6-Amino-2,3-dimethoxy-naphthalin | 56517-29-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-Amino-2,3-dimethoxy-naphthalin
• 英文别名: 2-Naphthalenamine, 6,7-dimethoxy-；6,7-dimethoxynaphthalen-2-amine
• CAS: 56517-29-4
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: JQGSFVRQRHRJRX-UHFFFAOYSA-N

物化性质

• 熔点：
  202-203 °C (sublm)
• 沸点：
  368.2±22.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  6-Amino-2,3-dimethoxy-naphthalin 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel inosine 5′-monophosphate dehydrogenase (IMPDH) inhibitors

  摘要：

  This study is based on our attempts to further explore the structure-activity relationship (SAR) of VX-148 (3) in an attempt to identify inosine 5'-mono-phosphate dehydrogenase (IMPDH) inhibitors superior to mycophenolic acid. A five-point pharmacophore developed using structurally diverse, known IMPDH inhibitors guided further design of novel analogs of 3. Several conventional as well as novel medicinal chemistry strategies were tried. The combined structure-and ligand-based approaches culminated in a few analogs with either retained or slightly higher potency. The compounds which retained the potency were also checked for their ability to inhibit human peripheral blood mononuclear cells proliferation. This study illuminates the stringent structural requirements and strict SAR for IMPDH II inhibition.

  DOI：

  10.3109/14756366.2013.793184
• 作为产物：
  描述：

  6-Nitro-2,3-dimethoxy-naphthalin 生成 6-Amino-2,3-dimethoxy-naphthalin
  参考文献：
  名称：

  一些抗肿瘤二苯并菲鎓盐的合成和生物活性。

  摘要：

  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。

  DOI：

  10.1021/jm00241a014

文献信息

• Design, synthesis and biological evaluation of novel inosine 5′-monophosphate dehydrogenase (IMPDH) inhibitors
  作者：Torsten Dunkern、Sunil Chavan、Digambar Bankar、Anuja Patil、Pritee Kulkarni、Prashant S. Kharkar、Arati Prabhu、Heike Goebel、Edith Rolser、Waltraud Burckhard-Boer、Premkumar Arumugam、Mahindra T. Makhija

  DOI：10.3109/14756366.2013.793184

  日期：2014.6.1

  This study is based on our attempts to further explore the structure-activity relationship (SAR) of VX-148 (3) in an attempt to identify inosine 5'-mono-phosphate dehydrogenase (IMPDH) inhibitors superior to mycophenolic acid. A five-point pharmacophore developed using structurally diverse, known IMPDH inhibitors guided further design of novel analogs of 3. Several conventional as well as novel medicinal chemistry strategies were tried. The combined structure-and ligand-based approaches culminated in a few analogs with either retained or slightly higher potency. The compounds which retained the potency were also checked for their ability to inhibit human peripheral blood mononuclear cells proliferation. This study illuminates the stringent structural requirements and strict SAR for IMPDH II inhibition.
• 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。