2'-O-acetyl-6-O-methyl-8a-aza-8a-homoerythromycin A | 412333-83-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-O-acetyl-6-O-methyl-8a-aza-8a-homoerythromycin A
• 英文别名: [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4-dihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-10-methoxy-3,5,8,10,12,14-hexamethyl-6,15-dioxo-1-oxa-7-azacyclopentadec-11-yl]oxy]-6-methyloxan-3-yl] acetate
• CAS: 412333-83-6
• 化学式: C₄₀H₇₂N₂O₁₄
• 分子量: 805.017
• InChiKey: WFCVKMYGHQJEND-AAPKTRAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  56
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  201
• 氢给体数：
  4
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2'-O-acetyl-6-O-methyl-8a-aza-8a-homoerythromycin A 、 3-氯丙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  4″-O-(ω-Quinolylamino-alkylamino)propionyl derivatives of selected macrolides with the activity against the key erythromycin resistant respiratory pathogens

  摘要：

  Four macrolides-6-O-methyl-8a-aza-8a-homoerythromycin, clarithromycin, azithromycin and azithromycin 11,12-cyclic carbonate, have been selected for the construction of a series of new quinolone derivatives. The quinolone moiety is connected to the macrolide scaffold via a diaminoaklyl 4"-O-propionyl ester chain of varying length. At the terminus the linker is attached via one of the nitrogen atoms in the linker at C(6) or C(7) of the quinolone. Many of compounds described, particularly clarithromycin derivative 37, and azithromycin derivatives 48 and 55, exhibited excellent antibacterial activity against a wide range of clinically relevant macrolide-resistant organisms, with profiles superior to that of telithromycin, an enhanced spectrum ketolide. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.049
• 作为产物：
  描述：

  6-O-methyl-8a-aza-8a-homoerythromycin A 、 乙酸酐 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2'-O-acetyl-6-O-methyl-8a-aza-8a-homoerythromycin A
  参考文献：
  名称：

  Synthesis and biological activity of 4″-O-acyl derivatives of 14- and 15-membered macrolides linked to ω-quinolone-carboxylic unit

  摘要：

  The synthesis and antimicrobial activity of a new class of macrolide antibiotics which consist of a macrolide scaffold and a quinolone unit covalently connected by an appropriate linker are described. Optimization of several synthetic steps and structural properties of lead compound 26 are discussed. Promising antibacterial properties of this compound and some of its analogues are reported. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.050

文献信息

• Ester Linked Macrolides Useful For The Treatment of Microbial Infections
  申请人：Alihodzic Sulejman

  公开号：US20080255060A1

  公开（公告）日：2008-10-16

  The present invention relates to 14- or 15-membered macrolides substituted at the 4″ position of formula (I) and pharmaceutically acceptable derivatives thereof, to processes for their preparation and their use in therapy or prophylaxis of systemic or topical microbial infections in a human or animal body.

  本发明涉及在式(I)的4"位置取代的14或15元大环内酯及其药学上可接受的衍生物，以及它们的制备方法和在人或动物体内治疗或预防系统性或局部微生物感染的用途。