6,7-二氯-4-羟基3-喹啉羧酸 | 26893-20-9

• 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
• 中文名称: 6,7-二氯-4-羟基3-喹啉羧酸
• 英文名称: base
• 英文别名: 6,7-dichloro-4-oxo-1H-quinoline-3-carboxylic acid
• CAS: 26893-20-9；51726-82-0
• 化学式: C₁₀H₅Cl₂NO₃
• 分子量: 258.061
• InChiKey: BFCGHXVOVSHPIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,7-二氯-4-羟基3-喹啉羧酸 在 硫酸氢铵 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.5h， 生成 6,7-dichloro-1,4-dihydro-4-oxoquinoline-1-β-D-ribofuranosyl-3-carboxylicacid sodium salt
  参考文献：
  名称：

  Quinolone Nucleosides: 6,7-Dihalo-N-β- and α-Glycosyl-l 4-dihydro-4-oxo-quinoline-3-carboxylic Acids and Derivatives. Synthesis, Antimicrobial and Antiviral Activity

  摘要：

  Reaction of the silylated 6,7-dihaloquinoline bases 10-12 with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (13) gave ethyl 7-chloro-6-flouro-1,4-dihydro-4-oxo-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)quinoline-3-carboxylate (14) and the free acids 15 and 16, respectively, which led on deblocking of the sugar moiety to the free nucleosides 17, 18 and 20, respectively. Treatment of 14 with methanolic ammonia afforded the amide derivative 19. Ribosylation of 11 with 1,2-di-O-acetyl-3-azido-3-deoxy-5-p-toluoyl-beta-D-ribofuranose (21) afforded the azido nucleoside 22, which was again converted into the free nucleoside 23. Analogously, reaction of 11 with the chloro deoxyribose derivative 24 led to a mixture of alpha / beta (2:1) anomers of 25. Deblocking and recrystallization of the product gave mainly the alpha-anomer 26. Compounds 17-19, 23 and 26 were evaluated against Escherichia coli and found inactive. Compound 16-18 and 22 were inactive aganist HIV-1 (III B) and HIV-2 (ROD) induced cytopathicity in human MT-4 lymphocyte cells.

  DOI：

  10.1080/07328319808004315
• 作为产物：
  描述：

  ethyl 6,7-dichloro-4-oxo-1,4-dihydroquinoline-3-carboxylate 在 sodium hydroxide 作用下， 以70%的产率得到基础
  参考文献：
  名称：

  Quinolone Nucleosides: 6,7-Dihalo-N-β- and α-Glycosyl-l 4-dihydro-4-oxo-quinoline-3-carboxylic Acids and Derivatives. Synthesis, Antimicrobial and Antiviral Activity

  摘要：

  Reaction of the silylated 6,7-dihaloquinoline bases 10-12 with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (13) gave ethyl 7-chloro-6-flouro-1,4-dihydro-4-oxo-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)quinoline-3-carboxylate (14) and the free acids 15 and 16, respectively, which led on deblocking of the sugar moiety to the free nucleosides 17, 18 and 20, respectively. Treatment of 14 with methanolic ammonia afforded the amide derivative 19. Ribosylation of 11 with 1,2-di-O-acetyl-3-azido-3-deoxy-5-p-toluoyl-beta-D-ribofuranose (21) afforded the azido nucleoside 22, which was again converted into the free nucleoside 23. Analogously, reaction of 11 with the chloro deoxyribose derivative 24 led to a mixture of alpha / beta (2:1) anomers of 25. Deblocking and recrystallization of the product gave mainly the alpha-anomer 26. Compounds 17-19, 23 and 26 were evaluated against Escherichia coli and found inactive. Compound 16-18 and 22 were inactive aganist HIV-1 (III B) and HIV-2 (ROD) induced cytopathicity in human MT-4 lymphocyte cells.

  DOI：

  10.1080/07328319808004315

文献信息

• Synthesis of acyclic 6,7-dihaloquinolone nucleoside analogues as potential antibacterial and antiviral agents
  作者：Najim A Al-Masoudi、Yaseen A Al-Soud、Michael Eherman、Erik De Clercq

  DOI：10.1016/s0968-0896(00)00067-5

  日期：2000.6

  Reaction of the quinolone carboxylic acids 1 and 2 with (2-acetoxyethoxy)methyl chloride 3 in the presence of n-Bu4NI afforded the N-alkylated products 4 and 6, which could be deblocked to the free nucleoside analogues 5 and 7, respectively. The alkylated quinolone carboxylic acids 9 and 10 were obtained by condensation of 1 and 2 with 1,4-dichlorobut-2-ene 8 in the presence of NaH. Hydrolysis of 9 gave the alcohol 11. Similar treatment of 1 with 8 in the presence of K2CO3 at relatively high temperature furnished 12. Prolonged heating of the ester 13 with 8 in NaH/DMF afforded the conjugated-diene 15. Treatment of 1 and 2 with dimethyl acetylenedicarboxylate 16 Furnished the pyrano[4,3-b]quinolones 17 and 18, respectively. Antibacterial and antiviral evaluations of the new products are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis and biological activity of new metronidazole derivatives
  作者：Najim A. Al-Masoudi、Zina A. A. Abbas

  DOI：10.1007/s00706-015-1612-7

  日期：2016.2

  The development of new antimicrobial and antiparasitic agents offers the possibility of generating structures of increased potency. To this end, three sulphonate ester derivatives of metronidazole were synthesized. Treatment of the tosylate analogue with NaSPh and NaN3 gave the thiophenolate and azide derivatives, respectively. Oxidation of phenylthio derivative with mCPBA afforded the sulfonyl analogue. Similarly, cycloaddition of azido-metronidazole with various symmetric acetylene compounds furnished the 1,2,3-triazole analogues. Treatment of dimethyl dicarboxylate metronidazole derivative with guanidine hydrochloride in the presence of base resulted in the formation of the ring-expanded (fat) derivative, triazolo-diazepam derivative of metronidazole. Treatment of chlorometronidazole with silylated quinolones gave the quinolone analogues of metronidazole. The antigardiasis and antifungal activities of the synthesized compounds were investigated. In addition, all synthesized compounds were evaluated for their in vitro anti-HIV activity in MT-4 cells as non-nucleoside reverse transcriptase inhibitors.[GRAPHICS].