1-(2-carboxyphenyl)-2-nitro-6,7-dimethoxy-3-methyl-3,4-dihydronaphthalene | 1315172-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-carboxyphenyl)-2-nitro-6,7-dimethoxy-3-methyl-3,4-dihydronaphthalene
• 英文别名: 2-(6,7-Dimethoxy-3-methyl-2-nitro-3,4-dihydronaphthalen-1-yl)benzoic acid
• CAS: 1315172-44-1
• 化学式: C₂₀H₁₉NO₆
• 分子量: 369.374
• InChiKey: PEHKXDIZMQALLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2-carboxyphenyl)-2-nitro-6,7-dimethoxy-3-methyl-3,4-dihydronaphthalene 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 生成 (+/-)-trans-1-(2-carboxyphenyl)-2-nitro-6,7-dimethoxy-3-methyl-3,4-dihydronaphthalene 、 (+/-)-trans-1-(2-carboxyphenyl)-2-nitro-6,7-dimethoxy-3-methyl-3,4-dihydronaphthalene
  参考文献：
  名称：

  Probing the Steric Space at the Floor of the D₁ Dopamine Receptor Orthosteric Binding Domain: 7α-, 7β-, 8α-, and 8β-Methyl Substituted Dihydrexidine Analogues

  摘要：

  To probe the space at the floor of the orthosteric ligand binding site in the dopamine D-1 receptor, four methylated analogues of dihydrexidine (DHX) were synthesized with substitutions at the 7 and 8 positions. The 8 alpha-axial, 8 beta-equatorial, and 7 alpha-equatorial were synthesized by photochemical cyclization of appropriately substituted N-benzoyl enamines, and the 7 beta-axial analogue was prepared by an intramolecular Henry reaction. All of the methylated analogues displayed losses in affinity when compared to DHX (20 nM): 8 beta-Me-ax-DHX (270 nM), 8 alpha-Me-eq-DHX (920 nM), 7 beta-Me-eq-DHX (6540 nM), and 7 alpha-Me-ax-DFLX (>10000 nM). Molecular modeling studies suggest that although the disruption of an aromatic interaction between Phe203(54.7) and Phe288(6.51) is the cause for the 14-fold loss in affinity associated with 8 beta-axial substitution, unfavorable steric interactions with Ser107(3.36) result in the more dramatic decreases in binding affinity suffered by the rest of the analogues.

  DOI：

  10.1021/jm200334c
• 作为产物：
  描述：

  Methyl 2-[4,5-dimethoxy-2-(2-methyl-3-nitropropyl)benzoyl]benzoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以96.9%的产率得到1-(2-carboxyphenyl)-2-nitro-6,7-dimethoxy-3-methyl-3,4-dihydronaphthalene
  参考文献：
  名称：

  Probing the Steric Space at the Floor of the D₁ Dopamine Receptor Orthosteric Binding Domain: 7α-, 7β-, 8α-, and 8β-Methyl Substituted Dihydrexidine Analogues

  摘要：

  To probe the space at the floor of the orthosteric ligand binding site in the dopamine D-1 receptor, four methylated analogues of dihydrexidine (DHX) were synthesized with substitutions at the 7 and 8 positions. The 8 alpha-axial, 8 beta-equatorial, and 7 alpha-equatorial were synthesized by photochemical cyclization of appropriately substituted N-benzoyl enamines, and the 7 beta-axial analogue was prepared by an intramolecular Henry reaction. All of the methylated analogues displayed losses in affinity when compared to DHX (20 nM): 8 beta-Me-ax-DHX (270 nM), 8 alpha-Me-eq-DHX (920 nM), 7 beta-Me-eq-DHX (6540 nM), and 7 alpha-Me-ax-DFLX (>10000 nM). Molecular modeling studies suggest that although the disruption of an aromatic interaction between Phe203(54.7) and Phe288(6.51) is the cause for the 14-fold loss in affinity associated with 8 beta-axial substitution, unfavorable steric interactions with Ser107(3.36) result in the more dramatic decreases in binding affinity suffered by the rest of the analogues.

  DOI：

  10.1021/jm200334c