5-O-(tert-butyldimethylsilyl)-13-O-[3-(2-azidobenzoylamino)propionyl]avermectin B1a aglycone | 261911-93-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 5-O-(tert-butyldimethylsilyl)-13-O-[3-(2-azidobenzoylamino)propionyl]avermectin B1a aglycone
• 英文别名: 5-O-(tert-butyldimethylsilyl)-13-O-[3-(2-azidobenzoylamino)propionyl]avermectin B_1a aglycone
• CAS: 261911-93-7
• 化学式: C₅₀H₇₀N₄O₁₀Si
• 分子量: 915.212
• InChiKey: QHQMPKWZZWMPBJ-GDGJLTOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.65
• 重原子数：
  65.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  187.61
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  5-O-(tert-butyldimethylsilyl)-13-O-[3-(2-azidobenzoylamino)propionyl]avermectin B1a aglycone 在 氟化氢吡啶 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以99%的产率得到
  参考文献：
  名称：

  Avermectin chemistry and action: ester- and ether-type candidate photoaffinity probes

  摘要：

  Avermectin B-1a (1) is a potent anthelmintic, insecticide, miticide and chloride channel activator on interaction with a specific nerve membrane site analyzed by binding assays with [H-3]1. Candidate photoaffinity probes were prepared replacing the dioleandrosyl substituent with potential isosteric esters and ethers approximating the original overall atom length and terminating in a phenyl moiety substituted with azido, iodo or hydroxy. Several of the candidates met the goal of high potency on mouse, housefly and fruit fly brain chloride channels with IC50 values of 7-57 nM in competing for the [H-3]1 binding site. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00259-x
• 作为产物：
  描述：

  5-O-(tert-butyldimethylsilyl)-13-O-[3-(2,2,2-trichloroethoxycarbonylamino)propionyl]avermectin B1a aglycone 在 水 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.5h， 生成 5-O-(tert-butyldimethylsilyl)-13-O-[3-(2-azidobenzoylamino)propionyl]avermectin B1a aglycone
  参考文献：
  名称：

  Avermectin chemistry and action: ester- and ether-type candidate photoaffinity probes

  摘要：

  Avermectin B-1a (1) is a potent anthelmintic, insecticide, miticide and chloride channel activator on interaction with a specific nerve membrane site analyzed by binding assays with [H-3]1. Candidate photoaffinity probes were prepared replacing the dioleandrosyl substituent with potential isosteric esters and ethers approximating the original overall atom length and terminating in a phenyl moiety substituted with azido, iodo or hydroxy. Several of the candidates met the goal of high potency on mouse, housefly and fruit fly brain chloride channels with IC50 values of 7-57 nM in competing for the [H-3]1 binding site. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00259-x