-ethenyl)-phenol, trifluoroacetate salt
  参考文献：
  名称：

  [EN] PYRAZOLE KINASE MODULATORS AND METHODS OF USE
  [FR] MODULATEURS DE KINASES A BASE DE PYRAZOLE ET LEURS PROCEDES D'UTILISATION

  摘要：

  公开号：

  WO2006033943A3
• 作为产物：
  描述：

  (E)-5-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)-1-phenylpent-4-ene-1,3-dione 在 四丁基氟化铵 作用下， 以 水 为溶剂， 以30%的产率得到(E)-5-(4-hydroxy-3-methoxyphenyl)-1-phenylpent-4-ene-1,3-dione
  参考文献：
  名称：

  [EN] PYRAZOLE KINASE MODULATORS AND METHODS OF USE
  [FR] MODULATEURS DE KINASES A BASE DE PYRAZOLE ET LEURS PROCEDES D'UTILISATION

  摘要：

  公开号：

  WO2006033943A3

文献信息

• The annular tautomerism of the curcuminoid NH-pyrazoles
  作者：Pilar Cornago、Pilar Cabildo、Rosa M. Claramunt、Latifa Bouissane、Elena Pinilla、M. Rosario Torres、José Elguero

  DOI：10.1039/b812018h

  日期：——

  The structures of four NH-pyrazoles, (E)-3,5-bis[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-1H-pyrazole (3), (E)-3(5)-[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-5(3)-methyl-1H-pyrazole (4), (E)-3(5)-[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-4,5(3)-dimethyl-1H-pyrazole (5) and (E)-3(5)-[β-(3,4-dimethoxyphenyl)-ethenyl]-4-methyl-5(3)-phenyl-1H-pyrazole (8), have been determined by X-ray crystallography. Compounds that have a phenol residue crystallize forming sheets that are stabilized by a complex pattern of hydrogen bonds between a unique tautomer (4), or by a 2 : 1 mixture of both tautomers (5) (these tautomers being identical in the case of 3). Pyrazole 8, which lacks OH groups, crystallizes in cyclic dimers that are stabilized by N–H⋯N hydrogen bonds. The tautomerism in solution and in the solid state was determined by 13C and 15N CPMAS NMR spectroscopy. For compounds 4, 5 and 8, the solid state results agree with those observed by crystallography; the most abundant tautomer in solution coincides with the tautomer present in the solid state (4 and 8) or with the most abundant tautomer in the crystal (5).

  四种 NH 吡唑的结构：(E)-3,5-双[β-(4-羟基-3-甲氧基苯基)-乙烯基]-1H-吡唑 (3)、(E)-3(5)-[β-(4-羟基-3-甲氧基苯基)-乙烯基]-5(3)-甲基-1H-吡唑 (4)、(E)-3(5)-[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-4,5(3)-dimethyl-1H-pyrazole (5) 和 (E)-3(5)-[β-(3,4-dimethoxyphenyl)-ethenyl]-4-methyl-5(3)-phenyl-1H-pyrazole (8) 已通过 X 射线晶体学测定。含有苯酚残基的化合物在结晶时会形成薄片，这些薄片通过独特的同分异构体（4）或两种同分异构体（5）的 2:1 混合物（3 的同分异构体完全相同）之间复杂的氢键模式来稳定。缺乏羟基的吡唑 8 结晶为环状二聚体，通过 N-H⋯N 氢键稳定。13C 和 15N CPMAS NMR 光谱测定了溶液和固态中的同分异构现象。对于化合物 4、5 和 8，固态结果与晶体学观察到的结果一致；溶液中含量最高的同分异构体与固态中的同分异构体（4 和 8）或晶体中含量最高的同分异构体（5）一致。
• Effects of Curcuminoid Pyrazoles on Cancer Cells and on the Expression of Telomerase Related Genes
  作者：Rosa Martí-Centelles、Eva Falomir、Miguel Carda、Carla I. Nieto、M. Pilar Cornago、Rosa M. Claramunt

  DOI：10.1002/ardp.201600067

  日期：2016.7

  group of 13 curcuminoid pyrazoles was investigated for their cytotoxicity on three tumoral cell lines (HT‐29, MCF‐7, and HeLa) and one non‐tumoral human cell line (HEK‐293). The values obtained were compared with those of curcumin. A subset of selected derivatives was also studied for their ability to downregulate expression of the hTERT and c‐Myc genes, which are both involved in telomerase activity

  研究了一组 13 种姜黄素吡唑对三种肿瘤细胞系（HT-29、MCF-7 和 HeLa）和一种非肿瘤人细胞系（HEK-293）的细胞毒性。将获得的值与姜黄素的值进行比较。还研究了一部分选定衍生物下调 hTERT 和 c-Myc 基因表达的能力，这两种基因都与端粒酶活性有关。
• Chemical Compounds
  申请人：Rees David Daryl

  公开号：US20080045591A1

  公开（公告）日：2008-02-21

  Compounds of general formula I: wherein: R 1 and R 2 are, independently of each other, selected from hydrogen, optionally substituted C 1-10 alkyl, optionally substituted —CO—(C 1-10 alkyl), optionally substituted C 3-10 cycloalkyl, optionally substituted —CO—(C 3-10 cycloalkyl), optionally substituted C 2-10 alkenyl, optionally substituted —CO—(C 2-10 alkenyl), optionally substituted aryl, and optionally substituted —CO-aryl, or R 1 and R 2 together represent an optionally substituted saturated or unsaturated C 1-10 alkylidene group, or an optionally substituted saturated or unsaturated C 3-10 cycloalkylidene group, or R 1 and R 2 together with the carbon atom to which they are attached represent an optionally substituted saturated or unsaturated organic ring containing 3, 4, 5, 6, 7 or 8 ring carbon atoms and optionally 1, 2 or 3 ring heteroatoms selected from O, N and S; R 3 , which may be the same as, or different from, either of R 1 and R 2 , is selected from optionally substituted C 1-10 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted C 2-10 alkenyl, and optionally substituted aryl; R 4 , R 5 and R 6 are, independently of each other, selected from hydrogen, optionally substituted C 1-10 alkyl, OH, optionally substituted C 1-10 alkoxy, halo, optionally substituted aryloxy, optionally substituted (C 1-10 alkyl)-S(O) n — where n=0, 1 or 2, optionally substituted aryl-S(O) n — where n=0, 1 or 2, or R 4 is hydrogen and R 5 and R 6 together represent an optionally substituted saturated or unsaturated organic chain containing 1, 2, 3, 4, 5, 6 or 7 chain carbon atoms and optionally 1, 2 or 3 chain heteroatoms selected from O, N and S, provided that the chain is at least 3 atoms long; with the proviso that, when R 1 ═R 2 =hydrogen, then any optionally substituted C 1-10 alkyl or optionally substituted C 2-10 alkenyl for R 3 must have a branch point at one or more of the α and β positions counted from the carbonyl group (or tautomeric form thereof) to which R 3 is attached; or a physiologically acceptable salt, complex or prodrug thereof; are disclosed per se and for use in the treatment or prophylaxis of hypersensitivity, smooth muscle disorders, spasmodic conditions, allergic conditions, inflammatory conditions and/or pain.

  通式I的化合物： 其中： R1和R2独立地选自氢，可选取代的C1-10烷基，可选取代的—CO—（C1-10烷基），可选取代的C3-10环烷基，可选取代的—CO—（C3-10环烷基），可选取代的C2-10烯基，可选取代的—CO—（C2-10烯基），可选取代的芳基和可选取代的—CO-芳基，或者R1和R2一起代表一个可选取代的饱和或不饱和的C1-10烷基亚基，或一个可选取代的饱和或不饱和的C3-10环烷基亚基，或者R1和R2与它们连接的碳原子一起代表一个可选取代的含有3、4、5、6、7或8个环碳原子和可选取代的1、2或3个从O、N和S中选取的环杂原子的饱和或不饱和的有机环； R3可以与R1和R2中的任何一个相同或不同，选自可选取代的C1-10烷基，可选取代的C3-10环烷基，可选取代的C2-10烯基和可选取代的芳基； R4、R5和R6独立地选自氢，可选取代的C1-10烷基，OH，可选取代的C1-10烷氧基，卤素，可选取代的芳氧基，可选取代的（C1-10烷基）-S（O）n-，其中n=0、1或2，可选取代的芳基-S（O）n-，其中n=0、1或2，或者R4为氢，R5和R6一起代表一个可选取代的含有1、2、3、4、5、6或7个链碳原子和可选取代的1、2或3个链杂原子的饱和或不饱和的有机链，前提是该链至少由3个原子组成； 但是，当R1=R2=氢时，R3必须选取一个可选取代的C1-10烷基或可选取代的C2-10烯基，其中至少有一个分支点位于从R3所连接的羰基（或其互变异构体）计算的α和β位置之一；或其生理上可接受的盐、络合物或前药，本发明公开了其本身和用于治疗或预防过敏、平滑肌障碍、痉挛性疾病、过敏性疾病、炎症性疾病和/或疼痛。
• Pyrazole Kinase Modulators And Methods Of Use
  申请人：Baik Tae-Gon

  公开号：US20070293507A1

  公开（公告）日：2007-12-20

  The present invention provides compounds for modulating protein kinase enzymatic activity for modulating cellular activities such as proliferation, differentiation, programmed cell death, migration and chemoinvasion. Compounds of the invention inhibit, regulate and/or modulate kinases. Methods of using the compounds and pharmaceutical compositions thereof to treat kinase-dependent diseases and conditions are also an aspect of the invention.

  本发明提供了用于调节蛋白激酶酶活性，以调节细胞活动（如增殖、分化、程序性细胞死亡、迁移和化学浸润）的化合物。本发明的化合物抑制、调节和/或调节激酶。使用这些化合物和制药组合物来治疗激酶依赖性疾病和状况也是本发明的一个方面。
• Highly diastereoselective annulation of 2-substituted 3-nitro-2<i>H</i>-chromenes with hemicurcuminoids and curcuminoids <i>via</i> a double and triple Michael reaction cascade
  作者：Nikolay S. Zimnitskiy、Alexey Yu. Barkov、Ivan A. Kochnev、Igor B. Kutyashev、Vladislav Yu. Korotaev、Vyacheslav Ya. Sosnovskikh

  DOI：10.1039/d2nj02019j

  日期：——

  72 h in the presence of Cs2CO3 proceeds by way of a triple Michael/Michael/oxa-Michael cascade leading to 3,6-diaryl-6a-nitro-2,3,5,6a,7,12b-hexahydro-1H,6H-chromeno[6,5-c]chromen-1-ones in 71–97% yields. 2-Phenyl-2-(trifluoromethyl)-3-nitro-2H-chromenes under the analogous conditions react with enediones to form 2-(2-phenyl-2-(trifluoromethyl)-2H-chromen-4-yl)-1,5-diarylpent-4-ene-1,3-diones as a result

  K 2 CO 3催化的 ( E )-1,5-二芳基-和 1-烷基-5-芳基戊-4-烯-1,3-二酮与 2-三氟甲基-和 2-苯基-取代的双迈克尔加成3-nitro-2 H -chromenes 在二氯甲烷中在室温下放置 48 小时，生成 10-aroyl(acyl)-7-aryl-6a-nitro-6,6a,7,8,10,10a-hexahydro-9 H -苯并[ c ]chromen-9-ones 以 75–98% 的产率作为单独的非对映异构体在 C-6、C-6a 和 C-7 原子和 H-9b 原子上相对于稠合三环体系具有顺式排列的取代基. 在 Cs 2 CO 3存在下，类姜黄素在氯仿中回流 72 小时的类似立体选择性过程通过三重 Michael/Michael/oxa-Michael 级联产生 3,6-diaryl-6a-nitro-2,3,5,6a,7,12b-hexahydro-1