4,6-dimethyl-7-hydroxyquinolin-2-one | 131195-66-9

• 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: 4,6-dimethyl-7-hydroxyquinolin-2-one
• 英文别名: 7-hydroxy-4,6-dimethylquinolin-2-one；7-hydroxy-4,6-dimethyl-1H-quinolin-2-one
• CAS: 131195-66-9
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: KGPQYCOXFZWWDU-UHFFFAOYSA-N

物化性质

• 熔点：
  328-329 °C
• 沸点：
  408.1±45.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,6-dimethyl-7-hydroxyquinolin-2-one 在 potassium carbonate 、 N,N-二乙基苯胺 作用下， 以 丙酮 为溶剂， 反应 43.0h， 生成 8-allyl-7-hydroxy-1,4,6-trimethylquinolin-2-one
  参考文献：
  名称：

  角呋喃喹啉酮，补骨脂素类似物：皮肤疾病的新型抗增殖剂。合成，生物活性，作用机理和计算机辅助研究。

  摘要：

  为了获得新的潜在的光化学治疗剂，具有增加的抗增殖活性和减少的不良作用，我们制备了一些新的呋喃喹啉酮。已对其中两个进行了详细的研究：1,4,6,8-四甲基-2H-呋喃[2,3-h]-喹啉-2-酮（8）和4,6,8,9-四甲基- 2H-呋喃[2,3-h]喹啉-2-一（10）。这些化合物与DNA形成分子复合物，在双链大分子内部进行插入，如线性流二色性所示。通过随后用UV-A光照射，络合的配体与大分子光结合，仅形成具有胸腺嘧啶的顺式-syn构型的单环加合物。为了评估由位置1的8中的氮原子引起的电子效应，已对4,6,4'-三甲基Angelicin（TMA）和8进行了半经验计算。所得结果并未明确区分两个分子，在此近似水平下，这两个分子显示了与8、3,4-和4'的3,4-和8,9-烯烃键同时发生光反应的可能性， TMA的5'键。在插层8的较低能构象中，呋喃环转向多核苷酸的小沟，从而有利于该环与胸腺嘧啶的

  DOI：

  10.1021/jm950585l
• 作为产物：
  描述：

  2,4-二氨基甲苯 在 硫酸 、 sodium nitrite 作用下， 生成 4,6-dimethyl-7-hydroxyquinolin-2-one
  参考文献：
  名称：

  New synthesis of pyrrolo [3,2,1-ij] quinolin-4-one derivatives

  摘要：

  A new convenient synthesis of pyrrolo[3,2,1-ij]quinolin-4-one derivatives is described. In this method, methyl-7-hydroxquinoline-2-ones are the starting materials onto which the third pyrrolo ring is condensed directly, yielding dehydrogenated methyl-9-hydroxypyrrolo[3,2,1-ij]quinolin-4-ones.

  DOI：

  10.1021/jo00003a016

文献信息

• Synthesis of some benzo[c][2,6]naphthyridin-5-ones and new tetracyclic benzofuro[4,5-c]-2,6-naphthyridin-5(6H)-ones
  作者：Adriana Chilin、Paolo Manzini、Alessia Confente、Giovanni Pastorini、Adriano Guiotto

  DOI：10.1016/s0040-4020(02)01325-x

  日期：2002.12

  methylbenzofuro[4,5-c]-2,6-naphthyridin-5(6H)-ones were synthesized, first building the pyridine nucleus on the appropriated quinolin-2-ones, and then condensing the furan ring on the preconstituted benzonaphthyridinones. The benzo[c][2,6]naphthyridinic nucleus was also interesting for its known pharmacological properties, as well as intermediate for the synthesis of natural product analogues.

  合成了一系列新颖的甲基苯并呋喃[4,5 - c ] -2,6-萘啶-5（6 H）-one，首先在合适的喹啉-2-ones上构建吡啶核，然后将呋喃环缩合在预制的苯并萘啶酮。苯并[ c ] [2,6]萘啶核也因其已知的药理特性以及用于合成天然产物类似物的中间体而引起人们的兴趣。
• DNA damage and biological effects induced by photosensitization with new N1-unsubstituted furo[2,3-h]quinolin-2(1H)-ones
  作者：Cristina Marzano、Adriana Chilin、Franco Bordin、Francarosa Baccichetti、Adriano Guiotto

  DOI：10.1016/s0968-0896(02)00145-1

  日期：2002.9

  New furoquinolinones unsubstituted at the N-1 position were prepared and their photobiological activities we re studied in comparison with 4.6.8.9-tetramethylfuro[2,3-h]quinotin-2(1H)-one (HFQ) and 8-MOP. The anti-proliferative activity of furoquinolinones 3a-f was tested upon UVA irradiation in mammalian cells, studying DNA synthesis and clonal growth capacity. and in micro-organisms, evaluating T2 infectivity. Almost all compounds appeared to be more active than 8-MOP, and free of any mutagenic activity and skin phototoxicity. Among them, compound 3b was the most effective one. Similarly to HFQ, compound 3b appeared to be very active also in DNA damaging, forming monoadducts and DPCL - 0. but no ISC and DPCL > 0, both responsible for furocoumarin genotoxicity and phototoxicity. Moreover, Ehrlich ascites cells, photoinactivated by the new furoquinolinone 3b and injected into recipient mice. proved to be capable of inducing protection against a successive challenge performed with the same tumor cells. For all these features. 3b seemed to be a new promising potential drug for PUVA therapy and photopheresis. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Photobiological properties of 1-(3′-hydroxypropyl)-4,6,8-trimethylfuro[2,3-h]quinolin-2(1H)-one, a new furocoumarin analogue
  作者：Christine Marzano、Adriana Chilin、Adriano Guiotto、Francarosa Baccichetti、Franco Carlassare、Franco Bordin

  DOI：10.1016/s0014-827x(00)00091-4

  日期：2000.11

  A new furoquinolinone derivative, 1-(3'-hydroxypropyl)-4,6,8-trimethylfuro[2,3-h]quinolin-2(1H)-one (HPFQ, 4), was prepared, in which the nitrogen atom in position 1 carries a hydroxypropyl chain. The antiproliferative activity of HPFQ was studied in comparison with its analogue 1,4,6, 8-tetramethylfuro[2, 3-h]quinolin-2(1H)-one (FQ) and g-methoxypsoralen (8-MOP). By incubation in the dark. HPFQ, although retaining antitopoisomerase II activity, appeared less effective than FQ. Upon UVA irradiation, HPFQ produced little amounts of singlet oxygen, but detectable levels of superoxide anion; like FQ, HPFQ induced numbers of DNA-protein cross-links, but no interstrand cross-links in mammalian cells. The HPFQ phototoxicity was comparable to that of FQ and g-MOP, while mutagenic activity, scored in two Escherichia coli strains, seemed much less remarkable. (C) 2000 Elsevier Science S.A. All rights reserved.
• CHILIN, A.;RODIGHIERO, P.;PASTORINI, G.;GUIOTTO, A., J. ORG. CHEM., 56,(1991) N, C. 980-983
  作者：CHILIN, A.、RODIGHIERO, P.、PASTORINI, G.、GUIOTTO, A.

  DOI：——

  日期：——
• New synthesis of pyrrolo [3,2,1-ij] quinolin-4-one derivatives
  作者：A. Chilin、P. Rodighiero、G. Pastorini、Adriano Guiotto

  DOI：10.1021/jo00003a016

  日期：1991.2

  A new convenient synthesis of pyrrolo[3,2,1-ij]quinolin-4-one derivatives is described. In this method, methyl-7-hydroxquinoline-2-ones are the starting materials onto which the third pyrrolo ring is condensed directly, yielding dehydrogenated methyl-9-hydroxypyrrolo[3,2,1-ij]quinolin-4-ones.