1,5-bis(isopropylamino)-9,10-anthraquinone | 33175-76-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,5-bis(isopropylamino)-9,10-anthraquinone
• 英文别名: 1,5-bis[(1-methylethylamino)]-9,10-anthracenedione；1.5-Di(2-propylamino)anthrachinon；1,5-Bis(isopropylamino)anthraquinone；9,10-Anthracenedione, 1,5-bis[(1-methylethyl)amino]-；1,5-bis(propan-2-ylamino)anthracene-9,10-dione
• CAS: 33175-76-7
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: UXQNNCXHZVVMHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,5-二氯蒽醌 、 异丙胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以65%的产率得到1,5-bis(isopropylamino)-9,10-anthraquinone
  参考文献：
  名称：

  基于结构的设计和合成的区域异构双取代氨基蒽醌衍生物作为潜在的抗癌药。

  摘要：

  继续进行有关细胞毒性物质的研究，我们报告了一系列具有潜在生物可还原基团的对称1,5-二氨基-9,10-蒽醌的合成和细胞毒性。1,5-二氯-9,10-蒽醌，在DMF的存在下适当的伯胺的氨基化对称布置的结构上相关的氨基蒽醌类似物1 - 19。使用大鼠神经胶质瘤C6细胞，人肝癌G2细胞和2.2.15细胞评估了它们的体外细胞毒性活性。在这些测定中，几种化合物表现出非常高的抗肿瘤活性。化合物4通过XTT比色测定法可以有效抑制C6细胞，人肝癌G2细胞和2.2.15细胞。4的抗增殖活性显着增强，达到了与强大的抗癌药米托蒽醌，阿霉素和顺铂相当的效力。讨论了这类新型氨基蒽醌类的生物学评估和结构/活性关系。

  DOI：

  10.1002/hlca.200490093

文献信息

• Synthesis and pharmaceuticals of novel bis-substituted anthraquinone derivatives
  申请人：Huang Hsu-Shan

  公开号：US20050009924A1

  公开（公告）日：2005-01-13

  This invention relates to novel anthraquinone compounds useful in the treatment of allergic, inflammatory conditions, antioxidant, tumor condition, stem cell application, tissue engineering, applied in treating age-associate tissue degeneration, reverse organ failure in chronic high-turnover disease and therapeutic compositions containing such compounds. The compounds of the present invention are 1,4-, 1,5- and 1,8-difunctionalized anthraquinones or analogs thereof. According to the practice of the invention, there are provided bis-symmetrical substituted anthraquinone compounds according to formula I: wherein R1, R2, R3 and R4 present a straight, aminoalkylamino side chains or branched chain alkyl group having 1 to 6 carbons which may be substituted with one or more groups of R5, or R1, R2, R3 and R4 present phenyl or benzyl which may be substituted with one or two groups of R6; wherein R5 is selected from the group consisting of halogen, —RNH 2 , —RNH 2 R, —ROH, —NO 2 , —OCH 3 , —OCH 2 CH 3 , and —OCH 2 CH 2 CH 3 ; and wherein R6 is selected from the group consisting of a straight or branched chain alkyl group having 1 to 4 carbons, halogen, —RNH 2 , —RNH 2 R, —ROH, —NO 2 , —OCH 3 , —OCH 2 CH 3 , —OCH 2 CH 2 CH 3 , —CH 2 Br, —CH 2 Cl, —CH 2 OH, —C(CH 3 ) 3 , —(CH 2 ) 2 0H, —(CH 2 ) 3 OH, —(CH 2 ) 4 OH, —CH 2 NH 2 , —(CH 2 ) 2 NH 2 , —(CH 2 ) 3 NH 2 , —(CH 2 ) 4 NH 2 , —(CH 2 ) 5 NH 2 , —CH 2 N(CH 3 ) 2 , —(CH 2 ) 2 N(CH 3 ) 2 , —(CH 2 ) 2 NH(CH 2 ) 2 OH, —(CH 2 ) 3 NH(CH 2 ) 2 OH, —(CH 2 ) 2 NHCH 2 OH, —(CH 2 ) 3 NHCH 2 OH, —CH 2 CH(CH 3 ) 2 , —CHCl 2 , —CH(CH 3 )Cl, —(CH 2 ) 2 Cl, —(CH 2 ) 3 Cl, —(CH 2 ) 3 Br, —(CH 2 ) 4 Br, and —(CH 2 ) 4 Cl. Chart 1. Activation of hTERT promoter-driven SEAP expression by c-Myc. About 1×10 7 hTERT-BJ1 cells were transfected with 13.5 μg each of plasmid pSEAP or pPhTERT-SEAP and of plasmid pMT2T or pMT2T-cMyc by electroporation. After 24 h, viable cells were harvested, and reinoculated at a density of 3×10 5 /mL, and the SEAP activity after 24 h at 37 □. The transfection efficiency of each experiment was determined by cotransfection with 1.5 μg of plasmid pCMVβ. The values were determined from three experiments. P<0.05 is presented by an asterisk.

  这项发明涉及新的蒽醌化合物，可用于治疗过敏、炎症症状、抗氧化、肿瘤病情、干细胞应用、组织工程学，用于治疗与年龄相关的组织退化、慢性高周转病的器官功能衰竭以及含有这种化合物的治疗性组合物。本发明的化合物是1,4-、1,5-和1,8-二官能蒽醌或其类似物。根据本发明的实践，提供了根据式I的双对称取代蒽醌化合物：其中R1、R2、R3和R4表示直链、氨基烷基氨基侧链或具有1至6个碳的支链烷基基团，可被一个或多个R5基团取代，或者R1、R2、R3和R4表示苯基或苄基，可被一个或两个R6基团取代；其中R5选自卤素、—RNH2、—RNH2R、—ROH、—NO2、—OCH3、—OCH2CH3和—OCH2CH2CH3组成的群；其中R6选自具有1至4个碳的直链或支链烷基基团、卤素、—RNH2、—RNH2R、—ROH、—NO2、—OCH3、—OCH2CH3、—OCH2CH2CH3、—CH2Br、—CH2Cl、—CH2OH、—C(CH3)3、—(CH2)20H、—(CH2)3OH、—(CH2)4OH、—CH2NH2、—(CH2)2NH2、—(CH2)3NH2、—(CH2)4NH2、—(CH2)5NH2、—CH2N(CH3)2、—(CH2)2N(CH3)2、—(CH2)2NH(CH2)2OH、—(CH2)3NH(CH2)2OH、—(CH2)2NHCH2OH、—(CH2)3NHCH2OH、—CH2CH(CH3)2、—CHCl2、—CH(CH3)Cl、—(CH2)2Cl、—(CH2)3Cl、—(CH2)3Br、—(CH2)4Br和—(CH2)4Cl。表1. c-Myc激活hTERT启动子驱动的SEAP表达。约1×107 hTERT-BJ1细胞通过电穿孔转染了13.5 μg的pSEAP或pPhTERT-SEAP质粒和pMT2T或pMT2T-cMyc质粒。24小时后，收集活细胞，并以3×105/mL的密度重新接种，37℃下培养24小时后测定SEAP活性。每次实验的转染效率通过与1.5 μg的pCMVβ质粒共转染确定。数值是根据三次实验确定的。P<0.05由星号表示。
• Limited play optical storage medium, method for making the same
  申请人：Sivakumar Krishnamoorthy

  公开号：US20050013232A1

  公开（公告）日：2005-01-20

  In one embodiment, a limited play optical storage medium for data comprises: a reflective layer, a control portion comprising an optically transparent polymeric resin and a light absorbing material, wherein the control portion has a light transmission of greater than or equal to about 70% at 650 nm, a curing index of greater than or equal to about 0.1 and a filtration index of greater than or equal to about 2.5, and wherein the light absorbing material has a minimum extinction coefficient (measured in CH 2 Cl 2 solution) at 600 nm of greater than or equal to 1,500 mol −1 ·cm −1 ·L, a maximum extinction coefficient (measured in CH 2 Cl 2 solution) at 650 nm of less than about 1,000 mol 1 ·cm −1 ·L, a ratio of extinction coefficient at 650 nm to 600 nm less than about 0.1, and a reactive layer disposed between the reflective layer and the control portion, wherein the reactive layer is designed to limit the time during which data on the medium (disposed on a side of the reactive layer opposite the control portion), can be accessed after exposure to oxygen.

  在一个实施方案中，一种有限播放数据的光学存储介质包括：反射层、由光学透明聚合树脂和光吸收材料组成的控制部分，其中控制部分在 650 纳米波长下的透光率大于或等于约 70%，固化指数大于或等于约 0.1，过滤指数大于或等于约 2.5，光吸收材料的最小消光系数（以 CH 2 Cl 2 溶液中测量）在 600 纳米波长处的最小消光系数大于或等于 1,500 mol -1 -厘米 -1 -L，最大消光系数（在 CH 2 Cl 2 溶液中）在 650 纳米波长处的最大消光系数小于约 1,000 mol 1 -厘米 -1 -在 650 纳米波长处的消光系数与 600 纳米波长处的消光系数之比小于约 0.1，以及设置在反射层和控制部分之间的反应层，其中反应层用于限制介质（设置在反应层与控制部分相对的一侧）上的数据在暴露于氧气后可被访问的时间。
• COLORED POLYMERIC RESIN COMPOSITION, ARTICLE MADE THEREFROM, AND METHOD FOR MAKING THE SAME
  申请人：GENERAL ELECTRIC COMPANY

  公开号：EP1646682A1

  公开（公告）日：2006-04-19
• LIMITED PLAY OPTICAL STORAGE MEDIUM, METHOD FOR MAKING THE SAME
  申请人：GENERAL ELECTRIC COMPANY

  公开号：EP1647011A1

  公开（公告）日：2006-04-19
• Colored polymeric resin composition, article made therefrom, and method for making the same
  申请人：Schottland Philippe

  公开号：US20050014878A1

  公开（公告）日：2005-01-20

  In one embodiment, a colored polymeric resin composition, comprises: a polymeric resin; and a 1,8-anthraquinone derivative having a purity of greater than or equal to about 90 wt % and having a Formula (VIII): wherein R 2 -R 7 are, individually, selected from the group consisting of a hydrogen atom, a hydroxyl group, an alkoxy group, an aryloxy group, an aliphatic group, an aromatic group, a heterocyclic group, a halogen atom, a cyano group, a nitro group, —COR 9 , —COOR 9 , —NR 9 R 10 , —NR 10 COR 11 , —NR 10 SO 2 R 11 , —CONR 9 R 10 , —CONHSO 2 R 11 , and —SO 2 NHCOR 11 ; in which R 9 and R 10 are, individually, selected from the group consisting of a hydrogen atom, an aliphatic group, an aromatic group, and a heterocyclic group; wherein R 11 is selected from the group consisting of an aliphatic group, an aromatic group, and a heterocyclic group; and wherein R is selected from the group consisting of hydrogen, an alkyl group containing 1 to 20 carbon atoms, a cycloalkyl group containing 3 to 20 carbon atoms, an allyl group containing 3 to 20 carbon atoms, a hydroxyl group, a 5-membered heterocyclic ring, and a 6-membered heterocyclic ring.