5-O-desosaminyl-9-deoxo-9-dihydro-9a-[N'-(β-phenylethyl)thiocarbamoyl-γ-aminopropyl]-9a-aza-9a-homoerythronolide A | 709653-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-desosaminyl-9-deoxo-9-dihydro-9a-[N'-(β-phenylethyl)thiocarbamoyl-γ-aminopropyl]-9a-aza-9a-homoerythronolide A
• 英文别名: 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-3,4,10,13-tetrahydroxy-3,5,8,10,12,14-hexamethyl-15-oxo-1-oxa-6-azacyclopentadec-6-yl]propyl]-3-(2-phenylethyl)thiourea
• CAS: 709653-10-1
• 化学式: C₄₁H₇₂N₄O₉S
• 分子量: 797.11
• InChiKey: PJEJHUKHQPAXEX-DWTLBQIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  55
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  209
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  阿奇霉素 A 在 盐酸 、 platinum on carbon 、 氢气 作用下， 以 二氯甲烷 、 水 为溶剂， 60.0 ℃ 、400.01 kPa 条件下， 反应 50.0h， 生成 5-O-desosaminyl-9-deoxo-9-dihydro-9a-[N'-(β-phenylethyl)thiocarbamoyl-γ-aminopropyl]-9a-aza-9a-homoerythronolide A
  参考文献：
  名称：

  Discovery of novel ureas and thioureas of 3-decladinosyl-3-hydroxy 15-membered azalides active against efflux-mediated resistant Streptococcus pneumoniae

  摘要：

  A series of novel ureas and thioureas of 3-decladinosyl-3-hydroxy 15-membered azalides, were discovered, structurally characterized and biologically evaluated. They have shown good antibacterial activity against selected Gram-positive and Gram-negative bacterial strains. These include N '' substituted 9a-(N'-carbamoyl-gamma-aminopropyl)- (6a,c), 9a-(N'-thiocarbamoyl-gamma-aminopropyl)- (7a,e), 9a-[N'-(beta-cyanoethyl)-N'-(carbamoyl-gamma-aminopropyl)]- (9a-c, 9g) 9a-[N'-(beta-cyanoethyl)-N'-(thiocarbamoyl-gamma-aminopropyl)]-derivatives (10d-f) of 5-O-desosaminyl-9-deoxo-9-dihydro-9a-aza-9a-homoerythronolide A (3).Among the synthesized compounds thiourea 7a and urea 9b have shown substantially improved activity comparable to azithromycin (1) and significantly better activity than the 3-decladinosyl-azithromycin (2) and the parent 3-cladinosyl analogues against efflux-mediated resistant S. pneumoniae. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.079

文献信息

• Discovery of novel ureas and thioureas of 3-decladinosyl-3-hydroxy 15-membered azalides active against efflux-mediated resistant Streptococcus pneumoniae
  作者：Mirjana Bukvić Krajačić、Miljenko Dumić、Predrag Novak、Mario Cindrić、Sanja Koštrun、Andrea Fajdetić、Sulejman Alihodžić、Karmen Brajša、Nedjeljko Kujundžić

  DOI：10.1016/j.bmcl.2010.11.079

  日期：2011.1

  A series of novel ureas and thioureas of 3-decladinosyl-3-hydroxy 15-membered azalides, were discovered, structurally characterized and biologically evaluated. They have shown good antibacterial activity against selected Gram-positive and Gram-negative bacterial strains. These include N '' substituted 9a-(N'-carbamoyl-gamma-aminopropyl)- (6a,c), 9a-(N'-thiocarbamoyl-gamma-aminopropyl)- (7a,e), 9a-[N'-(beta-cyanoethyl)-N'-(carbamoyl-gamma-aminopropyl)]- (9a-c, 9g) 9a-[N'-(beta-cyanoethyl)-N'-(thiocarbamoyl-gamma-aminopropyl)]-derivatives (10d-f) of 5-O-desosaminyl-9-deoxo-9-dihydro-9a-aza-9a-homoerythronolide A (3).Among the synthesized compounds thiourea 7a and urea 9b have shown substantially improved activity comparable to azithromycin (1) and significantly better activity than the 3-decladinosyl-azithromycin (2) and the parent 3-cladinosyl analogues against efflux-mediated resistant S. pneumoniae. (C) 2010 Elsevier Ltd. All rights reserved.