benzo[h]quinoline-6,7-dicarboxylic acid anhydride | 51301-38-3

• 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: benzo[h]quinoline-6,7-dicarboxylic acid anhydride
• 英文别名: Pyrido<2,3-c>naphthalin-1,8-dicarbonsaeurehydrazid；isochromeno[4,5-gh]isoquinoline-4,6-dione；Benzo[h]chinolin-6,7-dicarbonsaeure-anhydrid；5-Azaphenanthrene-1,10-dicarboxylic anhydride；11-oxa-3-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1,3,5,7,9(17),13,15-heptaene-10,12-dione
• CAS: 51301-38-3
• 化学式: C₁₅H₇NO₃
• 分子量: 249.225
• InChiKey: LJUBSQKPNGFPQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzo[h]quinoline-6,7-dicarboxylic acid anhydride 在 硫酸 、 硝酸 作用下， 生成 2-Nitro-5-oxa-11-aza-benzo[de]anthracene-4,6-dione
  参考文献：
  名称：

  The synthesis and antitumor evaluation of unsymmetrical bis-imides

  摘要：

  Unsymmetrical bis-imides 1 were synthesized and evaluated as potential antitumor agents. These novel bis-imides were assessed using three criteria: in vitro cytotoxicity (L1210), in vitro DNA binding, and in vivo studies with human tumor xenografts in mice. These studies identified DMP 315 as a potent, water soluble antitumor agent. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(96)00591-4
• 作为产物：
  描述：

  1,2-dihydroindeno[1,7-gh]quinoline 在 sodium dichromate 、 溶剂黄146 作用下， 反应 4.0h， 以82%的产率得到benzo[h]quinoline-6,7-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

文献信息

• Polycyclic and heterocyclic chromophores for bis-imide tumoricidals
  申请人：The Du Pont Merck Pharmaceutical Company

  公开号：US05416089A1

  公开（公告）日：1995-05-16

  Anticancer compounds of formula I: ##STR1## and pharmaceutically acceptable salts thereof, wherein: R.sup.1, R.sup.2 and R.sup.3 are independently selected H, CH.sub.3, NH.sub.2, NO.sub.2, and CN; R.sup.9 and R.sup.10 are H or alkyl or halo, X.sup.1 and Y.sup.1 or X.sup.2 and Y.sup.2, when present, join together to form, independently, a six membered 1N heterocycle substituted with 1-2 R.sup.3 ; or the group: ##STR2## wherein one of W or Z is C.dbd.O and the other is C.dbd.O, NH, S or O; or when X.sup.2 and Y.sup.2 are not joined together and when R.sup.2 is in the 4-position, then X.sup.2 and R.sup.2 may join together to form an ethylene bridge; are disclosed.

  公式I的抗癌化合物：##STR1##及其药学上可接受的盐，其中：R.sup.1、R.sup.2和R.sup.3独立选择H、CH.sub.3、NH.sub.2、NO.sub.2和CN；R.sup.9和R.sup.10为H或烷基或卤素，当存在X.sup.1和Y.sup.1或X.sup.2和Y.sup.2时，它们独立地结合在一起形成一个六元1N杂环，被1-2个R.sup.3取代；或者该基团：##STR2## 其中W或Z之一为C.dbd.O，另一个为C.dbd.O、NH、S或O；或者当X.sup.2和Y.sup.2没有结合在一起且R.sup.2在4位时，那么X.sup.2和R.sup.2可以结合在一起形成一个乙烯桥。
• Zinke; Raith, Monatshefte fur Chemie, 1919, vol. 40, p. 273
  作者：Zinke、Raith

  DOI：——

  日期：——
• Stewart, Journal of the Chemical Society, 1925, vol. 127, p. 1332
  作者：Stewart

  DOI：——

  日期：——
• Zincke; Raith, Monatshefte fur Chemie, 1919, vol. 40, p. 275
  作者：Zincke、Raith

  DOI：——

  日期：——
• US5416089A
  申请人：——

  公开号：US5416089A

  公开（公告）日：1995-05-16