10-methoxy-6H-chromeno[4,3-b]quinolin-6-one | 111222-30-1

• 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: 10-methoxy-6H-chromeno[4,3-b]quinolin-6-one
• 英文别名: 11-methoxy-6H-chromeno[4,3-b]quinolin-6-one；11-methoxychromeno[4,3-b]quinolin-6-one
• CAS: 111222-30-1
• 化学式: C₁₇H₁₁NO₃
• 分子量: 277.279
• InChiKey: LAFJJDHHMSFMOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻甲氧基苯胺 在 sodium hydroxide 、 三氯氧磷 作用下， 反应 3.5h， 生成 10-methoxy-6H-chromeno[4,3-b]quinolin-6-one
  参考文献：
  名称：

  A Novel Transformation of 4-Arylaminocoumarins to 6H-1-Benzopyrano[4,3-b]quinolin-6-ones Under V ilsmeier-Haack Conditions

  摘要：

  通过 4-羟基香豆素与适当的胺反应，制备出 4-芳基和 4-烷基氨基香豆素 1。在 Vilsmeier-Haack 条件下，4-烷基氨基香豆素可生成 3-甲酰基衍生物 3。

  DOI：

  10.1055/s-1987-27930

文献信息

• Ultrasound mediated catalyst free synthesis of 6H-1-benzopyrano[4,3-b]quinolin-6-ones leading to novel quinoline derivatives: Their evaluation as potential anti-cancer agents
  作者：Naveen Mulakayala、D. Rambabu、Mohan Rao Raja、Chaitanya M.、Chitta Suresh Kumar、Arunasree M. Kalle、G. Rama Krishna、C. Malla Reddy、M.V. Basaveswara Rao、Manojit Pal

  DOI：10.1016/j.bmc.2011.12.001

  日期：2012.1

  reaction of 4-chloro-2-oxo-2H-chromene-3-carbaldehyde with various aromatic amines in the presence of ultrasound. Some of these compounds were converted to the corresponding 2-(3-(hydroxymethyl)quinolin-2-yl)phenols and further structure elaboration of a representative quinoline derivative is presented. Molecular structure of two representative compounds was confirmed by single crystal X-ray diffraction

  通过4-氯-2-氧代-2 H的反应可轻松合成无催化的6 H -1-苯并吡喃并[4,3- b ]喹啉-6--苯甲基-3-甲醛与各种芳香胺在超声波的作用下。这些化合物中的一些被转化为相应的2-（3-（羟甲基）喹啉-2-基）苯酚，并给出了代表性喹啉衍生物的进一步结构详述。通过单晶X射线衍射研究证实了两种代表性化合物的分子结构。评估了其中许多化合物在体外对四种癌细胞系的抗增殖特性，发现几种化合物具有活性。进一步的体外研究表明，抑制沉默调节蛋白可能是这些分子起作用的可能机制。
• An efficient ultrasound promoted catalyst-free protocol for the synthesis of chromeno[4,3-b]quinolin-6-ones
  作者：J VENKATA PRASAD、J SATYANARAYANA REDDY、N RAVI KUMAR、K ANAND SOLOMON、G GOPIKRISHNA

  DOI：10.1007/s12039-011-0134-z

  日期：2011.9

  A convenient, catalyst-free protocol for the quantitative synthesis of fused chromeno[4,3-b]quinolin-6-ones has been developed by simple one-pot reaction of substituted anilines with 4-chloro-3-formylcoumarin using ultrasound irradiation. The protocol offers the advantages of mild reaction conditions, short reaction times and high yields.

  通过简单的分步反应将取代苯胺与4-氯-3-醛基香豆素在超声波照射下进行融合，开发了一种无需催化剂的方便程序，用于定量合成融合色烯[4,3-b]喹啉-6-酮。该方案具有反应条件温和、反应时间短和产率高的优点。
• Synthesis and biological evaluation of 6H-1-benzopyrano[4,3-b]quinolin-6-one derivatives as inhibitors of colon cancer cell growth
  作者：Tie-Ling Li、Hai-Feng Guo、Fu-Juan Li、Zhi-Guo Sun、Heng-Chun Zhang

  DOI：10.3329/bjp.v10i3.23645

  日期：——

  <p class="Abstract">A convenient synthesis of 6H-1-benzopyrano[4,3-b]quinolin-6-one derivatives was reported using 4-chloro-2-oxo-2H-chromene-3-carbaldehyde with different aromatic amines using silica sulfuric acid. The compounds were tested for their anticancer activity against colon (HCT-116 and S1-MI-80), prostate (PC3 and DU-145), breast (MCF-7 and MDAMB-231) cancer cells. These com-pounds showed more selectivity and potent cytotoxic activity against colon cancer cells. 3c was tested against five other colon cancer cell lines (HT-29, HCT-15, LS-180, LS-174, and LoVo), which had similar cytotoxicity and selectivity. 3c did not induce PXR-regulated ABCB1 or ABCG2 transporters. In fact, 3c induced cytotoxicity in HEK293 cells over expressing ABCB1 or ABCG2 to the same extent as in normal HEK293 cells. It was cytotoxic approximately 3- and 5-fold to resistant colon carcinoma S1-MI-80 cells. 3c also produced concentration-dependent changes in HCT-116 colon cancer cells, in mitochondrial membrane potential, leading to apoptosis, and sub-micromolar concentrations caused chromosomal DNA fragmentation. </p><p> </p>

  报告了使用4-氯-2-氧代-2H-咔喷-3-甲醛与不同芳香胺在硅硫酸的催化下，方便合成6H-1-苯并吡喃并[4,3-b]喹啉-6-酮衍生物。对这些化合物在结肠（HCT-116和S1-MI-80）、前列腺（PC3和DU-145）、乳腺（MCF-7和MDAMB-231）癌细胞的抗癌活性进行了测试。这些化合物对结肠癌细胞表现出更高的选择性和强效的细胞毒活性。3c对其他五种结肠癌细胞系（HT-29、HCT-15、LS-180、LS-174和LoVo）进行了测试，表现出类似的细胞毒性和选择性。3c不诱导PXR调节的ABCB1或ABCG2转运蛋白。事实上，3c在过表达ABCB1或ABCG2的HEK293细胞中引起的细胞毒性程度与正常HEK293细胞相同。在对耐药结肠癌S1-MI-80细胞中，3c的细胞毒性约为正常细胞的3-5倍。3c还在HCT-116结肠癌细胞中产生浓度依赖性的改变，导致线粒体膜电位的改变，进而导致凋亡，亚微摩尔浓度引起染色体DNA碎裂。
• Copper-Catalyzed Cyclization for Access to 6<i>H</i>-Chromeno[4,3-<i>b</i>]quinolin-6-ones Employing DMF as the Carbon Source
  作者：Yiyi Weng、Hao Zhou、Chen Sun、Yuanyuan Xie、Weike Su

  DOI：10.1021/acs.joc.7b01515

  日期：2017.9.1

  The first example of the copper-catalyzed cyclization of 4-(phenylamino)-2H-chromen-2-ones employing the N-methyl moiety of DMF as the source of the methine (CH) group has been developed, providing an efficient synthetic pathway to access novel functionalized 6H-chromeno[4,3-b]quinolin-6-ones in moderate to good yields.
• TABAKOVIC K.; TABAKOVIC I.; AJDINI N.; LECI O., SYNTHESIS,(1987) N 3, 308-310
  作者：TABAKOVIC K.、 TABAKOVIC I.、 AJDINI N.、 LECI O.

  DOI：——

  日期：——