7-chloro-3-(2,4-dichlorophenyl)-1,2,3,4,9,10-hexahydroacridine-1,9-dione | 91700-87-7

• 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: 7-chloro-3-(2,4-dichlorophenyl)-1,2,3,4,9,10-hexahydroacridine-1,9-dione
• 英文别名: 7-chloro-3-(2,4-dichlorophenyl)-3,4-dihydro-1,9(2H,10H)-acridinedione；3-(2,4-dichlorophenyl)-7-chloro-3,4-dihydroacridine-1,9(2H,10H)-dione；7-Chloro-3-[2,4-dichlorophenyl]-3,4-dihydro-1,9(2H,10H)-acridinedione；7-chloro-3-(2,4-dichlorophenyl)-2,3,4,10-tetrahydroacridine-1,9-dione
• CAS: 91700-87-7
• 化学式: C₁₉H₁₂Cl₃NO₂
• 分子量: 392.669
• InChiKey: SLRIULRRADAUHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-氨基丙基)吡咯烷 、 7-chloro-3-(2,4-dichlorophenyl)-1,2,3,4,9,10-hexahydroacridine-1,9-dione 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以74%的产率得到7-Chloro-3-(2,4-dichloro-phenyl)-1-[(E)-3-pyrrolidin-1-yl-propylimino]-1,3,4,10-tetrahydro-2H-acridin-9-one
  参考文献：
  名称：

  Antimalarial drugs. 64. Synthesis and antimalarial properties of 1-imino derivatives of 7-chloro-3-substituted-3,4-dihydro-1,9(2H,10H)-acridinediones and related structures

  摘要：

  To improve upon the activity and properties of the 3-aryl-7-chloro-3,4-dihydro-1,9(2H,10H)-acridinediones, a variety of 1-[(alkylamino)alkylene]imino derivatives (3) were prepared and shown to be highly active antimalarial agents in both rodents and primates. Among structural modifications prepared, including N-10-alkyl and C2-substituted analogs, removal of the C-9 oxygen, and introduction of an imino side chain at C-9, the imines of the N-10-H acridinediones were the most active compounds obtained. The [3-(NN-dimethylamino)propyl]imino derivative of 7-chloro-3-(2,4-dichlorophenyl)-3,4-dihydro-1,9(2H,10H)-acridinedione (9aa) proved to be highly active in advanced studies in primates.

  DOI：

  10.1021/jm00097a001
• 作为产物：
  描述：

  4-(2',4'-dichlorophenyl)-3-buten-2-one 在 sodium hydroxide 、 硫酸 、 sodium ethanolate 、 sodium hydride 作用下， 以 乙醇 为溶剂， 反应 17.5h， 生成 7-chloro-3-(2,4-dichlorophenyl)-1,2,3,4,9,10-hexahydroacridine-1,9-dione
  参考文献：
  名称：

  Antimalarial drugs. 64. Synthesis and antimalarial properties of 1-imino derivatives of 7-chloro-3-substituted-3,4-dihydro-1,9(2H,10H)-acridinediones and related structures

  摘要：

  To improve upon the activity and properties of the 3-aryl-7-chloro-3,4-dihydro-1,9(2H,10H)-acridinediones, a variety of 1-[(alkylamino)alkylene]imino derivatives (3) were prepared and shown to be highly active antimalarial agents in both rodents and primates. Among structural modifications prepared, including N-10-alkyl and C2-substituted analogs, removal of the C-9 oxygen, and introduction of an imino side chain at C-9, the imines of the N-10-H acridinediones were the most active compounds obtained. The [3-(NN-dimethylamino)propyl]imino derivative of 7-chloro-3-(2,4-dichlorophenyl)-3,4-dihydro-1,9(2H,10H)-acridinedione (9aa) proved to be highly active in advanced studies in primates.

  DOI：

  10.1021/jm00097a001

文献信息

• 7-Chloro-3-substituted aryl-3,4-dihydro-1,9(2H,10H) and 10 hydroxy
  申请人：Warner Lambert Company

  公开号：US04291034A1

  公开（公告）日：1981-09-22

  7-Chloro-3-substituted aryl-3,4-dihydro-1,9-(2H,1OH) and 10-hydroxy-acridinedioneimines and their pharmaceutically acceptable salts and a process for preparing them are disclosed and claimed. The compounds are useful in the treatment of protozoan diseases.

  揭示和声称了7-氯-3-取代基芳基-3,4-二氢-1,9-(2H,1OH)和10-羟基-喹啉二酮亚胺及其药用可接受盐的制备方法。这些化合物在原虫病的治疗中很有用。
• 7-Chloro-3-substituted aryl-3,4-dihydro-1,9(2H,10H) and 10-hydroxy acridinedioneimines, processes for producing the acridinedioneimines, and pharmaceutical compositions containing the acridinedioneimines
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0036718A2

  公开（公告）日：1981-09-30

  There are disclosed 7-chloro-3-substituted aryi-3,4-dihy- dro-1,9(2H,10H) and 10-hydroxy acridinedioneimines, processes for their production and pharmaceutical compositions containing such compounds. The novel compounds have the following formula: where Y is a hydrogen atom or hydroxy group; R1 is a hydrogen, fluorine, chlorine, bromine or iodine atom; each of R2 and R3, which are the same or different, is a hydrogen, fluorine, chlorine, bromine or iodine atom or a trifluoromethyl group; wherein n is zero or an integer from 1 to 5; each of R4 and R5, which are the same or different, is a hydrogen atom or an alkyl radical containing one to four carbon atoms, -CH2-CH2-OH, allyl, or R4 and R5 together are (CH2)4 to 5. or each of R6 and R7, which are the same or different, is hydrogen, methyl or ethyl; and R8 is hydrogen or methyl. The invention extends to the pharmaceutically acceptable salts of these compounds. The novel compounds and their salts are suitable for use in the prevention and cure of protozoal infections and have a high activity against malaria parasites.

  本发明公开了 7-氯-3-取代芳基-3,4-二氢-1,9(2H,10H)和 10-羟基吖啶二酮亚胺、其生产工艺以及含有此类化合物的药物组合物。这些新型化合物具有下式 其中 Y 是氢原子或羟基；R1 是氢、氟、氯、溴或碘原子；R2 和 R3（相同或不同）各自是氢、氟、氯、溴或碘原子或三氟甲基； 其中 n 为零或 1 至 5 的整数；R4 和 R5（相同或不同）各自为氢原子或含 1 至 4 个碳原子的烷基、-CH2-CH2-OH、 烯丙基，或 R4 和 R5 合在一起为 (CH2)4 至 5。 相同或不同的 R6 和 R7 各自为氢、甲基或乙基；以及 R8 为氢或甲基。本发明还包括这些化合物的药学上可接受的盐。这些新型化合物及其盐类适用于预防和治疗原生动物感染，对疟原虫有很高的活性。
• 3-Aryl-7-chlor-3,4-dihydro-acridin-1,9-(2H,10H)-dion-1-oxime und -1-hydrazonderivate, deren Salze, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0106284A1

  公开（公告）日：1984-04-25

  3-Aryl-7-chlor-3, 4-dihydro-acridin-1,9-(2H, 10H)-dion-1- oxime und -1-hydrazonderivate der Formel I und ihre physiologisch verträglichen Säureadditions- und Ammoniumsalze werden beschrieben sowie Verfahren zu deren Herstellung. Die neuen Verbindungen sind Chemotherapeutica und wirken gegen Protozoen, insbesondere Malaria-Plasmodien.

  式 I 的 3-芳基-7-氯-3,4-二氢-吖啶-1,9-(2H, 10H)-二酮-1-肟和-1-腙衍生物及其生理相容的酸加成盐和铵盐，以及它们的制备方法。 及其生理相容的酸加成盐和铵盐，以及它们的制备方法。这些新化合物是化疗药物，对原生动物，特别是疟疾疟原虫有效。
• A Versatile Synthesis of Acridine-1,9-Diones
  作者：Junjie Chen、Leslie W. Deady

  DOI：10.1080/00397919708004810

  日期：1997.1.1

  Alkylation of ethyl 2-(4-oxo-1,4-dihydroquinolin-2-yl)acetate by Michael addition with various alkenes has been carried out. The C-alpha alkylated intermediates so formed can be cyclized with hot polyphosphoric acid to acridine-1,9-diones.
• WERBEL, L. M.
  作者：WERBEL, L. M.

  DOI：——

  日期：——