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(-)-FLA 908 | 96393-00-9

中文名称
——
中文别名
——
英文名称
(-)-FLA 908
英文别名
FLA-908;(S)-5-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-6-methoxysalicylamide;5-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-hydroxy-6-methoxybenzamide;3-Bromo-N-(1-ethyl-pyrrolidin-2-ylmethyl)-6-hydroxy-2-methoxy-benzamide;3-bromo-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-6-hydroxy-2-methoxybenzamide
(-)-FLA 908化学式
CAS
96393-00-9
化学式
C15H21BrN2O3
mdl
——
分子量
357.247
InChiKey
QRMZHEDLUQMLGK-JTQLQIEISA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.3
  • 重原子数:
    21
  • 可旋转键数:
    5
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.53
  • 拓扑面积:
    61.8
  • 氢给体数:
    2
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    2,6-二甲氧基苯甲酸盐酸氯化亚砜三溴化硼N,N-二甲基甲酰胺 作用下, 以 二氯甲烷氯仿甲苯 为溶剂, 反应 2.5h, 生成 (-)-FLA 908
    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
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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.
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