10-chloro-6H-chromeno[4,3-b]quinolin-6-one | 100747-63-5

• 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: 10-chloro-6H-chromeno[4,3-b]quinolin-6-one
• 英文别名: 10-Chlorochromeno[4,3-b]quinolin-6-one
• CAS: 100747-63-5
• 化学式: C₁₆H₈ClNO₂
• 分子量: 281.698
• InChiKey: HXPUFYTXOSCJCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  496.0±25.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-3-(4-Chloro-phenyl)-acrylic acid 2-(2-oxo-[1,3,4]oxathiazol-5-yl)-phenyl ester 以8%的产率得到
  参考文献：
  名称：

  BROWNSORT, P. A.;PATON, R. M.;SUTHERLAND, A. G., TETRAHEDRON LETT., 1985, 26, N 31, 3727-3730

  摘要：

  DOI：

文献信息

• Intramolecular cycloaddition reactions involving nitrile sulphides
  作者：Peter A. Brownsort、R.Michael Paton、Alan G. Sutherland

  DOI：10.1016/s0040-4039(00)89234-5

  日期：1985.1

  ortho-(Phenylpropioloxy)benzonitrile sulphide, generated in situ by thermal decarboxylation of the oxathiazolone (1), undergoes intramolecular 1,3-dipolar cycloaddition forming the chromenoisothiazole (4a); ortho-cinnamoylbenzonitrile sulphides also yield (4), together with nitrile, chromenoquinoline and amino-chromene by-products.

  通过氧杂噻唑酮（1）的热脱羧原位生成的邻-（苯丙氧基）苯甲腈硫化物进行分子内的1,3-偶极环加成反应生成铬异噻唑（4a）；邻-肉桂酰基苄腈硫化物也与腈，色酚喹啉和氨基色烯副产物一起产生（4）。
• Aerobic, metal-free synthesis of 6<i>H</i>-chromeno[4,3-<i>b</i>]quinolin-6-ones
  作者：Nhan N. H. Ton、Ha V. Dang、Nam T. S. Phan、Tung T. Nguyen

  DOI：10.1039/c9ra02267h

  日期：——

  A Friedländer-based method for transition-metal free, aerobic synthesis of chromene-fused quinolinones is reported. The coupling of 4-hydrocoumarins and 2-aminobenzyl alcohols proceeds in the presence of acetic acid solvent and oxygen oxidant, affording 6H-chromeno[4,3-b]quinolin-6-ones in good to excellent yields. The reactions are tolerant of functionalities such as alkyl, methoxy, bromo, chloro

  报道了一种基于 Friedländer 的无过渡金属有氧合成色烯稠合喹啉酮的方法。4-hydrocoumarins 和 2-aminobenzyl alcohols 的偶联在乙酸溶剂和氧氧化剂的存在下进行，以良好至优异的产率提供 6 H- chromeno[4,3 - b ]quinolin-6-ones。该反应对烷基、甲氧基、溴、氯和N-杂环等官能团具有耐受性。等量环状 1,3-二酮和 2-氨基苯乙酮在反应条件下也产生稠合喹啉酮。本文的方法提供了迄今为止具有挑战性的N的快速和良性合成-杂环。据我们所知，这种获得色烯稠合喹啉酮的便捷途径在文献中尚不为人所知。
• 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。
• Substrate‐induced Selective <i>α</i>‐C(<i>sp</i>³)−H Activation of <i>N</i>‐alkyl Amines: Synthesis of Coumarin‐fused Quinolinones under Air
  作者：Zhou Zhang、Juan Wan、Lu Yin、Meitian Fu、Chao Huang

  DOI：10.1002/adsc.202301352

  日期：2024.3.19

  A substrate‐induced synthesis of coumarin‐fused quinolinones is achieved from 4‐(phenylamino)‐2H‐chromen‐2‐ones using N‐alkyl amines as the solvent and a carbon source under air conditions without any catalysts in one pot. This protocol highlights the special roles of 4‐(phenylamino)‐2H‐chromen‐2‐ones which were not only used as reactants but also as an internal oxidant selectively activated N‐α‐C(sp³)−H bond. This reaction features catalyst‐free, broad substrate scopes (N‐alkyl amines 27 examples and quinolinones 24 examples), operationally simple for the one‐step synthesis, and recovery and recycling of the solvent.

  摘要 以N-烷基胺为溶剂和碳源，在空气条件下，不使用任何催化剂，通过底物诱导合成了4-(苯基氨基)-2H-色烯-2-酮类香豆素融合喹啉酮。该方案突出了 4-(苯基氨基)-2H-苯并吡喃-2-酮的特殊作用，它不仅可用作反应物，还可用作选择性活化 N-α-C(sp3)-H 键的内部氧化剂。该反应具有无需催化剂、底物范围广（N-烷基胺类 27 例和喹啉酮类 24 例）、一步合成操作简单以及溶剂回收和循环利用等特点。
• BROWNSORT, P. A.;PATON, R. M.;SUTHERLAND, A. G., TETRAHEDRON LETT., 1985, 26, N 31, 3727-3730
  作者：BROWNSORT, P. A.、PATON, R. M.、SUTHERLAND, A. G.

  DOI：——

  日期：——