tetrahydro-1H-thieno<3',4':3,4>cyclobuta<1,2-c>pyrrole-4,6(3H,5H)-dione 2,2-dioxide | 33974-23-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: tetrahydro-1H-thieno<3',4':3,4>cyclobuta<1,2-c>pyrrole-4,6(3H,5H)-dione 2,2-dioxide
• 英文别名: 8,10-dioxo-4-thia-9-azatricyclo<5.3.0.0^2,6>decane 4,4-dioxide；2,2-dioxo-hexahydro-2λ⁶-thieno[3',4':3,4]cyclobuta[1,2-c]pyrrole-4,6-dione；tetrahydro-1H-thieno[3',4':3,4]cyclobuta[1,2-c]pyrrole-4,6(3H,5H)-dione 2,2-dioxide；4,4-Dioxo-4lambda6-thia-9-azatricyclo[5.3.0.02,6]decane-8,10-dione；4,4-dioxo-4λ6-thia-9-azatricyclo[5.3.0.02,6]decane-8,10-dione
• CAS: 33974-23-1
• 化学式: C₈H₉NO₄S
• 分子量: 215.23
• InChiKey: VKADSJHOPGIVBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tetrahydro-1H-thieno<3',4':3,4>cyclobuta<1,2-c>pyrrole-4,6(3H,5H)-dione 2,2-dioxide 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 5-[4-[4-(6-chloro-2-pyrazinyl)-1-piperazinyl]butyl]tetrahydro-1H-thieno[3',4':3,4]cyclobuta[1,2-c]pyrrole-4,6(3H,5H)-dione 2,2 dioxide
  参考文献：
  名称：

  Polycyclic aryl- and heteroarylpiperazinyl imides as 5-HT1A receptor ligands and potential anxiolytic agents: synthesis and structure-activity relationship studies

  摘要：

  A series of polycyclic aryl- and heteroarylpiperazinyl imides were prepared and tested in various receptor-binding and behavioral tests. Parameters measured included in vitro inhibition of D2 and 5-HT1A receptor binding, inhibition of apomorphine (APO) induced stereotyped and climbing behavior, and activity in blocking conditioned avoidance responding (CAR). Several compounds demonstrated moderate to high affinity for the 5-HT1A receptor binding site; compounds 27 and 36 containing the serotonin mimetic (o-methoxyphenyl)piperazinyl moiety and compounds 42 and 50 containing the 2-pyrimidinylpiperazinyl moiety displayed the highest affinity, being equal to that of the 5-HT1A agonist 8-OH-DPAT (Ki = 1-1.3 nM). In addition to affinity at 5-HT1A binding sites, many compounds were active in blocking CAR. Compound 34, 2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]hexahydro-4,7-etheno-1H- cyclobut[f]isoindole-1,3(2H)-dione, demonstrated 3 times the activity of buspirone, blocking CAR in rats with an AB50 of 13 mg/kg. It also displayed high affinity for the 5-HT1A receptor (Ki = 16 nM), which is at least 20 times higher than its affinity for D2 (Ki = 345 nM) and 5-HT2 (Ki = 458 nM) receptors. Compound 34 was selected for further preclinical and pharmacokinetic evaluations for possible development as an anxiolytic agent. Structure-activity relationships within this series are discussed.

  DOI：

  10.1021/jm00402a023
• 作为产物：
  描述：

  7-Carbamoyl-3,3-dioxo-3λ⁶-thia-bicyclo[3.2.0]heptane-6-carboxylic acid 生成 tetrahydro-1H-thieno<3',4':3,4>cyclobuta<1,2-c>pyrrole-4,6(3H,5H)-dione 2,2-dioxide
  参考文献：
  名称：

  Aitken, R. Alan; Cadogan, J. I. G.; Gosney, Ian, Journal of the Chemical Society. Perkin transactions I, 1999, # 5, p. 605 - 614

  摘要：

  DOI：

文献信息

• Shaikhrazieva,V.S. et al., Journal of Organic Chemistry USSR (English Translation), 1972, vol. 8, p. 377 - 381
  作者：Shaikhrazieva,V.S. et al.

  DOI：——

  日期：——
• SHAJXRAZIEVA V. SH.; ENIKEEV R. S.; TOLSTIKOV G. A., ORGAN. SOEDIN. SERY, T. 2, RIGA 1980, 150-156
  作者：SHAJXRAZIEVA V. SH.、 ENIKEEV R. S.、 TOLSTIKOV G. A.

  DOI：——

  日期：——
• ABOU-GHARBIA, MAGID;PATEL, USHA R.;WEBB, MICHAEL B.;MOYER, JOHN A.;ANDREE+, J. MED. CHEM., 31,(1988) N 7, 1382-1392
  作者：ABOU-GHARBIA, MAGID、PATEL, USHA R.、WEBB, MICHAEL B.、MOYER, JOHN A.、ANDREE+

  DOI：——

  日期：——
• US5053508A
  申请人：——

  公开号：US5053508A

  公开（公告）日：1991-10-01
• Aitken, R. Alan; Cadogan, J. I. G.; Gosney, Ian, Journal of the Chemical Society. Perkin transactions I, 1999, # 5, p. 605 - 614
  作者：Aitken, R. Alan、Cadogan, J. I. G.、Gosney, Ian、Humphries, Caroline M.、McLaughlin, Leo M.、Wyse, Stuart J.

  DOI：——

  日期：——