3-Bromo-2,6-dimethoxy-N-(1-propyl-pyrrolidin-2-ylmethyl)-benzamide | 84225-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Bromo-2,6-dimethoxy-N-(1-propyl-pyrrolidin-2-ylmethyl)-benzamide
• 英文别名: 3-bromo-2,6-dimethoxy-N-[[(2S)-1-propylpyrrolidin-2-yl]methyl]benzamide
• CAS: 84225-93-4
• 化学式: C₁₇H₂₅BrN₂O₃
• 分子量: 385.301
• InChiKey: PPAUVJZNYKISEQ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Bromo-2,6-dimethoxy-N-(1-propyl-pyrrolidin-2-ylmethyl)-benzamide 在 盐酸 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 以20%的产率得到3-Bromo-6-hydroxy-2-methoxy-N-(1-propyl-pyrrolidin-2-ylmethyl)-benzamide
  参考文献：
  名称：

  Potential neuroleptic agents. 3. Chemistry and antidopaminergic properties of substituted 6-methoxysalicylamides

  摘要：

  A series of substituted 6-methoxysalicylamides were synthesized from their corresponding 2,6-dimethoxybenzamides by demethylation of one methoxy group with boron tribromide. Substituted 6-methoxysalicylamides having a lipophilic aromatic substituent in the 3-position para with respect to the methoxy group, e.g. a bromo or an iodo atom or an ethyl or a propyl group, and having an (S)-N-(1-alkyl-2-pyrrolidinyl)methyl moiety as the side chain were found to be potent blockers of [3H]spiperone binding in vitro and potent inhibitors of the apomorphine syndrome in the rat. Similar to remoxipride but in contrast to haloperidol, some of the substituted salicylamides show a 10-20-fold separation between the dose that inhibits hyperactivity and that which inhibits stereotypy. It was concluded that, besides the requirement of a lipophilic substituent in the position para to the methoxy group for antidopamine activity in vivo, the formation of a coplanar six-membered pseudoring involving the amide moiety and the methoxy group is a structural requirement for activity in vitro.

  DOI：

  10.1021/jm00147a025
• 作为产物：
  描述：

  3-溴-2,6-二甲氧基苯甲酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 1.5h， 生成 3-Bromo-2,6-dimethoxy-N-(1-propyl-pyrrolidin-2-ylmethyl)-benzamide
  参考文献：
  名称：

  Potential neuroleptic agents. 3. Chemistry and antidopaminergic properties of substituted 6-methoxysalicylamides

  摘要：

  A series of substituted 6-methoxysalicylamides were synthesized from their corresponding 2,6-dimethoxybenzamides by demethylation of one methoxy group with boron tribromide. Substituted 6-methoxysalicylamides having a lipophilic aromatic substituent in the 3-position para with respect to the methoxy group, e.g. a bromo or an iodo atom or an ethyl or a propyl group, and having an (S)-N-(1-alkyl-2-pyrrolidinyl)methyl moiety as the side chain were found to be potent blockers of [3H]spiperone binding in vitro and potent inhibitors of the apomorphine syndrome in the rat. Similar to remoxipride but in contrast to haloperidol, some of the substituted salicylamides show a 10-20-fold separation between the dose that inhibits hyperactivity and that which inhibits stereotypy. It was concluded that, besides the requirement of a lipophilic substituent in the position para to the methoxy group for antidopamine activity in vivo, the formation of a coplanar six-membered pseudoring involving the amide moiety and the methoxy group is a structural requirement for activity in vitro.

  DOI：

  10.1021/jm00147a025

文献信息

• PAULIS, T. DE;KUMAR, YATENDRA;JOHANSSON, L.;RAEMSBY, S.;FLORVALL, L.;HALL+, J. MED. CHEM., 1985, 28, N 9, 1263-1269
  作者：PAULIS, T. DE、KUMAR, YATENDRA、JOHANSSON, L.、RAEMSBY, S.、FLORVALL, L.、HALL+

  DOI：——

  日期：——
• Potential neuroleptic agents. 3. Chemistry and antidopaminergic properties of substituted 6-methoxysalicylamides
  作者：Tomas De Paulis、Yatendra Kumar、Lars Johansson、Sten Raemsby、Lennart Florvall、Haakan Hall、Kristina Aengeby-Moeller、Sven Ove Oegren

  DOI：10.1021/jm00147a025

  日期：1985.9

  A series of substituted 6-methoxysalicylamides were synthesized from their corresponding 2,6-dimethoxybenzamides by demethylation of one methoxy group with boron tribromide. Substituted 6-methoxysalicylamides having a lipophilic aromatic substituent in the 3-position para with respect to the methoxy group, e.g. a bromo or an iodo atom or an ethyl or a propyl group, and having an (S)-N-(1-alkyl-2-pyrrolidinyl)methyl moiety as the side chain were found to be potent blockers of [3H]spiperone binding in vitro and potent inhibitors of the apomorphine syndrome in the rat. Similar to remoxipride but in contrast to haloperidol, some of the substituted salicylamides show a 10-20-fold separation between the dose that inhibits hyperactivity and that which inhibits stereotypy. It was concluded that, besides the requirement of a lipophilic substituent in the position para to the methoxy group for antidopamine activity in vivo, the formation of a coplanar six-membered pseudoring involving the amide moiety and the methoxy group is a structural requirement for activity in vitro.