7-isopropoxy-6-methoxy-1-naphthylamine | 56517-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-isopropoxy-6-methoxy-1-naphthylamine
• 英文别名: 2-methoxy-3-isopropoxy-5-naphthylamine；5-Amino-2-methoxy-3-isopropoxy-naphthalin；6-Methoxy-7-propan-2-yloxynaphthalen-1-amine
• CAS: 56517-28-3
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: NNQROXJBOLABKV-UHFFFAOYSA-N

物化性质

• 熔点：
  88-89 °C (sublm)
• 沸点：
  379.8±27.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-isopropoxy-6-methoxy-1-naphthylamine 在 吡啶 、 sodium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.5h， 生成 N-(2-bromobenzyl)-7-isopropoxy-6-methoxy-N-methyl-1-naphthylamine
  参考文献：
  名称：

  Novel Synthesis of a New Skeletal Compound Benzonaphthazepine by Regioselective C-H Activation Utilizing the Intramolecular Coordination of an Amine to Pd

  摘要：

  本研究描述了利用钯试剂从 N-溴苄基萘胺合成新骨架化合物苯并萘氮杂卓的新方法。在使用钯试剂对 N-溴苄基萘胺进行双芳基偶联反应时，苄基氨基与钯的分子内配位会导致相对于萘环上胺基的周位上的 C-H 发生区域选择性活化，从而以良好甚至极佳的收率生成苯并萘氮杂卓。萘环 C7 处取代基的体积会影响双芳基偶联反应的区域选择性。

  DOI：

  10.1055/s-2004-822371
• 作为产物：
  描述：

  6-Methoxy-1-nitro-7-propan-2-yloxynaphthalene 以99%的产率得到
  参考文献：
  名称：

  STERMITZ F. R.; GILLESPIE J. P.; AMOROS L. G.; ROMERO R.; STERMITZ T. A., J. MED. CHEM. , 1975, 18, NO 7, 708-713

  摘要：

  DOI：

文献信息

• Process for preparing benzo\x9bc!phenanthridinium derivatives, novel
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：US05747502A1

  公开（公告）日：1998-05-05

  The present invention relates to benzo\x9bc!phenanthridinium derivative of the general formula A: ##STR1## 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.sup.- represents an acid residue or a hydrogen acid residue, and R represents a lower alkyl group, and a process for preparing such derivatives. The compounds exhibit both potent antitumor activity and platelet aggregation inhibition activity, and are expected to be useful for the treatment of tumors. The process has good reproducibility and may be effected under moderate conditions, and therefore the process is practically useful. In addition, hydrogen salts of the present compounds have an enhanced stability, which is an advantage in formulating the same into pharmaceutical preparations.

  本发明涉及一般式A的苯并[中文字符]菲啉衍生物：其中M和N分别代表一个羟基或较低的烷氧基团，或者M和N同时代表一个氢原子或一起形成一个亚甲二氧基基团，X.sup.-代表一个酸残基或一个氢酸残基，R代表一个较低的烷基团，以及制备这种衍生物的方法。这些化合物表现出强大的抗肿瘤活性和抑制血小板聚集活性，预计对肿瘤治疗有用。该方法具有良好的可重复性，可以在适中条件下实施，因此该方法在实际中是有用的。此外，本化合物的氢盐具有增强的稳定性，这是将其配制成药物制剂的优势。
• Synthesis and biological activity of some antitumor benzophenanthridinium salts
  作者：Frank R. Stermitz、John P. Gillespie、Luis G. Amoros、Raquel Romero、Thomas A. Stermitz、Kenneth A. Larson、Steven Earl、James E. Ogg

  DOI：10.1021/jm00241a014

  日期：1975.7

  A facil synthesis of benzophenanthridinium salts has been developed and used for preparing a number of these compounds. The antitumor activities in mouse leukemia L1210 (LE) and P388 (PS) were determined as well as some selected antimicrobial activities. Although antitumor activity was exhibited by several of the derivatives, none was as active as the naturally occurring alkaloid fagaronine. Fagaronine

  已经开发了苯并菲鎓盐的简便合成方法，并将其用于制备许多这些化合物。确定了小鼠白血病L1210（LE）和P388（PS）中的抗肿瘤活性以及一些选定的抗微生物活性。尽管几种衍生物均表现出抗肿瘤活性，但没有一种活性与天然生物碱法加宁一样。通过改进的方法，可制成合成黄花碱。讨论了抗肿瘤苯并菲鎓盐之间的一些构效关系。
• 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。
• Benzo[C]phenanthridinium derivatives
  申请人：NIPPON KAYAKU KABUSHIKI KAISHA

  公开号：EP0487930B1

  公开（公告）日：1999-03-24
• US5747502A
  申请人：——

  公开号：US5747502A

  公开（公告）日：1998-05-05