carbonic acid 2-(10-allyloxyimino-14-ethyl-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,4-dioxo-oxacyclotetradec-6-yloxy)-4-(benzyloxycarbonyl-methyl-amino)-6-methyl-tetrahydro-pyran-3-yl ester benzyl ester | 860476-67-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: carbonic acid 2-(10-allyloxyimino-14-ethyl-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,4-dioxo-oxacyclotetradec-6-yloxy)-4-(benzyloxycarbonyl-methyl-amino)-6-methyl-tetrahydro-pyran-3-yl ester benzyl ester
• CAS: 860476-67-1
• 化学式: C₄₈H₆₈N₂O₁₄
• 分子量: 897.073
• InChiKey: XIWYKGDZUGDFEP-BIOBWWDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.78
• 重原子数：
  64.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  198.18
• 氢给体数：
  2.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  carbonic acid 2-(10-allyloxyimino-14-ethyl-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,4-dioxo-oxacyclotetradec-6-yloxy)-4-(benzyloxycarbonyl-methyl-amino)-6-methyl-tetrahydro-pyran-3-yl ester benzyl ester 在 palladium diacetate 吡啶 、 ruthenium trichloride 、 sodium periodate 、 甲酸 、 氯化亚砜 、 碳酸氢钠 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 四氯化碳 、 乙醇 、 水 、 乙腈 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  9-Oxime-3-ketolides: Modification at the C-11,12-diol moiety and antibacterial activities against key respiratory pathogens

  摘要：

  In the search for new types of ketolide antibiotics active against key respiratory pathogens including erythromycin-resistant strains, we conducted an extensive study on the modification at the C-11,12-diol moiety of 9-oxime-3-ketolide derivatives. Among the derivatives prepared, compound 6 with carbonate at the C-11, 12 position was found to have potent antibacterial activities against erythromycin-resistant Staphylococcus aureus as well as other erythromycin-susceptible strains. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.003
• 作为产物：
  描述：

  benzyl [(2S,3R,4S,6R)-2-[[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxo-10-prop-2-enoxyimino-oxacyclotetradec-6-yl]oxy]-6-methyl-4-[methyl(phenylmethoxycarbonyl)amino]oxan-3-yl] carbonate 在 盐酸 、 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 carbonic acid 2-(10-allyloxyimino-14-ethyl-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,4-dioxo-oxacyclotetradec-6-yloxy)-4-(benzyloxycarbonyl-methyl-amino)-6-methyl-tetrahydro-pyran-3-yl ester benzyl ester
  参考文献：
  名称：

  9-Oxime-3-ketolides: Modification at the C-11,12-diol moiety and antibacterial activities against key respiratory pathogens

  摘要：

  In the search for new types of ketolide antibiotics active against key respiratory pathogens including erythromycin-resistant strains, we conducted an extensive study on the modification at the C-11,12-diol moiety of 9-oxime-3-ketolide derivatives. Among the derivatives prepared, compound 6 with carbonate at the C-11, 12 position was found to have potent antibacterial activities against erythromycin-resistant Staphylococcus aureus as well as other erythromycin-susceptible strains. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.003

文献信息

• A new type of ketolides bearing an N-aryl-alkyl acetamide moiety at the C-9 iminoether synthesis and structure–activity relationships
  作者：Takashi Nomura、Tsutomu Iwaki、Tatsuro Yasukata、Koichi Nishi、Yukitoshi Narukawa、Koichi Uotani、Toshihiko Hori、Hideaki Miwa

  DOI：10.1016/j.bmc.2005.07.041

  日期：2005.12

  A new type of ketolides, bearing an N-aryl-alkyl acetamide moiety at the C-9 iminoether and a cyclic carbonate at the G 11, 12 position was prepared and the antibacterial activities of the compounds were evaluated. Some of the derivatives showed potent antibacterial activity against both Haemophilus influenzae and Streptococcus pneumoniae, which are clinically important respiratory tract pathogens. Among the derivatives prepared, compound 5s with a quinolin-4-yl moiety was found to have potent and well-balanced activity against S. pneumoniae and H. influenzae including erythromycin-resistant strains. (c) 2005 Elsevier Ltd. All rights reserved.