N-(4-bromo-2-butynyl)succinimide | 110826-55-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(4-bromo-2-butynyl)succinimide
• 英文别名: 1-(4-Bromobut-2-ynyl)pyrrolidine-2,5-dione
• CAS: 110826-55-6
• 化学式: C₈H₈BrNO₂
• 分子量: 230.061
• InChiKey: LFOUAIPTUPYBDZ-UHFFFAOYSA-N

物化性质

• 沸点：
  395.8±27.0 °C(Predicted)
• 密度：
  1.645±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-bromo-2-butynyl)succinimide 以73%的产率得到
  参考文献：
  名称：

  RINGDAHL, BJORN, J. MED. CHEM., 31,(1988) N 1, 164-168

  摘要：

  DOI：
• 作为产物：
  描述：

  DKJ 21 在 溴化氰 作用下， 以 氯仿 为溶剂， 以65%的产率得到N-(4-bromo-2-butynyl)succinimide
  参考文献：
  名称：

  Dimethylsulfonium and thiolanium analogs of the muscarinic agent oxotremorine

  摘要：

  Dimethylsulfonium (6a and 6b) and thiolanium analogues (7a and 7b) of oxotremorine were synthesized and found to be potent muscarinic agents in vivo and vitro. Compound 6a exceeded oxotremorine in potency. Their affinities for muscarinic receptors in the guinea pig ileum and urinary bladder, estimated pharmacologically, were higher than those of the corresponding trimethylammonium (8a and 8b) and N-methylpyrrolidinium compounds (9a and 9b). However, the new compounds had lower intrinsic efficacies than their quaternary ammonium analogues. The compounds also had high affinity for central muscarinic receptors as measured by displacement of specifically bound (-)-[3H]-N-methylscopolamine from homogenates of the rat cerebral cortex. Half-maximal occupation of cortical muscarinic receptors by 6a, 6b, 7a, and 7b was achieved at concentrations of 0.8, 5.4, 0.3, and 3.3 microM, respectively. The competition curves of 6a, 6b, and 7a were adequately described by a two-site binding equation. The ratio of low- and high-affinity dissociation constants agreed with relative efficacy estimated on the ileum. The thiolanium salt 7a was a fairly potent nicotinic agent on the frog rectus abdominis.

  DOI：

  10.1021/jm00396a025

文献信息

• ACETYLENIC IMIDAZOLES HAVING CENTRAL NERVOUS SYSTEM ACTIVITY
  申请人：THE UPJOHN COMPANY

  公开号：EP0426714B1

  公开（公告）日：1996-04-03
• US5100909A
  申请人：——

  公开号：US5100909A

  公开（公告）日：1992-03-31
• [EN] ACETYLENIC IMIDAZOLES HAVING CENTRAL NERVOUS SYSTEM ACTIVITY
  申请人：THE UPJOHN COMPANY

  公开号：WO1990001026A1

  公开（公告）日：1990-02-08

  (EN) Acetylenic imidazole compounds comprising structural formula (I) or a therapeutically acceptable salt thereof, wherein X is H2 or O; R1 is hydrogen, methyl, ethyl, methylamino, dimethylamino, methoxy or ethoxy; R2 is hydrogen, methyl or ethyl or R1 and R2 are joined to form a cyclic ring which can be methyl or carbonyl substituted; and R3, R4 and R5 are independently chosen from hydrogen, methyl, ethyl, fluorine, chlorine, bromine or iodine, having cholinergic agonist or antagonist activity useful in the treatment of mental disorders, extrapyramidal motor disorders, disorders of the parasympathetic nervous system and glaucoma or as analgesics for the treatment of pain. Typical central nervous system disorders for which the subject compounds can be used include cognitive disorders of all ages, including senile dementia, Alzheimer's disease and other related disorders. The compounds are particularly developed to improve mental performance when a mental deficiency is diagnosed.(FR) On a mis au point des composés d'imidazole acétylénique comprenant la formule structurelle (I) ou un de ses sels pharmaceutiquement acceptables, dans laquelle X représente H2 ou O; R1 représente hydrogène, méthyle, éthyle, méthylamino, diméthylamino, méthoxy ou éthoxy; R2 représente hydrogène, méthyle ou éthyle, ou R1 et R2 sont unis pour former un anneau cyclique, éventuellement à substitution par méthyle ou carbonyle; et R3, R4 et R5 sont choisis indépendamment parmi hydrogène, méthyle, éthyle, fluor, chlore, brome ou iode, présentant une activité d'agoniste ou d'antagoniste cholinergique utile dans le traitement de troubles mentaux, de troubles moteurs extrapyramidaux, de troubles du système nerveux parasympathique, et du glaucome, ou comme analgésiques pour le traitement des douleurs. Les troubles typiques du système nerveux central pour lesquels on peut utiliser lesdits composés comprennent les troubles cognitifs de tous les âges, y compris la démence sénile, la maladie d'Alzheimer et d'autres troubles apparentés. Lesdits composés sont en particulier conçus pour améliorer les capacités mentales lorsqu'une déficience mentale a été diagnostiquée.
• Dimethylsulfonium and thiolanium analogs of the muscarinic agent oxotremorine
  作者：Bjorn Ringdahl

  DOI：10.1021/jm00396a025

  日期：1988.1

  Dimethylsulfonium (6a and 6b) and thiolanium analogues (7a and 7b) of oxotremorine were synthesized and found to be potent muscarinic agents in vivo and vitro. Compound 6a exceeded oxotremorine in potency. Their affinities for muscarinic receptors in the guinea pig ileum and urinary bladder, estimated pharmacologically, were higher than those of the corresponding trimethylammonium (8a and 8b) and N-methylpyrrolidinium compounds (9a and 9b). However, the new compounds had lower intrinsic efficacies than their quaternary ammonium analogues. The compounds also had high affinity for central muscarinic receptors as measured by displacement of specifically bound (-)-[3H]-N-methylscopolamine from homogenates of the rat cerebral cortex. Half-maximal occupation of cortical muscarinic receptors by 6a, 6b, 7a, and 7b was achieved at concentrations of 0.8, 5.4, 0.3, and 3.3 microM, respectively. The competition curves of 6a, 6b, and 7a were adequately described by a two-site binding equation. The ratio of low- and high-affinity dissociation constants agreed with relative efficacy estimated on the ileum. The thiolanium salt 7a was a fairly potent nicotinic agent on the frog rectus abdominis.
• RINGDAHL, BJORN, J. MED. CHEM., 31,(1988) N 1, 164-168
  作者：RINGDAHL, BJORN

  DOI：——

  日期：——