3-(2-溴乙基)-1,3-苯并噁唑-2(3H)-酮 | 27170-93-0

• 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-(2-溴乙基)-1,3-苯并噁唑-2(3H)-酮
• 中文别名: 3-(2-溴乙基)苯并[D]恶唑-2(3H)-酮
• 英文名称: 3-(2-bromoethyl)benzo[d]oxazol-2(3H)-one
• 英文别名: 3-(2-bromoethyl)-1,3-benzoxazol-2-one
• CAS: 27170-93-0
• 化学式: C₉H₈BrNO₂
• mdl: MFCD06270899
• 分子量: 242.072
• InChiKey: ZXIXDDXYXCANPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-(2-溴乙基)-1,3-苯并噁唑-2(3H)-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-(2-(4-(4-(2-oxobenzo[d]oxazol-3(2H)-yl)butyl)piperazin-1-yl)ethyl)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 、 1,2-二溴乙烷 在 四丁基碘化铵 、 caesium carbonate 作用下， 反应 12.0h， 生成 3-(2-溴乙基)-1,3-苯并噁唑-2(3H)-酮
  参考文献：
  名称：

  N-(芳氨基乙基)苯并噁唑酮类化合物及其制备方法和用途

  摘要：

  本发明提供了一种用于农作物抑菌的N‑(芳氨基乙基)苯并噁唑酮类化合物及其制备方法和用途。该化合物是通过芳胺类化合物与N‑(2‑溴乙基)苯并噁唑酮进行反应制备获得的，该制备方法合成材料廉价易得，合成方法简单。同时该化合物对农作物病菌的活性具有良好的抑制作用，特别是对小麦赤霉病菌、黄瓜灰霉病菌、辣椒疫霉病菌、油菜菌核病菌、水稻纹枯病菌和稻瘟病菌等病菌的活性抑制效果显著。

  公开号：

  CN112174908B

文献信息

• 4-Phenyl- and 4-heteroaryl-4-anilidopiperidines. A novel class of analgesic and anesthetic agents
  作者：Linas V. Kudzma、Sherry A. Severnak、Mark J. Benvenga、Edward F. Ezell、Michael H. Ossipov、Valerie V. Knight、Frieda G. Rudo、H. Kenneth Spencer、Theodore C. Spaulding

  DOI：10.1021/jm00132a007

  日期：1989.12

  4-anilidopiperidines related to fentanyl (1) led to a novel class of potent opioid analgesic and anesthetic agents with a favorable pharmacological profile. The synthesis, analgesic activity, and anesthetic properties of a series of 4-phenyl-4-anilidopiperidines (13-29) are discussed. Isosteric replacement of the phenyl by various heteroaryl substituents extended the series to include 4-heteroaryl-4-anilidopiperidines

  在吗啡中发现的4-苯基哌啶药效基团并入与芬太尼相关的4-anilidopiperidines中（1）导致了一类新型的有效阿片类镇痛药和麻醉剂，具有良好的药理作用。讨论了一系列4-苯基-4-苯胺基哌啶（13-29）的合成，镇痛活性和麻醉性能。用各种杂芳基取代基对苯进行等位取代，将系列扩大到包括4-杂芳基-4-苯并哌啶（30-53）。在这一组中，1- [2-（1H-吡唑-1-基）乙基] -4-（4-甲基噻唑-2-基）-4-（N-苯基丙酰胺基）哌啶（48）具有较高的镇痛作用，作用时间短，麻醉剂量后运动协调迅速恢复，与目前临床使用的阿片类药物芬太尼（1）和阿芬太尼（2）相比，麻醉期间的心血管和呼吸安全性更高。这样的镇痛药对于临床医生在不断扩大的门诊外科手术领域中以及对患者控制的镇痛和计算机辅助的连续输注疼痛控制技术具有极大的实用性。
• Piperidine compounds
  申请人：ADIR ET COMPAGNIE

  公开号：US20020161228A1

  公开（公告）日：2002-10-31

  A compound selected from those of formula (I): 1 wherein: W represents optionally substituted naphthyl, or group of formula Y 2 as defined in the description, n represents an integer from 1 to 6 inclusive, Z represents single bond, oxygen, or optionally substituted nitrogen, A and Q each represent CH or nitrogen, M, together with carbon of phenyl to which it is bonded, represents thienyl, furyl, pyrrolyl or oxopyrrolyl, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof, and medicinal products containing the same are useful in the treatment of some CNS disorders.

  从式(I)中选择的化合物：其中：W代表可选取代的萘基或式Y2所定义的基团，n表示从1到6的整数，包括Z代表单键，氧或可选取代的氮，A和Q各自代表CH或氮，M与其结合的苯环上的碳一起，代表噻吩基，呋喃基，吡咯基或氧代吡咯基，其异构体和药学上可接受的酸或碱加盐物，以及含有它们的药物制品在治疗某些中枢神经系统疾病方面是有用的。
• 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.
• [EN] HIGHLY SELECTIVE SIGMA RECEPTOR LIGANDS<br/>[FR] LIGANDS DE RÉCEPTEUR SIGMA HAUTEMENT SÉLECTIFS
  申请人：UNIV MISSISSIPPI

  公开号：WO2009026227A3

  公开（公告）日：2009-04-09
• Zinner et al., Chemische Berichte, 1956, vol. 89, p. 2131,2132, 2135
  作者：Zinner et al.

  DOI：——

  日期：——