四氢咪唑并[1,5-a]吡啶-1,3(2H,5H)-二酮 | 4705-52-6

• 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: 四氢咪唑并[1,5-a]吡啶-1,3(2H,5H)-二酮
• 英文名称: 7.9-Dioxo-1.8-diaza-bicyclo <4.3.0> nonan
• 英文别名: tetrahydroimidazo[1,5-a]pyridine-1,3(2H,5H)-dione；6,7,8,8a-tetrahydro-5H-imidazo[1,5-a]pyridine-1,3-dione
• CAS: 4705-52-6
• 化学式: C₇H₁₀N₂O₂
• mdl: MFCD07843119
• 分子量: 154.169
• InChiKey: QBCSJOKGNDNJKE-UHFFFAOYSA-N

物化性质

• 熔点：
  123-124 °C(Solv: methanol (67-56-1))
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  四氢咪唑并[1,5-a]吡啶-1,3(2H,5H)-二酮 在 sodium hydride 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.5h， 生成 2-(3-{4-[3-(trifluoromethyl)phenyl]-1-piperazinyl}propyl)tetrahydroimidazo[1,5-a]pyridine-1,3(2H,5H)-dione
  参考文献：
  名称：

  2-[4-(o-methoxyphenyl)piperazin-1-ylmethyl]-1,3-dioxoperhydroimidazo[1,5-a]pyridine as a new selective 5-HT1A receptor ligand

  摘要：

  A series of 2-[omega-(4-arylpiperazin-1-yl)alkyl]-1,3-dioxoperhydroimidazo[1,5-a]pyridine derivatives was prepared and evaluated for affinity at 5-HT1A and alpha(1) receptors. The most promising analogue Im bound at 5-HT1A sites with nanomolar affinity (K-i=31.7) and high selectivity over alpha(1), D-2 and 5-HT2A receptors (K-i>1000, K-i>10 000, K-i>1000 nM, respectively). Preliminary studies showed that this agent is a presynaptic 5-HT1A agonist, and it displayed activity in the face to face behavioural model.

  DOI：

  10.1016/0960-894x(96)00081-9
• 作为产物：
  描述：

  potassium cyanide 、 methyl pipecolinecarboxylate hydrochloride 以 水 为溶剂， 以22%的产率得到四氢咪唑并[1,5-a]吡啶-1,3(2H,5H)-二酮
  参考文献：
  名称：

  IMIDAZOLIDINE CARBOXAMIDE DERIVATIVES AS LIPASE AND PHOSPHOLIPASE INHIBITORS

  摘要：

  本发明涉及一般式I的咪唑啉羧酰胺衍生物，其中R、R1、R2、X和Y如本文所定义，或其药用盐以及其作为药用物质的用途。

  公开号：

  US20100105719A1

文献信息

• Design and synthesis of S-(−)-2-[[4-(napht-1-yl)piperazin-1-yl]methyl]-1,4-dioxoperhydropyrrolo[1,2-a]pyrazine (CSP-2503) using computational simulation. A 5-HT1A receptor agonist
  作者：Marı́a L López-Rodrı́guez、Ma José Morcillo、Esther Fernández、Bellinda Benhamú、Ignacio Tejada、David Ayala、Alma Viso、Mireia Olivella、Leonardo Pardo、Mercedes Delgado、Jorge Manzanares、José A Fuentes

  DOI：10.1016/s0960-894x(03)00160-4

  日期：2003.4

  Based on a computational model for 5-HT(1A)R-ligand interaction and QSAR studies, we have designed and synthesized a new series of arylpiperazines 2-8 which exhibit high 5-HT(1A)R affinity and selectivity over alpha(1)-adrenergic receptors. Among them, compound CSP-2503 (4) has been pharmacologically characterized as a 5-HT(1A)R agonist at somatodendritic and postsynaptic sites, endowed with anxiolytic

  基于5-HT（1A）R-配体相互作用的计算模型和QSAR研究，我们设计和合成了一系列新的芳基哌嗪2-8，它们在α（1）上具有较高的5-HT（1A）R亲和力和选择性肾上腺素能受体。其中，化合物CSP-2503（4）的药理学特征是在体树突状和突触后部位具有抗焦虑特性的5-HT（1A）R激动剂。
• Synthesis and Structure−Activity Relationships of a New Model of Arylpiperazines. 3. 2-[ω-(4-Arylpiperazin-1-yl)alkyl]perhydropyrrolo- [1,2-<i>c</i>]imidazoles and -perhydroimidazo[1,5-<i>a</i>]pyridines:  Study of the Influence of the Terminal Amide Fragment on 5-HT_1A Affinity/Selectivity
  作者：María L. López-Rodríguez、M. José Morcillo、Esther Fernández、Esther Porras、Marta Murcia、Antonio M. Sanz、Luis Orensanz

  DOI：10.1021/jm970216k

  日期：1997.8.1

  A series of new arylpiperazine derivatives 2, which are devoid of the terminal amide fragment present in related 5-HT1A ligands, was prepared and evaluated for affinity at 5-HT1A and alpha 1 receptors. All the compounds 2 demonstrated high affinity for the 5-HT1A receptor and moderate affinity for alpha 1 receptor binding sites. Structure-activity relationship (SAR) studies suggest that there is influence

  制备了一系列新的芳基哌嗪衍生物2，这些衍生物没有相关的5-HT1A配体中存在的末端酰胺片段，并评估了对5-HT1A和α1受体的亲和力。所有化合物2对5-HT1A受体都表现出高亲和力，对α1受体结合位点具有中等亲和力。结构-活性关系（SAR）研究表明，电子因素对alpha 1受体位点的非药效学部分有影响。但是，电子相互作用对5-HT1A受体-配体复合物的稳定性没有影响。
• N-heteroaryl-substituted pyridine derivatives and their use as herbicides
  申请人：Syngenta Crop Properties, Inc.

  公开号：US06369002B1

  公开（公告）日：2002-04-09

  Compounds of formula 1 wherein R1 is hydrogen, fluorine, chlorine, bromine or methyl; R2 is C1-C4alkyl, C1-C4halogenalkyl, halogen, hydroxy, C1-C4alkoxy, C1-C4halogenalkoxy, nitro, amino or cyano; R3, R15 to R39 and X6 to X19 are as defined in claim 1, and the agrochemically acceptable salts and stereoisomers of these compounds of formula I are suitable for use as herbicides.

  式1的化合物，其中R1为氢，氟，氯，溴或甲基；R2为C1-C4烷基，C1-C4卤代烷基，卤素，羟基，C1-C4烷氧基，C1-C4卤代烷氧基，硝基，氨基或氰基；R3，R15到R39和X6到X19如权利要求1所定义的，以及公认为农药可接受的盐和立体异构体的I式化合物，适用于作为除草剂使用。
• Novel herbicides
  申请人：——

  公开号：US20020156285A1

  公开（公告）日：2002-10-24

  Compounds of formula 1 1 R 1 is hydrogen, fluorine, chlorine, bromine or methyl; R 2 is C 1 -C 4 alkyl, C 1 -C 4 halogenalkyl, halogen, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 halogenalkoxy, nitro, amino or cyano; 2 R 3 , R 15 to R 39 and X 6 to X 19 are as defined in claim 1, and the agrochemically acceptable salts and stereoisomers of these compounds of formula I are suitable for use as herbicides.

  化合物的公式为11R1，其中R1是氢，氟，氯，溴或甲基；R2是C1-C4烷基，C1-C4卤代烷基，卤素，羟基，C1-C4烷氧基，C1-C4卤代烷氧基，硝基，氨基或氰基；2R3，R15到R39和X6到X19如权利要求1所定义，并且这些公式I的化合物的农药可接受盐和立体异构体适用于作为除草剂使用。
• Pyridine compounds as inhibitors of dipeptidyl peptidase IV
  申请人：Oi Satoru

  公开号：US20070037807A1

  公开（公告）日：2007-02-15

  A compound represented by the formula wherein R 1 and R 2 are the same or different and each is an optionally substituted hydrocarbon group or an optionally substituted hydroxy group; R 3 is an optionally substituted aromatic group; R 4 is an optionally substituted amino group; L is a divalent chain hydrocarbon group; Q is a bond or a divalent chain hydrocarbon group; and X is a hydrogen atom, a cyano group, a nitro group, an acyl group, a substituted hydroxy group, an optionally substituted thiol group, an optionally substituted amino group or an optionally substituted cyclic group; provided that when X is an ethoxycarbonyl group, then Q is a divalent chain hydrocarbon group. The compound has a peptidase inhibitory action, is useful as an agent for the prophylaxis or treatment of diabetes and the like, and is superior in efficacy, duration of action, specificity, lower toxicity and the like.

  该化合物的化学式为其中R1和R2是相同或不同的可选择取代的烃基或可选择取代的羟基；R3是可选择取代的芳香基；R4是可选择取代的氨基；L是二价链烃基；Q是键或二价链烃基；X是氢原子、氰基、硝基、酰基、可选择取代的羟基、可选择取代的硫醇基、可选择取代的氨基或可选择取代的环状基；但当X是乙氧羰基时，Q是二价链烃基。该化合物具有肽酶抑制作用，可用作预防或治疗糖尿病等药物，具有优异的疗效、持续时间、特异性、低毒性等特点。