7-amino-1,2,3,4-tetrahydroanthracene | 160555-08-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 7-amino-1,2,3,4-tetrahydroanthracene
• 英文别名: 5,6,7,8-tetrahydroanthracen-2-amine
• CAS: 160555-08-8
• 化学式: C₁₄H₁₅N
• 分子量: 197.28
• InChiKey: QSICEHYCBQABMY-UHFFFAOYSA-N

物化性质

• 沸点：
  396.2±11.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-amino-1,2,3,4-tetrahydroanthracene 在 二硫化碳 、 sodium hydroxide 、 三氯化铝 、 双氧水 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 9.0h， 生成 2-acetylaminoanthracene-1,9-dicarboxylic acid anhydride
  参考文献：
  名称：

  Analogues of Amonafide and Azonafide with Novel Ring Systems

  摘要：

  Three new types of amonafide and azonafide analogues were synthesized and screened in a panel of human solid tumor cells and murine L1210 leukemia cells. The structural types included tetrahydroazonafides, which have the naphthalene chromophore of amonafide within the anthracene nucleus of azonafide; phenanthrene analogues, in which the linear anthracene nucleus is replaced by the bent phenanthrene nucleus; and azaphenanthrenes. The tetrahydroazonafides were generally intermediate in potencies between amonafide and azonafide against the tumor cells, but some of them had high potencies against the L1210 cells and were more potent against the MDR strain than the sensitive strain. The phenanthrene and azaphenanthrene analogues showed no improvement on the potencies of the anthracenes.

  DOI：

  10.1021/jm9905817
• 作为产物：
  描述：

  2-氨基蒽醌 在 氨 、 水 、 氢气 、 镍 、 萘烷 、 锌 作用下， 生成 7-amino-1,2,3,4-tetrahydroanthracene
  参考文献：
  名称：

  v. Braun; Bayer, Justus Liebigs Annalen der Chemie, 1929, vol. 472, p. 104

  摘要：

  DOI：

文献信息

• 2-[2‘-(Dimethylamino)ethyl]-1,2-dihydro-3<i>H</i>-dibenz[<i>de</i>,<i>h</i>]isoquinoline-1,3-diones with Substituents at Positions 4, 8, 9, 10, and 11. Synthesis, Antitumor Activity, and Quantitative Structure−Activity Relationships
  作者：Salah M. Sami、Robert T. Dorr、David S. Alberts、Anikó M. Sólyom、William A. Remers

  DOI：10.1021/jm960623g

  日期：1996.1.1

  New 2-[2'-(dimethylamino)ethyl]-1,2-dihydro-3H-dibenz[de,h]isoquinoline-1,3- diones with substituents at the 4, 8, 9, 10, and 11 positions were synthesized. Diazonium salts prepared from aminoazonafides were key intermediates for many of the analogues. Six of the new compounds were more potent than azonafide in a panel of tumor cells including human melanoma and ovarian carcinoma and murine L1210 leukemias

  新的2- [2'-（二甲基氨基）乙基] -1,2-二氢-3H-二苯并[de，h]异喹啉-1,3-二酮在4、8、9、10和11位带有取代基合成的。由氨基氮杂胺制备的重氮盐是许多类似物的关键中间体。在包括人类黑素瘤和卵巢癌以及鼠L1210白血病在内的一系列肿瘤细胞中，六种新化合物比阿扎那非更有效。这些化合物中的三种，即10-OCH3、10-OC2H5和10-F类似物，其心脏毒性与肿瘤细胞毒性的比率比阿扎那非好。八种化合物对MDR L1210白血病没有交叉耐药性，而且10-CN类似物对实体瘤细胞的作用比对白血病细胞的作用更强。9-OH，10-CN，和10-F类似物对MFX 7乳腺癌和WiDr结肠癌以及敏感性A599肺癌的敏感和耐药细胞系均具有高效力。在小鼠的P388白血病中，10-Cl，10-NH2和10-CN类似物优于阿扎那非的优势是显而易见的，在这种测定中，10-CN类似物比阿霉素更有效。定
• 1, 2-dihydro-3H-dibenzisoquinoline-1,3-dione anticancer agents
  申请人：Research Corporation Technologies, Inc.

  公开号：US05635506A1

  公开（公告）日：1997-06-03

  This invention relates to a compound useful for the treatment of tumors having the formula: ##STR1##

  这项发明涉及一种用于治疗具有以下化学式的肿瘤的化合物：##STR1##
• Aerobic Oxidative Homocoupling of Aryl Amines Using Heterogeneous Rhodium Catalysts
  作者：Kenji Matsumoto、Kento Dougomori、Shohei Tachikawa、Takanori Ishii、Mitsuru Shindo

  DOI：10.1021/ol502197p

  日期：2014.9.19

  The first heterogeneous catalyzed oxidative coupling of aryl amines is reported. Aryl amines were dimerized at room temperature under air using a heterogeneous Rh/C catalyst in the presence of acids. By choosing a suitable acidic solvent, biaryl compounds and carbazoles were selectively prepared in good yields. This reaction is operationally simple and provides an efficient synthetic methodology for the preparation of biaryl diamines via oxidative C-H activation.
• Amino-Substituted 2-[2-(Dimethylamino)ethyl]-1,2-dihydro-3H-dibenz[de,h]isoquinoline-1,3-diones. Synthesis, Antitumor Activity, and Quantitative Structure-Activity Relationship
  作者：Salah M. Sami、Robert T. Dorr、Aniko M. Solyom、David S. Alberts、William A. Remers

  DOI：10.1021/jm00006a018

  日期：1995.3

  Sets of 2-[2'-(dimethylamino)ethyl]-1,2-dihydro-3H-dibenz[de,h]isoquinoline-1,3-diones with amino and actylamino groups at each of the eight positions on the anthracene nucleus were synthesized from appropriately substituted anthracenes. Their evaluation in in vitro antitumor and cardiotoxicity assays revealed a very strong dependence of potency on the position of substitution. Certain compounds, including the 4-, 5-, 7-, and 9-amino derivatives, showed significantly higher potency than the unsubstituted parent compound, azonafide. Among them, 7-aminoazonafide had low cardiotoxicity relative to cytotoxicity. In general, the acetylamino analogues were less potent than the amino derivatives against tumor cells and neonatal rat heart myocytes; however, 5-(acetylamino)azonafide was highly cardiotoxic. 9-Aminoazonafide was more efficacious than azonafide or amonafide against P388 leukemia in mice. Statistically significant correlations were made between the ability of amino analogues to increase the transition melt temperature (Delta T-m) of DNA and their potency against solid tumors, leukemia cells, or cardiac myocytes.
• 1,2 DIHYDRO-3-H-DIBENZ(de,h) ISOQUINOLINE 1,3 DIONE AND THEIR USE AS ANTICANCER AGENTS
  申请人：RESEARCH CORPORATION TECHNOLOGIES

  公开号：EP0660824A1

  公开（公告）日：1995-07-05