2,4-喹啉二醇 | 1677-36-7

• 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
• 中文名称: 2,4-喹啉二醇
• 中文别名: 2,4,6-三(2-丙烯基氧基)-1,3,5-三嗪；2,4-二羟基喹啉
• 英文名称: 6-chloro-4-hydroxyquinolin-2(1H)-one
• 英文别名: 6-Chlor-4-hydroxy-carbostyril；6-chloro-4-hydroxy-1H-quinolin-2-one；6-chloro-4-hydroxyquinoline-2(1H)-one
• CAS: 1677-36-7
• 化学式: C₉H₆ClNO₂
• mdl: MFCD04037761
• 分子量: 195.605
• InChiKey: XLRWZGHILAGXMB-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C(lit.)
• 沸点：
  439.1±45.0 °C(Predicted)
• 密度：
  1.516±0.06 g/cm3(Predicted)
• 溶解度：
  碱性溶液（微溶），DMSO（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36/37/38
• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：室温、避光、干燥且密封保存。

反应信息

• 作为反应物：
  描述：

  2,4-喹啉二醇 在 四磷十氧化物 、 四丁基溴化铵 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以32%的产率得到2,4-dibromo-6-chloroquinoline
  参考文献：
  名称：

  Novel coumarin- and quinolinone-based polycycles as cell division cycle 25-A and -C phosphatases inhibitors induce proliferation arrest and apoptosis in cancer cells

  摘要：

  Cell division cycle phosphatases CDC25 A, B and C are involved in modulating cell cycle processes and are found overexpressed in a large panel of cancer typology. Here, we describe the development of two novel quinone-polycycle series of CDC25A and C inhibitors on the one hand la-k, coumarin-based, and on the other 2a-g, quinolinone-based, which inhibit either enzymes up to a sub-micro molar level and at single digit micro molar concentrations, respectively. When tested in six different cancer cell lines, compound 2c displayed the highest efficacy to arrest cell viability, showing in almost all cell lines sub-micro molar IC50 values, a profile even better than the reference compound NCS95397. To investigate the putative binding mode of the inhibitors and to develop quantitative structure-activity relationships, molecular docking and 3-D QSAR studies were also carried out. Four selected inhibitors, la, ld, 2a and 2c have been also tested in A431 cancer cells; among them, compound 2c was the most potent one leading to cell proliferation arrest and decreased CDC25C protein levels together with its splicing variant. Compound 2c displayed increased phosphorylation levels of histone H3, induction of PARP and caspase 3 cleavage, highlighting its contribution to cell death through pro-apoptotic effects. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.04.012
• 作为产物：
  描述：

  对氯苯胺 在 polyphosphoric acid 作用下， 反应 7.0h， 生成 2,4-喹啉二醇
  参考文献：
  名称：

  6-chloro-4-hydroxyquinoline-2(1 H)-one衍生的一些偶氮染料的合成、结构解析、溶剂化显色和光谱性质

  摘要：

  摘要 以多磷酸为催化剂，对氯苯胺衍生的丙二苯胺(I)以中等收率环化为6-氯-4-羟基喹啉-2(1 H)-酮(II)。然后将该化合物与一些重氮化的芳香胺偶联，得到相应的偶氮分散染料 1-12。对溶剂、酸、碱和 pH 值对染料 1-12 电子吸收光谱的影响进行了系统研究。在 DMSO、DMF、CH 3 CN、CHCl 3 、乙醇和酸性介质（CH 3 COOH，酸化乙醇）中，这些理论上可能参与偶氮腙互变异构现象的染料仅作为腙互变异构体 T 1 和 T 2 被检测到。在室温和 0.1 的离子强度下，在 80 vol% 乙醇-水溶液中测量染料的酸解离常数。

  DOI：

  10.1016/j.molstruc.2015.12.001

文献信息

• Identification and molecular modeling of new quinolin-2-one thiosemicarbazide scaffold with antimicrobial urease inhibitory activity
  作者：Mohammed A. I. Elbastawesy、Yaseen A. M. M. El-Shaier、Mohamed Ramadan、Alan B. Brown、Ashraf A. Aly、Gamal El-Din A. Abuo-Rahma

  DOI：10.1007/s11030-019-10021-0

  日期：2021.2

  A new series of 6-substituted quinolin-2-one thiosemicarbazides 6a–j has been synthesized. The structure of the target compounds was proved by different spectroscopic and elemental analyses. All the designed final compounds were evaluated for their in vitro activity against the urease-producing R. mucilaginosa and Proteus mirabilis bacteria as fungal and bacterial pathogens, respectively. Moreover, all compounds were in vitro tested as potential urease inhibitors using the cup-plate diffusion method. Compounds 6a and 6b were the most active with (IC50 = 0.58 ± 0.15 and 0.43 ± 0.09 µM), respectively, in comparison with lead compound I (IC50 = 1.13 ± 0.00 µM). Also, the designed compounds were docked into urease proteins (ID: 3LA4 and ID: 4UBP) using Open Eye® software to understand correctly about ligand–receptor interactions. The docking results revealed that the designed compounds can interact with the active site of the enzyme through multiple strong hydrogen bonds. Moreover, rapid overlay of chemical structures’ analysis was described to understand the 3D QSAR of synthesized compounds as urease inhibitors. The results emphasize the importance of polar thiosemicarbazide directly linked to 6-substituted quinolone moieties as promising antimicrobial urease inhibitors.

  一系列6-取代的喹啉-2-酮硫脲6a–j已被合成。目标化合物的结构通过不同的光谱和元素分析得到证实。所有设计的最终化合物分别对产生脲酶的R. muciLAginoSA和Proteus mirabilis细菌作为真菌和细菌病原体的体外活性进行了评估。此外，所有化合物在体外采用杯盘扩散法作为潜在的脲酶抑制剂进行了测试。化合物6a和6b活性最强，分别为（IC50 = 0.58 ± 0.15和0.43 ± 0.09μM），与先导化合物I（IC50 = 1.13 ± 0.00μM）相比。此外，设计的化合物通过Open Eye®软件对接入脲酶蛋白（ID：3LA4和ID：4UBP），以正确理解配体-受体相互作用。对接结果显示，设计的化合物可以通过多个强氢键与酶的活性位点相互作用。此外，还描述了化学结构的快速叠加分析，以理解合成的化合物作为脲酶抑制剂的3D QSAR。结果强调了直接连接到6-取代喹诺酮部分的极性硫脲作为有前途的抗菌脲酶抑制剂的重要性。
• New Quinoline-2-one/thiazolium bromide Derivatives; Synthesis, Characterization and Mechanism of Formation
  作者：Sara M. Mostafa、Ashraf A. Aly、Samia M. Sayed、Mohamed A. Raslan、Amira E. Ahmed、Ayman Nafady、Esam A. Ishak、Ahmed M. Shawky、El-Shimaa M.N. Abdelhafez

  DOI：10.1016/j.molstruc.2021.130501

  日期：2021.9

  We report on the formation of new quinoline-2-one derived by thiazolium bromides from the reaction of 3-thiosemicarbazides derived by 2-quinolones with 2-bromoacetophenones. The structure of products was elucidated by mass, IR and NMR spectra together with elemental analysis. The mechanism of products formation was discussed.

  我们报道了由噻唑溴化物衍生的新喹啉-2-酮的形成，该喹啉-2-酮是由2-喹诺酮与2-溴苯乙酮衍生的3-硫代氨基脲的反应。通过质量，IR和NMR光谱以及元素分析来阐明产物的结构。讨论了产品形成的机理。
• Synthesis and colon anticancer activity of some novel thiazole/-2-quinolone derivatives
  作者：Ashraf A. Aly、Asmaa H. Mohamed、Mohamed Ramadan

  DOI：10.1016/j.molstruc.2020.127798

  日期：2020.5

  Abstract We direct for the synthesis of 1,6,7-trisubstituted-4-phenylthiazol-2(3H)-ylidene)hydrazono)methyl)quinolin-2-one derivatives by the reaction of corresponding thiosemicarbazone derived by 2-quinolone derivatives with 2-bromoacetophenones in presence of triethylamine at room temperature. The mechanism of the formed products was discussed. The structure of the obtained products was fully characterized

  摘要 我们指导了 1,6,7-三取代-4-苯基噻唑-2(3H)-ylidene)hydrazono)methyl)quinolin-2-one 衍生物的合成，通过 2-quinolone 衍生物衍生的相应缩氨基硫脲与 2 -溴苯乙酮在室温下三乙胺存在下。讨论了形成产物的机理。使用不同的光谱技术，包括红外 (IR)、核磁共振 (NMR) 和质谱 (MS) 以及元素分析，对所得产物的结构进行了全面表征。新合成的化合物显示出中等的结肠抗癌活性。
• Synthesis of novel 1,2-bis-quinolinyl-1,4-naphthoquinones: ERK2 inhibition, cytotoxicity and molecular docking studies
  作者：Ashraf A. Aly、Essmat M. El-Sheref、Momtaz E.M. Bakheet、Mai A.E. Mourad、Alan B. Brown、Stefan Bräse、Martin Nieger、Mahmoud A.A. Ibrahim

  DOI：10.1016/j.bioorg.2018.09.017

  日期：2018.12

  pathway inhibition together with molecular docking using ATP-binding site of ERK2. The results revealed that compounds 3a, 3b and 4f inhibited ETS-1 phosphorylation by ERK2 in a dose dependent manner. Also, compound 4f showed highest potency for ERK2 inhibition with ATP-competitive inhibition mechanism which was confirmed by the formation of three hydrogen bond in the molecular docking studies. The synthesized

  N -2,3-双（6-取代的-4-羟基-2-羟基-2-氧代-1,2-二氢喹啉-3-基）萘-1,4-二酮3a-d和取代的N-（甲基）的两个新系列（乙基）双喹啉酮三乙基铵盐4e，f已成功合成。合成的化合物可作为具有明显抗肿瘤活性的细胞外信号调节激酶1/2（ERK1 / 2）的新候选物。合成涉及乙醇/二甲基甲酰胺（1：1）的混合物中的2当量的4-羟基-2（1 H）-喹啉酮1a - f和1当量的1,4-萘醌（2）的反应和0.5 mL Et 3N.在6-甲基-4-羟基喹诺酮1b与2的反应中，获得第二系列的副产物4b。通常，游离NH-喹诺酮的存在给出了第一系列的单一化合物，而N-甲基/乙基喹诺酮1e，f与2的反应增强了第二系列化合物的形成。通过不同的光谱技术，例如IR，NMR（2D-NMR）和质谱，元素分析和X射线晶体学，证明了新化合物的结构。为了进一步阐明这些新合成的化合物，化合物3a，3b，4e和
• CONVENIENT ROUTE TO 2H-FURO[3,2-c]QUINOLIN-4-ONE FRAMEWORK USING Mn(III)-BASED OXIDATIVE RADICAL CYCLIZATION
  作者：Ryoukou Kumabe、Hiroshi Nishino

  DOI：10.1515/hc.2004.10.2-3.135

  日期：2004.1

  The oxidation of a mixture of 1.1-disubstituted ethenes 1 with 4-hydroxy-2-quinolinone derivatives 2 with manganese(III) acetate in boiling glacial acetic acid was investigated. The reaction of 3-substituted quinolinones 2 gave 9b-hydroxy-3,3a,5,9b-tetrahydro-2//-furo[3,2-c]quinolin-4-ones 3 and 3-(2.2-diarvlethenyl)quinoline-2,4-diones 4 in moderate to good yields. On the other hand, 3,5-dihydro-2//-furo[3

  研究了 1.1-二取代的乙烯 1 与 4-羟基-2-喹啉酮衍生物 2 与乙酸锰 (III) 在沸腾冰醋酸中的氧化反应。3-取代喹啉酮2反应得到9b-羟基-3,3a,5,9b-四氢-2//-呋喃[3,2-c]喹啉-4-酮3和3-(2.2-二亚乙烯基)喹啉-2,4-二酮 4 中等至良好的收率。另一方面，3,5-dihydro-2//-furo[3,2-c]quinolin-4-ones 5 主要在 3-位无取代基的喹啉酮 2 反应过程中产生。讨论了反应途径和反应的应用。喹啉酮是一类非常重要的杂环化合物。喹啉酮环存在于许多天然产物中，大量喹啉酮衍生物显示出令人感兴趣的生物活性。最近，我们发现了一种独特的过氧化物形成，使用锰 (III) 催化的 4-羟基喹啉-2-酮在烯烃存在下的有氧氧化。有氧氧化产生 3,3-双（2 氢过氧乙基）喹啉二酮和 [4.4.3] 丙烷型环状过氧化物。从抗疟活性的角度来看