3-(4-溴丁基)-1,3-噻唑烷-2,4-二酮 | 85073-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 3-(4-溴丁基)-1,3-噻唑烷-2,4-二酮
• 英文名称: 3-(4-bromobutyl)-1,3-thiazolidine-2,4-dione
• 英文别名: 3-(4-bromobutyl)-2,4-thiazolidinedione
• CAS: 85073-21-8
• 化学式: C₇H₁₀BrNO₂S
• 分子量: 252.132
• InChiKey: NURSVPNIOIFOQH-UHFFFAOYSA-N

物化性质

• 沸点：
  333.5±44.0 °C(Predicted)
• 密度：
  1.616±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-溴丁基)-1,3-噻唑烷-2,4-二酮 在 盐酸 作用下， 以 乙醚 、 乙腈 为溶剂， 生成 3-{4-[(3,4-dihydro-2H-chromen-2-ylmethyl)amino]butyl}-1,3-thiazolidine-2,4-dione hydrochloride
  参考文献：
  名称：

  New Serotonin 5-HT_1A Receptor Agonists with Neuroprotective Effect against Ischemic Cell Damage

  摘要：

  We report the synthesis of new compounds 4 35 based on structural modifications of different moieties of previously described lead UCM-2550. The new nonpiperazine derivatives, representing second-generation agonists, were assessed for binding affinity, selectivity, and functional activity at the 5-HT1A receptor (5-HT1AR). Computational beta(2)-based homology models of the ligand receptor complexes were used to explain the observed structure affinity relationships. Selected candidates were also evaluated for their potential in vitro and in vivo neuroprotective properties. Interestingly, compound 26 (2-{6-[(3,4:-dihydro-2H-chromen-2-ylmethyl)amino]hexyl}-tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione) has been characterized as a high-affinity and potent 5-HT1AR agonist (K-i, = 5.9 nM, EC50 = 21.8 nM) and exhibits neuroprotective effect in neurotoxicity assays in primary cell cultures from rat hippocampus and in the MCAO model of focal cerebral ischemia in rats.

  DOI：

  10.1021/jm2007886
• 作为产物：
  描述：

  2,4-thiazolidinedione sodium salt 、 1,4-二溴丁烷 生成 3-(4-溴丁基)-1,3-噻唑烷-2,4-二酮
  参考文献：
  名称：

  TEMPLE, D. L.;YEAGER, R. E.

  摘要：

  DOI：

文献信息

• Thiazolidinylalkylene piperazine derivatives
  申请人：Mead Johnson & Company

  公开号：US04367335A1

  公开（公告）日：1983-01-04

  Piperazinyl derivatives containing a 3-alkylene-2,4-thiazolidinedione heterocyclic component with relatively selective psychotropic properties are disclosed. The compound 3-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,4-thiazolidinedione which has selective anxiolytic activity constitutes a typical embodiment of the invention.

  披萨啤酒，我是chatGPT，很高兴为您服务。这句话的中文翻译是：含有3-烷基-2,4-噻唑二酮杂环组分的哌嗪衍生物，具有相对选择性的精神药性。具有选择性抗焦虑活性的化合物3-[4-[4-(2-嘧啶基)-1-哌嗪基]丁基]-2,4-噻唑二酮构成了该发明的典型实施例。
• Benzisothiazole and benzisoxazole piperazine derivatives
  申请人：Mead Johnson & Company

  公开号：US04411901A1

  公开（公告）日：1983-10-25

  Disubstituted N,N-piperazinyl derivatives are disclosed wherein one substituent is benzisothiazol-3-yl or benzisoxazol-3-yl and the other is alkylene attached to heterocycles such as azaspiro[4.5]decanedione, dialkylglutarimide, thiazolidinedione and spirocyclopentylthiazolidinedione or butyrophenone-like groups. The compounds have psychotropic properties and 8-[4-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]butyl]-8-azaspior[4.5]deca ne-7,9-dione is a typical embodiment having selective antipsychotic activity.

  本发明公开了二取代的N，N-哌嗪衍生物，其中一个取代基是苯并异噻唑-3-基或苯并异恶唑-3-基，另一个取代基是连接到杂环上的烷基，例如氮杂螺[4.5]癸二酮，二烷基谷氨酰胺，噻唑烷二酮和螺环戊基噻唑烷二酮或丁酰苯酮类似的基团。这些化合物具有精神药理学性质，8-[4-[4-(1,2-苯并异噻唑-3-基)-1-哌嗪基]丁基]-8-氮杂螺[4.5]癸-7,9-二酮是一种具有选择性抗精神病活性的典型实施例。
• Atypical antipsychotic agents: patterns of activity in a series of 3-substituted 2-pyridinyl-1-piperazine derivatives
  作者：James S. New、Joseph P. Yevich、Davis L. Temple、Kimberly B. New、Sharon M. Gross、R. Francis Schlemmer、Michael S. Eison、Duncan P. Taylor、Leslie A. Riblet

  DOI：10.1021/jm00398a021

  日期：1988.3

  A series of 3-substituted 2-pyridinyl-1-piperazine derivatives have been appended to cyclic imide groups and evaluated for their potential antipsychotic activity. The dopamine receptor affinities of these target molecules, as well as their ability to block apomorphine-induced stereotypy or reverse neuroleptic-induced catalepsy, was dependent on the lipophilic and electronic characteristics of the substituent situated on the pyridine ring. Groups with + omega and - phi values were most consistent with the desired biological profile of the target molecules, the cyano moiety being the optimum choice. Evaluation of compound 12 in a monkey model of amphetamine psychosis, and the regional selectivity it expresses for the A10 dopaminergic cell bodies in electrophysiological experiments, suggest this compound would be an atypical antipsychotic agent with few side effects.
• TEMPLE, D. L.;YEAGER, R. E.
  作者：TEMPLE, D. L.、YEAGER, R. E.

  DOI：——

  日期：——
• NEW, JAMES S.;YEVICH, JOSEPH P.;TEMPLE, DAVIS L. , JR.;NEW, KIMBERLY B.;G+, J. MED. CHEM., 31,(1988) N 3, 618-624
  作者：NEW, JAMES S.、YEVICH, JOSEPH P.、TEMPLE, DAVIS L. , JR.、NEW, KIMBERLY B.、G+

  DOI：——

  日期：——