7-Hydroxy-4-(4-hydroxyphenyl)-6-(4-methoxy-6-oxopyran-2-yl)-5-methyl-3,4-dihydrochromen-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 7-Hydroxy-4-(4-hydroxyphenyl)-6-(4-methoxy-6-oxopyran-2-yl)-5-methyl-3,4-dihydrochromen-2-one
• 英文别名: 7-hydroxy-4-(4-hydroxyphenyl)-6-(4-methoxy-6-oxopyran-2-yl)-5-methyl-3,4-dihydrochromen-2-one
• 化学式: C₂HCl₃NOPol
• 分子量: 394.4
• InChiKey: IZLDEMGPMNPSSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-Hydroxy-4-(4-hydroxyphenyl)-6-(4-methoxy-6-oxopyran-2-yl)-5-methyl-3,4-dihydrochromen-2-one 、 (napht-2-yl)methyl 2-azido-3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-glucopyranoside 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 4-amino-N-((2R,3R,4R,5S,6R)-5-hydroxy-6-(methoxymethyl)-4-(naphthalen-2-ylmethoxy)-2-phenethoxytetrahydro-2H-pyran-3-yl)butanamide
  参考文献：
  名称：

  A Versatile Synthetic Approach toward Diversity Libraries using Monosaccharide Scaffolds

  摘要：

  The pyranose scaffold is unique in its ability to position pharmacophore substituents in various ways in 3D space, and unique pharmacophore scanning libraries could be envisaged that focus on scanning topography rather than diversity in the type Of substituents. Approaches have been described that make use of amine and acid functionalities on the pyranose scaffolds to append substituents, and this has enabled the generation of libraries of significant structural diversity. Our general aim was to generate libraries of pyranose-based drug-like mimetics, where the substituents are held close to the scaffold, in order to obtain molecules with better defined positions for the pharmacophore substituents. Here we describe the development of a versatile synthetic route toward peptide mimetics build oil 2-amino pyranose scaffolds. The method allows introduction of a wide range of substituent types, it is regio- and stereospecific, and the later diversity steps are performed on solid phase. Further, the same process was applied oil glucose mid allose scaffolds, in the exemplified cases, and is likely adaptable to other pyranose building blocks. The methods developed in this work give access to molecules that position the three selected binding elements in various 3D orientations oil a pyranose scaffold and have been applied for the production of a systematically diverse library of several hundred monosaccharide-based mimetics.

  DOI：

  10.1021/jo9021919
• 作为产物：
  描述：

  三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 7-Hydroxy-4-(4-hydroxyphenyl)-6-(4-methoxy-6-oxopyran-2-yl)-5-methyl-3,4-dihydrochromen-2-one
  参考文献：
  名称：

  嘌呤在固相上直接CH杂化反应及其在化学文库合成中的应用

  摘要：

  描述了固定在Wang树脂上的嘌呤衍生物的C 8 -H直接芳基化。嘌呤骨架是通过用聚合物负载的胺进行的C 6-区域选择性2，6-二氯嘌呤取代固定的。在用两种不同的烷基碘进行N 9烷基化并用两种选定的胺取代C 2之后，C 8的反应条件开发并优化了-H芳基化。各种芳基溴化物和芳基碘化物用于反应，以非常好的纯度提供目标2,6,8,9-四取代嘌呤。相同的反应条件也适用于2,6,8-三取代嘌呤的合成，但是收率较低。该方法适用于由嘌呤支架组成的化学文库的高通量合成。

  DOI：

  10.1021/co200075r
• 作为试剂：
  描述：

  2-(N-芴甲氧羰基氨基)乙醇 在 7-Hydroxy-4-(4-hydroxyphenyl)-6-(4-methoxy-6-oxopyran-2-yl)-5-methyl-3,4-dihydrochromen-2-one 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 caffeic acid cinnamyl ester
  参考文献：
  名称：

  嘌呤在固相上直接CH杂化反应及其在化学文库合成中的应用

  摘要：

  描述了固定在Wang树脂上的嘌呤衍生物的C 8 -H直接芳基化。嘌呤骨架是通过用聚合物负载的胺进行的C 6-区域选择性2，6-二氯嘌呤取代固定的。在用两种不同的烷基碘进行N 9烷基化并用两种选定的胺取代C 2之后，C 8的反应条件开发并优化了-H芳基化。各种芳基溴化物和芳基碘化物用于反应，以非常好的纯度提供目标2,6,8,9-四取代嘌呤。相同的反应条件也适用于2,6,8-三取代嘌呤的合成，但是收率较低。该方法适用于由嘌呤支架组成的化学文库的高通量合成。

  DOI：

  10.1021/co200075r

文献信息

• Solid-Phase Synthesis and Chemical Properties of 2-(2-Amino/hydroxyethyl)-1-aryl-3,4-dihydropyrazino[1, 2-<i>b</i>]indazol-2-iums
  作者：Jan Kočí、Viktor Krchňák

  DOI：10.1021/cc9001422

  日期：2010.1.11

  Amino alcohols, diamines, benzenesulfonyl chlorides, and bromoketones were used to prepare polymer-supported 2-(2-(2-(amino/hydroxyl)ethylamino)ethyl)-3-benzoyl-2H-indazoles. Acid-mediated release yielded 2-((amino/hydroxyl)ethyl)-1-aryl-3,4-dihydropyrazino[1,2-b]indazole-2-iums. In neutral pH, iminiums spontaneously cyclized to complex fused heterocycles 3,6,9,10-tetraazatetracyclo[7.7.0.0(2,6).0(11,16)]hexadeca-11,13,15-trienes, 3-oxa-6,9,10-triazatetracyclo[7.7.0.0(2,6).0(11,16)]hexadeca-11,13,15-trienes, and 3,7,10,11-tetraazatetracyclo[8.7.0.0(2,7).0(12,17)]heptadeca-12,14,16-trienes. Transformations were carried out under mild conditions and tolerated diverse substitution patterns.
• Screening of polymeric supports and enzymes for the development of an endo enzyme cleavable linker
  作者：Ana Chiva、David E. Williams、Alethea B. Tabor、Helen C. Hailes

  DOI：10.1016/j.tetlet.2010.03.040

  日期：2010.5

  Several polymeric supports possessing an ester moiety were prepared and a range of enzymes was investigated to hydrolyse the ester linkage and release a signalling group into solution for applications in immunoassays. Pseudomonas lipases were found to most readily cleave the solution-phase analogue and this observation translated well to the corresponding polymeric supports, where the most effective were PEGA resins and the LPOS support PEG-6000. (C) 2010 Elsevier Ltd. All rights reserved.
• Biological Diversity from a Structurally Diverse Library: Systematically Scanning Conformational Space Using a Pyranose Scaffold
  作者：Giovanni Abbenante、Bernd Becker、Sébastien Blanc、Chris Clark、Glenn Condie、Graeme Fraser、Matthias Grathwohl、Judy Halliday、Senka Henderson、Ann Lam、Ligong Liu、Maretta Mann、Craig Muldoon、Andrew Pearson、Rajaratnam Premraj、Tracie Ramsdale、Tony Rossetti、Karl Schafer、Giang Le Thanh、Gerald Tometzki、Frank Vari、Géraldine Verquin、Jennifer Waanders、Michael West、Norbert Wimmer、Annika Yau、Johannes Zuegg、Wim Meutermans

  DOI：10.1021/jm1002777

  日期：2010.8.12

  Success in discovering bioactive peptide mimetics is often limited by the difficulties in correctly transposing known binding elements of the active peptide onto a small and metabolically more stable scaffold while maintaining bioactivity. Here we describe a scanning approach using a library of pyranose-based peptidomimetics that is structurally diverse in a systematic manner, designed to cover all possible conformations of tripeptide motifs containing two aromatic groups and one positive charge. Structural diversity was achieved by efficient selection of various chemoforms, characterized by a choice of pyranose scaffold of defined chirality and substitution pattern. A systematic scanning library of 490 compounds was thus designed, produced, and screened in vitro for activity at the somatostatin (sst(1-5)) and melanin-concentrating hormone (MCH1) receptors. Bioactive compounds were found for each target, with specific chemoform preferences identified in each case, which can be used to guide follow-on drug discovery projects without the need for scaffold hopping.
• A Versatile Synthetic Approach toward Diversity Libraries using Monosaccharide Scaffolds
  作者：Giang Le Thanh、Giovanni Abbenante、George Adamson、Bernd Becker、Chris Clark、Glenn Condie、Tania Falzun、Matthias Grathwohl、Praveer Gupta、Michael Hanson、Ngoc Huynh、Peter Katavic、Krystle Kuipers、Ann Lam、Ligong Liu、Maretta Mann、Jeff Mason、Declan McKeveney、Craig Muldoon、Andrew Pearson、Premraj Rajaratnam、Sarah Ryan、Gerry Tometzki、Geraldine Verquin、Jennifer Waanders、Michael West、Neil Wilcox、Norbert Wimmer、Annika Yau、Johannes Zuegg、Wim Meutermans

  DOI：10.1021/jo9021919

  日期：2010.1.1

  The pyranose scaffold is unique in its ability to position pharmacophore substituents in various ways in 3D space, and unique pharmacophore scanning libraries could be envisaged that focus on scanning topography rather than diversity in the type Of substituents. Approaches have been described that make use of amine and acid functionalities on the pyranose scaffolds to append substituents, and this has enabled the generation of libraries of significant structural diversity. Our general aim was to generate libraries of pyranose-based drug-like mimetics, where the substituents are held close to the scaffold, in order to obtain molecules with better defined positions for the pharmacophore substituents. Here we describe the development of a versatile synthetic route toward peptide mimetics build oil 2-amino pyranose scaffolds. The method allows introduction of a wide range of substituent types, it is regio- and stereospecific, and the later diversity steps are performed on solid phase. Further, the same process was applied oil glucose mid allose scaffolds, in the exemplified cases, and is likely adaptable to other pyranose building blocks. The methods developed in this work give access to molecules that position the three selected binding elements in various 3D orientations oil a pyranose scaffold and have been applied for the production of a systematically diverse library of several hundred monosaccharide-based mimetics.
• Direct C–H Arylation of Purine on Solid Phase and Its Use for Chemical Libraries Synthesis
  作者：Barbora Vaňková、Viktor Krchňák、Miroslav Soural、Jan Hlaváč

  DOI：10.1021/co200075r

  日期：2011.9.12

  skeleton was immobilized via C6-regioselective substitution of 2,6-dichloropurine with polymer-supported amines. After N9-alkylation with two different alkyl iodides and C2 substitution with two selected amines, reaction conditions for C8–H arylation were developed and optimized. Various aryl bromides and aryl iodides were used for the reaction affording the target 2,6,8,9-tetrasubstituted purines in

  描述了固定在Wang树脂上的嘌呤衍生物的C 8 -H直接芳基化。嘌呤骨架是通过用聚合物负载的胺进行的C 6-区域选择性2，6-二氯嘌呤取代固定的。在用两种不同的烷基碘进行N 9烷基化并用两种选定的胺取代C 2之后，C 8的反应条件开发并优化了-H芳基化。各种芳基溴化物和芳基碘化物用于反应，以非常好的纯度提供目标2,6,8,9-四取代嘌呤。相同的反应条件也适用于2,6,8-三取代嘌呤的合成，但是收率较低。该方法适用于由嘌呤支架组成的化学文库的高通量合成。