Acetic acid (2S,3R,4S,6R)-4-dimethylamino-2-((1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,17S)-3-ethyl-2,7,10-trihydroxy-2,6,8,10,12,17-hexamethyl-5,15-dioxo-4,14,16-trioxa-bicyclo[11.3.1]heptadec-9-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester | 223660-85-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3R,4S,6R)-4-dimethylamino-2-((1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,17S)-3-ethyl-2,7,10-trihydroxy-2,6,8,10,12,17-hexamethyl-5,15-dioxo-4,14,16-trioxa-bicyclo[11.3.1]heptadec-9-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester
• CAS: 223660-85-3
• 化学式: C₃₂H₅₅NO₁₂
• 分子量: 645.788
• InChiKey: JJIGPJORTZGCJA-VGYGQCEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  45.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  170.52
• 氢给体数：
  3.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4S,6R)-4-dimethylamino-2-((1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,17S)-3-ethyl-2,7,10-trihydroxy-2,6,8,10,12,17-hexamethyl-5,15-dioxo-4,14,16-trioxa-bicyclo[11.3.1]heptadec-9-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester 在 甲醇 、 三甲基乙酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 (9S)-5-O-desosaminyl-9-dihydro-3-O-(3-pyridyl)acetylerythronolide A 9,11-cyclic carbonate
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of a Novel Series of Acylides:  3-O-(3-Pyridyl)acetylerythromycin A Derivatives

  摘要：

  A novel series of acylides, 3-O-(aryl)acetylerythromycin A derivatives, were synthesized and evaluated. These compounds have significant potent antibacterial activity against not only Gram-positive pathogens, including inducibly macrolide-lincosamide-streptogramin B (MLSB)-resistant and efflux-resistant strains, but also Gram-negative pathogens, such as H. influenzae. 6,9:11,12-Dicarbonate acylide 47 (FMA0122) was twice as active against H. influenzae than azithromycin, whereas it showed only moderate in vivo efficacy in mouse protection tests. However, the 11,12-carbamate acylide 19 (TEA0929), which showed potent antibacterial activity against almost all of the main causative pathogens of community-acquired pneumonia tested, exhibited excellent in vivo efficacy comparable to those of second-generation macrolides.

  DOI：

  10.1021/jm020568d
• 作为产物：
  描述：

  (9S)-9-dihydroerythromycin A 9,11-cyclic carbonate 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 Acetic acid (2S,3R,4S,6R)-4-dimethylamino-2-((1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,17S)-3-ethyl-2,7,10-trihydroxy-2,6,8,10,12,17-hexamethyl-5,15-dioxo-4,14,16-trioxa-bicyclo[11.3.1]heptadec-9-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of a Novel Series of Acylides:  3-O-(3-Pyridyl)acetylerythromycin A Derivatives

  摘要：

  A novel series of acylides, 3-O-(aryl)acetylerythromycin A derivatives, were synthesized and evaluated. These compounds have significant potent antibacterial activity against not only Gram-positive pathogens, including inducibly macrolide-lincosamide-streptogramin B (MLSB)-resistant and efflux-resistant strains, but also Gram-negative pathogens, such as H. influenzae. 6,9:11,12-Dicarbonate acylide 47 (FMA0122) was twice as active against H. influenzae than azithromycin, whereas it showed only moderate in vivo efficacy in mouse protection tests. However, the 11,12-carbamate acylide 19 (TEA0929), which showed potent antibacterial activity against almost all of the main causative pathogens of community-acquired pneumonia tested, exhibited excellent in vivo efficacy comparable to those of second-generation macrolides.

  DOI：

  10.1021/jm020568d