methyl 2-methyl-5-(pyridin-3-yl)furan-3-carboxylate | 1130431-48-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: methyl 2-methyl-5-(pyridin-3-yl)furan-3-carboxylate
• 英文别名: Methyl 2-methyl-5-pyridin-3-ylfuran-3-carboxylate；methyl 2-methyl-5-pyridin-3-ylfuran-3-carboxylate
• CAS: 1130431-48-9
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: UZKZEVLUKSXQAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-methyl-5-(pyridin-3-yl)furan-3-carboxylate 在 4-二甲氨基吡啶 、 水 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-(5,6-dihydro-4H-cyclopenta[d][1,3]thiazol-2-yl)-2-methyl-5-pyridin-3-ylfuran-3-carboxamide
  参考文献：
  名称：

  Discovery and hit-to-lead optimization of novel allosteric glucokinase activators

  摘要：

  We report on a hit generation and hit-to-lead program of a novel class of glucokinase activators (GKAs). Hit compounds, activators at low glucose concentration only were identified by vHTS. Scaffold modification reliably afforded activators also at high substrate level. Potency was increased by introduction of a hydrogen bond acceptor as proposed by molecular docking. Replacement of the initial alkylene linkers with a rigid 1,2-phenylene motif followed by further studies eventually furnished a series of potent lead compounds exhibiting steep SAR. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.128
• 作为产物：
  描述：

  2-甲基-3-糠酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 methyl 2-methyl-5-(pyridin-3-yl)furan-3-carboxylate
  参考文献：
  名称：

  Discovery and hit-to-lead optimization of novel allosteric glucokinase activators

  摘要：

  We report on a hit generation and hit-to-lead program of a novel class of glucokinase activators (GKAs). Hit compounds, activators at low glucose concentration only were identified by vHTS. Scaffold modification reliably afforded activators also at high substrate level. Potency was increased by introduction of a hydrogen bond acceptor as proposed by molecular docking. Replacement of the initial alkylene linkers with a rigid 1,2-phenylene motif followed by further studies eventually furnished a series of potent lead compounds exhibiting steep SAR. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.128

文献信息

• Palladium-catalyzed direct heteroarylation of chloropyridines and chloroquinolines
  作者：Fazia Derridj、Julien Roger、Florence Geneste、Safia Djebbar、Henri Doucet

  DOI：10.1016/j.jorganchem.2008.11.032

  日期：2009.2

  PdCl(dppb)(C3H5) as a catalyst, a range of heteroaryl derivatives undergoes coupling via C–H bond activation/functionalization reaction with chloropyridines or chloroquinolines in low to high yields. This air-stable catalyst can be used with a wide variety of substrates. The position of the chloro substituent on pyridines has a minor influence on the yields. On the other hand, the nature on the heteroaryl derivative

  芳基氯化物与杂芳烃的直接偶联将具有可持续发展的巨大优势，因为它们的成本更低，质量更轻，可用化合物的多样性更大，并且还因为仅形成了与副产物碱有关的HCl和减少制备这些化合物的步骤数。我们观察到通过使用PdCl（dppb）（C 3 H 5）作为催化剂，一系列杂芳基衍生物通过C–H键活化/官能化反应与氯吡啶或氯喹啉进行低至高收率的偶联。这种空气稳定的催化剂可与多种基材一起使用。吡啶上氯取代基的位置对收率影响很小。另一方面，杂芳基衍生物的性质具有很大的影响。使用苯并恶唑，噻吩或噻唑衍生物可获得最高的收率。氯吡啶与呋喃的偶联也得到了预期的产物，但是产率低至中等。
• Low catalyst loading ligand-free palladium-catalyzed direct arylation of furans: an economically and environmentally attractive access to 5-arylfurans
  作者：Jia Jia Dong、Julien Roger、Franc Požgan、Henri Doucet

  DOI：10.1039/b915290n

  日期：——

  The direct 5-arylation of furans at very low catalyst loading using Pd(OAc)2 as catalyst without added ligand proceed in high yields. Turnover numbers up to 10000 have been obtained for the coupling of several activated aryl bromides. A wide range of functions on the furan or aryl bromide is tolerated.

  的直接5-芳基化 呋喃 在非常低的位置 催化剂使用Pd（OAc）2作为催化剂 没有添加 配体以高产进行。对于几种活化的芳基溴化物的偶联，已经获得了高达10000的周转率。上的多种功能呋喃 或可以容忍芳基溴化物。
• 噻二唑酰胺类化合物及其应用
  申请人：浙江大学

  公开号：CN113444081B

  公开（公告）日：2022-07-05

  本发明公开了噻二唑酰胺类化合物及其应用，属于医药领域。所述化合物的结构通式如式(Ⅰ)所示，为一类具有雄激素受体拮抗活性的新型化合物，其中关键靶标之一是雄激素受体配体结合域二聚体界面间的结合口袋，能够阻断雄激素受体二聚化而发挥拮抗雄激素受体的作用。本发明提供的化合物具有较高的拮抗雄激素受体转录的活性，在分子水平、细胞水平和动物水平均表现较好的生物学活性，且具有较好的安全性。因此，可以将其应用于制备治疗雄激素受体异常表达肿瘤包括但不限于前列腺癌、转移性前列腺癌，去势抵抗性前列腺癌、乳腺癌、卵巢癌的药物中。
• Furan Synthesis via Triplet Sensitization of Acceptor/Acceptor Diazoalkanes
  作者：Siqi Zhu、Fang Li、Claire Empel、Sripati Jana、Chao Pei、Rene M. Koenigs

  DOI：10.1002/adsc.202200654

  日期：2022.9.20

  reaction of acceptor/acceptor diazoalkanes with terminal alkynes. Experimental and computational studies suggest the formation of a key triplet carbene intermediate that undergoes an addition reaction to the alkyne followed by cyclization to give furan heterocycles (31 to 90% yield). This reaction was studied with a broad range of alkynes and acceptor/acceptor diazoalkanes and now provides access to furans

  在此，我们报道了受体/受体重氮烷烃与末端炔烃的光催化反应。实验和计算研究表明形成了一个关键的三线态卡宾中间体，该中间体与炔烃发生加成反应，然后环化得到呋喃杂环（31% 至 90% 的产率）。该反应用广泛的炔烃和受体/受体重氮烷烃进行了研究，现在可以在温和的反应条件下获得呋喃。
• Discovery and hit-to-lead optimization of novel allosteric glucokinase activators
  作者：Martin Lang、Markus H.-J. Seifert、Kristina K. Wolf、Andrea Aschenbrenner、Roland Baumgartner、Tanja Wieber、Viola Trentinaglia、Marcus Blisse、Nobumitsu Tajima、Tokuyuki Yamashita、Daniel Vitt、Hitoshi Noda

  DOI：10.1016/j.bmcl.2011.06.128

  日期：2011.9

  We report on a hit generation and hit-to-lead program of a novel class of glucokinase activators (GKAs). Hit compounds, activators at low glucose concentration only were identified by vHTS. Scaffold modification reliably afforded activators also at high substrate level. Potency was increased by introduction of a hydrogen bond acceptor as proposed by molecular docking. Replacement of the initial alkylene linkers with a rigid 1,2-phenylene motif followed by further studies eventually furnished a series of potent lead compounds exhibiting steep SAR. (C) 2011 Elsevier Ltd. All rights reserved.