AG-690/36482004 | 130186-64-0

• 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: AG-690/36482004
• 英文别名: 9-amino-3,3-dimethyl-1,2,3,4-tetrahydroacridin-1-one；9-amino-3,3-dimethyl-3,4-dihydroacridin-1(2H)-one；9-amino-3,3-dimethyl-3,4-dihydroacridine-1(2H)-one；9-amino-3,3-dimethyl-1-oxo-1,2,3,4-tetrahydroacridine；9-Amino-3,3-dimethyl-3,4-dihydro-1(2H)-acridinone；9-amino-3,3-dimethyl-2,4-dihydroacridin-1-one
• CAS: 130186-64-0
• 化学式: C₁₅H₁₆N₂O
• mdl: MFCD00445032
• 分子量: 240.305
• InChiKey: RFXDMILSJZCTDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  56
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  AG-690/36482004 、 2-氨基苯甲腈 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以63%的产率得到2-[(9-Amino-3,3-dimethyl-2,4-dihydroacridin-1-ylidene)amino]benzonitrile
  参考文献：
  名称：

  Synthesis and Crystal Structure of 7,8-Dihydroquinolino[2,3-a]acridine Derivatives

  摘要：

  Novel 9-amino-3-substituted-1,2,3,4-acridin-1-one derivatives and 9,14-diamino-7-substituted-7,8-dihydroquinolino[2,3-a]acridine derivatives were synthesized by the condensation reaction of 5-substituted-1,3-cyclohexanedione with 2-aminobenzonitrile and substituted 2-aminobenzonitrile using p-toluenesulfonic acid, K2CO3, and Cu2Cl2 as catalysts. The structures of all compounds were characterized by elemental analysis, infrared, mass spectrometry, and 1H and 13C NMR spectra. The crystal and molecular structures of 6, 14-diamino-3,4,11,12-tetramethoxy-7-phenyl-7,8-dihydroquinolino[2,3-a]acridine 5a have been determined by single-crystal x-ray diffraction analysis. The crystal of compound 5a belongs to triclinic with space group P-1, a=1.06168(15) nm, b=1.16951(17) nm, c=1.6020(2) nm, =71.380(3)degrees, =77.686(3)degrees, =66.743(3)degrees, Z=2, V=1.7231(4) nm3, R1=0.1060, and wR2=0.2192.

  DOI：

  10.1080/00397910802656042
• 作为产物：
  描述：

  N-(5,5-dimethyl-3-oxo-cyclohexen-1-yl)-2-aminobenzonitrile 在 potassium carbonate 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以78%的产率得到AG-690/36482004
  参考文献：
  名称：

  Synthesis and Crystal Structure of 7,8-Dihydroquinolino[2,3-a]acridine Derivatives

  摘要：

  Novel 9-amino-3-substituted-1,2,3,4-acridin-1-one derivatives and 9,14-diamino-7-substituted-7,8-dihydroquinolino[2,3-a]acridine derivatives were synthesized by the condensation reaction of 5-substituted-1,3-cyclohexanedione with 2-aminobenzonitrile and substituted 2-aminobenzonitrile using p-toluenesulfonic acid, K2CO3, and Cu2Cl2 as catalysts. The structures of all compounds were characterized by elemental analysis, infrared, mass spectrometry, and 1H and 13C NMR spectra. The crystal and molecular structures of 6, 14-diamino-3,4,11,12-tetramethoxy-7-phenyl-7,8-dihydroquinolino[2,3-a]acridine 5a have been determined by single-crystal x-ray diffraction analysis. The crystal of compound 5a belongs to triclinic with space group P-1, a=1.06168(15) nm, b=1.16951(17) nm, c=1.6020(2) nm, =71.380(3)degrees, =77.686(3)degrees, =66.743(3)degrees, Z=2, V=1.7231(4) nm3, R1=0.1060, and wR2=0.2192.

  DOI：

  10.1080/00397910802656042

文献信息

• Sulfuric acid-modified PEG-6000 (PEG-OSO3H): an efficient, bio-degradable and reusable polymeric catalyst for the solvent-free synthesis of poly-substituted quinolines under microwave irradiation
  作者：Alireza Hasaninejad、Abdolkarim Zare、Mohsen Shekouhy、Javad Ameri-Rad

  DOI：10.1039/c0gc00953a

  日期：——

  acid-modified polyethylene glycol 6000 (PEG-OSO3H) is applied as an efficient and eco-friendly polymeric catalyst for Friedländer synthesis of poly-substituted quinolines from 2-aminoaryl ketones (or anthranilonitrile) and carbonyl compounds possessing a reactive methylene group under microwave irradiation and solvent-free conditions. The reactions are completed in short times, and the products are obtained

  硫酸改性聚乙二醇6000（PEG-OSO 3 H）被用作一种高效且环保的聚合物催化剂 Friedländer合成多取代基 喹啉 由2-氨基芳基 酮类 （或者 蒽腈） 和 羰基化合物 在微波辐射下具有反应性亚甲基 溶剂无条件。反应在短时间内完成，并且以良好至优异的产率获得产物。
• Acridine derivatives
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0371388A3

  公开（公告）日：1991-01-09

  A compound of the formula : wherein R¹ is hydrogen, halogen, hydroxy, lower alkoxy, lower alkyl or mono(or di or tri)halo(lower)alkyl, and (in which R² and R³ are each lower alkyl), and a pharmaceutically acceptable salt thereof, processes for their preparation and pharmaceutical compositions comprising them as an active ingredient in admixture with pharmaceutically acceptable carriers. The invention also relates to intermediates of the formula

  该化合物的化学式为： 其中R¹为氢、卤素、羟基、较低的烷氧基、较低的烷基或单(或二或三)卤代(较低)烷基，以及 (其中R²和R³各自为较低的烷基)， 以及其药学上可接受的盐，其制备方法以及包含它们作为活性成分与药学上可接受的载体混合物的药物组合物。该发明还涉及该化合物的中间体的化学式。
• Synthesis of 4-methyl-2,3-disubstituted quinoline scaffolds via environmentally benign Fe(<scp>iii</scp>) catalysed sequential condensation, cyclization and aromatization of 1,3-diketone and 2-ethynylaniline
  作者：Mahalingam Sivaraman、Paramasivan T. Perumal

  DOI：10.1039/c4ra03666b

  日期：——

  Environmentally benign Fe(III)-catalysed sequential condensation, cyclization and aromatization of 1,3-diketone and 2-ethynylaniline derivatives to the substituted quinoline scaffolds with good to excellent yield in shorter reaction time is described.

  本文描述了一种环境友好的铁(III)催化1,3-二酮与2-乙炔基苯胺衍生物的顺序缩合、环化和芳构化反应，以较短的反应时间获得了高至优异产率的取代喹啉骨架。
• DERIVATIVES OF 9-AMINOACRIDINE HAVING PSYCHOTROPIC, ANTIAMNESTIC AND LIPID REGULATING PROPERTIES
  申请人：VSESOJUZNY NAUCHNY TSENTR PO BEZOPASNOTI BIOLOGICHESKI ACTIVNYKH VESHCHESTV

  公开号：EP0633251A1

  公开（公告）日：1995-01-11

  New chemical compounds, derivatives of 9-aminoacridine of general formula (I) where R = H, CH₃; R¹ = H, CH₃, Br; R² = H, CH₃; R³ = alkyl-C₁-C₅, arylmethyl, diethylaminoethyl; X = C = O, CHOH; Y = CH₂; X + Y = CH = CH; and their salts with organic and non-organic acids. The desired compounds are obtained by interaction of substituted nitriles of antranyl acid with dimedone with subsequent cyclization of intermediate enaminonitriles into corresponding ketones of 9-aminoacridine after the reduction of which and of their derivatives alkylated or aralkylated on the 9-amino group, the corresponding alcohols are obtained, after hydration of which 9-amino-3,4-dihydroacridines are obtained. When experimented on animals, the said derivatives of 9-aminoacridine have shown psychotropic, antiamnestic and lipid regulating properties, as well as a lower toxicity in comparison with known preparations.

  新的化合物，是9-氨基蒽醌的衍生物，其通式为(I)，其中R = H、CH₃；R¹ = H、CH₃、Br；R² = H、CH₃；R³ = 烷基-C₁-C₅、芳基甲基、二乙氨基乙基；X = C = O、CHOH；Y = CH₂；X + Y = CH = CH；以及它们与有机和非有机酸的盐。所需化合物是通过将替代的蒽酰胺基酸腈与二甲酮反应，随后将中间体烯胺腈环化成相应的9-氨基蒽醌酮，还原后得到它们及其衍生物烷基化或芳基烷基化的相应醇，水合后得到9-氨基-3,4-二氢蒽醌。在动物实验中，所述9-氨基蒽醌的衍生物表现出精神药理、抗遗忘和调脂作用，并且与已知制剂相比毒性更低。
• JPH02167267A
  申请人：——

  公开号：JPH02167267A

  公开（公告）日：1990-06-27