4-(Piperazin-1-yl)-2,1,3-benzoxadiazole | 105685-14-1

• 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: 4-(Piperazin-1-yl)-2,1,3-benzoxadiazole
• 英文别名: 4-piperazin-1-yl-2,1,3-benzoxadiazole
• CAS: 105685-14-1
• 化学式: C₁₀H₁₂N₄O
• 分子量: 204.231
• InChiKey: TXXKTDZWBMTHEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(Piperazin-1-yl)-2,1,3-benzoxadiazole 、 (3R,4aR,10aR)-6-methoxy-1-methyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-3-carboxylic acid, sodium salt 在 吡啶 、 propylphosphonic anhydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到[(3R,4aR,10aR)-6-methoxy-1-methyl-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinolin-3-yl]-[4-(2,1,3-benzoxadiazol-4-yl)piperazin-1-yl]methanone
  参考文献：
  名称：

  SAR of the arylpiperazine moiety of obeline somatostatin sst1 receptor antagonists

  摘要：

  The SAR of over 50 derivatives of octahydrobenzo[g]quinoline (obeline)-type somatostatin sst, receptor antagonist 1 is presented, focusing on the modification of its arylpiperazine moiety. sst(1) affinities in this series cover a range of five orders of magnitude with the best derivatives displaying subnanomolar sst, affinities and > 10,000-fold selectivities over the sst, receptor subtype as well as promising pharmacokinetic properties. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.078
• 作为产物：
  描述：

  哌嗪 、 4-氯苯并呋喃 在 N,N-二甲基甲酰胺 作用下， 以 甲醇 为溶剂， 以7%的产率得到4-(Piperazin-1-yl)-2,1,3-benzoxadiazole
  参考文献：
  名称：

  SAR of the arylpiperazine moiety of obeline somatostatin sst1 receptor antagonists

  摘要：

  The SAR of over 50 derivatives of octahydrobenzo[g]quinoline (obeline)-type somatostatin sst, receptor antagonist 1 is presented, focusing on the modification of its arylpiperazine moiety. sst(1) affinities in this series cover a range of five orders of magnitude with the best derivatives displaying subnanomolar sst, affinities and > 10,000-fold selectivities over the sst, receptor subtype as well as promising pharmacokinetic properties. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.078

文献信息

• Novel N-acylated heterocycles
  申请人：Recordati S.A.

  公开号：US20030162777A1

  公开（公告）日：2003-08-28

  Described are compositions comprising a muscarinic receptor antagonist and an N-acylated heterocycle derivative having affinity for serotonergic receptors, and enantiomers, diastereoisomers, N-oxides, polymorphs, solvates and pharmaceutically acceptable salts thereof. The combination of a muscarinic receptor antagonist and an N-acylated heterocycle, or an enantiomer, diastereoisomer, N-oxide, polymorph, solvate or pharmaceutically acceptable salt thereof, is useful in the treatment of patients with neuromuscular dysfunction of the lower urinary tract and diseases related to 5-HT 1A receptors.

  描述了包含一种肌氨酸受体拮抗剂和一种对5-HT 1A 受体具有亲和力的N-酰化杂环衍生物的组合物，以及它们的对映体、二对映体、N-氧化物、多型体、溶剂合物和药用可接受盐。肌氨酸受体拮抗剂和N-酰化杂环，或其对映体、二对映体、N-氧化物、多型体、溶剂合物或药用可接受盐的组合，在治疗患有下尿路神经肌肉功能障碍和与5-HT 1A 受体相关疾病的患者中是有用的。
• Decahydroisoquinoline derivatives as novel non-peptidic, potent and subtype-selective somatostatin sst3 receptor antagonists
  作者：Thomas Troxler、Konstanze Hurth、Karl-Heinrich Schuh、Philippe Schoeffter、Daniel Langenegger、Albert Enz、Daniel Hoyer

  DOI：10.1016/j.bmcl.2010.01.063

  日期：2010.3

  Starting from non-peptidic sst(1)-selective somatostatin receptor antagonists, first compounds with mixed sst(1)/sst(3) affinity were identified by directed structural modifications. Systematic optimization of these initial leads afforded novel, enantiomerically pure, highly potent and sst(3)-subtype selective somatostatin antagonists based on a (4S,4aS,8aR)-decahydroisoquinoline-4-carboxylic acid core moiety. These compounds can efficiently be synthesized and show promising PK properties in rodents. (C) 2010 Elsevier Ltd. All rights reserved.
• SAR of the arylpiperazine moiety of obeline somatostatin sst1 receptor antagonists
  作者：Konstanze Hurth、Albert Enz、Philipp Floersheim、Conrad Gentsch、Daniel Hoyer、Daniel Langenegger、Peter Neumann、Paul Pfäffli、Dieter Sorg、Robert Swoboda、Annick Vassout、Thomas Troxler

  DOI：10.1016/j.bmcl.2007.04.078

  日期：2007.7

  The SAR of over 50 derivatives of octahydrobenzo[g]quinoline (obeline)-type somatostatin sst, receptor antagonist 1 is presented, focusing on the modification of its arylpiperazine moiety. sst(1) affinities in this series cover a range of five orders of magnitude with the best derivatives displaying subnanomolar sst, affinities and > 10,000-fold selectivities over the sst, receptor subtype as well as promising pharmacokinetic properties. (C) 2007 Elsevier Ltd. All rights reserved.