methyl 6-nitro-1-naphthoate | 59866-99-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 6-nitro-1-naphthoate
• 英文别名: 6-Nitro-naphthoesaeure-1-methylester；methyl 6-nitronaphthalene-1-carboxylate
• CAS: 59866-99-8
• 化学式: C₁₂H₉NO₄
• 分子量: 231.208
• InChiKey: UWOUNIVGBDIJLD-UHFFFAOYSA-N

物化性质

• 沸点：
  389.4±15.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 6-nitro-1-naphthoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到6-nitro-1-naphthoic acid
  参考文献：
  名称：

  (Aminoalkyl)indole Isothiocyanates as Potential Electrophilic Affinity Ligands for the Brain Cannabinoid Receptor

  摘要：

  A series of (aminoalkyl)indole compounds, naphthalene analogs of pravadoline (1), has been shown to exhibit cannabinoid agonist activities such as antinociception in animals, inhibition of adenylate cyclase in brain membranes, and binding to the cannabinoid receptor. These pravadoline analogs were selected for the preparation of potential electrophilic affinity ligands based on the synthesis of isothiocyanate derivatives. One isothiocyanatonaphthalene derivative (8) displaced [H-3]CP-55940 binding to a rat brain P2 membrane preparation with an IC50 of 690 nM, which was 10-fold less potent than the parent molecule (IC50 = 73 nM). Isothiocyanate substitution at various positions on the naphthalene moiety of the desmethyl analog 10 gave compounds that displaced [H-3]CP-55940 with IC50 values between 400 and 1000 nM, compared with 46 nM for the parent compound 10. However, 6-isothiocyanato substitution on the indole ring of the desmethyl analog provided isothiocyanate 12 that displaced [H-3]CP-55940 binding with an IC50 of 160 nM. After pretreatment of brain membranes with this high-affinity isothiocyanato ligand followed by washing out the ligand, the membranes were depleted of 90% of the cannabinoid receptor binding capacity. Loss of receptor binding capacity was half-maximal at 300 nM of the derivative under standard assay conditions. As a control, pretreatment with the parent compound at concentrations that were 20 times the K-d failed to alter subsequent binding activity. This study demonstrates that an isothiocyanato (aminoalkyl)-indole (12) can behave as an affinity ligand which binds irreversibly to the cannabinoid receptor in brain and which precludes subsequent binding of the cannabinoid ligand [H-3]CP-55940.

  DOI：

  10.1021/jm950932r
• 作为产物：
  描述：

  甲醇 、 3-硝基-1,8-萘二甲酸酐 在 盐酸 、 sodium hydroxide 、 氯化亚砜 、 mercury(II) diacetate 作用下， 生成 methyl 6-nitro-1-naphthoate 、 3-硝基-1-萘酸甲酯
  参考文献：
  名称：

  (Aminoalkyl)indole Isothiocyanates as Potential Electrophilic Affinity Ligands for the Brain Cannabinoid Receptor

  摘要：

  A series of (aminoalkyl)indole compounds, naphthalene analogs of pravadoline (1), has been shown to exhibit cannabinoid agonist activities such as antinociception in animals, inhibition of adenylate cyclase in brain membranes, and binding to the cannabinoid receptor. These pravadoline analogs were selected for the preparation of potential electrophilic affinity ligands based on the synthesis of isothiocyanate derivatives. One isothiocyanatonaphthalene derivative (8) displaced [H-3]CP-55940 binding to a rat brain P2 membrane preparation with an IC50 of 690 nM, which was 10-fold less potent than the parent molecule (IC50 = 73 nM). Isothiocyanate substitution at various positions on the naphthalene moiety of the desmethyl analog 10 gave compounds that displaced [H-3]CP-55940 with IC50 values between 400 and 1000 nM, compared with 46 nM for the parent compound 10. However, 6-isothiocyanato substitution on the indole ring of the desmethyl analog provided isothiocyanate 12 that displaced [H-3]CP-55940 binding with an IC50 of 160 nM. After pretreatment of brain membranes with this high-affinity isothiocyanato ligand followed by washing out the ligand, the membranes were depleted of 90% of the cannabinoid receptor binding capacity. Loss of receptor binding capacity was half-maximal at 300 nM of the derivative under standard assay conditions. As a control, pretreatment with the parent compound at concentrations that were 20 times the K-d failed to alter subsequent binding activity. This study demonstrates that an isothiocyanato (aminoalkyl)-indole (12) can behave as an affinity ligand which binds irreversibly to the cannabinoid receptor in brain and which precludes subsequent binding of the cannabinoid ligand [H-3]CP-55940.

  DOI：

  10.1021/jm950932r

文献信息

• The mercury-mediated decarboxylation (Pesci reaction) of naphthoic anhydrides investigated by microwave synthesis
  作者：Jonathan D. Moseley、John P. Gilday

  DOI：10.1016/j.tet.2005.12.064

  日期：2006.5

  The mercury-mediated decarboxylation (Pesci reaction) of several substituted naphthoic anhydrides has been investigated by microwave synthesis. A laboratory microwave reactor was found to be ideal for small-scale preparations of this slow reaction, reducing reaction times from typically four days to less than 1 h for the three-step process. The ionic reaction medium rapidly heated to high temperatures under microwave heating and could be efficiently maintained by low microwave power settings. Generation of stoichiometric CO2 was safely contained within the reaction tubes. A simplified reaction procedure has been developed. For substituted naphthoic anhydrides, H-1 NMR analysis of the naphthoate ester derivatives indicated no change in the regioisomer ratio compared to previously reported thermal values. (c) 2006 Published by Elsevier Ltd.
• (Aminoalkyl)indole Isothiocyanates as Potential Electrophilic Affinity Ligands for the Brain Cannabinoid Receptor
  作者：Koichiro Yamada、Kenner C. Rice、Judith L. Flippen-Anderson、Michael A. Eissenstat、Susan J. Ward、M. Ross Johnson、Allyn C. Howlett

  DOI：10.1021/jm950932r

  日期：1996.1.1

  A series of (aminoalkyl)indole compounds, naphthalene analogs of pravadoline (1), has been shown to exhibit cannabinoid agonist activities such as antinociception in animals, inhibition of adenylate cyclase in brain membranes, and binding to the cannabinoid receptor. These pravadoline analogs were selected for the preparation of potential electrophilic affinity ligands based on the synthesis of isothiocyanate derivatives. One isothiocyanatonaphthalene derivative (8) displaced [H-3]CP-55940 binding to a rat brain P2 membrane preparation with an IC50 of 690 nM, which was 10-fold less potent than the parent molecule (IC50 = 73 nM). Isothiocyanate substitution at various positions on the naphthalene moiety of the desmethyl analog 10 gave compounds that displaced [H-3]CP-55940 with IC50 values between 400 and 1000 nM, compared with 46 nM for the parent compound 10. However, 6-isothiocyanato substitution on the indole ring of the desmethyl analog provided isothiocyanate 12 that displaced [H-3]CP-55940 binding with an IC50 of 160 nM. After pretreatment of brain membranes with this high-affinity isothiocyanato ligand followed by washing out the ligand, the membranes were depleted of 90% of the cannabinoid receptor binding capacity. Loss of receptor binding capacity was half-maximal at 300 nM of the derivative under standard assay conditions. As a control, pretreatment with the parent compound at concentrations that were 20 times the K-d failed to alter subsequent binding activity. This study demonstrates that an isothiocyanato (aminoalkyl)-indole (12) can behave as an affinity ligand which binds irreversibly to the cannabinoid receptor in brain and which precludes subsequent binding of the cannabinoid ligand [H-3]CP-55940.