2-hydroxy-6-bromobenzopyridin-4-one | 138964-51-9

• 物质功能分类: 医药中间体 - 喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-hydroxy-6-bromobenzopyridin-4-one
• 英文别名: 6-bromoquinoline-2,4(1H, 3H)-dione；6-Bromoquinoline-2,4(1H,3H)-dione；6-bromo-1H-quinoline-2,4-dione
• CAS: 138964-51-9
• 化学式: C₉H₆BrNO₂
• 分子量: 240.056
• InChiKey: VWPAGBJORSHCDO-UHFFFAOYSA-N

物化性质

• 沸点：
  442.2±45.0 °C(Predicted)
• 密度：
  1.696±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-hydroxy-6-bromobenzopyridin-4-one 在 sodium hydroxide 、 三氯氧磷 作用下， 反应 2.0h， 以96 g的产率得到6-溴-2,4-二氯喹啉
  参考文献：
  名称：

  Discovery, Synthesis, and Biological Evaluation of Thiazoloquin(az)olin(on)es as Potent CD38 Inhibitors

  摘要：

  A series of thiazoloquin(az)olinones were synthesized and found to have potent inhibitory activity against CD38. Several of these compounds were also shown to have good pharmacokinetic properties and demonstrated the ability to elevate NAD levels in plasma, liver, and muscle tissue. In particular, compound 78c was given to diet induced obese (DIO) C57Bl6 mice, elevating NAD > 5-fold in liver and >1.2-fold in muscle versus control animals at a 2 h time point. The compounds described herein possess the most potent CD38 inhibitory activity of any small molecules described in the literature to date. The inhibitors should allow for a more detailed assessment of how NAD elevation via CD38 inhibition affects physiology in NAD deficient states.

  DOI：

  10.1021/jm502009h
• 作为产物：
  描述：

  3-(4-溴苯胺基)-3-氧代丙酸甲酯 在 甲烷磺酸 、 四磷十氧化物 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.33h， 生成 2-hydroxy-6-bromobenzopyridin-4-one
  参考文献：
  名称：

  Discovery, Synthesis, and Biological Evaluation of Thiazoloquin(az)olin(on)es as Potent CD38 Inhibitors

  摘要：

  A series of thiazoloquin(az)olinones were synthesized and found to have potent inhibitory activity against CD38. Several of these compounds were also shown to have good pharmacokinetic properties and demonstrated the ability to elevate NAD levels in plasma, liver, and muscle tissue. In particular, compound 78c was given to diet induced obese (DIO) C57Bl6 mice, elevating NAD > 5-fold in liver and >1.2-fold in muscle versus control animals at a 2 h time point. The compounds described herein possess the most potent CD38 inhibitory activity of any small molecules described in the literature to date. The inhibitors should allow for a more detailed assessment of how NAD elevation via CD38 inhibition affects physiology in NAD deficient states.

  DOI：

  10.1021/jm502009h

文献信息

• New quinoline-2-one/pyrazole derivatives; design, synthesis, molecular docking, anti-apoptotic evaluation, and caspase-3 inhibition assay
  作者：Ashraf A. Aly、Samia M. Sayed、El-Shimaa M.N. Abdelhafez、Sara Mohamed Naguib Abdelhafez、Walaa Yehia Abdelzaher、Mohamed A. Raslan、Amira E. Ahmed、Khaled Thabet、Ahmed A.M. El-Reedy、Alan B. Brown、Stefan Bräse

  DOI：10.1016/j.bioorg.2019.103348

  日期：2020.1

  cells while compound 6e showed dilated blood vessels with more apoptotic cells if compared with NAC. Caspase-3 inhibition assay revealed that compounds 6a, 6b and 6d weaken caspase-3 expression to an extent higher than NAC (1.063, 0.430, 0.731 and 1.115, respectively). Docking studies with caspase-3 revealed that most of the tested compounds showed good binding with the enzyme especially for compound

  我们报告了新的喹啉-2-一/吡唑杂化物的合成及其抗凋亡活性。使用N-乙酰半胱氨酸（NAC）作为抗凋亡参考，研究了减少I / R诱导的大鼠结肠组织损伤的效果。与模型组相比，化合物6a，6c和6f的氧化应激参数MDA，SOD，GSH和NOx表现出显着改善，并且比参考NAC（N-乙酰半胱氨酸）更大，而化合物6d和6e与模型组相比显示出较弱的抗氧化活性。参考NAC。此外，与模型组相比，化合物6a，6c和6f显示出炎性介质TNFα和CRB的降低显着大于NAC，尤其是化合物6c，其与conc 2.13mg / dL的NAC相比发现CRB为1.90（mg / dL）。此外，对所有目标化合物进行了结肠组织病理学研究，结果表明，与NAC相比，化合物6a和6f的H＆E切片显示明显的正常结肠细胞，而化合物6e显示的血管扩张，凋亡细胞更多。Caspase-3抑制分析表明，化合物6a，6b和6d减弱caspase-3的表达的程度高于NAC（分别为1
• Synthesis of spiro[indoline-3,4′-pyrano[3,2-c]quinolone]-3′-carbonitriles
  作者：Ashraf A. Aly、Essmat M. El-Sheref、Aboul-Fetouh E. Mourad、Alan B. Brown、Stefan Bräse、Momtaz E. M. Bakheet、Martin Nieger

  DOI：10.1007/s00706-017-2078-6

  日期：2018.3

  2′-amino-2,5′-dioxo-5′,6′-dihydrospiro(indoline-3,4′-pyrano[3,2-c]quinoline)-3′-carbonitriles in good to excellent yields. The structures of all new products were proven using one- and two-dimensional NMR, IR, and mass spectral data, and in five cases X-ray structural analyses. The possible mechanism for the reaction is also discussed. Graphical abstract

  摘要喹啉-2,4-二酮与吡啶中的2-（2-氧代-1,2-二氢吲哚-3-亚烷基）丙二腈反应生成2'-氨基-2,5'-二氧代-5'，6'-二氢螺基（二氢吲哚-3,4'-吡喃并[3,2- c ]喹啉）-3'-腈的收率良好。使用一维和二维NMR，IR和质谱数据以及五种情况下的X射线结构分析证明了所有新产品的结构。还讨论了反应的可能机理。 图形概要
• 一种糖精衍生物有机颜料及制备方法
  申请人：江苏丽王科技股份有限公司

  公开号：CN113861180A

  公开（公告）日：2021-12-31

  本发明提供一种糖精衍生物有机颜料及制备方法，将糖精、苯并吡啶‑4‑酮及衍生物按摩尔比1:1投入到反应器中，选用溶剂水、甲醇、乙醇、丙醇、异丙醇、吡啶、正丁醇等作为溶剂，在64‑140℃搅拌反应3‑36小时，得到有机颜料。本发明制备的有机颜料合成过程简单，合成产物收率高，结构中有丰富的羰基，酰胺基，磺酰基，吡啶酮和苯环结构，所得到的颜料耐溶剂、耐日晒，耐温性能优异。
• Synthesis of pyrano[3,2-c]quinoline-4-carboxylates and 2-(4-oxo-1,4-dihydroquinolin-3-yl)fumarates
  作者：Essmat M. El-Sheref、Ashraf A. Aly、Aboul-Fetouh E. Mourad、Alan B. Brown、Stefan Bräse、Momtaz E. M. Bakheet

  DOI：10.1007/s11696-017-0269-6

  日期：2018.1

  Reaction of equimolar amounts of 2,4(1H,3H)-quinolinediones and diethyl acetylenedicarboxylate in absolute ethanol, containing catalytic triethylamine, gave ethyl 5,6-dihydro-2,5-dioxo-6,9-disubstituted-2H-pyrano[3,2-c]quinoline-4-carboxylates in good yields. In a different manner, reaction of two equivalents of dialkyl acetylenedicarboxylates with one equivalent of 2,4(1H,3H)-quinolinediones afforded dialkyl 2(4-oxo-1,4-dihydroquinolin-3-yl)fumarates in good yields. The structures of the products were elucidated by 1H NMR, 13C NMR, two-dimensional NMR, IR, mass spectra and elemental analyses.

  等摩尔量的 2,4(1H,3H)-喹啉二酮和乙炔二甲酸二乙酯在含有三乙胺催化剂的绝对乙醇中反应，得到 5,6-二氢-2,5-二氧代-6,9-二取代-2H-吡喃并[3,2-c]喹啉-4-羧酸乙酯，产率良好。用另一种方法，将两个等量的乙炔二羧酸二烷基酯与一个等量的 2,4(1H,3H)-喹啉二酮反应，可以得到 2(4-氧代-1,4-二氢喹啉-3-基)富马酸二烷基酯，收率很高。产品的结构通过 1H NMR、13C NMR、二维 NMR、IR、质谱和元素分析得以阐明。
• Intramolecular Diels–Alder Cycloaddition of Furan-Derived β-Enamino Diketones: An Entry to Diastereoselective Synthesis of Polycyclic Pyrano[3,2-<i>c</i>]quinolin-5-one Derivatives
  作者：Sivanna Chithanna、Ding-Yah Yang

  DOI：10.1021/acs.joc.1c03163

  日期：2022.4.15

  target compounds were generated via the formation of β-enamino diketone as a key intermediate, followed by intramolecular Diels–Alder cycloaddition. The prepared molecules bearing a quinoline-2,4-dione moiety could be further brominated with N-bromosuccinimide and diastereoselectively reduced by NaBH4 to afford pyrano[3,2-c]quinolin-5-one-derived heterocycles with six vicinal stereogenic centers.

  通过1,4-二氮杂双环[2.2.2]辛烷催化、CH 3 NO 2介导的 1,3 三组分反应合成了一系列 1,3-环二酮和四氢环氧异吲哚稠合的 β-烯氨基二羰基杂环。 -环二酮、糠醛和烯丙胺的甲苯溶液。目标化合物是通过形成 β-烯氨基二酮作为关键中间体，然后进行分子内 Diels-Alder 环加成反应生成的。制备的带有 quinoline-2,4-dione 部分的分子可以进一步用N-溴代琥珀酰亚胺溴化并被 NaBH 4非对映选择性还原得到吡喃[3,2- c]quinolin-5-one 衍生的杂环，具有六个邻位立体中心。