N-((4aS,11aR,12aS,13S)-3,7-bis(benzyloxy)-4a-((tert-butyldimethylsilyl)oxy)-10-chloro-13-(dimethylamino)-5-hydroxy-4,6-dioxo-4,4a,6,11,11a,12,12a,13-octahydroisoxazolo[5',4':6,7]naphtho[2,3-g]isoquinolin-8-yl)-2-bromoacetamide | 1268248-40-3

• 分子结构分类: 有机化合物
• 英文名称: N-((4aS,11aR,12aS,13S)-3,7-bis(benzyloxy)-4a-((tert-butyldimethylsilyl)oxy)-10-chloro-13-(dimethylamino)-5-hydroxy-4,6-dioxo-4,4a,6,11,11a,12,12a,13-octahydroisoxazolo[5',4':6,7]naphtho[2,3-g]isoquinolin-8-yl)-2-bromoacetamide
• CAS: 1268248-40-3
• 化学式: C₄₂H₄₆BrClN₄O₈Si
• 分子量: 878.292
• InChiKey: JFIOKMQCBHTSRY-XRRWOWLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.66
• 重原子数：
  57.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  153.32
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-((4aS,11aR,12aS,13S)-3,7-bis(benzyloxy)-4a-((tert-butyldimethylsilyl)oxy)-10-chloro-13-(dimethylamino)-5-hydroxy-4,6-dioxo-4,4a,6,11,11a,12,12a,13-octahydroisoxazolo[5',4':6,7]naphtho[2,3-g]isoquinolin-8-yl)-2-bromoacetamide 在 盐酸 、 palladium 10% on activated carbon 、 氢氟酸 、 氢气 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 乙腈 为溶剂， 反应 19.0h， 生成 9-[2-(tert-butylamino)acetamido]-7-chloro-6-demethyl-6-deoxy-8-azatetracycline dihydrochloride
  参考文献：
  名称：

  8-Azatetracyclines: Synthesis and Evaluation of a Novel Class of Tetracycline Antibacterial Agents

  摘要：

  A novel series of fully synthetic 8-azatetracyclines was prepared and evaluated for antibacterial activity. Compounds were identified that overcome both efflux (tet(K)) and ribosomal protection (tet(M)) tetracycline resistance mechanisms and are active against Gram-positive and Gram-negative organisms. Two compounds were identified that exhibit comparable efficacy to marketed tetracyclines in in vivo models of bacterial infection.

  DOI：

  10.1021/jm1015389
• 作为产物：
  描述：

  phenyl 3-(benzyloxy)-2-bromo-6-chloro-5-methylisonicotinate 在 盐酸 、 tris-(dibenzylideneacetone)dipalladium(0) 、 anhydrous dipotassium phosphate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 5.17h， 生成 N-((4aS,11aR,12aS,13S)-3,7-bis(benzyloxy)-4a-((tert-butyldimethylsilyl)oxy)-10-chloro-13-(dimethylamino)-5-hydroxy-4,6-dioxo-4,4a,6,11,11a,12,12a,13-octahydroisoxazolo[5',4':6,7]naphtho[2,3-g]isoquinolin-8-yl)-2-bromoacetamide
  参考文献：
  名称：

  8-Azatetracyclines: Synthesis and Evaluation of a Novel Class of Tetracycline Antibacterial Agents

  摘要：

  A novel series of fully synthetic 8-azatetracyclines was prepared and evaluated for antibacterial activity. Compounds were identified that overcome both efflux (tet(K)) and ribosomal protection (tet(M)) tetracycline resistance mechanisms and are active against Gram-positive and Gram-negative organisms. Two compounds were identified that exhibit comparable efficacy to marketed tetracyclines in in vivo models of bacterial infection.

  DOI：

  10.1021/jm1015389