7-氯-3-(3,4-二氯苯基)-3,4-二氢-10-羟基-1,9-(2H,10H)-吖啶二酮 | 75618-33-6

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

7-氯-3-(3,4-二氯苯基)-3,4-二氢-10-羟基-1,9-(2H,10H)-吖啶二酮

中文别名

——

英文名称

7-chloro-3-(3,4-dichlorophenyl)-3,4-dihydro-10-hydroxy-1,9(2H,10H)-acridinedione

英文别名

3-(3,4-dichlorophenyl)-7-chloro-10-hydroxy-3,4-dihydroacridine-1,9(2H,10H)-dione；7-chloro-3-(3,4-dichlorophenyl)-10-hydroxy-3,4-dihydro-2H-acridine-1,9-dione

7-氯-3-(3,4-二氯苯基)-3,4-二氢-10-羟基-1,9-(2H,10H)-吖啶二酮化学式

CAS

75618-33-6

化学式

C₁₉H₁₂Cl₃NO₃

mdl

——

分子量

408.668

InChiKey

UKEQLQYAEAYLCA-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

584.2±50.0 °C(Predicted)
密度：

1.62±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

3.8
重原子数：

26
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：

57.6
氢给体数：

1
氢受体数：

4

上下游信息

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	7-chloro-3-(3,4-dichlorophenyl)-3,4-dihydro-1,9(2H,10H)-acridinedione	80092-91-7	C₁₉H₁₂Cl₃NO₂	392.669
——	9(2H)-Acridinone,7-chloro-3-(3,4-dichlorophenyl)-1,3,4,10-tetrahydro-10-hydroxy-1-(methylimino)-	144128-41-6	C₂₀H₁₅Cl₃N₂O₂	421.71
——	7-chloro-3-(3,4-dichlorophenyl)-1-[[3-(dimethylamino)propyl]imino]-1,3,4,10-tetrahydro-10-hydroxy-9(2H)acridinone	80092-32-6	C₂₄H₂₄Cl₃N₃O₂	492.832
——	7-chloro-3-(3,4-dichlorophenyl)-1-[[3-(dimethylamino)propyl]imino]-1,3,4,10-tetrahydro-10-hydroxy-9(2H)acridinone	80092-32-6	C₂₄H₂₄Cl₃N₃O₂	492.832
——	7-chloro-3-(3,4-dichlorophenyl)-10-hydroxy-1-[3-(4-methylpiperazin-1-yl)propylimino]-3,4-dihydro-2H-acridin-9-one	80108-14-1	C₂₇H₂₉Cl₃N₄O₂	547.912
——	7-Chloro-3-(3,4-dichloro-phenyl)-1-[(E)-3-diethylamino-propylimino]-10-hydroxy-1,3,4,10-tetrahydro-2H-acridin-9-one	80092-35-9	C₂₆H₂₈Cl₃N₃O₂	520.886
——	7-chloro-3-(3,4-dichlorophenyl)-1-[[2-(diethylamino)ethyl]imino]-1,3,4,10-tetrahydro-10-hydroxy-9(2H)acridinone	80092-34-8	C₂₅H₂₆Cl₃N₃O₂	506.859
——	7-Chloro-3-(3,4-dichloro-phenyl)-1-{(E)-3-[ethyl-(2-hydroxy-ethyl)-amino]-propylimino}-10-hydroxy-1,3,4,10-tetrahydro-2H-acridin-9-one	80092-49-5	C₂₆H₂₈Cl₃N₃O₃	536.886
——	1-{(E)-3-[Bis-(2-hydroxy-ethyl)-amino]-propylimino}-7-chloro-3-(3,4-dichloro-phenyl)-10-hydroxy-1,3,4,10-tetrahydro-2H-acridin-9-one	80092-43-9	C₂₆H₂₈Cl₃N₃O₄	552.885
——	7-Chloro-3-(3,4-dichloro-phenyl)-10-hydroxy-1-[(E)-3-piperidin-1-yl-propylimino]-1,3,4,10-tetrahydro-2H-acridin-9-one	80092-38-2	C₂₇H₂₈Cl₃N₃O₂	532.897
——	1-[(E)-3-Butylamino-propylimino]-7-chloro-3-(3,4-dichloro-phenyl)-10-hydroxy-1,3,4,10-tetrahydro-2H-acridin-9-one	80092-48-4	C₂₆H₂₈Cl₃N₃O₂	520.886
——	7-Chloro-3-(3,4-dichloro-phenyl)-10-hydroxy-1-[(E)-3-(2-hydroxy-ethylamino)-propylimino]-1,3,4,10-tetrahydro-2H-acridin-9-one	80092-44-0	C₂₄H₂₄Cl₃N₃O₃	508.832
——	7-Chloro-3-(3,4-dichloro-phenyl)-1-[(E)-7-dimethylamino-heptylimino]-10-hydroxy-1,3,4,10-tetrahydro-2H-acridin-9-one	80092-37-1	C₂₈H₃₂Cl₃N₃O₂	548.94
——	(1E)-7-chloro-3-(3,4-dichlorophenyl)-1-[2-(diethylamino)ethoxyimino]-10-hydroxy-3,4-dihydro-2H-acridin-9-one	144128-30-3	C₂₅H₂₆Cl₃N₃O₃	522.859
——	7-Chloro-3-(3,4-dichloro-phenyl)-1-[(E)-2-diisobutylamino-ethylimino]-10-hydroxy-1,3,4,10-tetrahydro-2H-acridin-9-one	80092-42-8	C₂₉H₃₄Cl₃N₃O₂	562.967
——	7-Chloro-3-(3,4-dichloro-phenyl)-1-[(E)-3-diethylamino-2,2-dimethyl-propylimino]-10-hydroxy-1,3,4,10-tetrahydro-2H-acridin-9-one	80092-50-8	C₂₈H₃₂Cl₃N₃O₂	548.94
——	7-Chloro-3-(3,4-dichloro-phenyl)-1-[(E)-4-diethylamino-1-methyl-butylimino]-10-hydroxy-1,3,4,10-tetrahydro-2H-acridin-9-one	80092-39-3	C₂₈H₃₂Cl₃N₃O₂	548.94
——	7-Chloro-3-(3,4-dichloro-phenyl)-1-{(E)-2-[ethyl-(2-hydroxy-2-methyl-propyl)-amino]-ethylimino}-10-hydroxy-1,3,4,10-tetrahydro-2H-acridin-9-one	80092-41-7	C₂₇H₃₀Cl₃N₃O₃	550.912
——	7-Chloro-3-(3,4-dichloro-phenyl)-1-[(E)-3-diethylaminomethyl-phenylimino]-10-hydroxy-1,3,4,10-tetrahydro-2H-acridin-9-one	144128-45-0	C₃₀H₂₈Cl₃N₃O₂	568.93
——	9(2H)-Acridinone,7-chloro-3-(3,4-dichlorophenyl)-1-[[4-(diethylamino)cyclohexyl]imino]-1,3,4,10-tetrahydro-10-hydroxy-	144128-43-8	C₂₉H₃₂Cl₃N₃O₂	560.951
——	7-chloro-3-(3,4-dichlorophenyl)-1-(1-ethylpiperidin-3-yl)imino-10-hydroxy-3,4-dihydro-2H-acridin-9-one	144128-42-7	C₂₆H₂₆Cl₃N₃O₂	518.87
——	4-(acetyloxy)-7-chloro-3-(3,4-dichlorophenyl)-3,4-dihydro-1,9(2H,10H)-acridinedione	144128-82-5	C₂₁H₁₄Cl₃NO₄	450.705
——	7-Chloro-3-(3,4-dichloro-phenyl)-1-[(E)-3-dimethylamino-propylimino]-1,3,4,10-tetrahydro-2H-acridin-9-one	80092-61-1	C₂₄H₂₄Cl₃N₃O	476.833
——	1-[(E)-Butylimino]-7-chloro-3-(3,4-dichloro-phenyl)-1,3,4,10-tetrahydro-2H-acridin-9-one	144155-29-3	C₂₃H₂₁Cl₃N₂O	447.792
——	7-chloro-3-(3,4-dichlorophenyl)-1-[[2-(diethylamino)ethyl]imino]-1,3,4,10-tetrahydro-9(2H)acridinone	80092-63-3	C₂₅H₂₆Cl₃N₃O	490.86

反应信息

作为反应物：

描述：

7-氯-3-(3,4-二氯苯基)-3,4-二氢-10-羟基-1,9-(2H,10H)-吖啶二酮在三氯化磷作用下，以氯仿为溶剂，反应 1.0h，以34%的产率得到7-chloro-3-(3,4-dichlorophenyl)-3,4-dihydro-1,9(2H,10H)-acridinedione

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：

5-(3,4-二氯苯基)环己烷-1,3-二酮、邻硝基苯甲醛在盐酸作用下，以溶剂黄146 为溶剂，以71%的产率得到7-氯-3-(3,4-二氯苯基)-3,4-二氢-10-羟基-1,9-(2H,10H)-吖啶二酮

参考文献：

名称：

Duerckheimer; Raether; Seliger, Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 7, p. 1041 - 1046

摘要：

DOI：

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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。
Winkelmann; Raether, Arzneimittel-Forschung/Drug Research, 1987, vol. 37, # 6, p. 647 - 661

作者：Winkelmann、Raether

DOI：——

日期：——
Werbel; Hung; McNamara, European Journal of Medicinal Chemistry, 1985, vol. 20, # 4, p. 363 - 370

作者：Werbel、Hung、McNamara、Ortwine

DOI：——

日期：——