3-(Phenylmethoxy)-5-isoxazolemethanamine | 14423-93-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(Phenylmethoxy)-5-isoxazolemethanamine
• 英文别名: (3-phenylmethoxy-1,2-oxazol-5-yl)methanamine
• CAS: 14423-93-9
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: MBTTWUDVHGZSIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(Phenylmethoxy)-5-isoxazolemethanamine 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 以179 mg的产率得到蝇蕈醇溴酸盐
  参考文献：
  名称：

  4,5-Substituted 3-Isoxazolols with Insecticidal Activity Act as Competitive Antagonists of Housefly GABA Receptors

  摘要：

  The insect GABA receptor (GABAR), which-is composed of five RDL subunits, represents an important target for insecticides. A series of 4,5-disubstituted 3-isoxazolols, including muscimol, analogues; were synthesized and examined for their activities against four splice variants (ac, ad, bc, and bd) of housefly GABARs expressed in Xenopus oocytes. Muscimol was a more potent agonist than GABA in all four splice variants, whereas Synthesized analogues did, not exhibit agonism but rather antagonism in housefly GABARs. The introduction of bicyclic aromatic groups at the 4-position of muscimol and the simultaneous replacement Of the aminomethyl group with a carbamoyl group at the 5-position to afford six 4-aryl-5-carbamoyl-3-isoxazolols resulted in Compounds that exhibited significantly enhanced antagonism with IC50 value in the low micromolar range in the ac variant. The inhibition of GABA-induced currents by 100 mu M analogues was approximately 1.5-4-fold greater in the ac and bc variants than in the ad and bd variants. 4-(3-Biphenylyl)-5-carbamoyl-3-isoxazolol displayed Competitive antagonism, with IC50 values of 30, 34, 1:07, and 96 mu M in the ac, bc, ad, and bd variants, respectively, and exhibited Moderate insecticidal activity against houseflies, with an LD50, value of 5.6 nmol/fly. These findings suggest that these 3-isoxazolol analogues are novel lead compounds for the design and development of insecticides that target the orthosteric site of housefly GABARs.

  DOI：

  10.1021/acs.jafc.5b01843
• 作为产物：
  描述：

  3-苄氧基异噁唑-5-羧酸甲酯 在 ammonium hydroxide 、 硼烷四氢呋喃络合物 作用下， 反应 12.0h， 生成 3-(Phenylmethoxy)-5-isoxazolemethanamine
  参考文献：
  名称：

  4,5-Substituted 3-Isoxazolols with Insecticidal Activity Act as Competitive Antagonists of Housefly GABA Receptors

  摘要：

  The insect GABA receptor (GABAR), which-is composed of five RDL subunits, represents an important target for insecticides. A series of 4,5-disubstituted 3-isoxazolols, including muscimol, analogues; were synthesized and examined for their activities against four splice variants (ac, ad, bc, and bd) of housefly GABARs expressed in Xenopus oocytes. Muscimol was a more potent agonist than GABA in all four splice variants, whereas Synthesized analogues did, not exhibit agonism but rather antagonism in housefly GABARs. The introduction of bicyclic aromatic groups at the 4-position of muscimol and the simultaneous replacement Of the aminomethyl group with a carbamoyl group at the 5-position to afford six 4-aryl-5-carbamoyl-3-isoxazolols resulted in Compounds that exhibited significantly enhanced antagonism with IC50 value in the low micromolar range in the ac variant. The inhibition of GABA-induced currents by 100 mu M analogues was approximately 1.5-4-fold greater in the ac and bc variants than in the ad and bd variants. 4-(3-Biphenylyl)-5-carbamoyl-3-isoxazolol displayed Competitive antagonism, with IC50 values of 30, 34, 1:07, and 96 mu M in the ac, bc, ad, and bd variants, respectively, and exhibited Moderate insecticidal activity against houseflies, with an LD50, value of 5.6 nmol/fly. These findings suggest that these 3-isoxazolol analogues are novel lead compounds for the design and development of insecticides that target the orthosteric site of housefly GABARs.

  DOI：

  10.1021/acs.jafc.5b01843

文献信息

• Tetracycline Derivatives with Reduced Antibiotic Activity and Neuroprotective Benefits
  申请人：Duncan Iain W.

  公开号：US20100009981A1

  公开（公告）日：2010-01-14

  The present disclosure is directed to compositions and methods which utilize the tetracycline scaffold, preferably the scaffold of tetracycline or minocycline, and which significantly lack antibiotic activity. The compounds have neuroprotective attributes without interfering with the drugs capacity to pass through the blood brain barrier. These compounds have neuroprotective activity because of their inhibition of neuronal cell cycle progression. The compounds are characterized in part by a fifth ring joining positions 9 and 10.

  本公开涉及利用四环素骨架的组合物和方法，优选是四环素或米诺环素的骨架，并且明显缺乏抗生素活性。这些化合物具有神经保护特性，而不会干扰药物通过血脑屏障的能力。这些化合物由于抑制神经元细胞周期进展而具有神经保护活性。这些化合物部分地以第五环连接9和10位置为特征。
• TETRACYCLINE DERIVATIVES WITH REDUCED ANTIBIOTIC ACTIVITY AND NEUROPROTECTIVE BENEFITS
  申请人：Neumedics

  公开号：US20170144979A1

  公开（公告）日：2017-05-25

  The present disclosure is directed to compositions and methods which utilize the tetracycline scaffold, preferably the scaffold of tetracycline or minocycline, and which significantly lack antibiotic activity. The compounds have neuroprotective attributes without interfering with the drugs capacity to pass through the blood brain barrier. These compounds have neuroprotective activity because of their inhibition of neuronal cell cycle progression. The compounds are characterized in part by a fifth ring joining positions 9 and 10.
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