7,8-naphthoquinoline-2,4-dicarboxylic acid | 1548708-58-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 7,8-naphthoquinoline-2,4-dicarboxylic acid
• 英文别名: Naphtho[2,3-h]quinoline-2,4-dicarboxylic acid；naphtho[2,3-h]quinoline-2,4-dicarboxylic acid
• CAS: 1548708-58-2
• 化学式: C₁₉H₁₁NO₄
• 分子量: 317.301
• InChiKey: FNFOCLDEQKVHRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以15 mg的产率得到7,8-naphthoquinoline-2,4-dicarboxylic acid
  参考文献：
  名称：

  The development of benzo- and naphtho-fused quinoline-2,4-dicarboxylic acids as vesicular glutamate transporter (VGLUT) inhibitors reveals a possible role for neuroactive steroids

  摘要：

  Substituted quinoline-2,4-dicarboxylates (QDCs) are conformationally-restricted mimics of glutamate that were previously reported to selectively block the glutamate vesicular transporters (VGLUTs). We find that expanding the QDC scaffold to benzoquinoline dicarboxylic acids (BQDC) and naphthoquinoline dicarboxylic acids (NQDCs) improves inhibitory activity with the NQDCs showing IC50 similar to 70 mu M. Modeling overlay studies showed that the polycyclic QDCs resembled steroid structures and led to the identification and testing of estrone sulfate, pregnenolone sulfate and pregnanolone sulfate that blocked the uptake of L-Glu by 50%, 70% and 85% of control, respectively. Pregnanolone sulfate was further characterized by kinetic pharmacological determinations that demonstrated competitive inhibition and a K-i of approximate to 20 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.086

文献信息

• The development of benzo- and naphtho-fused quinoline-2,4-dicarboxylic acids as vesicular glutamate transporter (VGLUT) inhibitors reveals a possible role for neuroactive steroids
  作者：Christina N. Carrigan、Sarjubhai A. Patel、Holly D. Cox、Erin S. Bolstad、John M. Gerdes、Wesley E. Smith、Richard J. Bridges、Charles M. Thompson

  DOI：10.1016/j.bmcl.2013.12.086

  日期：2014.2

  Substituted quinoline-2,4-dicarboxylates (QDCs) are conformationally-restricted mimics of glutamate that were previously reported to selectively block the glutamate vesicular transporters (VGLUTs). We find that expanding the QDC scaffold to benzoquinoline dicarboxylic acids (BQDC) and naphthoquinoline dicarboxylic acids (NQDCs) improves inhibitory activity with the NQDCs showing IC50 similar to 70 mu M. Modeling overlay studies showed that the polycyclic QDCs resembled steroid structures and led to the identification and testing of estrone sulfate, pregnenolone sulfate and pregnanolone sulfate that blocked the uptake of L-Glu by 50%, 70% and 85% of control, respectively. Pregnanolone sulfate was further characterized by kinetic pharmacological determinations that demonstrated competitive inhibition and a K-i of approximate to 20 mu M. (C) 2013 Elsevier Ltd. All rights reserved.