2'-O-acetyl-4"-deoxyerythromycin B | 150785-60-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-O-acetyl-4"-deoxyerythromycin B
• 英文别名: 2'-O-acetyl-4''-deoxy-erythromycin B；[(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,4S,5S,6R,7R,9R,11R,12S,13R,14R)-14-ethyl-7,12-dihydroxy-4-[(2S,4S,6S)-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] acetate
• CAS: 150785-60-7
• 化学式: C₃₉H₆₉NO₁₂
• 分子量: 743.976
• InChiKey: AJWVTIXPROHLDP-ZDJHGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  52
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  160
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2'-O-acetyl-4"-deoxyerythromycin B 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 acetic acid 2-[5-ethyl-3-hydroxy-9-(4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-2,4,8,10,12,14-hexamethyl-7-oxo-6,15-dioxa-bicyclo[10.2.1]pentadec-1⁽¹⁴⁾-en-11-yloxy]-6-methyl-4-methylamino-tetrahydro-pyran-3-yl ester; hydrochloride
  参考文献：
  名称：

  Facile N-demethylation of erythromycins

  摘要：

  4 "-Deoxyerythromycin B reacts with 1-chloroethyl chloroformate to give the corresponding N-demethyl N-chloroethyl carbamate, Mild methanolysis removes the chloroethyl group giving the N-demethyl erythromycin derivative while also forming the 6,9-enol ether moiety. Further manipulation gives ABT-229, a potential prokinetic agent. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00244-0
• 作为产物：
  描述：

  红霉素B 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 26.75h， 生成 2'-O-acetyl-4"-deoxyerythromycin B
  参考文献：
  名称：

  Synthesis of 4''-Deoxy Motilides: Identification of a Potent and Orally Active Prokinetic Drug Candidate

  摘要：

  As an approach to discovering highly potent motilides with oral activity, novel 4''-deoxy derivatives of 8,9-anhydroerythromycin 6,9-hemiacetal were designed, synthesized, and evaluated for their gastrointestinal prokinetic activities. These compounds were orders of magnitude more potent than their 4''-hydroxy analogs in inducing smooth muscle contractions in an in vitro rabbit duodenal assay. Removal of the 12-hydroxy group, which was aimed at improving oral bioavailability, also afforded further potentiation in in vitro activity, leading to the identification of 8,9-anhydro-4''-deoxy-3'-N-desmethyl-3'-N-ethylerythromycin B 6,9-hemiacetal (ABT-229) as a potential prokinetic drug. ABT-229 was >300 000 times more potent than erythromycin in, vitro and had 39% oral bioavailability in dog compared to its 4'';12-dihydroxy congener (EM-523), which was only 400 times more potent than erythromycin and had relatively low (1.4%) oral bioavailability.

  DOI：

  10.1021/jm00010a024