1-(1-Methyl-5-tetraazolyl)piperazine | 119639-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(1-Methyl-5-tetraazolyl)piperazine
• 英文别名: 1-(1-Methyltetrazol-5-yl)piperazine
• CAS: 119639-49-5
• 化学式: C₆H₁₂N₆
• mdl: MFCD05182222
• 分子量: 168.201
• InChiKey: SQJDMBCPQVISRB-UHFFFAOYSA-N

物化性质

• 沸点：
  330.1±52.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[4-溴丁基]糖精 、 1-(1-Methyl-5-tetraazolyl)piperazine 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[4-[4-(1-Methyltetrazol-5-yl)piperazin-1-yl]butyl]-1,1-dioxo-1,2-benzothiazol-3-one
  参考文献：
  名称：

  取代的四氢-和六氢-1,2-苯并噻唑-3-酮1,1,2-二氧化物和噻二嗪酮的合成及其构效关系：潜在的抗焦虑药。

  摘要：

  制备了几种新颖的取代的四氢-和六氢-1,2-苯并噻唑-3-一和1,1-二氧化物和噻二嗪酮，并在一系列体外和体内试验中进行了研究，以确定它们的药理作用。大多数化合物在阻止条件性回避反应（CAR）方面具有口服活性，但不能拮抗阿扑吗啡引起的刻板印象。几种化合物对5-HT1A受体的结合位点表现出中等至高的亲和力，其中含有2-嘧啶基哌嗪基和[3-（三氟甲基）苯基]哌嗪基部分的化合物37和38和含有2-吡嗪基哌嗪基部分的化合物47表现出最高的亲和力（ Ki值分别为10、4和9 nM。化合物37，3- [4- [4-（2-嘧啶基）-1-哌嗪基]丁基]六氢-4，7-乙炔基-1H-环丁[[f] -1,2-苯并噻唑-3（2H）- 1,1-二氧化物 丁螺环酮和ipsapirone的神经化学和行为特征相似。它们在阻断CAR方面的功效相似，AB50分别为39、32和42 mg / kg。他们还显示了对5-HT1A受体位点的高亲和力和选择性（Ki

  DOI：

  10.1021/jm00125a016

文献信息

• Polycyclic aryl- and heteroarylpiperazinyl imides as 5-HT1A receptor ligands and potential anxiolytic agents: synthesis and structure-activity relationship studies
  作者：Magid Abou-Gharbia、Usha R. Patel、Michael B. Webb、John A. Moyer、Terrance H. Andree、Eric A. Muth

  DOI：10.1021/jm00402a023

  日期：1988.7

  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.
• 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：——
• Synthesis and structure-activity relationship of substituted tetrahydro- and hexahydro-1,2-benzisothiazol-3-one 1,1-dioxides and thiadiazinones: potential anxiolytic agents
  作者：Magid Abou-Gharbia、John A. Moyer、Usha Patel、Michael Webb、Guy Schiehser、Terrance Andree、J. Thomas Haskins

  DOI：10.1021/jm00125a016

  日期：1989.5

  Several novel substituted tetrahydro- and hexahydro-1,2-benzisothiazol-3-one 1,1-dioxides and thiadiazinones were prepared and examined in a series of in vitro and in vivo tests to determine their pharmacological profile. Most compounds were orally active in blocking the conditioned avoidance response (CAR) but did not antagonize apomorphine-induced stereotyped behavior. Several compounds demonstrated

  制备了几种新颖的取代的四氢-和六氢-1,2-苯并噻唑-3-一和1,1-二氧化物和噻二嗪酮，并在一系列体外和体内试验中进行了研究，以确定它们的药理作用。大多数化合物在阻止条件性回避反应（CAR）方面具有口服活性，但不能拮抗阿扑吗啡引起的刻板印象。几种化合物对5-HT1A受体的结合位点表现出中等至高的亲和力，其中含有2-嘧啶基哌嗪基和[3-（三氟甲基）苯基]哌嗪基部分的化合物37和38和含有2-吡嗪基哌嗪基部分的化合物47表现出最高的亲和力（ Ki值分别为10、4和9 nM。化合物37，3- [4- [4-（2-嘧啶基）-1-哌嗪基]丁基]六氢-4，7-乙炔基-1H-环丁[[f] -1,2-苯并噻唑-3（2H）- 1,1-二氧化物 丁螺环酮和ipsapirone的神经化学和行为特征相似。它们在阻断CAR方面的功效相似，AB50分别为39、32和42 mg / kg。他们还显示了对5-HT1A受体位点的高亲和力和选择性（Ki