5-bromo-2-methoxybenzaldehyde oxime | 452280-22-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-bromo-2-methoxybenzaldehyde oxime
• 英文别名: N-[(5-bromo-2-methoxyphenyl)methylidene]hydroxylamine
• CAS: 452280-22-7
• 化学式: C₈H₈BrNO₂
• mdl: MFCD03931941
• 分子量: 230.061
• InChiKey: FOPPMJDZHLMQIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-2-methoxybenzaldehyde oxime 在 N-氯代丁二酰亚胺 、 四(三苯基膦)钯 、 sodium hydride 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-(5-allyl-2-methoxyphenyl)-5-((allyloxy)methyl)isoxazole
  参考文献：
  名称：

  Synthesis and anti-neuroinflammatory activity of N-heterocyclic analogs based on natural biphenyl-neolignan honokiol

  摘要：

  Novel isoxazole and pyrazole analogs based on natural biphenyl-neolignan honokiol were synthesized and evaluated for their inhibitory activities against nitric oxide production in lipopolysaccharide-activated BV-2 microglial cells. The isoxazole skeleton was constructed via nitrile oxide cycloaddition from oxime 3 and pyrazole was generated by condensation of 4-chromone and alkylhydrazine. Among the analogs, 13b and 14a showed stronger inhibitory activities with IC50 values of 8.9 and 1.2 mu M, respectively, than honokiol.

  DOI：

  10.1016/j.bmcl.2018.11.014
• 作为产物：
  描述：

  5-溴-2-甲氧基苯甲醛 在 盐酸羟胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5-bromo-2-methoxybenzaldehyde oxime
  参考文献：
  名称：

  An efficient one-pot synthesis of 3-aryl-5-methylisoxazoles from aryl aldehydes

  摘要：

  An efficient protocol for the one-pot preparation of alkyl 3-aryl-5-methylisoxazole-4-carboxylates from aryl aldehydes is described. This method is readily amenable to the large scale preparation of isoxazoles as well as the parallel synthesis of isoxazole libraries. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.104

文献信息

• An efficient one-pot synthesis of 3-aryl-5-methylisoxazoles from aryl aldehydes
  作者：Shirong Zhu、Shuhao Shi、Samuel W. Gerritz

  DOI：10.1016/j.tetlet.2011.05.104

  日期：2011.8

  An efficient protocol for the one-pot preparation of alkyl 3-aryl-5-methylisoxazole-4-carboxylates from aryl aldehydes is described. This method is readily amenable to the large scale preparation of isoxazoles as well as the parallel synthesis of isoxazole libraries. (C) 2011 Elsevier Ltd. All rights reserved.
• Discovery of 3-Amino-4-Chlorophenyl P1 as a novel and potent benzamidine mimic via solid-phase synthesis of an isoxazoline library
  作者：Patrick Y.S. Lam、Jessica J. Adams、Charles G. Clark、W.Jason Calhoun、Joseph M. Luettgen、Robert M. Knabb、Ruth R. Wexler

  DOI：10.1016/s0960-894x(03)00130-6

  日期：2003.5

  In an effort to identify orally bioavailable factor Xa inhibitors, two isoxazolines libraries were prepared to scan for novel P1 ligands. From this work, 4-chloro-3-aniline was identified as a novel and potent benzamidine mimic. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Design and synthesis of 4-O-methylhonokiol analogs as inhibitors of cyclooxygenase-2 (COX-2) and PGF1 production
  作者：Bit Lee、Jae-Hwan Kwak、Shin-Won Huang、Jae-Yong Jang、Sanglae Lim、Young-Shin Kwak、Kiho Lee、Hyung Sook Kim、Sang-Bae Han、Jin-Tae Hong、Heesoon Lee、Sukgil Song、Seung-Yong Seo、Jae-Kyung Jung

  DOI：10.1016/j.bmc.2012.03.028

  日期：2012.5

  A series of novel 4-O-methylhonokiol analogs were synthesized in light of revealing structure-activity relationship for inhibitory effect of COX-2 enzyme. The key strategy of the molecular design was oriented towards modification of the potential metabolic soft spots (e. g., phenol and olefin) or by altering the polar surface area via incorporating heterocycles such as isoxazole and triazole. Most of all exhibited the inhibitory effects on COX-2 and PGF(1) production but not macrophage NO production. Especially, aryl carbamates 10 and 11 exhibited more potent inhibitory activity against COX-2 and PGF(1) production. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.
• Synthesis and anti-neuroinflammatory activity of N-heterocyclic analogs based on natural biphenyl-neolignan honokiol
  作者：Yue Yuan、Lalita Subedi、Daesung Lim、Jae-Kyung Jung、Sun Yeou Kim、Seung-Yong Seo

  DOI：10.1016/j.bmcl.2018.11.014

  日期：2019.1

  Novel isoxazole and pyrazole analogs based on natural biphenyl-neolignan honokiol were synthesized and evaluated for their inhibitory activities against nitric oxide production in lipopolysaccharide-activated BV-2 microglial cells. The isoxazole skeleton was constructed via nitrile oxide cycloaddition from oxime 3 and pyrazole was generated by condensation of 4-chromone and alkylhydrazine. Among the analogs, 13b and 14a showed stronger inhibitory activities with IC50 values of 8.9 and 1.2 mu M, respectively, than honokiol.