[(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(1S,2S,3R,7R,8R,11R,12S,13S,14R,15R,19R)-8-ethyl-12-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-2,7,11,13,15,19-hexamethyl-5,10,17-trioxo-4,6,9,16,18-pentaoxatricyclo[13.3.2.03,7]icosan-14-yl]oxy]-6-methyloxan-3-yl] acetate | 561327-21-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(1S,2S,3R,7R,8R,11R,12S,13S,14R,15R,19R)-8-ethyl-12-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-2,7,11,13,15,19-hexamethyl-5,10,17-trioxo-4,6,9,16,18-pentaoxatricyclo[13.3.2.03,7]icosan-14-yl]oxy]-6-methyloxan-3-yl] acetate
• CAS: 561327-21-7
• 化学式: C₄₁H₆₇NO₁₆
• 分子量: 829.98
• InChiKey: ZWABKZBAJZRHSC-RRYOOMOLSA-N

物化性质

• 沸点：
  884.2±65.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  58
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  193
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(1S,2S,3R,7R,8R,11R,12S,13S,14R,15R,19R)-8-ethyl-12-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-2,7,11,13,15,19-hexamethyl-5,10,17-trioxo-4,6,9,16,18-pentaoxatricyclo[13.3.2.03,7]icosan-14-yl]oxy]-6-methyloxan-3-yl] acetate 在 盐酸 、 甲醇 作用下， 以 丙酮 为溶剂， 反应 23.0h， 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
• 作为产物：
  描述：

  (9S)-9-dihydroerythromycin A 11,12-cyclic carbonate 在 吡啶 、 丙酮 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(1S,2S,3R,7R,8R,11R,12S,13S,14R,15R,19R)-8-ethyl-12-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-2,7,11,13,15,19-hexamethyl-5,10,17-trioxo-4,6,9,16,18-pentaoxatricyclo[13.3.2.03,7]icosan-14-yl]oxy]-6-methyloxan-3-yl] acetate
  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

文献信息

• C-4" POSITION SUBSTITUTED MACROLIDE DERIVATIVE
  申请人：Sugimoto Tomohiro

  公开号：US20140046043A1

  公开（公告）日：2014-02-13

  A macrolide compound represented by the formula (I) effective against erythromycin resistant bacteria (for example, resistant pneumococci, streptococci and mycoplasmas).

  一种大环内酯化合物，化学式为（I），对红霉素耐药的细菌有效（例如，耐药的肺炎球菌，链球菌和支原体）。
• US9139609B2
  申请人：——

  公开号：US9139609B2

  公开（公告）日：2015-09-22