3-(3-溴丙基)-2,3-二氢-1,3-苯并噁唑-2-酮 | 509148-27-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: 3-(3-溴丙基)-2,3-二氢-1,3-苯并噁唑-2-酮
• 英文名称: 3-(3-bromopropyl)benzo[d]oxazol-2(3H)-one
• 英文别名: 3-(3-bromopropyl)-3H-benzooxazol-2-one；3-(3-bromopropyl)-1,3-benzoxazol-2-one
• CAS: 509148-27-0
• 化学式: C₁₀H₁₀BrNO₂
• 分子量: 256.099
• InChiKey: OMCQBXJRMGMJEE-UHFFFAOYSA-N

物化性质

• 沸点：
  339.2±44.0 °C(Predicted)
• 密度：
  1.557±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-溴丙基)-2,3-二氢-1,3-苯并噁唑-2-酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 3-(3-(4-(4-(2-oxobenzo[d]oxazol-3(2H)-yl)butyl)piperazin-1-yl)propyl)benzo[d]oxazol-2(3H)-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of bivalent benzoxazolone and benzothiazolone ligands as potential anti-inflammatory/analgesic agents

  摘要：

  Benzoxazolone and benzothiazolone were used as template blocks to develop two series of dimers as anti-inflammatory and analgesic agents based on the concept of bivalent ligands. The first series (I) involved varying the carbon chain lengths extending from the piperazine core to the nitrogen atom of the dibenzo[d]oxazol-2(3H)-one or dibenzo[d]thiazol-2(3H)-one. The second series (II) was designed by changing the attachment point. All compounds were screened for their in vitro anti-inflammatory activity in terms of the inhibition of inducible nitric oxide synthase (iNOS) and nuclear factor kappa B (NF-kappa B). Seventeen compounds inhibited both targets. Eleven of them exhibited IC50 values below 3 mu M while five compounds showed IC50 values of 1 mu M or below. Most of the compounds were found to be devoid of cytotoxicity against mammalian kidney and solid tumors cell lines up to 25 mu g/mL. In vivo anti-inflammatory and antinociceptive studies revealed that compounds 3j, 5t and 8b have significant anti-inflammatory and analgesic activity comparable to that of indomethacin and ketorolac, respectively. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.057
• 作为产物：
  描述：

  2-苯并唑啉酮 、 1,3-二溴丙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以31%的产率得到3-(3-溴丙基)-2,3-二氢-1,3-苯并噁唑-2-酮
  参考文献：
  名称：

  Conversion of a Highly Selective Sigma-1 Receptor–Ligand to Sigma-2 Receptor Preferring Ligands with Anticocaine Activity

  摘要：

  Cocaine's toxicity can be mitigated by blocking its interaction with sigma-1 receptors. The involvement of sigma-2 receptors remains unclear. To investigate their potential role, we have designed compounds through a convergent synthesis utilizing a highly selective sigma-1 ligand and elements of a selective sigma-2 ligand. Among the synthesized compounds was produced a subnanomolar sigma-2 ligand with an 11-fold preference over sigma-1 receptors. These compounds may be useful in developing effective pharmacotherapies for cocaine toxicity.

  DOI：

  10.1021/jm701357m

文献信息

• Benzimidazolidinone derivatives as muscarinic agents
  申请人：——

  公开号：US20030100545A1

  公开（公告）日：2003-05-29

  Benzimidazolidinone derivative compounds, which increase acetylcholine signaling or effect in the brain, and highly selective muscarinic agonists, particularly for the M 1 and/or M 4 receptor subtypes, pharmaceutical compositions comprising the same, as well as methods of treating psychosis using these compounds are disclosed.

  苯并咪唑啉酮衍生物化合物，可增加乙酰胆碱在大脑中的信号传导或作用，并且高度选择性的肌碱受体激动剂，特别是针对M1和/或M4受体亚型，还公开了包含这些化合物的药物组合物，以及使用这些化合物治疗精神病的方法。
• Conversion of a Highly Selective Sigma-1 Receptor–Ligand to Sigma-2 Receptor Preferring Ligands with Anticocaine Activity
  作者：Christophe Mésangeau、Sanju Narayanan、Andrea M. Green、Jamaluddin Shaikh、Nidhi Kaushal、Eddy Viard、Yan-Tong Xu、James A. Fishback、Jacques H. Poupaert、Rae R. Matsumoto、Christopher R. McCurdy

  DOI：10.1021/jm701357m

  日期：2008.3.13

  Cocaine's toxicity can be mitigated by blocking its interaction with sigma-1 receptors. The involvement of sigma-2 receptors remains unclear. To investigate their potential role, we have designed compounds through a convergent synthesis utilizing a highly selective sigma-1 ligand and elements of a selective sigma-2 ligand. Among the synthesized compounds was produced a subnanomolar sigma-2 ligand with an 11-fold preference over sigma-1 receptors. These compounds may be useful in developing effective pharmacotherapies for cocaine toxicity.
• Discovery of <i>N</i>-{1-[3-(3-Oxo-2,3-dihydrobenzo[1,4]oxazin-4-yl)propyl]piperidin-4-yl}-2-phenylacetamide (Lu AE51090): An Allosteric Muscarinic M₁ Receptor Agonist with Unprecedented Selectivity and Procognitive Potential
  作者：Anette G. Sams、Morten Hentzer、Gitte K. Mikkelsen、Krestian Larsen、Christoffer Bundgaard、Niels Plath、Claus T. Christoffersen、Benny Bang-Andersen

  DOI：10.1021/jm100697g

  日期：2010.9.9

  The discovery and structure activity relationship (SAR) of a series of allosteric muscarinic M, receptor agonists are described. Compound 17 (Lu AE51090) was identified as a representative compound from the series, based on its high selectivity as an agonist at the muscarinic M-1 receptor across a panel of muscarinic receptor subtypes. Furthermore, 17 displayed a high degree of selectivity when tested in a broad panel of G-protein-coupled receptors, ion channels, transporters, and enzymes, and 17 showed an acceptable pharmacokinetic profile and sufficient brain exposure in rodents in order to characterize the compound in vivo. Hence, in a rodent model of learning and memory, 17 reversed delay-induced natural forgetting, suggesting a procognitive potential of 17.
• EP1432420A4
  申请人：——

  公开号：EP1432420A4

  公开（公告）日：2005-11-09
• BENZIMIDAZOLIDINONE DERIVATIVES AS MUSCARINIC AGENTS
  申请人：Acadia Pharmaceuticals Inc.

  公开号：EP1432420B1

  公开（公告）日：2011-07-13