(Z)-3-(2-Hydroxy-naphthalen-1-ylamino)-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester | 216501-07-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-3-(2-Hydroxy-naphthalen-1-ylamino)-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester
• 英文别名: ethyl 3-[(2-hydroxynaphthalen-1-yl)amino]-2-(2,3,4,5-tetrafluorobenzoyl)prop-2-enoate
• CAS: 216501-07-4
• 化学式: C₂₂H₁₅F₄NO₄
• 分子量: 433.359
• InChiKey: ZVBMYQRLTPCLEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-(2-Hydroxy-naphthalen-1-ylamino)-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester 在 吡啶 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 60.75h， 生成 Ethyl 15-fluoro-14-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]-18-oxo-12-oxa-1-azapentacyclo[11.7.1.02,11.03,8.017,21]henicosa-2(11),3,5,7,9,13(21),14,16,19-nonaene-19-carboxylate
  参考文献：
  名称：

  Design of New Topoisomerase II Inhibitors Based upon a Quinobenzoxazine Self-Assembly Model

  摘要：

  A new class of pyridobenzophenoxazine compounds has been developed as topoisomerase II inhibitors for anticancer chemotherapy. These compounds were designed based on a proposed model of a quinobenzoxazine self-assembly complex on DNA. They showed excellent inhibitory effects on several tumor cell lines with nanomolar IC50 values. Their cytotoxic potency correlates with their ability to unwind DNA and inhibit topoisomerase II.

  DOI：

  10.1021/jm980265c
• 作为产物：
  描述：

  左氧氟单酯 在 吡啶 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (Z)-3-(2-Hydroxy-naphthalen-1-ylamino)-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester
  参考文献：
  名称：

  Design of New Topoisomerase II Inhibitors Based upon a Quinobenzoxazine Self-Assembly Model

  摘要：

  A new class of pyridobenzophenoxazine compounds has been developed as topoisomerase II inhibitors for anticancer chemotherapy. These compounds were designed based on a proposed model of a quinobenzoxazine self-assembly complex on DNA. They showed excellent inhibitory effects on several tumor cell lines with nanomolar IC50 values. Their cytotoxic potency correlates with their ability to unwind DNA and inhibit topoisomerase II.

  DOI：

  10.1021/jm980265c

文献信息

• Synthesis of quinobenzoxazine analogues with topoisomerase II and quadruplex interactions for use as antineoplastic agents
  申请人：Board of Regents, The University of Texas System

  公开号：US06528517B1

  公开（公告）日：2003-03-04

  The present invention discloses a novel quinobenzoxazine self-assembly complex on DNA and on the topoisomerase II-DNA complex. The related model is used to design a new series of quinobenzoxazines, pyridobenzophenoxazines, pyrridonaphthophenoxazines, and other related compounds that may exhibit anticancer or antibiotic activity. The anticancer activity of these compounds is thought to operate via stabilization of the topoisomerase II-DNA complex and/or interaction with G-quadruplexes, while the antibiotic activity of these compounds derives from their ability to inhibit gyrase, the bacterial type II topoisomerase.

  本发明揭示了一种新型的喹诺苯并噁嗪自组装复合物，可作用于DNA和拓扑异构酶II-DNA复合物。相关模型用于设计一系列新的喹诺苯并噁嗪、吡啶苯并苯噁嗪、吡啶萘苯噁嗪和其他相关化合物，这些化合物可能表现出抗癌或抗生素活性。这些化合物的抗癌活性被认为是通过稳定拓扑异构酶II-DNA复合物和/或与G四链体相互作用来发挥作用的，而这些化合物的抗生素活性则源于它们抑制细菌类型II拓扑异构酶酶的能力。