N-(10,11-dihydro-5H-dibenzocyclohepten-5-yl)phthalimide | 59631-14-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: N-(10,11-dihydro-5H-dibenzocyclohepten-5-yl)phthalimide
• 英文别名: N-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-phthalimide；2-(2-Tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenyl)isoindole-1,3-dione
• CAS: 59631-14-0
• 化学式: C₂₃H₁₇NO₂
• 分子量: 339.393
• InChiKey: GUOXEFWVQACCIM-UHFFFAOYSA-N

物化性质

• 沸点：
  498.5±34.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(10,11-dihydro-5H-dibenzocyclohepten-5-yl)phthalimide 在 一水合肼 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.0h， 以22%的产率得到5-氨基二苯并环庚烷
  参考文献：
  名称：

  Design, Synthesis, and in Vitro Activity of Catamphiphilic Reverters of Multidrug Resistance:  Discovery of a Selective, Highly Efficacious Chemosensitizer with Potency in the Nanomolar Range

  摘要：

  On the basis of the results obtained in previous research, three series of compounds (A-C), derived from verapamil, were designed and synthesized to obtain drugs able to revert multidrug resistance (MDR), an acquired resistance that frequently impairs cancer chemotherapy. The ability of the obtained compounds to revert MDR was evaluated on anthracycline-resistant erythroleukemia K 562 cells, measuring the uptake of THP-adriamycin (pirarubicin) by continuous spectrofluorometric monitoring of the decrease of the fluorescence signal of the anthracycline at 590 nm (lambda(ex) = 480 nm), after incubation with cells. Cardiovascular activity, which is responsible for unwanted side effects, was also evaluated. The results obtained show that many of the compounds studied are potent reverters of MDR and are endowed with reduced cardiovascular activity. One of the compounds (7, MM36) presents a pharmacological profile (unprecedented nanomolar potency, high reversal of MDR, low cardiovascular activity) that makes it a promising drug candidate to treat MDR and a useful tool for studying P-glycoprotein.

  DOI：

  10.1021/jm980440p
• 作为产物：
  描述：

  potassium phtalimide 、 二苯并环庚烯酮基氯 在 18-冠醚-6 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以99%的产率得到N-(10,11-dihydro-5H-dibenzocyclohepten-5-yl)phthalimide
  参考文献：
  名称：

  Design, Synthesis, and in Vitro Activity of Catamphiphilic Reverters of Multidrug Resistance:  Discovery of a Selective, Highly Efficacious Chemosensitizer with Potency in the Nanomolar Range

  摘要：

  On the basis of the results obtained in previous research, three series of compounds (A-C), derived from verapamil, were designed and synthesized to obtain drugs able to revert multidrug resistance (MDR), an acquired resistance that frequently impairs cancer chemotherapy. The ability of the obtained compounds to revert MDR was evaluated on anthracycline-resistant erythroleukemia K 562 cells, measuring the uptake of THP-adriamycin (pirarubicin) by continuous spectrofluorometric monitoring of the decrease of the fluorescence signal of the anthracycline at 590 nm (lambda(ex) = 480 nm), after incubation with cells. Cardiovascular activity, which is responsible for unwanted side effects, was also evaluated. The results obtained show that many of the compounds studied are potent reverters of MDR and are endowed with reduced cardiovascular activity. One of the compounds (7, MM36) presents a pharmacological profile (unprecedented nanomolar potency, high reversal of MDR, low cardiovascular activity) that makes it a promising drug candidate to treat MDR and a useful tool for studying P-glycoprotein.

  DOI：

  10.1021/jm980440p

文献信息

• Synthesis and evaluation of novel phthalimide mimics as anti-angiogenic
  申请人：——

  公开号：US20040122030A1

  公开（公告）日：2004-06-24

  The present invention is directed to novel thalidomide derivative compounds that have activity as anti-angiogenic compounds. More particularly the compounds have the general structure: where R 1 is selected from the group consisting of H, halo, alkyl, haloalkyl, —NH 2 , hydroxy and alkoxy; R 2 is selected from the group consisting of optionally substituted bicyclic, optionally substituted aryl, and R 6 is H, or C 1 -C 8 alkyl; R 19 is optionally substituted aryl; and m is 0-6. 1

  本发明涉及具有抗血管生成活性的新型沙利度胺衍生物化合物。更具体地说，这些化合物具有以下一般结构： 其中 R 1 选自由 H、卤素、烷基、卤代烷基、-NH 2 、羟基和烷氧基 2 选自由取代的双环化合物、自由取代的芳基化合物和 R 6 是 H 或 C 1 -C 8 烷基；R 19 是任选取代的芳基；m 是 0-6。 1
• US7893071B2
  申请人：——

  公开号：US7893071B2

  公开（公告）日：2011-02-22
• Design, Synthesis, and in Vitro Activity of Catamphiphilic Reverters of Multidrug Resistance:  Discovery of a Selective, Highly Efficacious Chemosensitizer with Potency in the Nanomolar Range
  作者：Elisabetta Teodori、Silvia Dei、Patricia Quidu、Roberta Budriesi、Alberto Chiarini、Arlette Garnier-Suillerot、Fulvio Gualtieri、Dina Manetti、Maria Novella Romanelli、Serena Scapecchi

  DOI：10.1021/jm980440p

  日期：1999.5.1

  On the basis of the results obtained in previous research, three series of compounds (A-C), derived from verapamil, were designed and synthesized to obtain drugs able to revert multidrug resistance (MDR), an acquired resistance that frequently impairs cancer chemotherapy. The ability of the obtained compounds to revert MDR was evaluated on anthracycline-resistant erythroleukemia K 562 cells, measuring the uptake of THP-adriamycin (pirarubicin) by continuous spectrofluorometric monitoring of the decrease of the fluorescence signal of the anthracycline at 590 nm (lambda(ex) = 480 nm), after incubation with cells. Cardiovascular activity, which is responsible for unwanted side effects, was also evaluated. The results obtained show that many of the compounds studied are potent reverters of MDR and are endowed with reduced cardiovascular activity. One of the compounds (7, MM36) presents a pharmacological profile (unprecedented nanomolar potency, high reversal of MDR, low cardiovascular activity) that makes it a promising drug candidate to treat MDR and a useful tool for studying P-glycoprotein.