LUF5492 | 247206-91-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: LUF5492
• 英文别名: 4-(2-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carbonyl)-benzoic acid methyl ester；methyl 4-(2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonyl)benzoate
• CAS: 247206-91-3
• 化学式: C₁₇H₁₇NO₃S
• 分子量: 315.393
• InChiKey: DSQPVVJMEVDVMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  97.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  LUF5492 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以93%的产率得到4-(2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonyl)benzoic acid
  参考文献：
  名称：

  Allosteric Modulation of the Adenosine A₁ Receptor. Synthesis and Biological Evaluation of Novel 2-Amino-3-benzoylthiophenes as Allosteric Enhancers of Agonist Binding

  摘要：

  Novel allosteric enhancers of agonist binding to the rat adenosine Al receptor are described. The lead compound for the new series was PD 81,723 ((2-amino-4,5-dimethyl-3-thienyl)[3(trifluoromethyl)phenyl]methanone), a compound previously reported by Bruns and co-workers (Mol. Pharmacol. 1990, 38, 950-958). The 4,5-dimethyl group and the benzoyl moiety were targets for further modifications, leading to series of 4,5-dialkyl (12a-g), of tetrahydrobenzo (12h-u), and of tetrahydropyridine (13a-g) derivatives. A number of compounds, in particular 12b, 12e, 12j, 12n, and 12u, proved superior to PD 81,723, Their EC50 values for enhancing the binding of the adenosine Al receptor agonist N-6-cyclopentyladenosine to the receptor were lower, and/or their antagonistic activity on the adenosine Al receptor was shown to be diminished.

  DOI：

  10.1021/jm991051d
• 作为产物：
  描述：

  4-(氰基乙酰)苯甲酸甲酯 、 环己酮 在 sulfur 、 二乙胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以15%的产率得到LUF5492
  参考文献：
  名称：

  Allosteric Modulation of the Adenosine A₁ Receptor. Synthesis and Biological Evaluation of Novel 2-Amino-3-benzoylthiophenes as Allosteric Enhancers of Agonist Binding

  摘要：

  Novel allosteric enhancers of agonist binding to the rat adenosine Al receptor are described. The lead compound for the new series was PD 81,723 ((2-amino-4,5-dimethyl-3-thienyl)[3(trifluoromethyl)phenyl]methanone), a compound previously reported by Bruns and co-workers (Mol. Pharmacol. 1990, 38, 950-958). The 4,5-dimethyl group and the benzoyl moiety were targets for further modifications, leading to series of 4,5-dialkyl (12a-g), of tetrahydrobenzo (12h-u), and of tetrahydropyridine (13a-g) derivatives. A number of compounds, in particular 12b, 12e, 12j, 12n, and 12u, proved superior to PD 81,723, Their EC50 values for enhancing the binding of the adenosine Al receptor agonist N-6-cyclopentyladenosine to the receptor were lower, and/or their antagonistic activity on the adenosine Al receptor was shown to be diminished.

  DOI：

  10.1021/jm991051d

文献信息

• Thieno-pyridine derivatives as allosteric enhancers of the GABAB receptors
  申请人：Malherbe Parichehr

  公开号：US20060135552A1

  公开（公告）日：2006-06-22

  The present invention relates to compounds of formula I wherein R 1 , R 2 , R 3 , R 4 , and R 5 are as defined in the specification. Compounds of the invention are active on the GABAB receptor and are useful for treating a variety of CNS disorders, including anxiety, depression, epilepsy, schizophrenia, cognitive disorders, spasticity-and skeletal muscle rigidity, spinal cord injury, multiple sclerosis, amyotrophic lateral sclerosis, cerebral palsy, neuropathic pain and craving associated with cocaine and nicotine, psychosis, panic disorder, posttraumatic stress disorders and gastrointestinal disorders.

  本发明涉及式I化合物，其中R1、R2、R3、R4和R5如规范中所定义。本发明的化合物在GABAB受体上具有活性，并可用于治疗多种中枢神经系统疾病，包括焦虑、抑郁、癫痫、精神分裂症、认知障碍、痉挛和骨骼肌强直、脊髓损伤、多发性硬化症、肌萎缩性侧索硬化、脑瘫、神经病性疼痛和与可卡因和尼古丁有关的渴望、精神病、惊恐障碍、创伤后应激障碍和胃肠疾病。
• WO2006/63732
  申请人：——

  公开号：——

  公开（公告）日：——
• THIENO-PYRIDINE DERIVATIVES AS GABA-B ALLOSTERIC ENHANCERS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1828199B1

  公开（公告）日：2009-05-06
• CONTINUOUS CHEMICAL PROCESSES IN CENTRIFUGAL CONTACT SEPARATORS
  申请人：DSM IP Assets B.V.

  公开号：EP1931463B1

  公开（公告）日：2009-04-22
• Continuous Chemical Proceses in Centrifugal Contact Separators
  申请人：De Vries Johannes Gerardus

  公开号：US20090298141A1

  公开（公告）日：2009-12-03

  The invention relates to the use of a centrifugal contact-separator for carrying out a non-radioactive reaction in a liquid-liquid emulsion formed from two immiscible liquids. The invention also relates to a process for carrying out a reaction in a centrifugal contact-separator, and to a process for carrying out a catalytic reaction in a centrifugal contact-separator. An example of a process for carrying out a reaction, comprising the following steps: i) continuously introducing a liquid phase A and a liquid phase B into at least one first centrifugal contact separator, where in liquid phases A and B are immiscible and wherein phase A and/or phase B comprise at least one reactant ii) mixing phase A and phase B thereby allowing an emulsion to be formed iii) applying a centrifugal force that allows phase separation of the emulsion, such that phases A′ and B′ are obtained; iv) optionally, recovering a reaction product from at least one or the phases A′ and B′.