3-acetyl-7-[(2,3-O-carbonyl-6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one | 200727-44-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-acetyl-7-[(2,3-O-carbonyl-6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one
• 英文别名: 7-[[(3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxo-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]oxy]-3-acetyl-4-hydroxy-8-methylchromen-2-one
• CAS: 200727-44-2
• 化学式: C₂₁H₂₂O₁₀
• 分子量: 434.4
• InChiKey: JJBIKOLXPOYZDF-DODZYUBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  环丙胺 、 3-acetyl-7-[(2,3-O-carbonyl-6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 6.0h， 生成 cyclopropyl-carbamic acid-3'-ester of 3-acetyl-7-[(6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Aromatic derivatives substituted by a ribose, their method of preparation and application as medicine

  摘要：

  发明的主题是公式(I)的化合物：R1＝H, OH, 烷基，烯基或炔基可选地被取代或烷氧基，R2＝H, 卤素，R3＝H, 烷基，卤素，Rg和Rh：H, 烷基，芳基，杂环，R5＝H或O-烷基，R6＝烷基或CH2—O-烷基，R7＝H或烷基。公式(I)的化合物具有抗生素性质。

  公开号：

  US06350733B1
• 作为产物：
  描述：

  (+)-6-deoxy-5-C,4-O-dimethyl-L-xylo-hexopyranose 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-acetyl-7-[(2,3-O-carbonyl-6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Improved antibacterial activities of coumarin antibiotics bearing 5′,5′-dialkylnoviose: biological activity of RU79115

  摘要：

  A new series of coumarin inhibitors of DNA gyrase B bearing a N-propargyloxycarbamate at C-3' of various 5',5'-dialkylnoviose, including RU79115, were synthesised and their antibacterial activities have been delineated. Introduction of dialkyl substituents at 5'5'-position of noviose leads to coumarin analogues with improved in vitro and in vivo antibacterial activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00304-8

文献信息

• Aromatic derivatives substituted by a ribose, their method of preparation and application as medicine
  申请人：Aventis Pharma S.A.

  公开号：US06350733B1

  公开（公告）日：2002-02-26

  A subject of the invention is the compounds of formula (I): R1=H, OH, alkyl, alkenyl or alkynyl optionally substituted or alkoxy, R2=H, Hal, R3=H, alkyl, Hal, Rg and Rh: H, alkyl, aryl heterocycle, R5=H or O-alkyl, R6=alkyl or CH2—O-alkyl, R7=H or alkyl. The compounds of formula (I) have antibiotic properties.

  发明的主题是公式(I)的化合物：R1＝H, OH, 烷基，烯基或炔基可选地被取代或烷氧基，R2＝H, 卤素，R3＝H, 烷基，卤素，Rg和Rh：H, 烷基，芳基，杂环，R5＝H或O-烷基，R6＝烷基或CH2—O-烷基，R7＝H或烷基。公式(I)的化合物具有抗生素性质。
• Improved antibacterial activities of coumarin antibiotics bearing 5′,5′-dialkylnoviose: biological activity of RU79115
  作者：Branislav Musicki、Anne-Marie Periers、Patrick Laurin、Didier Ferroud、Yannick Benedetti、Sylvette Lachaud、Fabienne Chatreaux、Jean-Luc Haesslein、Alain Iltis、Christine Pierre、Jean Khider、Nicole Tessot、Marlene Airault、Jacques Demassey、Claudine Dupuis-Hamelin、Patrice Lassaigne、Alain Bonnefoy、Pascale Vicat、Michel Klich

  DOI：10.1016/s0960-894x(00)00304-8

  日期：2000.8

  A new series of coumarin inhibitors of DNA gyrase B bearing a N-propargyloxycarbamate at C-3' of various 5',5'-dialkylnoviose, including RU79115, were synthesised and their antibacterial activities have been delineated. Introduction of dialkyl substituents at 5'5'-position of noviose leads to coumarin analogues with improved in vitro and in vivo antibacterial activity. (C) 2000 Elsevier Science Ltd. All rights reserved.