[(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-3-acetyloxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-4-yl] 2-phenylacetate | 382606-10-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-3-acetyloxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-4-yl] 2-phenylacetate
• CAS: 382606-10-2
• 化学式: C₄₀H₆₃NO₁₂
• 分子量: 749.94
• InChiKey: LPZNVJXAUPCQAE-SCDDCLFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  53
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  167
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-3-acetyloxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-4-yl] 2-phenylacetate 以 甲醇 为溶剂， 反应 6.0h， 以71%的产率得到5-O-desosaminyl-3-O-phenylacetyl-6-O-methylerythronolide A
  参考文献：
  名称：

  酰化物（3-O-酰基-红霉素衍生物）的合成和抗菌活性：一类新的大环内酯类抗生素。

  摘要：

  将酰基引入红霉素A衍生物而不是L-cladinose的3-O-位导致了一类新的大环内酯类抗生素，我们将其命名为“酰化物”。3-O-硝基苯基乙酰基衍生物TEA0777不仅对易感红霉素的革兰氏阳性病原体而且对可诱导大环内酯类，林可酰胺类，链霉菌素B（MLS（B））的金黄色葡萄球菌和对外排毒的肺炎链球菌均显示出显着的有效活性。这些结果表明酰化物具有作为下一代大环内酯类抗生素的潜力。

  DOI：

  10.1021/jm015566s
• 作为产物：
  描述：

  克拉红霉素EP杂质I 在 4-二甲氨基吡啶 作用下， 以 吡啶 、 丙酮 为溶剂， 反应 28.0h， 生成 [(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-3-acetyloxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-4-yl] 2-phenylacetate
  参考文献：
  名称：

  酰化物（3-O-酰基-红霉素衍生物）的合成和抗菌活性：一类新的大环内酯类抗生素。

  摘要：

  将酰基引入红霉素A衍生物而不是L-cladinose的3-O-位导致了一类新的大环内酯类抗生素，我们将其命名为“酰化物”。3-O-硝基苯基乙酰基衍生物TEA0777不仅对易感红霉素的革兰氏阳性病原体而且对可诱导大环内酯类，林可酰胺类，链霉菌素B（MLS（B））的金黄色葡萄球菌和对外排毒的肺炎链球菌均显示出显着的有效活性。这些结果表明酰化物具有作为下一代大环内酯类抗生素的潜力。

  DOI：

  10.1021/jm015566s

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.