9-deoxo-9-dihydro-9a-(N'-(β-cyanoethyl)-N'-(1-naphthyl)carbamoyl-γ-aminopropyl)-9a-aza-9a-homoerythromycin A | 709653-17-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-deoxo-9-dihydro-9a-(N'-(β-cyanoethyl)-N'-(1-naphthyl)carbamoyl-γ-aminopropyl)-9a-aza-9a-homoerythromycin A
• 英文别名: 1-(2-cyanoethyl)-1-[3-[(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-15-oxo-1-oxa-6-azacyclopentadec-6-yl]propyl]-3-naphthalen-1-ylurea
• CAS: 709653-17-8
• 化学式: C₅₄H₈₇N₅O₁₃
• 分子量: 1014.31
• InChiKey: YYZLEZBKLBXPPP-VUKDABBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  72
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  236
• 氢给体数：
  6
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  9-deoxo-9-dihydro-9a-(N'-(β-cyanoethyl)-N'-(1-naphthyl)carbamoyl-γ-aminopropyl)-9a-aza-9a-homoerythromycin A 在 盐酸 、 水 作用下， 反应 12.0h， 以80.2%的产率得到5-O-desosaminyl-9-deoxo-9-dihydro-9a-[N'-(β-cyanoethyl)-N'-(1-naphthyl)carbamoyl-γ-aminopropyl]-9a-aza-9a-homoerythronolide A
  参考文献：
  名称：

  Novel ureas and thioureas of 15-membered azalides with antibacterial activity against key respiratory pathogens

  摘要：

  The new ureas and thioureas of 15-membered azalides, N ''-substituted 9a-(N'-carbamoyl-gamma-aminopropyl) (4), 9a-(N'-thiocarbamoyl-gamma-aminopropyl) (6), 9a-[N'-(beta-cyanoethyl)-N'-(carbamoyl-gamma-aminopropyl)] (8) and 9a-[N'-(beta-cyanoethyl)-N'-(thiocarbamoyl-gamma-aminopropyl)] (10) of 9-deoxo-9-dihydro-9a-aza-9a-homoerythromycin A (2), were synthesized and structurally characterized by NMR and IR spectroscopic methods and mass spectrometry. The new compounds were evaluated in vitro against a panel of erythromycin susceptible and erythromycin-resistant Gram-positive and Gram-negative bacterial strains. These compounds displayed an excellent overall antibacterial in vitro activity against erythromycin sensitive Gram-positive strains, Streptococcus pneumoniae, Streptococcus pyogenes, Staphylococcus aureus, and good against negative strains, Moraxella catarrhalis and Haemophilus influenzae. In addition, several ureas with naphthyl substituents (4f, 4g, 4h) showed better activity in comparison to azithromycin against inducible resistant S. pyogenes. Ureas with naphthyl substituents 4g, 4h and thiourea 8h displayed moderate activity against constitutively resistant S. pneumoniae. (C) 2009 Elsevier Masson SAS. All rights reserved

  DOI：

  10.1016/j.ejmech.2009.02.001
• 作为产物：
  描述：

  9-deoxo-9-dihydro-9a-N-[N'-(β-cyanoethyl)-γ-aminopropyl]-9a-aza-9a-homoerithromycin A 、 1-Alapha-萘异氰酸酯 以 二氯甲烷 为溶剂， 反应 1.0h， 以36.1%的产率得到9-deoxo-9-dihydro-9a-(N'-(β-cyanoethyl)-N'-(1-naphthyl)carbamoyl-γ-aminopropyl)-9a-aza-9a-homoerythromycin A
  参考文献：
  名称：

  Novel ureas and thioureas of 15-membered azalides with antibacterial activity against key respiratory pathogens

  摘要：

  The new ureas and thioureas of 15-membered azalides, N ''-substituted 9a-(N'-carbamoyl-gamma-aminopropyl) (4), 9a-(N'-thiocarbamoyl-gamma-aminopropyl) (6), 9a-[N'-(beta-cyanoethyl)-N'-(carbamoyl-gamma-aminopropyl)] (8) and 9a-[N'-(beta-cyanoethyl)-N'-(thiocarbamoyl-gamma-aminopropyl)] (10) of 9-deoxo-9-dihydro-9a-aza-9a-homoerythromycin A (2), were synthesized and structurally characterized by NMR and IR spectroscopic methods and mass spectrometry. The new compounds were evaluated in vitro against a panel of erythromycin susceptible and erythromycin-resistant Gram-positive and Gram-negative bacterial strains. These compounds displayed an excellent overall antibacterial in vitro activity against erythromycin sensitive Gram-positive strains, Streptococcus pneumoniae, Streptococcus pyogenes, Staphylococcus aureus, and good against negative strains, Moraxella catarrhalis and Haemophilus influenzae. In addition, several ureas with naphthyl substituents (4f, 4g, 4h) showed better activity in comparison to azithromycin against inducible resistant S. pyogenes. Ureas with naphthyl substituents 4g, 4h and thiourea 8h displayed moderate activity against constitutively resistant S. pneumoniae. (C) 2009 Elsevier Masson SAS. All rights reserved

  DOI：

  10.1016/j.ejmech.2009.02.001

文献信息

• 9A-Carbamoyl-Y-Aminopropyl- And 9A-Thiocabamoyl-Y-Aminopropyl-Azalides With Antimalarial Activity
  申请人：Ivezic Zrinka

  公开号：US20080113926A1

  公开（公告）日：2008-05-15

  9a-Carbamoyl-γ-aminopropyl- and 9a-thiocarbamoyl-γ-aminopropyl-azalides and their pharmaceutically acceptable derivatives are useful for treatment and prevention of malaria.
• Novel ureas and thioureas of 15-membered azalides with antibacterial activity against key respiratory pathogens
  作者：Mirjana Bukvić Krajačić、Predrag Novak、Miljenko Dumić、Mario Cindrić、Hana Čipčić Paljetak、Nedjeljko Kujundžić

  DOI：10.1016/j.ejmech.2009.02.001

  日期：2009.9

  The new ureas and thioureas of 15-membered azalides, N ''-substituted 9a-(N'-carbamoyl-gamma-aminopropyl) (4), 9a-(N'-thiocarbamoyl-gamma-aminopropyl) (6), 9a-[N'-(beta-cyanoethyl)-N'-(carbamoyl-gamma-aminopropyl)] (8) and 9a-[N'-(beta-cyanoethyl)-N'-(thiocarbamoyl-gamma-aminopropyl)] (10) of 9-deoxo-9-dihydro-9a-aza-9a-homoerythromycin A (2), were synthesized and structurally characterized by NMR and IR spectroscopic methods and mass spectrometry. The new compounds were evaluated in vitro against a panel of erythromycin susceptible and erythromycin-resistant Gram-positive and Gram-negative bacterial strains. These compounds displayed an excellent overall antibacterial in vitro activity against erythromycin sensitive Gram-positive strains, Streptococcus pneumoniae, Streptococcus pyogenes, Staphylococcus aureus, and good against negative strains, Moraxella catarrhalis and Haemophilus influenzae. In addition, several ureas with naphthyl substituents (4f, 4g, 4h) showed better activity in comparison to azithromycin against inducible resistant S. pyogenes. Ureas with naphthyl substituents 4g, 4h and thiourea 8h displayed moderate activity against constitutively resistant S. pneumoniae. (C) 2009 Elsevier Masson SAS. All rights reserved