12-acetylbenzo[f]pyrido[1,2-a]indole-6,11-dione | 98596-11-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 12-acetylbenzo[f]pyrido[1,2-a]indole-6,11-dione
• 英文别名: 12-Acetylnaphtho[2,3-b]indolizine-6,11-dione
• CAS: 98596-11-3
• 化学式: C₁₈H₁₁NO₃
• 分子量: 289.29
• InChiKey: OLBAGJDDSBANJY-UHFFFAOYSA-N

物化性质

• 熔点：
  205-206 °C(Solv: acetic acid (64-19-7))
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  12-acetylbenzo[f]pyrido[1,2-a]indole-6,11-dione 在 吡啶 、 sodium hydroxide 、 碘 作用下， 生成 6,11-dioxo-6,11-dihydrobenzo[f]pyrido[1,2-a]indole-12-carboxylic acid
  参考文献：
  名称：

  Reactions of Naphthoquinones with Malonic Ester and its Analogs. III. 1-Substituted Phthaloyl- and Phthaloylbenzopyrrocolines¹

  摘要：

  DOI：

  10.1021/ja01562a048
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 1-吡啶-2-基-2-丙酮 在 乙醇 、 sodium ethanolate 作用下， 生成 12-acetylbenzo[f]pyrido[1,2-a]indole-6,11-dione
  参考文献：
  名称：

  Reactions of Naphthoquinones with Malonic Ester and its Analogs. III. 1-Substituted Phthaloyl- and Phthaloylbenzopyrrocolines¹

  摘要：

  DOI：

  10.1021/ja01562a048

文献信息

• Synthesis of benzo[f]pyrido[1,2-a]indole-6,11-diones via the I2-promoted reactions of methyl ketones with pyridines and 1,4-naphthoquinone
  作者：Yun Liu、Hui Xu、Hui Wu

  DOI：10.1016/j.tetlet.2021.153235

  日期：2021.8

  synthesis of benzo[f]pyrido[1,2-a]indole-6,11-diones has been achieved via the I2-promoted reactions of methyl ketones, pyridines and 1,4-naphthoquinone. In this reaction, either aromatic or aliphatic methyl ketones proceeded well. The advantages of this method include a broad substrate scope, metal-free reaction conditions, and high atom- and step-economy.

  苯并[ f ]吡啶并[1,2 - a ]吲哚-6,11-二酮的有效合成已通过甲基酮、吡啶和1,4-萘醌的I 2促进反应实现。在该反应中，芳香族或脂肪族甲基酮都进行得很好。该方法的优点包括底物范围广、反应条件无金属、原子经济和步骤经济性高。
• 6,11-Dioxobenzo[<i>f</i>]pyrido[1,2-<i>a</i>]indoles Kill <i>Mycobacterium tuberculosis</i> by Targeting Iron–Sulfur Protein Rv0338c (IspQ), A Putative Redox Sensor
  作者：Rita Székely、Monica Rengifo-Gonzalez、Vinayak Singh、Olga Riabova、Andrej Benjak、Jérémie Piton、Mena Cimino、Etienne Kornobis、Valerie Mizrahi、Kai Johnsson、Giulia Manina、Vadim Makarov、Stewart T. Cole

  DOI：10.1021/acsinfecdis.0c00531

  日期：2020.11.13

  Screening of a diversity-oriented compound library led to the identification of two 6,11-dioxobenzo[f]pyrido[1,2-a]indoles (DBPI) that displayed low micromolar bactericidal activity against the Erdman strain of Mycobacterium tuberculosis in vitro. The activity of these hit compounds was limited to tubercle bacilli, including the nonreplicating form, and to Mycobacterium marinum. On hit expansion and investigation of the structure activity relationship, selected modifications to the dioxo moiety of the DBPI scaffold were either neutral or led to reduction or abolition of antimycobacterial activity. To find the target, DBPI-resistant mutants of M. tuberculosis Erdman were raised and characterized first microbiologically and then by whole genome sequencing. Four different mutations, all affecting highly conserved residues, were uncovered in the essential gene rv0338c (ispQ) that encodes a membrane-bound protein, named IspQ, with 2Fe-2S and 4Fe-4S centers and putative iron-sulfur-binding reductase activity. With the help of a structural model, two of the mutations were localized close to the 2Fe-2S domain in IspQ and another in transmembrane segment 3. The mutant genes were recessive to the wild type in complementation experiments and further confirmation of the hit-target relationship was obtained using a conditional knockdown mutant of rv0338c in M. tuberculosis H37Rv. More mechanistic insight was obtained from transcriptome analysis, following exposure of M. tuberculosis to two different DBPI; this revealed strong upregulation of the redox-sensitive SigK regulon and genes induced by oxidative and thiol-stress. The findings of this investigation pharmacologically validate a novel target in tubercle bacilli and open a new vista for tuberculosis drug discovery.
• BIOLOGICAL ACTIVITIES AND CORRELATIONS TENDENCY OF ELECTROCHEMICAL PROPERTIES OF SOME INDOLIZINO&amp;#091;1,2-B]QUINOLINE DERIVATIVES
  作者：A CAÑETE、F ARMIJO、M. A DEL VALLE、R.A TAPIA、C THEODULOZ、C. D PESSOA、L CANTUARIAS、G RECABARREN

  DOI：10.4067/s0717-97072012000200015

  日期：——

  We report the preparation of a series of indolylquinone and pyridine derivatives in order to evaluate structure-activity relationships in human gastric (AGS), lung (SK-MES-1), bladder (J82) cancer cell lines and human normal lung fibroblasts (MCR-5). Two correlations tendency between half-wave redox potentials against their antineoplasic activity were found making it possible to establish that for epithelial human gastric cancer (AGS) cell lines and human normal lung fibroblasts (MCR-5). The quinone bioreduction should correspond to a one electron process under normomix conditions, whilst for all other lines this process should correspond to a two electron attachment via a hypoxic process.
• Suryanarayana; Tilak, Proceedings - Indian Academy of Sciences, Section A, 1954, vol. 39, p. 185,194
  作者：Suryanarayana、Tilak

  DOI：——

  日期：——
• AYYANGAR, N. R.;KOLHE, P. Y.;TILAK, B. D., INDIAN J. CHEM., 1980, 19, N 10, 836-843
  作者：AYYANGAR, N. R.、KOLHE, P. Y.、TILAK, B. D.

  DOI：——

  日期：——

表征谱图