2-[2-[(4R,5S,6S,7R,9R,11E,13E,15S,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-5,9,13,15-tetramethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]ethyl]isoindole-1,3-dione | 93416-86-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[2-[(4R,5S,6S,7R,9R,11E,13E,15S,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-5,9,13,15-tetramethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]ethyl]isoindole-1,3-dione
• CAS: 93416-86-5
• 化学式: C₄₆H₆₈N₂O₁₃
• 分子量: 857.052
• InChiKey: JUUVBPZDMRIZMA-FVOBSFDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  61
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  202
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2-[2-[(4R,5S,6S,7R,9R,11E,13E,15S,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-5,9,13,15-tetramethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]ethyl]isoindole-1,3-dione 在 硫酸 作用下， 反应 1.0h， 以60%的产率得到2-{2-[(11E,13E)-(4R,5S,6S,7R,9R,15S,16R)-6-((2R,3R,4S,5S,6R)-4-Dimethylamino-3,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-16-ethyl-4-hydroxy-5,9,13,15-tetramethyl-2,10-dioxo-oxacyclohexadeca-11,13-dien-7-yl]-ethyl}-isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis and evaluation of tylosin-related macrolides modified at the aldehyde function: a new series of orally effective antibiotics

  摘要：

  Modification of the aldehyde group in tylosin and related macrolide antibiotics dramatically enhanced the oral efficacy of the derivatives against experimental infections caused by susceptible bacteria in laboratory animals. A large number and wide variety of aldehyde-modified macrolide derivatives were prepared, utilizing the Mitsunobu reaction and other chemical transformations. Evaluation of in vitro and in vivo antimicrobial activity indicated that derivatives of demycarosyltylosin (desmycosin) combined the broadest spectrum of antimicrobial activity with the best efficacy and bioavailability after oral administration.

  DOI：

  10.1021/jm00403a025
• 作为产物：
  描述：

  (4R,5S,6S,7R,9R,11E,13E,15S,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-7-(2-hydroxyethyl)-5,9,13,15-tetramethyl-1-oxacyclohexadeca-11,13-diene-2,10-dione 、 邻苯二甲酸亚胺 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以57%的产率得到2-[2-[(4R,5S,6S,7R,9R,11E,13E,15S,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-5,9,13,15-tetramethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]ethyl]isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis and evaluation of tylosin-related macrolides modified at the aldehyde function: a new series of orally effective antibiotics

  摘要：

  Modification of the aldehyde group in tylosin and related macrolide antibiotics dramatically enhanced the oral efficacy of the derivatives against experimental infections caused by susceptible bacteria in laboratory animals. A large number and wide variety of aldehyde-modified macrolide derivatives were prepared, utilizing the Mitsunobu reaction and other chemical transformations. Evaluation of in vitro and in vivo antimicrobial activity indicated that derivatives of demycarosyltylosin (desmycosin) combined the broadest spectrum of antimicrobial activity with the best efficacy and bioavailability after oral administration.

  DOI：

  10.1021/jm00403a025

文献信息

• KIRST, HERBERT A.;TOTH, JOHN E.;DEBONO, MANUEL;WILLARD, KEVIN E.;TRUEDELL+, J. MED. CHEM., 31,(1988) N 8, C. 1631-1641
  作者：KIRST, HERBERT A.、TOTH, JOHN E.、DEBONO, MANUEL、WILLARD, KEVIN E.、TRUEDELL+

  DOI：——

  日期：——