6-methyl-11H-indeno[1,2-b]quinoxalin-11-one | 154457-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-methyl-11H-indeno[1,2-b]quinoxalin-11-one
• 英文别名: 6-Methyl-indeno[1,2-b]quinoxalin-11-one；6-methylindeno[1,2-b]quinoxalin-11-one
• CAS: 154457-99-5
• 化学式: C₁₆H₁₀N₂O
• mdl: MFCD00430527
• 分子量: 246.268
• InChiKey: GRMXZXPXUQERMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methyl-11H-indeno[1,2-b]quinoxalin-11-one 在 硫酸羟胺 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以95%的产率得到6-methyl-11H-indeno[2,3-b]quinoxalin-11-one oxime
  参考文献：
  名称：

  合成，生物学评估和分子模拟的11 H-茚并[1,2-b]喹喔啉-11-1衍生物和类胰蛋白酶-6-肟作为c-Jun N端激酶抑制剂。

  摘要：

  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。

  DOI：

  10.1016/j.ejmech.2018.10.023
• 作为产物：
  描述：

  11-methyl-5,6-dioxobenzo[a]phenazine 7-oxide 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以83%的产率得到6-methyl-11H-indeno[1,2-b]quinoxalin-11-one
  参考文献：
  名称：

  苯并[a]吩嗪-5,6-二酮7-氧化物与甲醇碱和吡咯烷的反应活性

  摘要：

  当用甲醇碱，苯并[处理а ]吩嗪-5,6-二酮-7-氧化物转化成11 Н -茚并[1,2- b ]喹喔啉11酮，而11-羟基-11-（吡咯烷-1-羰基）-11 Н -茚并[1,2- b ]喹喔啉10氧化物形成在与吡咯烷治疗。

  DOI：

  10.1007/s10593-015-1676-7

文献信息

• Novel c-Jun N-Terminal Kinase (JNK) Inhibitors with an 11H-Indeno[1,2-b]quinoxalin-11-one Scaffold
  作者：Serhii A. Liakhov、Igor A. Schepetkin、Olexander S. Karpenko、Hanna I. Duma、Nadiia M. Haidarzhy、Liliya N. Kirpotina、Anastasia R. Kovrizhina、Andrei I. Khlebnikov、Irina Y. Bagryanskaya、Mark T. Quinn

  DOI：10.3390/molecules26185688

  日期：——

  c-Jun N-terminal kinase (JNK) plays a central role in stress signaling pathways implicated in important pathological processes, including rheumatoid arthritis and ischemia-reperfusion injury. Therefore, inhibition of JNK is of interest for molecular targeted therapy to treat various diseases. We synthesized 13 derivatives of our reported JNK inhibitor 11H-indeno[1,2-b]quinoxalin-11-one oxime and evaluated

  c-Jun N 末端激酶 (JNK) 在涉及重要病理过程的应激信号通路中发挥核心作用，包括类风湿性关节炎和缺血再灌注损伤。因此，抑制 JNK 对治疗各种疾病的分子靶向治疗具有重要意义。我们合成了我们报道的 JNK 抑制剂 11 H -indeno[1,2- b] 的13 种衍生物]quinoxalin-11-one 肟并评估了它们与三种 JNK 亚型的结合及其生物学效应。八种化合物对至少一种 JNK 异构体表现出亚微摩尔结合亲和力。大多数这些化合物还抑制脂多糖 (LPS) 诱导的核因子-κB/活化蛋白 1 (NF-κB/AP-1) 活化和白细胞介素 6 (IL-6) 在人单核细胞 THP1-Blue 细胞和人 MonoMac 中的产生-6 个单元格，分别。选定的化合物（4f和4m）还抑制了 MonoMac-6 细胞中 LPS 诱导的 c-Jun 磷酸化，直接证实了 JNK 抑制。我们得出结论，基于茚并喹喔啉的肟可以作为
• Activator free diastereoselective 1,3-dipolar cycloaddition: a quick access to coumarin based spiro multi heterocyclic adducts
  作者：Nagender Thadem、Manda Rajesh、Saibal Das

  DOI：10.1039/d1ra05070b

  日期：——

  A formal diastereoselective 1,3-dipolar cycloaddition of azomethine ylide and coumarin derivatives to construct coumarin based spiro multi heterocyclics has been described. The in situ generation of azo-ylide was achieved for various heterocyclic carbonyls (indenoquinoxaline and isatin). This transformation is also suitable for maleimide dipolarophiles for the synthesis of hydro-maleimide derivatives

  已经描述了偶氮甲碱叶立德和香豆素衍生物的正式非对映选择性1,3-偶极环加成，以构建香豆素基螺环多杂环。各种杂环羰基化合物（茚并喹喔啉和靛红）实现了偶氮叶立德的原位生成。该转化也适用于马来酰亚胺亲偶极物，用于合成氢马来酰亚胺衍生物。这些脱羧成环既不需要任何催化剂也不需要任何活化剂。此外，在环境条件下反应后，通过过滤从反应混合物中分离出纯产物。
• Discovery of indeno[1,2- b ]quinoxaline derivatives as potential anticancer agents
  作者：Chih-Hua Tseng、You-Ren Chen、Cherng-Chyi Tzeng、Wangta Liu、Chon-Kit Chou、Chien-Chih Chiu、Yeh-Long Chen

  DOI：10.1016/j.ejmech.2015.11.031

  日期：2016.1

  We have synthesized certain indeno[1,2-b]quinoxaline derivatives for antiproliferative evaluation. Among them, 11-[3-(dimethylamino)propoxy]imino}-N-[3-(dimethylamino) propyl]-11H-indeno(1,2-b] quinoxaline-6-carboxamide (10a) was active against the growth of MDA-MB231, PC-3, and Huh-7 with IC50 values of 0.87 (selectivity index, SI = 36.22), 0.82 (SI = 38.43), and 0.64 mu M (SI = 49.23) respectively. Compound 10a was inactive against the growth of normal human fetal lung fibroblast cell line (MRC-5) with an IC50 value of 31.51 mu M. Its analogs, 10b and 10c, were also active against the growth of MB231, PC-3, and Huh-7 with IC50 values of <1.0.mu M in each case. Our results have also indicated compounds 10a-10c exhibited comparable inhibitory activities against topo I and topo II with the positive compound 2 at a concentration of 10 mu M. Mechanism studies indicated that compound 10a induced cell cycle arrest at S phase via activation of caspase-3, -7 and an increase in the protein expression of Bad and Bax but a decrease in expression of Bcl-2 and PARP, which consequently cause cell death. In addition, compound 10a attenuated the levels of phosphorylated Src, Akt-1, and Akt-2 protein levels but did not affect the total protein expression of Akt. We have also implanted human hepatocellular carcinoma cells into the yolk sac of zebrafish larvae and incubated larvae with various concentrations of 10a. Our results of the zebrafish xenograft assay confirmed the anti-tumor effect of 10a in vivo. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Quantitative Reaction Cascades of Ninhydrin in the Solid State
  作者：Gerd Kaupp、M. Reza Naimi-Jamal、Jens Schmeyers

  DOI：10.1002/1521-3765(20020201)8:3<594::aid-chem594>3.0.co;2-5

  日期：2002.2.1

  Crystalline ninhydrin (1) undergoes waste-free solid-state cascade reactions with dimedone, L-proline, three omicron-phenyienediamines, omicron-mercaptoaniline, two ureas, three thioureas, and methyl 3-aminocrotonate. The yields are quantitative and give pure crystalline products without workup just by milling stoichiometric mixtures of the crystalline reagents. The structures of the new and the previously obtained products with lower yields from solutions are established or confirmed by spectroscopic data and density functional calculations at the B3LYP/6-31G* level. The success of 3- and 4-cascade reactions in the crystal without melting is unusual and of unmatched atom economy. They are mechanistically investigated with atomic force microscopy techniques (AFM) on six different faces of 1 when omicron-phenylenediamine was the reagent (substitution, elimination, cyclization, elimination) and interpreted on the basis of known crystal structure data. Strict correlations to the crystal packings are observed. The characteristic surface features grow to mum heights in some cases at distances of 0.5 mm. from the contact edge of the reacting crystals. The waste-free and easy syntheses of highly functionalized (C=O; O-H, C=N) heterocycles or of a tetraketone are also of interest for synthetic use.
• Synthesis of some 11H-indeno[1,2-b]quinoxalin-11-ones
  作者：Leslie W Deady、José Desneves、Andrew C Ross

  DOI：10.1016/s0040-4020(01)80184-8

  日期：1993.1

  Condensation of substituted o-phenylene diamines and ninhydrins gave the tide compounds. The substituent orientation in the products was determined by H-1 NMR analysis of the chemical shifts brought about by N5-oxidation. Reduction of the 8-nitro to 8-amino compound was achieved both with and without reduction of the carbonyl group. Nitration of the 8-carboxylic acid occurred in the 2-position.