NK109 | 98325-17-8

• 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: NK109
• 英文别名: 1-hydroxy-2-methoxy-12-methyl-[1,3]dioxolo[4′,5′:4,5]-benzo[1,2-c]phenanthridin-12-ium chloride；Benzophenanthridinium；2-methoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium-1-ol;chloride
• CAS: 98325-17-8
• 化学式: C₂₀H₁₆NO₄*Cl
• 分子量: 369.804
• InChiKey: CUXBKFBSLWHZGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  48
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  氧基白屈菜季铵碱 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 碘 、 potassium acetate 、 对甲苯磺酸 、 silver(I) chloride 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 3.0h， 生成 NK109
  参考文献：
  名称：

  Hanaoka, Miyoji; Yamagishi, Hiroshi; Mukai, Chisato, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 4, p. 1763 - 1765

  摘要：

  DOI：

文献信息

• Process for preparing benzo[C]phenanthridinium derivatives, and novel compounds prepared by said process
  申请人：NIPPON KAYAKU KABUSHIKI KAISHA

  公开号：EP0487930A1

  公开（公告）日：1992-06-03

  The present invention relates to a process for preparing benzo[c]phenanthridinium derivatives of the general formula A: wherein M and N individually represent a hydroxyl or lower alkoxy group, or M and N simultaneously represent a hydrogen atom or together form a methylenedioxy group, X⁻ represents an acid residue or a hydrogen acid residue, and R represents a lower alkyl group. This process has good reproducibility and may be effected under moderate conditions, and therefore the process is practically useful. Also, it has been found that certain novel benzo[c]phenanthridinium derivatives, prepared by the present process, have not only an antitumor activity but also an inhibition activity on blood platelet aggregation. In addition, hydrogen salts of the present compounds have an enhanced stability, which is an advantage in formulating into phamaceutical preparations.

  本发明涉及一种制备通式 A 的苯并[c]菲啶鎓衍生物的工艺： 其中 M 和 N 分别代表羟基或低级烷氧基，或 M 和 N 同时代表氢原子或共同形成亚甲基二氧基，X- 代表酸残基或氢酸残基，R 代表低级烷基。该工艺具有良好的重现性，可在中等条件下进行，因此该工艺非常实用。此外，还发现通过本工艺制备的某些新型苯并[c]菲啶衍生物不仅具有抗肿瘤活性，还具有抑制血小板聚集的活性。此外，本发明化合物的氢盐具有更高的稳定性，这在配制成医药制剂方面具有优势。
• NOVEL PHENANETHRIDINIUM DERIVATIVES
  申请人：NIPPON KAYAKU KABUSHIKI KAISHA

  公开号：EP0947514A1

  公开（公告）日：1999-10-06

  A novel phenanthridinium derivative represented by general formula (A): wherein R1 is a substituted or unsubstituted lower aliphatic hydrocarbon group; R is an aliphatic hydrocarbon chain having 2 to 6 carbon atoms which may optionally be substituted with a substituent selected from the group consisting of a lower alkyl group, a halogen and a hydroxy group; each of Y and Z independently represents a hydrogen, a hydroxy or a lower alkoxy group; or Y and Z are combined together to form methylenedioxy or a phenyl ring; and, X- is an acid residue or a hydrogen acid residue, exhibits an antitumor activity and has resistance to chemical reduction as well as biological metabolic reactions and is thus advantageous for use as a medicine.

  通式(A)代表的新型菲啶衍生物： 其中 R1 是取代或未取代的低级脂肪族烃基；R 是具有 2 至 6 个碳原子的脂肪族烃链，可任选被选自低级烷基、卤素和羟基的取代基取代；Y 和 Z 各自独立地代表氢、羟基或低级烷氧基；或 Y 和 Z 结合在一起形成亚甲基二氧基或苯基环； X-是酸残基或氢酸残基，具有抗肿瘤活性，耐化学还原和生物代谢反应，因此有利于用作药物。
• Benzo[C]phenanthridinium derivatives
  申请人：NIPPON KAYAKU KABUSHIKI KAISHA

  公开号：EP0487930B1

  公开（公告）日：1999-03-24
• Revision of the Structure of Fagaridine Based on the Comparison of UV and NMR Data of Synthetic Compounds
  作者：Takeshi Nakanishi、Masanobu Suzuki

  DOI：10.1021/np980193s

  日期：1998.10.1

  Fagaridine is a quaternary benzo[c]phenanthridine alkaloid, originally isolated from Fagara xanthoxyloides in 1973. The assigned structure of this alkaloid was 7-hydroxy-8-methoxy-5-methyl-2,3-(methylenedioxy)-benzo[c]phenanthridinium (1). We have synthesized this compound, coded NK109, aiming at a practical antitumor drug, and during synthetic studies we questioned the original assigned structure. Thus, we synthesized 8-hydroxy-7-methoxy-5-methyl-2,3-(methylenedioxy)benzo[c]phenanthridinium (2), isomer of the assigned structure, and compared the spectroscopic data of both 1 and 2. The NMR data of 1 and 2 were very similar, but the UV spectra were completely different. The UV data for fagaridine agreed with these for 2; consequently, the true structure of fagaridine is 2, not 1.
• Antitumor agent
  申请人：NIPPON KAYAKU KABUSHIKI KAISHA

  公开号：EP0432630B1

  公开（公告）日：1994-03-16