reevesianine-A | 109030-96-8

• 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: reevesianine-A
• 英文别名: 2-(4-Hydroxyphenyl)-1-methylquinolin-4-one
• CAS: 109030-96-8
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: IVVGAXUISDFFMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  433.7±45.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  reevesianine-A 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以47%的产率得到2-(4-甲氧基苯基)-1-甲基喹啉-4-酮
  参考文献：
  名称：

  Evolution from a Natural Flavones Nucleus to Obtain 2-(4-Propoxyphenyl)quinoline Derivatives As Potent Inhibitors of the S. aureus NorA Efflux Pump

  摘要：

  Overexpression of efflux pumps is an important mechanism by which bacteria evade the effects of substrate antimicrobial agents. Inhibition of such pumps is a promising strategy to circumvent this resistance mechanism. NorA is a Staphylococcus aureus efflux pump that confers reduced susceptibility to many structurally unrelated agents, including fluoroquinolones, resulting in a multidrug resistant phenotype. In this work, a series of 2-phenyl-4(1H)-quinolone and 2-phenyl-4-hydroxyquinoline derivatives, obtained by modifying the flavone nucleus of known efflux pump inhibitors (EPIs), were synthesized in an effort to identify more potent S. aureus NorA EPIs. The 2-phenyl-4-hydroxyquinoline derivatives 28f and 29f display potent EPI activity against SA-1199B, a strain that overexpresses norA, in an ethidium bromide efflux inhibition assay. The same compounds, in combination with ciprofloxacin, were able to completely restore its antibacterial activity against both S. aureus SA-K2378 and SA-1199B, narA-overexpressing strains.

  DOI：

  10.1021/jm200370y
• 作为产物：
  描述：

  2-(4-甲氧基苯基)-喹啉 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 reevesianine-A
  参考文献：
  名称：

  Synthesis of 2-Arylquinoline and 2-Aryl-4-quinolone Alkaloids via Diels-Alder Reaction of 1,2,3-Benzotriazine with Enamines.

  摘要：

  2-芳基喹啉生物碱、2-苯基喹啉和杜巴敏，以及 2-芳基喹啉酮生物碱、1-甲基-2-苯基-4-喹啉酮、graveoline、reevesiamine-A 和 eduline 的合成是通过 1, 2, 3-苯并三嗪与烯胺的 Diels-Alder 反应完成的。

  DOI：

  10.1248/cpb.47.1038

文献信息

• Synthesis and cytotoxicity of 1,6,7,8-substituted 2-(4'-substituted phenyl)-4-quinolones and related compounds: identification as antimitotic agents interacting with tubulin
  作者：Sheng Chu Kuo、Hong Zin Lee、Jung Pin Juang、Yih Tyng Lin、Tian Shung Wu、Jer Jang Chang、Dan Lednicer、Kenneth D. Paull、Chii M. Lin

  DOI：10.1021/jm00061a005

  日期：1993.4

  A series of 1,6,7,8-substituted 2-(4'-substituted phenyl)-4-quinolones and related compounds have been synthesized and evaluated as cytotoxic compounds and as antimitotic agents interacting with tubulin. The 2-phenyl-4-quinolones (22-30) with substituents (e.g. F, Cl, and OCH3) at C-6, C-7, and C-8 show, in general, potent cytotoxicity against human lung carcinoma (A-549), ileocecal carcinoma (HCT-8)

  已合成了一系列的1,6,7,8-取代的2-（4'-取代的苯基）-4-喹诺酮和相关化合物，并作为细胞毒性化合物和与微管蛋白相互作用的抗有丝分裂剂进行了评估。通常，在C-6，C-7和C-8处带有取代基（例如F，Cl和OCH3）的2-苯基-4-喹诺酮类化合物（22-30）对人肺癌具有有效的细胞毒性（A -549），回盲肠癌（HCT-8），黑素瘤（RPMI-7951）和鼻咽表皮样癌（KB）和两个鼠白血病系（P-388和L1210）。在N-1或C-4氧处引入烷基会导致失活的化合物（35-43和50）。此外，化合物24、26和27在美国国家癌症研究所的60种人类肿瘤细胞系的体外筛选中进行了评估。这些化合物在两种结肠癌细胞系（COLO-205和KM-20L2）和中枢神经系统肿瘤细胞系（SF-539）的筛选中显示出最显着的效果，其中化合物26是这三种药物中最有效的。化合物24、26和27是微管蛋白聚合的有
• Alkaloids and coumarins of Skimmia reevesiana
  作者：Tian Shung Wu

  DOI：10.1016/s0031-9422(00)84814-1

  日期：1987.1

  Two new quinolone alkaloids, reevesianine-A and -B, along with five known furoquinoline alkaloids, 7-isopentenyloxy-γ-fagarine, skimmianine, haplopine, evodine, evoxine, and nine known coumarins, 7-isopentenyloxy-8-isopentenylcoumarin, auraptene, osthol, isomeranzin, pranferin, R-(−)-columbianetin, umbelliferone, meranzin hydrate and skimmin, were isolated from the root and stem bark of Skimmia reevesiana

  摘要 两种新的喹诺酮类生物碱 Reevesianine-A 和 -B，以及五种已知的呋喃喹啉类生物碱 7-isopentenyloxy-γ-fagarine、skimmianine、haplopine、evodine、evoxine 和九种已知的香豆素、7-isopentenyloxy-8-isopentenylapturene从台湾收集的Skimmia reevesiana的根和茎皮中分离出蛇胆素、异美兰素、普兰费林、R-(-)-columbianetin、伞形酮、meranzin hydrate和skimmin。Reevesianine-A 和-B 的结构是通过化学和光谱方法确定的。
• [EN] 2-ARYL-4-QUINOLONES AS ANTITUMOR COMPOUNDS<br/>[FR] 2-ARYL-4-QUINOLONES UTILISEES COMME COMPOSES ANTITUMORAUX
  申请人：——

  公开号：WO1994002145A2

  公开（公告）日：1994-02-03

  [EN] A method of inhibiting tumor-cell growth, by administering a pharmaceutically effective amount of a 2-aryl-4-quinolone compound, is disclosed. The 2-aryl-4-quinolone compound is effective to inhibit tumor cell growth in tumors in which multiple drug resistance is encountered. Also disclosed are novel 2-aryl-4-quinolone anti-tumor compounds.
  [FR] L'invention se rapporte à un procédé pour inhiber la croissance de cellules tumorales, qui consiste à administrer une quantité pharmaceutiquement efficace d'un composé de 2-aryl-4-quinolone. Ce composé de 2-aryl-4-quinolone a pour effet d'inhiber la croissance des cellules tumorales dans des tumeurs dans lesquelles on rencontre des résistances multiples aux médicaments. L'invention décrit également de nouveaux composés antitumoraux à base de 2-aryl-4-quinolone.
• Evolution from a Natural Flavones Nucleus to Obtain 2-(4-Propoxyphenyl)quinoline Derivatives As Potent Inhibitors of the <i>S. aureus</i> NorA Efflux Pump
  作者：Stefano Sabatini、Francesca Gosetto、Giuseppe Manfroni、Oriana Tabarrini、Glenn W. Kaatz、Diixa Patel、Violetta Cecchetti

  DOI：10.1021/jm200370y

  日期：2011.8.25

  Overexpression of efflux pumps is an important mechanism by which bacteria evade the effects of substrate antimicrobial agents. Inhibition of such pumps is a promising strategy to circumvent this resistance mechanism. NorA is a Staphylococcus aureus efflux pump that confers reduced susceptibility to many structurally unrelated agents, including fluoroquinolones, resulting in a multidrug resistant phenotype. In this work, a series of 2-phenyl-4(1H)-quinolone and 2-phenyl-4-hydroxyquinoline derivatives, obtained by modifying the flavone nucleus of known efflux pump inhibitors (EPIs), were synthesized in an effort to identify more potent S. aureus NorA EPIs. The 2-phenyl-4-hydroxyquinoline derivatives 28f and 29f display potent EPI activity against SA-1199B, a strain that overexpresses norA, in an ethidium bromide efflux inhibition assay. The same compounds, in combination with ciprofloxacin, were able to completely restore its antibacterial activity against both S. aureus SA-K2378 and SA-1199B, narA-overexpressing strains.
• Synthesis of 2-Arylquinoline and 2-Aryl-4-quinolone Alkaloids via Diels-Alder Reaction of 1,2,3-Benzotriazine with Enamines.
  作者：Junko KOYAMA、Izumi TOYOKUNI、Kiyoshi TAGAHARA

  DOI：10.1248/cpb.47.1038

  日期：——

  Synthesis of the 2-arylquinoline alkaloids, 2-phenylquinoline and dubamine, and the 2-arylquinolone alkaloids, 1-methyl-2-phenyl-4-quinolone, graveoline, reevesiamine-A, and eduline, was accomplished by the Diels-Alder reaction of 1, 2, 3-benzotriazine with enamines as a kye step.

  2-芳基喹啉生物碱、2-苯基喹啉和杜巴敏，以及 2-芳基喹啉酮生物碱、1-甲基-2-苯基-4-喹啉酮、graveoline、reevesiamine-A 和 eduline 的合成是通过 1, 2, 3-苯并三嗪与烯胺的 Diels-Alder 反应完成的。