(9S)-5-O-desosaminyl-9-dihydroerythronolide A | 50896-25-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (9S)-5-O-desosaminyl-9-dihydroerythronolide A
• 英文别名: (9S)-O⁵-(3-dimethylamino-β-D-xylo-3,4,6-trideoxy-hexopyranosyl)-9-hydroxy-9-deoxo-erythronolide-A；(3R)-14t-ethyl-6t-(3-dimethylamino-β-D-xylo-3,4,6-trideoxy-hexopyranosyloxy)-4t,7c,10c,12t,13c-pentahydroxy-3r,5c,7t,9t,11c,13t-hexamethyl-oxacyclotetradecan-2-one；(3R)-14t-Aethyl-6t-(3-dimethylamino-β-D-xylo-3,4,6-tridesoxy-hexopyranosyloxy)-4t,7c,10c,12t,13c-pentahydroxy-3r,5c,7t,9t,11c,13t-hexamethyl-oxacyclotetradecan-2-on；O⁵-β-D-desosaminyl-dihydro-erythronolide-A；(3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-4,7,10,12,13-pentahydroxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
• CAS: 50896-25-8
• 化学式: C₂₉H₅₅NO₁₀
• 分子量: 577.756
• InChiKey: SOFQQJHDVFEJIQ-QMHPMPFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  169
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (9S)-5-O-desosaminyl-9-dihydroerythronolide A 、 苯硼酸 以 丙酮 为溶剂， 生成 (9S)-O⁵-(3-dimethylamino-β-D-xylo-3,4,6-trideoxy-hexopyranosyl)-9-hydroxy-O⁹,O¹¹-phenylboranediyl-9-deoxo-erythronolide-A
  参考文献：
  名称：

  megalomicins。第四部分 megalomicins A，B，C 1和C 2的结构

  摘要：

  阐明了巨果霉素A，B，C 1和C 2的结构和绝对立体化学，这是由巨果单孢菌（Micromonospora megalomicea sp。）精心制作的一组大环内酯类抗生素。描述。巨型霉素A已显示为（2 R，3 S，4 S，5 R，6 R，8 R，10 R 11 R，12 S，13 R）-3-（2,6-二脱氧-3- C甲基α-大号-核糖-hexopyranosyloxy）-6,12 -二羟基4,6,8,10,12六甲基-9-氧代-11-（2,3,6-三脱氧-3- dimethylalmino -β- d -来苏-hexopyranosyloxy）-5-（3,4,6-三脱氧-3-二甲基氨基- β- d -木糖- hexopyranosyloxy）十五烷-13-内酯。业已证明，巨果霉素B，C 1和C 2是在3-糖基系统中被酰化的巨果霉素A的衍生物。

  DOI：

  10.1039/p19730001374
• 作为产物：
  描述：

  红霉素 在 盐酸 、 甲醇 、 硼酸三钠 作用下， 生成 (9S)-5-O-desosaminyl-9-dihydroerythronolide A
  参考文献：
  名称：

  Erythromycin. VI. Degradation Studies¹

  摘要：

  DOI：

  10.1021/ja01583a038

文献信息

• Synthesis and Antibacterial Activity of a Novel Series of Acylides:  3-<i>O</i>-(3-Pyridyl)acetylerythromycin A Derivatives
  作者：Tetsuya Tanikawa、Toshifumi Asaka、Masato Kashimura、Keiko Suzuki、Hiroyuki Sugiyama、Masakazu Sato、Kazuya Kameo、Shigeo Morimoto、Atsushi Nishida

  DOI：10.1021/jm020568d

  日期：2003.6.1

  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.