3-O-decladinosyl-6-O-methyl-9-deoxo-9a-aza-9a-homoerythromycin A | 944474-44-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-decladinosyl-6-O-methyl-9-deoxo-9a-aza-9a-homoerythromycin A
• CAS: 944474-44-6
• 化学式: C₃₀H₅₈N₂O₉
• 分子量: 590.799
• InChiKey: NSOIGBMTVZSHKW-NZMWSZMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  41.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  150.18
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3-O-decladinosyl-6-O-methyl-9-deoxo-9a-aza-9a-homoerythromycin A 、 2,4-二氯苯基异氰酸酯 以 乙腈 为溶剂， 反应 0.5h， 以63%的产率得到(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-N-(2,4-dichlorophenyl)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,13-trihydroxy-10-methoxy-3,5,8,10,12,14-hexamethyl-15-oxo-1-oxa-6-azacyclopentadecane-6-carboxamide
  参考文献：
  名称：

  Novel 9a-carbamoyl- and 9a-thiocarbamoyl-3-decladinosyl-6-hydroxy and 6-methoxy derivatives of 15-membered macrolides

  摘要：

  An efficient method for the synthesis of diverse 9a-carbamoyl- and 9a-thiocarbamoyl-3-decladinosyl-6-hydroxy and 3-decladinosyl-6-methoxy derivatives of 15-membered azalides has been developed. These derivatives bear various alkyl and aryl groups attached to macrolide scaffold through urea or thiourea moieties at 9a position. Chemical transformations of hydroxy group at position C-3 afforded range of ketolides, anhydrolides, herniketals, cyclic ethers, and acylides. It has been shown that 6-hydroxy and 6-methoxy derivatives undergo different chemical transformations under otherwise identical reaction conditions. Antimicrobial properties of prepared compounds were evaluated. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.021
• 作为产物：
  描述：

  6-O-methyl-9-deoxo-9-dihydro-9a-aza-9a-homoerythromycin A 在 盐酸 作用下， 反应 24.0h， 以46%的产率得到3-O-decladinosyl-6-O-methyl-9-deoxo-9a-aza-9a-homoerythromycin A
  参考文献：
  名称：

  Novel 9a-carbamoyl- and 9a-thiocarbamoyl-3-decladinosyl-6-hydroxy and 6-methoxy derivatives of 15-membered macrolides

  摘要：

  An efficient method for the synthesis of diverse 9a-carbamoyl- and 9a-thiocarbamoyl-3-decladinosyl-6-hydroxy and 3-decladinosyl-6-methoxy derivatives of 15-membered azalides has been developed. These derivatives bear various alkyl and aryl groups attached to macrolide scaffold through urea or thiourea moieties at 9a position. Chemical transformations of hydroxy group at position C-3 afforded range of ketolides, anhydrolides, herniketals, cyclic ethers, and acylides. It has been shown that 6-hydroxy and 6-methoxy derivatives undergo different chemical transformations under otherwise identical reaction conditions. Antimicrobial properties of prepared compounds were evaluated. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.021

文献信息

• Novel 9a,11-bridged azalides: One-pot synthesis of N′-substituted 2-imino-1,3-oxazolidines condensed to an azalide aglycone
  作者：Zorica Marušić Ištuk、Ana Čikoš、Dubravka Gembarovski、Gorjana Lazarevski、Ivica Đilović、Dubravka Matković-Čalogović、Goran Kragol

  DOI：10.1016/j.bmc.2010.10.061

  日期：2011.1

  An efficient one-pot method for the synthesis of novel 9a,11-bridged 15-membered 9a-aza-9-deoxo-9a-homoerythromycin A and its 6-O-methyl analogue has been developed. The novel bicyclic azalide scaffold is characterized by an N'-substituted-2-imino-1,3-oxazolidine moiety bound to a macrolactone ring between positions 9a and 11. Removal of the cladinose sugar from the starting compounds allows easy preparation of a small series of such bicyclic 3-keto and 3,6-hemiketal azalide derivatives. A mechanism for the formation of N'-substituted-2-imino-1,3-oxazolidines is discussed. Antibacterial properties of the prepared compounds were evaluated. (C) 2010 Elsevier Ltd. All rights reserved.