5-[(dimethylamino)methylene]-6,7-dihydro-1-benzofuran-4(5H)-one | 84661-71-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 5-[(dimethylamino)methylene]-6,7-dihydro-1-benzofuran-4(5H)-one
• 英文别名: (E)-5-((dimethylamino)methylene)-6,7-dihydrobenzofuran-4(5H)-one；5-[(Dimethylamino)methylidene]-4,5,6,7-tetrahydro-1-benzofuran-4-one；(5E)-5-(dimethylaminomethylidene)-6,7-dihydro-1-benzofuran-4-one
• CAS: 84661-71-2
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: WYLQWUCWHMRGAF-BQYQJAHWSA-N

物化性质

• 沸点：
  292.7±40.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  33.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[(dimethylamino)methylene]-6,7-dihydro-1-benzofuran-4(5H)-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 72.0h， 生成 methyl 2-oxo-1,2-dihydrofuro[2,3-h]quinoline-3-carboxylate
  参考文献：
  名称：

  Novel angular furo and thieno-quinolinones: synthesis and preliminary photobiological studies

  摘要：

  A number of new furo and thienoquinolinones carrying an electron-withdrawing function or unsubstituted at the position 3 were synthesized in order to obtain new potential photochemotherapeutic agents with increased anti proliferative activity and decreased toxic side effects. Our interest in studying the SAR of these derivatives also prompted us to investigate the influence of N-methylation on biological activity, by preparing N-methyl derivatives. The antiproliferative activity of all the newly synthesized compounds was evaluated and compared to 8-methoxypsoralen (8-MOP), the drug widely used in PUVA-therapy. The 3-unsubstituted thienoquinolinones were generally the most potent derivatives, followed by the furo-analogues. In particular. the unsubstituted thieno[2.3-h]quinoline-2(1H)one showed the highest activity in T2 bacteriophage, HeLa cells and Ehrlich cells tests. All the compounds, assayed on Escherichia coli WP2 TM9, showed a similar mutagenic activity, very close to that of 8-MOP. Except for 2-oxo-1,2-dihydrothieno[2.3-h]quinoline-3-carboxylic acid, which appeared to be very effective, all compounds generated singlet oxygen to slightly larger amounts when compared to 8-MOP. The N-methyl analogues only induced moderate skin erythemas on albino guinea pigs, while all other derivatives appeared to be entirely inactive. On the basis of these results, the unsubstituted thieno[2,3h]quinoline 2(1H)one seems to be the most interesting potential drug for PUVA photochemotherapy and photopheresis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00328-5
• 作为产物：
  描述：

  Bredereck 试剂 、 6,7-二氢-4(5H)-苯并呋喃酮 以 甲苯 为溶剂， 反应 96.0h， 生成 5-[(dimethylamino)methylene]-6,7-dihydro-1-benzofuran-4(5H)-one
  参考文献：
  名称：

  [EN] SUBSTITUTED PYRAZOLO [3, 4-B] PYRIDINE COMPOUNDS
  [FR] COMPOSÉS DE PYRAZOLO[3,4-B]PYRIDINE SUBSTITUÉS

  摘要：

  本发明涉及替代咪唑基-5,6-二氢苯并[ｎ]异喹啉化合物及合成这些化合物的方法。本发明还涉及含有替代咪唑基-5,6-二氢苯并[ｎ]异喹啉化合物的药物组合物，以及通过向需要的受试者投予这些化合物和药物组合物来治疗细胞增殖性疾病，如癌症的方法。

  公开号：

  WO2010078427A1

文献信息

• Reaction of ketenes with<i>N,N</i>-disubstituted α-aminomethyleneketones.<b>XIX</b>. Synthesis of<i>N,N</i>-disubstituted 4-amino-3-phenyl-2<i>H</i>-furo[2,3-<i>h]</i>-1-benzopyran-2-ones (4-amino-3-phenylangelicins). Crystal and molecular structure of 3-Phenylangelicin
  作者：Luisa Mosti、Pietro Schenone、Giulia Menozzi、Fernando Sancassan、Francarosa Baccichetti、Franco Benetollo、Gabriella Bombieri

  DOI：10.1002/jhet.5570250211

  日期：1988.3

  phenylchloroketene to N,N-disubstituted 5-aminomethylene-6,7-dihydrobenzo[b]- furan-4(5H)-ones gave the corresponding adducts, namely N,N-disubstituted 4-amino-3-chloro-3,4,5,6-tetra- hydro-3-phenyl-2H-furo[2,3-h]-l-benzopyran-2-ones II, which were dehydrochlorinated with DBN to N,N-disubstituted 4-amino-5,6-dihydro-3-phenyl-2H-furo[2,3-h]-1-benzopyran-2-ones III. Compounds III afforded the title compounds

  苯氯乙烯酮的1,4-环加成至N，N-二取代的5-氨基亚甲基-6,7-二氢苯并[ b ]-呋喃-4（5 H）-ones得到相应的加合物，即N，N-二取代的4-氨基- 3-氯-3,4,5,6-四氢-3-苯基-2 H-呋喃并[2,3 - h ] -1-苯并吡喃-2-酮s II，用DBN脱氯化氢成N，N -二取代的4-氨基-5,6-二氢-3-苯基-2 H-呋喃并[2,3 - h ] -1-苯并吡喃-2-酮III。化合物III通过用DDQ脱氢得到标题化合物IV。在环加成步骤中，3-苯基AngelicinV几乎总是形成的，其结构由1 H-nmr迁移试剂数据和X射线晶体结构确定，可能是从II开始，通过二取代氨基的脱氯化氢，脱氢和氢解作用而形成的。在环加成步骤中，或者在大多数情况下，在脱氯化氢步骤中，通过氧化铝色谱法实现V的分离。
• SUBSTITUTED IMIDAZOLYL-5,6-DIHYDROBENZO[N]ISOQUINOLINE COMPOUNDS
  申请人：Ali Syed M.

  公开号：US20100239526A1

  公开（公告）日：2010-09-23

  The present invention relates to substituted imidazolyl-5,6-dihydrobenzo[n]isoquinoline compounds and methods of synthesizing these compounds. The present invention also relates to pharmaceutical compositions containing substituted imidazolyl-5,6-dihydrobenzo[n]isoquinoline compounds and methods of treating cell proliferative disorders, such as cancer, by administering these compounds and pharmaceutical compositions to subjects in need thereof.

  本发明涉及取代的咪唑基-5,6-二氢苯并[n]异喹啉化合物及其合成方法。本发明还涉及含有取代的咪唑基-5,6-二氢苯并[n]异喹啉化合物的制药组合物，以及通过向需要治疗细胞增殖性疾病（如癌症）的受试者施用这些化合物和制药组合物来治疗的方法。
• Mosti; Schenone; Menozzi, European Journal of Medicinal Chemistry, 1983, vol. 18, # 2, p. 113 - 120
  作者：Mosti、Schenone、Menozzi、et al.

  DOI：——

  日期：——
• Mosti, Luisa; Schenone, Pietro; Menozzi, Giulia, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1227 - 1229
  作者：Mosti, Luisa、Schenone, Pietro、Menozzi, Giulia、Romussi, Giovanni、Baccichetti, Francarosa

  DOI：——

  日期：——
• MOSTI, L.;SCHENONE, P.;MENOZZI, G.;ROMUSSI, G.;BACCICHETTI, F., J. HETEROCYCL. CHEM., 1982, 19, N 5, 1227-1229
  作者：MOSTI, L.、SCHENONE, P.、MENOZZI, G.、ROMUSSI, G.、BACCICHETTI, F.

  DOI：——

  日期：——