4-hydroxy-6-methoxy-3-phenylquinolin-2(1H)-one | 28563-21-5

• 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: 4-hydroxy-6-methoxy-3-phenylquinolin-2(1H)-one
• 英文别名: 4-Hydroxy-6-methoxy-3-phenyl-1h-quinolin-2-one
• CAS: 28563-21-5
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: YUGCKEYUTQREGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6-methoxy-3-phenylquinolin-2(1H)-one 在 甲烷磺酸 、 sodium 4-methylbenzenesulfinate 、 三氯氧磷 作用下， 以 水 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 95.0h， 生成 2-chloro-6-methoxy-3-phenylquinoline-4-carbonitrile
  参考文献：
  名称：

  3-芳基-6-甲氧基-2-氧-1,2-二氢喹啉-4-腈作为溶剂和不依赖pH值的绿色荧光染料

  摘要：

  高度荧光和稳定3-芳基-6-甲氧基-2-氧代喹啉-4-甲腈6（λ EXC = 408 nm和λ EM = 510 nm）的合成从合适的起始arylmalonates 2。与对茴香胺的闭环反应得到4-羟基喹诺酮3，可将其双氯化以生成喹啉4。区域选择性水解产生的活性4- chloroquinolones 5，将其转化为绿色荧光4-氰基喹诺酮6用toluenesulfinates作为催化剂。

  DOI：

  10.1002/jhet.1084
• 作为产物：
  描述：

  甲氧苯胺 、 苯基丙二酸二乙酯 反应 0.25h， 以40%的产率得到4-hydroxy-6-methoxy-3-phenylquinolin-2(1H)-one
  参考文献：
  名称：

  在无溶剂条件下快速微波增强4-羟基喹啉酮的合成

  摘要：

  3-Aryl-4-hydroxyquinolin-2（1 H）-ones是有效的，选择性的，具有药用价值的甘氨酸位点NMDA受体拮抗剂。已经开发了在无溶剂条件下这种喹啉酮的新型微波增强合成方法。由于丙二酸酯衍生物与苯胺的正式酰胺化反应和随后的中间体丙二烯环化反应，可以通过一锅法轻松获得喹啉酮。

  DOI：

  10.1016/s0040-4039(00)02244-9

文献信息

• Substituent effects on absorption and fluorescence spectra of carbostyrils
  作者：Walter M.F. Fabian、Karlheinz S. Niederreiter、Georg Uray、Wolfgang Stadlbauer

  DOI：10.1016/s0022-2860(98)00616-4

  日期：1999.3

  Abstract Absorption and fluorescence spectra as well as quantum yields of a series of differently substituted carbostyrils (quinolin-2(1H)-ones) are reported. Especially for compounds containing donor substituents in position 6, substantial bathochromic shifts (comparable to analogous coumarins) of both absorption as well as fluorescence transitions are obtained. High absorption intensities and quantum

  摘要 报告了一系列不同取代的喹诺酮 (quinolin-2(1H)-ones) 的吸收光谱和荧光光谱以及量子产率。特别是对于在 6 位含有供体取代基的化合物，获得了吸收和荧光跃迁的显着红移（与类似香豆素相当）。7 供体取代异构体具有高吸收强度和量子产率。半经验分子轨道计算（AM1 表示结构，ZINDO 表示电子跃迁能）被证明是预测这些化合物的吸收和荧光特性的合适工具。从头算和密度泛函计算确定内酰胺形式作为母体喹啉-2(1H)-one 的主要互变异构体。
• Rapid microwave-enhanced synthesis of 4-hydroxyquinolinones under solvent-free conditions
  作者：Jos H.M Lange、Peter C Verveer、Stefan J.M Osnabrug、Geb M Visser

  DOI：10.1016/s0040-4039(00)02244-9

  日期：2001.2

  potent and selective glycine-site NMDA receptor antagonists of pharmaceutical interest. A novel microwave-enhanced synthesis of such quinolinones under solvent-free conditions has been developed. The quinolinones are easily obtained in a one-pot procedure as a result of the formal amidation of a malonic ester derivative with an aniline and subsequent cyclisation of the intermediate malondianilides

  3-Aryl-4-hydroxyquinolin-2（1 H）-ones是有效的，选择性的，具有药用价值的甘氨酸位点NMDA受体拮抗剂。已经开发了在无溶剂条件下这种喹啉酮的新型微波增强合成方法。由于丙二酸酯衍生物与苯胺的正式酰胺化反应和随后的中间体丙二烯环化反应，可以通过一锅法轻松获得喹啉酮。
• Copper(I)-Catalyzed [ 3+ 2] Cycloaddition of 3-Azidoquinoline-2,4(1H,3H)-diones with Terminal Alkynes
  作者：Stanislav Kafka、Sylvia Hauke、Arjana Salcinovic、Otto Soidinsalo、Damijana Urankar、Janez Kosmrlj

  DOI：10.3390/molecules16054070

  日期：——

  are readily available from 4-hydroxyquinolin-2(1H)-ones 4 via 3-chloroquinoline-2,4(1H,3H)-diones 5, afford, in copper(I)-catalyzed [3 + 2] cycloaddition reaction with terminal acetylenes, 1,4-disubstituted 1,2,3-triazoles 3 in moderate to excellent yields. The structures of compounds 3 were confirmed by 1H and 13C-NMR spectroscopy, combustion analyses and mass spectrometry.

  3-叠氮喹啉-2,4(1H,3H)-二酮 1 可通过 3-氯喹啉-2,4(1H,3H)-二酮 5 从 4-羟基喹啉-2(1H)-酮 4 轻松获得，提供, 在铜 (I) 催化的 [3 + 2] 环加成反应与末端乙炔中，1,4-二取代的 1,2,3-三唑 3 以中等至极好的收率进行。化合物3的结构经1H和13C-NMR光谱、燃烧分析和质谱证实。
• Halogenation reactions in position 3 of quinoline-2,4-dione systems by electrophilic substitution and halogen exchange
  作者：Wolfgang Stadlbauer、Rita Laschober、Herbert Lutschouig、Gerda Schindler、Thomas Kappe

  DOI：10.1007/bf00816857

  日期：——

  3-Substituted 4-hydroxy-2(1 H)-quinolones 3, 5, 7 are halogenated with bromine or sulfuryl chloride to yield the quinolinediones 9 or 10. Reaction of 3, 5, 7 with chloroform gives the dichloromethyl quinolinediones 11. Halogen exchange leads from the chloro quinolinediones 10 to fluoro quinolinedones 12 and to azido quinolinediones 13. Similarly the dichloro quinolinedione 10 an reacts to the difluoro quinolinedione 14, which is reduced to the 3-fluoro-4-hydroxyquinolone 16 and reacts again with sulfuryl chloride to give the mixed 3-chloro-3-fluoroquinolinedione 15.
• Synthesis and cytotoxic activity evaluation of indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones and 6-anilinoindoloquinoline derivatives
  作者：Yeh-Long Chen、Chao-Ho Chung、I.-Li Chen、Po-Hsu Chen、Haw-Yaun Jeng

  DOI：10.1016/s0968-0896(02)00111-6

  日期：2002.8

  Certain indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones 4a,b, 6, 8, 16a-c and 6-anilinoindoloquinoline derivatives 10a,b, 11a,b, 12a,b have been synthesized and evaluated in vitro against a 3-cell lines panel consisting of MCF7 (Breast), NCI-H460 (Lung), and SF-268 (CNS). Those active compounds 4a,b, 6, 8, 10a,b, 11a,b, 12a,b were then evaluated in the full panel of 60 human tumor cell lines derived from nine cancer cell types. The results have shown that cytotoxicity decreases in the order of 6-anilinoindoloquinolines>indoloquinolin-2(1H)-ones>pyrroloquinolin-2(1H)-ones>benzofuroquinolin-2(1H)-ones. Among them, 1-[3-(11H-indolo[3,2-c]quinolin-6ylamino)phenyl]ethanone oxime hydrochloride (14a) and its 2-chloro derivative (11b) were most active, with mean GI(50) values of 1.70 and 1.35 muM, respectively. Both compounds 11a,b were also found to inhibit the growth of SNB-75 (CNS cancer cell) with a GI(50) value of less than 0.01 muM, and, therefore, were selected for further evaluation for in vivo antitumor activity. (C) 2002 Published by Elsevier Science Ltd.