6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one | 37436-54-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶吡嗪类
• 英文名称: 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one
• 英文别名: 2,7,9-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1,3(8),4,6,9,11,13,15-octaen-17-one
• CAS: 37436-54-7
• 化学式: C₁₄H₇N₃O
• 分子量: 233.229
• InChiKey: FNOHEHFDTZVGNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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：
  55.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one 、 L-羟基脯氨酸 在 phosphomolybdic acid on silica gel 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以80%的产率得到6-(1H-pyrrol-1-yl)-6H-indeno-[1,2-b]pyrido[3,2-e]pyrazine
  参考文献：
  名称：

  磷钼酸/SiO2作为多相固体酸催化剂用于快速合成N-取代吡咯

  摘要：

  摘要 靛红在 10 mol% PMA/SiO2 的乙腈/水 (4:1) 溶液中在回流条件下与 4-羟基脯氨酸有效反应，以优异的产率提供 N-取代的吡咯。同样，11H-茚并[1,2-b]quinoxalin-11-ones也参与了该反应。

  DOI：

  10.1080/00397910802157843
• 作为产物：
  描述：

  2,3-二氨基吡啶 、 1,2,3-茚满三酮 在 poly(N,N′-dibromo-N-ethylnaphthyl-2,7-disulfonamide 作用下， 以 neat (no solvent) 为溶剂， 反应 0.12h， 以93%的产率得到6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one
  参考文献：
  名称：

  Synthesis of Bisindolylindeno[1,2-b]quinoxaline and Bisindolylindeno[3,4-b]pyrazine with Poly(N,N′-dibromo-N-ethylnaphthyl-2,7-disulfonamide)

  摘要：

  Poly(N,N-dibromo-N-ethylnaphthyl-2,7-disulfonamide) (PBNS) as novel reagent was synthesized. Bisindolylindeno[1,2-b]quinoxaline and bisindolylindeno[3,4-b]pyrazine derivatives were synthesized in a simple and efficient method from the three-component condensation reaction of indole, indane-1,2,3-trione, and diamine aromatic compounds by PBNS under solvent-free conditions at 80 degrees C in good to excellent yields, short reaction times, and a simple procedure for new derivatives. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications((R)) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.829237

文献信息

• Nanomagnetically modified thioglycolic acid (γ‐Fe₂O₃@SiO₂‐SCH₂CO₂H): Efficient and reusable green catalyst for the one‐pot domino synthesis of spiro[benzo[<i>a</i>]benzo[6,7]chromeno[2,3‐<i>c</i>]phenazine] and benzo[<i>a</i>]benzo[6,7]chromeno[2,3‐<i>c</i>]phenazines
  作者：Sajjad Abbasi Pour、Afshin Yazdani‐Elah‐Abadi、Mojgan Afradi

  DOI：10.1002/aoc.3791

  日期：2017.11

  Superparamagnetic nanoparticles of modified thioglycolic acid (γ‐Fe2O3@SiO2‐SCH2CO2H) represent a new, efficient and green catalyst for the one‐pot synthesis of novel spiro[benzo[a]benzo[6,7]chromeno[2,3‐c]phenazine] derivatives via domino Knoevenagel–Michael–cyclization reaction of 2‐hydroxynaphthalene‐1,4‐dione, benzene‐1,2‐diamines, ninhydrin and isatin. This novel magnetic organocatalyst was easily

  改性巯基乙酸（γ-铁的顺磁纳米颗粒2 ö 3 @SiO 2 -SCH 2 CO 2 2H）代表用于一锅合成新颖螺〔苯并[一种新的，有效的和绿色的催化剂一]苯并[6,7 ] chromeno [2,3‐ c[吩嗪]衍生物通过2-羟基萘-1,4-二酮，苯1,2-二胺，茚三酮和靛红的多米诺Knoevenagel–Michael–环化反应而生成。通过使用外部磁体的磁倾析，可以容易地从反应混合物中分离出这种新型的磁性有机催化剂，并且可以重复使用至少六次而不会显着降低其活性。使用各种技术对催化剂进行了充分表征。该方法也成功地用于合成苯并[ a ]苯并[6,7]色酚[2,3- c ]吩嗪。
• Theophylline as a new and green catalyst for the one-pot synthesis of spiro[benzo[ a ]pyrano[2,3- c ]phenazine] and benzo[ a ]pyrano[2,3- c ]phenazine derivatives under solvent-free conditions
  作者：Afshin Yazdani-Elah-Abadi、Malek-Taher Maghsoodlou、Razieh Mohebat、Reza Heydari

  DOI：10.1016/j.cclet.2016.09.016

  日期：2017.2

  A green, convenient, high yielding and one-pot procedure for the synthesis of novel spiro[benzo[a]pyrano[2,3-c]phenazine] derivatives by domino multi-component condensation reaction between 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamines, ninhydrine, and malononitrile in the presence of a catalytic amount of 1,3-dimethyl-7H-purine-2,6-dione (theophylline) as an expedient, eco-friendly and reusable

  通过2-羟基萘-1,4-之间多米诺骨牌多组分缩合反应合成新型螺[苯并[a]吡喃并[2,3-c]吩嗪]衍生物的绿色简便方法催化量的1,3-二甲基-7H-嘌呤-2,6-二酮（茶碱）的存在下，二酮，苯1,2-二胺，茚三酮和丙二腈作为一种方便，生态友好且可重复使用的固体碱催化剂在热，微波辐射和无溶剂条件下。该方法也已成功用于苯并[a]吡喃并[2,3-c]吩嗪的合成。
• Design, synthesis and antitumor activity of non-camptothecin topoisomerase I inhibitors
  作者：Chao Zhang、Shasha Li、Liyan Ji、Shan Liu、Zhongjun Li、Shuchun Li、Xiangbao Meng

  DOI：10.1016/j.bmcl.2015.06.042

  日期：2015.10

  Three groups of non-camptothecin compounds with four to five fused rings have been designed and synthesized. Their in vitro anti-proliferative activity has been evaluated with five different cancer cell lines (HCT116, PC3, U87MG, HepG2, SK-OV-3). Compounds B-2 and B-3 showed the most potent cell growth inhibition with IC50 of 169 nM and 325 nM against U87MG cell line correspondingly.

  已经设计并合成了三组具有四个至五个稠合环的非喜树碱化合物。已经用五种不同的癌细胞系（HCT116，PC3，U87MG，HepG2，SK-OV-3）评估了它们的体外抗增殖活性。化合物B-2和B-3对U87MG细胞系的生长抑制作用最强，IC50分别为169 nM和325 nM。
• Synthesis, biological evaluation, and molecular modeling of 11H-indeno[1,2-b]quinoxalin-11-one derivatives and tryptanthrin-6-oxime as c-Jun N-terminal kinase inhibitors
  作者：Igor A. Schepetkin、Andrei I. Khlebnikov、Andrei S. Potapov、Anastasia R. Kovrizhina、Vladislava V. Matveevskaya、Maxim L. Belyanin、Dmitriy N. Atochin、Svitlana O. Zanoza、Nadiya M. Gaidarzhy、Sergiy A. Lyakhov、Liliya N. Kirpotina、Mark T. Quinn

  DOI：10.1016/j.ejmech.2018.10.023

  日期：2019.1

  pathologic processes. We synthesized novel 11H-indeno[1,2-b]quinoxalin-11-one oxime analogs and tryptanthrin-6-oxime (indolo[2,1-b]quinazoline-6,12-dion-6-oxime) and evaluated their effects on JNK activity. Several compounds exhibited sub-micromolar JNK binding affinity and were selective for JNK1/JNK3 versus JNK2. The most potent compounds were 10c (11H-indeno[1,2-b]quinoxalin-11-one O-(O-ethylcarboxymethyl)

  c-Jun N末端激酶（JNK）在许多生理和病理过程中起着核心作用。我们合成了新型11H-茚并[1,2-b]喹喔啉-11-一肟类似物和色胺素6-肟（吲哚[2,1-b]喹唑啉-6,12-dion-6-肟），并对其进行了评估。对JNK活性的影响。几种化合物表现出亚微摩尔的JNK结合亲和力，对JNK1 / JNK3和JNK2具有选择性。最有效的化合物是10c（11H-茚并[1,2-b]喹喔啉-11-一个O-（O-乙基羧甲基）肟）和色胺酮-6-肟，它们的JNK1和JNK3的解离常数（Kd）为分别为22和76 nM，以及150和275 nM。分子建模表明在JNK催化位点的结合相互作用的模式，并且所选的肟衍生物是潜在的竞争性JNK抑制剂。化合物的JNK结合活性与其抑制脂多糖（LPS）诱导的人单核THP-1Blue细胞和白介素6（IL-β）中核因子-κB/活化蛋白1（NF-κB/ AP-1）活化的能力有关。
• Regio- and stereoselective 1,3-dipolar cycloaddition of indenoquinoxalinone azomethine ylides to β-nitrostyrenes: synthesis of spiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizidines] and spiro[indeno[1,2-b]quinoxaline-11,2'-pyrrolidines]
  作者：Aleksey Yi. Barkov、Nikolay S. Zimnitskiy、Vladislav Yu. Korotaev、Igor B. Kutyashev、Vladimir S. Moshkin、Vyacheslav Ya. Sosnovskikh

  DOI：10.1007/s10593-017-2074-0

  日期：2017.4

  from proline or sarcosine and indenoquinoxalinones reacted with nitrostyrenes upon heating in isopropanol for 4–5 days, resulting in the formation of spiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizidines] and spiro[indeno[1,2-b]-quinoxaline-11,2'-pyrrolidines] with various regiochemistry.

  在脯氨酸或肌氨酸和茚并喹喔啉酮中原位 获得的甲亚胺基化物在异丙醇中加热4-5天后与硝基苯乙烯反应，从而形成螺[茚并[1,2 - b ]喹喔啉-11,3'-吡咯并核苷]和螺[茚并[1,2 - b ]-喹喔啉-1,2'-吡咯烷]具有多种区域化学作用。