Acetic acid (2S,3R,4S,6R)-4-dimethylamino-2-((1S,2S,3R,7R,8R,11R,12S,13S,14R,15R,19R)-8-ethyl-12-hydroxy-2,7,11,13,15,19-hexamethyl-5,10,17-trioxo-4,6,9,16,18-pentaoxa-tricyclo[13.3.2.03,7]icos-14-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester | 205320-32-7

• 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-((1S,2S,3R,7R,8R,11R,12S,13S,14R,15R,19R)-8-ethyl-12-hydroxy-2,7,11,13,15,19-hexamethyl-5,10,17-trioxo-4,6,9,16,18-pentaoxa-tricyclo[13.3.2.03,7]icos-14-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester
• CAS: 205320-32-7
• 化学式: C₃₃H₅₃NO₁₃
• 分子量: 671.783
• InChiKey: IUMBIAJNFHMNIA-KMHODRDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  47.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  165.59
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4S,6R)-4-dimethylamino-2-((1S,2S,3R,7R,8R,11R,12S,13S,14R,15R,19R)-8-ethyl-12-hydroxy-2,7,11,13,15,19-hexamethyl-5,10,17-trioxo-4,6,9,16,18-pentaoxa-tricyclo[13.3.2.03,7]icos-14-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester 在 甲醇 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 144.0h， 生成 (9S)-5-desosaminyl-9-dihydro-3-O-(4-pyridyl)acetylerythronolide A 6,9:11,12-dicyclic 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：

  [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(1R,2R,5R,6S,7S,8R,9R,11R,12S,13S,14R)-2-ethyl-9,12-dihydroxy-6-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-1,5,7,9,11,13-hexamethyl-4,16-dioxo-3,15,17-trioxabicyclo[12.3.0]heptadecan-8-yl]oxy]-6-methyloxan-3-yl] acetate 在 吡啶 、 盐酸 、 甲醇 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 28.0h， 生成 Acetic acid (2S,3R,4S,6R)-4-dimethylamino-2-((1S,2S,3R,7R,8R,11R,12S,13S,14R,15R,19R)-8-ethyl-12-hydroxy-2,7,11,13,15,19-hexamethyl-5,10,17-trioxo-4,6,9,16,18-pentaoxa-tricyclo[13.3.2.03,7]icos-14-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