pyridin-3-yl-acetic acid 10-(3-acetoxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-14-hydroxyimino-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6-dioxo-dodecahydro-1,3,5-trioxa-cyclopentacyclotetradecen-8-yl ester | 561327-29-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pyridin-3-yl-acetic acid 10-(3-acetoxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-14-hydroxyimino-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6-dioxo-dodecahydro-1,3,5-trioxa-cyclopentacyclotetradecen-8-yl ester
• CAS: 561327-29-5
• 化学式: C₄₀H₆₁N₃O₁₃
• 分子量: 791.937
• InChiKey: NBFHDRLKZCHDSR-ZCUWGHGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  56.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  190.84
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  pyridin-3-yl-acetic acid 10-(3-acetoxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-14-hydroxyimino-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6-dioxo-dodecahydro-1,3,5-trioxa-cyclopentacyclotetradecen-8-yl ester 在 甲醇 作用下， 反应 3.0h， 以79%的产率得到(E)-5-O-desosaminyl-3-O-(3-pyridyl)acetyl-6-O-methylerythronolide A 9-oxime 11,12-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：

  3-吡啶乙酸 在 吡啶 、 甲醇 、 三甲基乙酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 14.0h， 生成 pyridin-3-yl-acetic acid 10-(3-acetoxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-14-hydroxyimino-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6-dioxo-dodecahydro-1,3,5-trioxa-cyclopentacyclotetradecen-8-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