<1>benzopyrano<3,2-b>indol-11(10H)-one | 53277-25-1

• 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: <1>benzopyrano<3,2-b>indol-11(10H)-one
• 英文别名: chromeno[3,2-b]indol-11(10H)-one；<1>Benzopyrano<3,2-b>indol-11-on；Chromono<3,2-b>-indol；10H-chromeno[3,2-b]indol-11-one；10H-chromeno[3,2-b]indol-11-one
• CAS: 53277-25-1
• 化学式: C₁₅H₉NO₂
• 分子量: 235.242
• InChiKey: IPVHEJWKQYHCHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 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：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-hydroxy-2-(2-hydroxybenzoyl)indole 在 PPA 作用下， 生成 <1>benzopyrano<3,2-b>indol-11(10H)-one
  参考文献：
  名称：

  来自杂环 1,3-二羰基化合物的稠合色酮

  摘要：

  杂环 1,3-二羰基化合物 2b、2d、6c 和 9b 可以与多磷酸 (PPS) 环化得到色酮 3a、3b、7 和 10。1,3-二羰基化合物2、6、9、11完全烯醇化；讨论了烯醇化和氢键的方向。二苯甲酰甲烷衍生物5c以螯合二酮形式存在。结构证明是用光谱方法进行的。

  DOI：

  10.1002/ardp.19743070706

文献信息

• Synthesis of heterocyclic-fused benzofurans via C–H functionalization of flavones and coumarins
  作者：Youngtaek Moon、Yechan Kim、Hyerim Hong、Sungwoo Hong

  DOI：10.1039/c3cc44456b

  日期：——

  An efficient method to effect C-O cyclization was developed via the C-H functionalization of chromones and coumarins, affording heterocyclic-fused benzofurans.

  通过色酮和香豆素的CH官能化开发了一种有效的CO环化方法，提供了杂环稠合的苯并呋喃。
• The 1,3-dihydroxy-5-oxonia-11-azabenzo[b]fluorene cation; a synthetic nitrogenous anthocyanidin
  作者：Francis M. Dean、Chachanat Patamapongse

  DOI：10.1039/p19740000952

  日期：——

  The chalcone formed from salicylaldehyde and indoxyl cyclises in warm trifluoroacetic acid to yield the 5-oxonia-11-azabenzo[b]fluorene cation (Ib). The constitution of this has been confirmed by oxidation with hydrogen peroxide to the related flavone, [1]benzopyrano[3,2-b]indol-11-one (XI), also accessible by heating 2′-nitroflavone with ethyl phosphite.

  在温暖的三氟乙酸中，由水杨醛和吲哚基环化形成的查耳酮，生成5-氧代十一氮杂氮杂苯并[ b ]芴阳离子（I b）。通过用过氧化氢氧化成相关的黄酮[1]苯并吡喃并[3,2 - b ]吲哚-11-酮（XI），也可以通过将2'-硝基黄酮与亚磷酸乙酯加热而得到证实。
• Synthesis and in vitro cytotoxicity of a series of 3-aminoflavones
  作者：D Dauzonne、B Folléas、L Martinez、GG Chabot

  DOI：10.1016/s0223-5234(97)84363-2

  日期：1997.1

  To further understand the molecular requirements for the antiproliferative activity of flavonoids, a series of 3-aminoflavones and some of their derivatives were prepared and evaluated using L1210 murine leukemia. Our novel five-step synthetic approach required easily available substituted aromatic aldehydes as starting materials and proved more convenient and more general than previously reported methods. Our results in the 3-aminoflavones series indicated that the 4'-methoxy group is important for cytotoxic activity. Moreover, for the flavone-8-acetic analogs, a marked increase in potency was observed with the addition of a 3-amino or a 3-nitro group, Methoxy groups on the 6 and 7 positions of flavonoids (as in cirsiliol) also appear to be important for antiproliferative activity. These results are essential for the further understanding of the critical molecular requirements that lead to antiproliferative properties in the flavonoid series.