5H-indeno[1,2-b]quinolin-10(11H)-one | 38105-54-3

• 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: 5H-indeno[1,2-b]quinolin-10(11H)-one
• 英文别名: 5H-indeno[1,2-b]quinolin-10-one；5,11-dihydro-indeno[1,2-b]quinolin-10-one；5,11-dihydroindeno[1,2-b]quinolin-10-one
• CAS: 38105-54-3
• 化学式: C₁₆H₁₁NO
• 分子量: 233.269
• InChiKey: VSSBKIZSYSOAIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5H-indeno[1,2-b]quinolin-10(11H)-one 在 palladium on activated charcoal 氢气 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 110.0 ℃ 、344.74 kPa 条件下， 反应 9.0h， 生成 11H-indeno[1,2-b]quinoline
  参考文献：
  名称：

  Synthesis and evaluation of isosteres of N-methyl indolo[3,2-b]-quinoline (cryptolepine) as new antiinfective agents

  摘要：

  Isosteres of cryptolepine (1) were synthesized and evaluated for their antiinfective activities. Overall, the sulfur isostere, 5-methyl benzothieno[3,2-b]quinolinium salt (5b), was equipotent to 1 and has shown no cytotoxicity at 23.8 mu g/mL. Compound 5b was also found to have a broad spectrum of activity. Both the carbon and oxygen isosteres were less potent than cryptolepine. A limited library of 2-substituted analogs of 5b has been synthesized and evaluated in antifungal screens but did not show increase in potency compared to the unsubstituted 5b. Similarly, evaluation of tricyclic benzothieno[3,2-b]pyridines while showing promise in individual screens did not produce an overall increase in potency. Overall, the evaluation of the activities of 5b compared with standard antifungal/anti-protozoal agents suggests that the benzothienoquinoline scaffold could serve as a lead for optimization. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.062
• 作为产物：
  描述：

  12-[hydroxyl(phenyl)methyl]-11,12-dihydro-5H-dibenzo[b,g]azonine-6,13-dione 在 盐酸 作用下， 以 水 为溶剂， 以52%的产率得到5H-indeno[1,2-b]quinolin-10(11H)-one
  参考文献：
  名称：

  功能化11,12-二氢-5H-二苯并[b,g]氮酮的合成及一些反应

  摘要：

  摘要 Dihydro-5H-dibenzo[b,g]azonine-6,13-​​dione (2) 已被用作合成吲哚[2,3-e]dibenzo[b,g]azonine 和tribenzo[ b,g,j][1,6]二氮杂环十二烷环系统 6 和 7 分别通过 Fischer 吲哚化/高碘酸盐氧化序列。(1,4-苯二肼)衍生物8的Fischer吲哚化得到多环体系9。2的施密特反应导致苯并咪唑[1,2-b] [2]苯并氮杂环体系的形成11.曼尼希反应2 导致了螺环系统 15。2 与醛亚胺和芳香醛的反应也进行了研究。

  DOI：

  10.1515/znb-2014-0271

文献信息

• Antihyperglycemic Activities of Cryptolepine Analogues:  An Ethnobotanical Lead Structure Isolated from <i>Cryptolepis sanguinolenta</i>
  作者：Donald E. Bierer、Larisa G. Dubenko、Pingsheng Zhang、Qing Lu、Patricia A. Imbach、Albert W. Garofalo、Puay-Wah Phuan、Diana M. Fort、Joane Litvak、R. Eric Gerber、Barbara Sloan、Jian Luo、Raymond Cooper、Gerald M. Reaven

  DOI：10.1021/jm970735n

  日期：1998.7.1

  Cryptolepine (1) is a rare example of a natural product whose synthesis was reported prior to its isolation from nature. In the previous paper we reported the discovery of cryptolepine's antihyperglycemic properties. As part of a medicinal chemistry program designed to optimize natural product lead structures originating from our ethnobotanical and ethnomedical field research, a series of substituted and heterosubstituted

  Cryptolepine（1）是天然产物的稀有实例，其合成被报道是在与自然分离之前进行的。在先前的论文中，我们报道了隐氯平的抗高血糖特性的发现。作为旨在优化源自我们民族植物学和民族医学领域研究的天然产物铅结构的药物化学计划的一部分，合成了一系列取代和杂合取代的隐氯仿类似物。在体外和NIDDM小鼠模型中测量了降血糖活性，以进行有关隐肾上腺核的首次结构生物活性研究。
• 一种新的[1,2,b]茚并喹啉类衍生物及其制备 方法和在抗肿瘤药物中的应用
  申请人：广西师范大学

  公开号：CN105622508B

  公开（公告）日：2018-08-21

  本发明公开了一种新的茚并[1,2,b]喹啉类衍生物及其制备方法，衍生物的结构通式为：这种衍生物具有良好的体内、外抗肿瘤活性，可以制备成抗肿瘤的药物。
• Anellierte Chinoline, 4. Mitt. 11-Oxo-5,11-dihydro-benzothieno[3,2-b][1] chinoline, S,S-Dioxide und Thionierungsprodukte
  作者：Klaus Görlitzer、Josef Weber

  DOI：10.1002/ardp.19813140115

  日期：——

  Die Amide 3 cyclisieren beim Erhitzen mit Polyphosphorsäure (PPS) zu den Titelverbindungen 4, aus denen mit H2O2 die S,S‐Dioxide 6 erhalten werden. Es wird über die Darstellung der Thione 12 und der Thioether 13 berichtet.

  酰胺3与多磷酸(PPS)加热环化，得到标题化合物4，用H 2 O 2 从中得到S，S-二氧化物6。报告了硫酮 12 和硫醚 13 的存在。
• ５，１０−ジヒドロ−１１Ｈ−インデノ〔１，２−ｂ〕キノリン−１０−オン誘導体
  申请人：丸石製薬株式会社

  公开号：JP2001089455A

  公开（公告）日：2001-04-03

  PROBLEM TO BE SOLVED: To provide a new 5,10-dihydro-11H-indeno[1,2-blquinolin-10-one derivative having antiviral activity. SOLUTION: A 5,10-dihydro-11H-indeno[1,2-b]quinolin-10-one derivative of formula (I) [R1 is a lower alkyl; R2 is a lower alkyl or a lower alkoxy; R3 is H or a lower alkyl; and in R4 and R5, one is H, and the other is amino, a lower alkanoylamino, hydroxy, an alkyl or phenyl, or one is hydroxy or a lower alkoxy, and the other is a lower alkyl or phenyl, or both together form oxo, hydroxyimino or a lower alkoxyimino].

  需要解决的问题：提供一种具有抗病毒活性的新型5,10-二氢-11H-吲哚并[1,2-bl]喹啉-10-酮衍生物。解决方案：公式（I）中的5,10-二氢-11H-吲哚并[1,2-b]喹啉-10-酮衍生物[R1是较低的烷基；R2是较低的烷基或较低的烷氧基；R3是H或较低的烷基；在R4和R5中，一个是H，另一个是氨基，较低的烷酰胺基，羟基，烷基或苯基，或一个是羟基或较低的烷氧基，另一个是较低的烷基或苯基，或两者合并形成氧代基，羟基亚胺基或较低的烷氧基亚胺基]。
• Cryptolepine and aromathecin based mimics as potent G-quadruplex-binding, DNA-cleavage and anticancer agents: Design, synthesis and DNA targeting-induced apoptosis
  作者：Jing-Mei Yuan、Kai Wei、Guo-Hai Zhang、Nan-Ying Chen、Xin-Wei Wei、Cheng-Xue Pan、Dong-Liang Mo、Gui-Fa Su

  DOI：10.1016/j.ejmech.2019.02.072

  日期：2019.5

  Thirty Cryptolepine and Aromathecin based mimics were designed and synthesized. Their cytotoxicity was evaluated in four human cancer cell lines (HepG-2, T24, NCI-H460 and MGC-803) and one normal human cell line (HL-7702). Most compounds exhibited potent anticancer activity with IC50 values from 0.31 to 11.97 mu M. 8-Fluoro-10-(N-3-dimethylaminopropyl)amino-11H-indeno[1,2-b]quinoline (5b) was identified as the most promising candidate in view of its anticancer activity. Molecular mechanism studies suggested that 5b not only could strongly bind to G-quadruplex, but intercalate into supercoil DNA and resulted in significant DNA double-strand break as well. Furthermore, 5b caused cell cycle arrest at S/G2 phase and induced apoptosis. After treatment with 5b, pro-apoptotic proteins Bak, Bax and Bim were up-regulated, anti-apoptotic proteins Bcl-2 and Bcl-xL were down-regulated, and the effector caspase-3/9 was activated to initiate apoptosis. The anticancer activity of 5b was finally validated in a MGC-803 xenograft tumor model with tumor growth inhibition (TGI) up to 53.2%, while displaying no obvious toxicity. Taken together, these results suggest that 5b may be a potential candidate of cytotoxic antineoplastic drugs for cancer therapy. (C) 2019 Elsevier Masson SAS. All rights reserved.