methyl 5,10-dioxo-5,10-dihydrobenzo[f]pyridazino[6,1-a]isoindole-11-carboxylate | 615582-75-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: methyl 5,10-dioxo-5,10-dihydrobenzo[f]pyridazino[6,1-a]isoindole-11-carboxylate
• 英文别名: Methyl 2,9-dioxo-15,16-diazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(17),3,5,7,10,12,14-heptaene-17-carboxylate；methyl 2,9-dioxo-15,16-diazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(17),3,5,7,10,12,14-heptaene-17-carboxylate
• CAS: 615582-75-7
• 化学式: C₁₇H₁₀N₂O₄
• 分子量: 306.277
• InChiKey: CYUOFFULRTZQFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,4-萘醌 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 0.02h， 以60%的产率得到methyl 5,10-dioxo-5,10-dihydrobenzo[f]pyridazino[6,1-a]isoindole-11-carboxylate
  参考文献：
  名称：

  Ultrasound and microwave assisted synthesis of isoindolo-1,2-diazine: A comparative study

  摘要：

  A comparative study, ultrasound (US) versus microwave (MW) versus conventional thermal heating (TH), for synthesis of isoindolo-1,2-diazine is described. The reaction pathway is fast, efficient and straight applicable, involving a Huisgen [3 + 2] dipolar cycloaddition of cycloimmonium ylides to 1,4-naphthoquinone. A feasible reaction mechanism for the obtaining of the fully aromatized tetra- and penta- cyclic isoindolo-1,2-diazine is presented. Under US irradiation the yields are much higher (sometimes substantially, by almost double), the reaction time decreases substantially, the reaction conditions are milder. The use of a generator with a higher nominal power induces higher yields and short reaction times. Overall the use of US it proved to be more efficient than MW or TH. A feasible explication for US efficiency is presented. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2012.02.012

文献信息

• Synthesis, structure, and in vitro anticancer activity of new polycyclic 1,2-diazines
  作者：Dorina Mantu、Dan Maftei、Dorina Iurea、Cornelia Ursu、Vasilichia Bejan

  DOI：10.1007/s00044-013-0878-8

  日期：2014.6

  AbstractThe synthesis, structure, and in vitro anticancer activity of a new class of anticancer derivatives with dihydrobenzo[5,6]isoindolo[1,2-a]phthalazine and dihydrobenzo[f]pyridazino[6,1-a]isoindole skeletons are presented. The preparation is straight and efficient, involving two steps only: a N-alkylation of the pyridazine or phthalazine heterocycle, followed by a [3 + 2] dipolar cycloaddition

  摘要提出了具有二氢苯并[5,6]异吲哚并[1,2- a ]酞嗪和二氢苯并[ f ]哒嗪并[6,1- a ]异吲哚骨架的新型抗癌衍生物的合成，结构和体外抗癌活性。。准备工作是直接而有效的，仅涉及两个步骤：N-哒嗪或酞嗪杂环的-烷基化，然后将1,2-二叠氮基的[3 + 2]偶极环加成成相应的偶极亲和剂。合成是在微波和超声（US）辐射以及常规热加热下进行的。发现在产率和时间方面最有效的条件是US辐照。评价五环和四环1,2-二嗪的体外抗癌活性。五环1,2-二嗪衍生物对非小细胞肺癌NCI-H460，白血病MOLT-4，白血病CCRF-CEM和乳腺癌MCF7具有显着的抗癌活性。已经提供了五环1,2-二嗪类抗癌功效的可行解释，并与作用机理相关。 图形概要提出了新型的具有多环1,2-二嗪骨架的新型抗癌分子的合成（常规热加热，微波和超声辐射），结构和体外抗癌活性。
• Ultrasound and microwave assisted synthesis of isoindolo-1,2-diazine: A comparative study
  作者：Vasilichia Bejan、Dorina Mantu、Ionel I. Mangalagiu

  DOI：10.1016/j.ultsonch.2012.02.012

  日期：2012.9

  A comparative study, ultrasound (US) versus microwave (MW) versus conventional thermal heating (TH), for synthesis of isoindolo-1,2-diazine is described. The reaction pathway is fast, efficient and straight applicable, involving a Huisgen [3 + 2] dipolar cycloaddition of cycloimmonium ylides to 1,4-naphthoquinone. A feasible reaction mechanism for the obtaining of the fully aromatized tetra- and penta- cyclic isoindolo-1,2-diazine is presented. Under US irradiation the yields are much higher (sometimes substantially, by almost double), the reaction time decreases substantially, the reaction conditions are milder. The use of a generator with a higher nominal power induces higher yields and short reaction times. Overall the use of US it proved to be more efficient than MW or TH. A feasible explication for US efficiency is presented. (C) 2012 Elsevier B.V. All rights reserved.