6-iodo-4-oxo-1-(2-propen-1-yl)-1,4-dihydro-3-quinolinecarboxylic acid | 869310-78-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-iodo-4-oxo-1-(2-propen-1-yl)-1,4-dihydro-3-quinolinecarboxylic acid
• 英文别名: 1-allyl-6-iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid；6-Iodo-4-oxo-1-prop-2-enylquinoline-3-carboxylic acid
• CAS: 869310-78-1
• 化学式: C₁₃H₁₀INO₃
• 分子量: 355.132
• InChiKey: JFBWZRNNIPOXNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-iodo-4-oxo-1-(2-propen-1-yl)-1,4-dihydro-3-quinolinecarboxylic acid 、 ((2-(prop-2-yn-1-yloxy)ethoxy)methyl)benzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以80%的产率得到4-oxo-6-[3-({2-[(phenylmethyl)oxy]ethyl}oxy)-1-propyn-1-yl]-1-(2-propen-1-yl)-1,4-dihydro-3-quinolinecarboxylic acid
  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
• 作为产物：
  描述：

  ethyl 6-iodo-4-oxo-1-(2-propen-1-yl)-1,4-dihydro-3-quinolinecarboxylate 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以93%的产率得到6-iodo-4-oxo-1-(2-propen-1-yl)-1,4-dihydro-3-quinolinecarboxylic acid
  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。
• Synthesis and properties of macrolones characterized by two ether bonds in the linker
  作者：Ivana Palej Jakopović、Goran Kragol、Andrew K. Forrest、Catherine S.V. Frydrych、Vlado Štimac、Samra Kapić、Maja Matanović Škugor、Marina Ilijaš、Hana Čipčić Paljetak、Dubravko Jelić、David J. Holmes、Deirdre M.B. Hickey、Donatella Verbanac、Vesna Eraković Haber、Sulejman Alihodžić

  DOI：10.1016/j.bmc.2010.07.007

  日期：2010.9

  In this paper synthesis of macrolones 1-18 starting from azithromycin is reported. Two key steps in the construction of the linker between macrolide and quinolone moiety, are formation of central ether bond by alkylation of unactivated OH group, and formation of terminal C-C bond at 6-position of the quinolone unit. Due to the difficulty in formation of these two bonds the study of alternative synthetic methodologies and optimization of the conditions for the selected routes was required. Formation of C-4"-O-ether bond was completed by modified Michael addition, whereas O-alkylation via diazonium cation proved to be the most effective in formation of the central allylic or propargylic ether bond. Comparison of Heck and Sonogashira reaction revealed the former as preferred route to the C-C bond formation at C(6) position of the quinolone unit. Most of the target compounds exhibited highly favorable antibacterial activity against common respiratory pathogens, without significant cytotoxicity profile when tested in vitro on eukaryotic cell lines. (C) 2010 Elsevier Ltd. All rights reserved.
• ESTER LINKED MACROLIDES USEFUL FOR THE TREATMENT OF MICROBIAL INFECTIONS
  申请人：GlaxoSmithKline istrazivacki centar Zagreb d.o.o.

  公开号：EP1756135B1

  公开（公告）日：2009-08-12