9-tert-butyl-2-iodo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one | 1003869-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 9-tert-butyl-2-iodo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
• 英文别名: 9-tert-butyl-2-iodo-7,12-dihydro-5H-indolo[3,2-d][1]benzazepin-6-one
• CAS: 1003869-22-4
• 化学式: C₂₀H₁₉IN₂O
• 分子量: 430.288
• InChiKey: NENBYNYHVZIGBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-tert-butyl-2-iodo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 硫酸 、 mercury(II) diacetate 、 四丁基氟化铵 、 水 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 194.41h， 生成 9-tert-butyl-2-[(2E)-3-phenylprop-2-enoyl]-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
  参考文献：
  名称：

  2-Arylpaullones are selective antitrypanosomal agents

  摘要：

  Antileishmanial paullone-chalcone hybrid molecules display antiparasitic activity against Trypanosoma brucei rhodesiense blood stream forms, albeit with low selectivity against human THP-1 cells. In order to develop less toxic analogues, paullones with acrylamide or aryl substituents in 2-position were synthesized, of which the latter exhibited potent antiparasitic activity with excellent selectivity profiles. The most potent compound identified in this study was 9-tert-butyl-2-(4-morpholinophenyl)paullone (3i) which inhibited the parasites at submicromolar concentrations (GI(50) = 510 nM) with a selectivity index of 157. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.065
• 作为产物：
  描述：

  4-特丁基苯肼盐酸盐 、 7-iodo-3,4-dihydro-1H-1-benzazepine-2,5-dione 在 sodium acetate 、 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以61%的产率得到9-tert-butyl-2-iodo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
  参考文献：
  名称：

  2-(3-Aryl-3-oxopropen-1-yl)-9-tert-butyl-paullones: A New Antileishmanial Chemotype

  摘要：

  A screening program directed to find new agents against Leishmania donovani, the parasite causing visceral leishmaniasis, revealed that paullones attenuate the proliferation of axenic amastigotes. Because these structures were not active in a test system involving infected macrophages, a structure optimization campaign was carried out. Concomitant introduction of an unsaturated side chain into the 2-position and a tert-butyl substituent into the 9-position of the parent scaffold led to compounds inhibiting also parasites dwelling in macrophages. By inclusion of the so elaborated scaffold into a chalcone substructure, the toxicity against uninfected host cells was significantly reduced. For the synthesis of this new compound class, a novel modification of the Heck-type palladium-catalyzed C,C-cross coupling strategy was used, employing a ketone Mannich base as precursor for the alkene reactant. The so-prepared compounds exhibited improved antileishmanial activity both on axenic amastigotes (GI(50) < 1 mu M) as well as on parasites in infected macrophages.

  DOI：

  10.1021/jm7012166

文献信息

• Synthesis of 11H-Indolo[3,2-c]quinoline-6-carboxylic Acids by Cascade Autoxidation-Ring Contractions
  作者：Conrad Kunick、Anja Becker、Simone Kohfeld、Tanja Pies、Karen Wieking、Lutz Preu

  DOI：10.1055/s-0028-1088014

  日期：2009.4

  11H-Indolo[3,2-c]quinoline-6-carboxylic acids are prepared in moderate yields from paullones [7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-ones] by reaction with molecular oxygen in the presence of N-hydroxyphthalimide and cobalt(II) acetate. A reaction mechanism is suggested comprising initial autoxidation reaction with subsequent ring contraction.

  通过 paullones [7,12-二氢吲哚并[3,2-d][1]苯并氮杂-6(5H)-酮]反应以中等收率制备 11H-吲哚[3,2-c]喹啉-6-羧酸在 N-羟基邻苯二甲酰亚胺和乙酸钴 (II) 存在下与分子氧反应。建议的反应机制包括最初的自氧化反应和随后的环收缩。
• [EN] PAULLONE DERIVATIVES AND ITS USE<br/>[FR] DÉRIVÉS DE PAULLONE ET LEURS UTILISATION
  申请人：UNIV BRAUNSCHWEIG TECH CAROLO WILHELMINA

  公开号：WO2009010298A2

  公开（公告）日：2009-01-22

  The present invention relates to new paullone derivatives. In particular, the present invention relates to new paullone derivatives having anti-protozoan activity, in particular, anti-leishmanial activity. In a further aspect, the present invention relates to pharmaceutical compositions containing said paullones.