4,11-二甲基-5H-吲哚并(2,3-b)喹啉 | 114414-79-8

• 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
• 中文名称: 4,11-二甲基-5H-吲哚并(2,3-b)喹啉
• 英文名称: 5,11-Dimethyl-5H-indolo<2,3-b>quinoline
• 英文别名: 5,11-dimethyl-5H-indolo[2,3-b]quinoline；5,11-dimethylindolo[2,3-b]quinoline；11-methylneocryptolepine；DiMIQ；5,11-dimethyl-6H-indolo[2,3-b]quinolinium betaine；5,11-Dimethyl-6H-indolo[2,3-b]chinolinium-betain；5,11-Dimethyl-5H-quinindoline
• CAS: 114414-79-8
• 化学式: C₁₇H₁₄N₂
• 分子量: 246.312
• InChiKey: HPNJLBZRPMSGCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-苄基吲哚 在 aluminum (III) chloride 、 碘 、 caesium carbonate 作用下， 以 乙腈 、 苯 为溶剂， 反应 36.0h， 生成 4,11-二甲基-5H-吲哚并(2,3-b)喹啉
  参考文献：
  名称：

  One-Pot Access to Indolo[2,3-b]quinolines by Electrophile-Triggered Cross-Amination/Friedel–Crafts Alkylation of Indoles with 1-(2-Tosylaminophenyl)ketones

  摘要：

  Activation of C2 and C3 of indoles by molecular iodine (I-2) and base followed by in situ reaction with 1-(2-tosylaminophenyl)ketones or 2-tosylaminobenzaldehyde can afford highly substituted indolo(2,3-b)quinolines in moderate to excellent yields (up to 99%). The reaction provides a metal-free selective difunctionalization of indoles. The synthetic potential of the protocol has been illustrated by the synthesis. of neocryptolepine and its 11-methyl analogue.

  DOI：

  10.1021/jo202035p

文献信息

• Revisiting Furodiindolines: One-Pot Synthesis of Furodiindolines Using Indole 2,3-Epoxide Surrogates and Their Synthetic Applications
  作者：Takumi Abe、Sakura Aoyama、Masami Ohmura、Masato Taniguchi、Koji Yamada

  DOI：10.1021/acs.orglett.9b01108

  日期：2019.5.3

  Furodiindolines have emerged as versatile intermediates in various transformations, which are easily obtained from indole 2,3-epoxide surrogates via a one-pot procedure and allowed access to heterocyclic compounds with structural diversity and complexity. Four types of transformations from the furodiindolines have been achieved: (i) dehydrative rearrangement to afford 2,3′-biindoles, (ii) hydrolysis/cyclization

  呋喃二氢吲哚已成为各种转化中的多用途中间体，很容易通过一锅法从吲哚2，3-环氧代用品中获得，并能获得具有结构多样性和复杂性的杂环化合物。从呋喃二氢吲哚获得了四种类型的转化：（i）脱水重排，得到2,3'-双吲哚，（ii）水解/环化，得到3,4-二取代的喹啉，（iii）开环/环化，得到吡咯并二氢吲哚，和（iv）经氨基裂解得到3，3-二取代的2-氧吲哚。
• An efficient iron-promoted synthesis of 6H-indolo[2,3-b]quinolines and neocryptolepine derivatives
  作者：Zicong Yan、Changfeng Wan、Jianyong Wan、Zhiyong Wang

  DOI：10.1039/c6ob00469e

  日期：——

  A facile and practical method for the preparation of 6H-indolo[2,3-b]quinolines and neocryptolepines was developed under the promotion of the easily available ferric trichloride, affording the desired products with moderate to good yields.

  在容易获得的三氯化铁的促进下，开发了一种简便实用的制备6 H-吲哚并[2,3- b ]喹啉和新隐油菜碱的方法，从而以中等至良好的收率提供了所需的产物。
• Synthesis and Structure-Activity Relationship of Methyl-Substituted Indolo[2,3-b]quinolines: Novel Cytotoxic, DNA Topoisomerase II Inhibitors
  作者：Wanda Peczynska-Czoch、Francois Pognan、Lukasz Kaczmarek、Janusz Boratynski

  DOI：10.1021/jm00047a008

  日期：1994.10

  bacteria and pathogenic fungi at MIC range 3 x 10(-2) to 2.5 x 10(-1) mumol/mL, displayed cytotoxicity against KB cells ID50 in the range 2 x 10(-3) to 9 x 10(-3) mumol/mL, and stimulated the formation of calf thymus topoisomerase II mediated DNA cleavage at concentration between 0.4 and 10 microM. None of the indolo[2,3-b]quinolines belonging to the 6H series, i.e., lacking a methyl group on the pyridine

  为了进一步开展有关稠合氮杂芳族化合物的化学和抗肿瘤活性的SAR研究，根据修饰的Graebe-合成了一系列5H-和6H-吲哚并[2,3-b]喹啉的线性，甲基取代的衍生物。乌尔曼反应。为了建立吲哚[2,3-b]喹啉的理化和生物学活性之间的关系，它们的亲脂性，细胞毒性和抗菌活性以及在体外诱导拓扑异构酶II依赖性pSP65 DNA裂解的能力，我们进行了研究。我们发现吲哚[2,3-b]喹啉的抗微生物和细胞毒性活性受到位置的强烈影响，甲基取代基的数量和吡啶氮上甲基的存在对于这些化合物的细胞毒性至关重要。全部indolo [2，属于5H系列的3-b]喹啉，即在吡啶氮上带有甲基，对原核和真核生物显示出显着的活性。它们在MIC范围3 x 10（-2）至2.5 x 10（-1）mumol / mL时抑制革兰氏阳性细菌和致病真菌的生长，对KB细胞ID50的细胞毒性显示在2 x 10（-3）范围内至9 x 10（-3）mumol
• Heteroatom directed photoannulation: synthesis of indoloquinoline alkaloids: cryptolepine, cryptotackieine, cryptosanguinolentine, and their methyl derivatives
  作者：T. Dhanabal、R. Sangeetha、P.S. Mohan

  DOI：10.1016/j.tet.2006.04.050

  日期：2006.6

  indoloquinoline alkaloids is described. The reaction of 2,3 and 4-substituted haloquinolines with anilines afforded the respective anilinoquinolines, which upon photocyclization gave the indoloquinolines. By regioselective methylation on quinoline nitrogen, furnished the alkaloids cryptotackieine, cryptosanguinolentine, cryptolepine, and the synthetic isomer isoneocryptolepine. Their methyl derivatives

  描述了吲哚喹啉生物碱的三步合成。2，3和4-取代的卤代喹啉与苯胺的反应得到各自的苯胺喹啉，其在光环化后得到吲哚喹啉。通过在喹啉氮上的区域选择性甲基化，提供了生物碱隐tackieine，隐sanguinolentine，隐lepinepine和合成异构体isooneocryptolepine。还合成了它们的甲基衍生物，以寻找新的抗疟原虫药物和DNA嵌入剂。
• Cancerostatics, VI. Synthesis and Antineoplastic Properties of Some Benzo-iso-α-carbolines
  作者：Łukasz Kaczmarek、Roman Balicki、Paweł Nantka-Namirski、Wanda Peczyńska-Czoch、Marian Mordarski

  DOI：10.1002/ardp.19883210807

  日期：——

  Some benzo‐iso‐α‐carbolines were synthesized by modification of the Graebe‐Ullmann reaction and examined for antineoplastic activity. The linear, tetracyclic 5,11‐dimethyl‐5H‐indolo[2,3‐b]quinoline 13b, that is related to ellipticine, showed significant antitumor activity against mice P 388 and L 1210 leukemias and against melanoma B 16.

  通过改进 Graebe-Ullmann 反应合成了一些苯并 - 异 - α - 咔啉，并检测了其抗肿瘤活性。与玫瑰树碱相关的线性四环 5,11-二甲基-5H-吲哚 [2,3-b] 喹啉 13b 对小鼠 P 388 和 L 1210 白血病以及黑色素瘤 B 16 显示出显着的抗肿瘤活性。