1-cyclopropyl-6,8-difluoro-7-(1-methyltetrazol-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 124256-12-8

• 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: 1-cyclopropyl-6,8-difluoro-7-(1-methyltetrazol-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-Cyclopropyl-6,8-difluoro-7-(1-methyltetrazol-5-yl)sulfanyl-4-oxoquinoline-3-carboxylic acid
• CAS: 124256-12-8
• 化学式: C₁₅H₁₁F₂N₅O₃S
• 分子量: 379.347
• InChiKey: FDJCIFRDZWOVBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1-环丙基-6,7,8-三氟-4-氧代-1,4-二氢喹啉-3-羧酸 、 1-甲基-5-巯基-1H-四氮唑 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以17%的产率得到1-cyclopropyl-6,8-difluoro-7-(1-methyltetrazol-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Pyridonecarboxylic acid antibacterial agents. Part XV. Synthesis of 7-thio-substituted 4-oxoquinoline-3-carboxylic acids with antibacterial activity.

  摘要：

  制备并测试了一系列 C-7 硫代 1-环丙基-1，4-二氢-4-氧代喹啉-3-羧酸的抗菌活性。讨论了与 C-5 和 C-7 取代基相关的结构-活性关系。在 C-7 取代基（包括烷基硫代、芳基硫代、杂芳基硫代和环状硫代氨基）中，2-氨基乙基硫代最能提高体外抗菌活性。C-5 变体提高活性的顺序为 OH

  DOI：

  10.1248/cpb.38.2190

文献信息

• Pyridonecarboxylic acid antibacterial agents. Part XV. Synthesis of 7-thio-substituted 4-oxoquinoline-3-carboxylic acids with antibacterial activity.
  作者：Yoshiro NISHIMURA、Tohru HIROSE、Hidetsugu OKADA、Koh-ichiro SHIBAMORI、Junji NAKANO、Jun-ichi MATSUMOTO

  DOI：10.1248/cpb.38.2190

  日期：——

  A series of C-7 thio-substituted 1-cyclopropyl-1, 4-dihydro-4-oxoquinoline-3-carboxylic acids were prepared and tested for their antibacterial activity. Structure-activity relationships associated with the C-5 and C-7 substituents were discussed. Among the C-7 substituents including alkylthio, arylthio, heteroarylthio, and cyclic aminothio groups, a 2-aminoethylthio group was the best for enhancing in vitro antibacterial activity. The C-5 variants increased activity in the order OH

  制备并测试了一系列 C-7 硫代 1-环丙基-1，4-二氢-4-氧代喹啉-3-羧酸的抗菌活性。讨论了与 C-5 和 C-7 取代基相关的结构-活性关系。在 C-7 取代基（包括烷基硫代、芳基硫代、杂芳基硫代和环状硫代氨基）中，2-氨基乙基硫代最能提高体外抗菌活性。C-5 变体提高活性的顺序为 OH
• Synthesis and antibacterial activities of new quinolone derivatives utilizing 1-azabicyclo[1.1.0]butane
  作者：Yoshifumi Ikee、Kana Hashimoto、Masaaki Nakashima、Kazuhiko Hayashi、Shigeki Sano、Motoo Shiro、Yoshimitsu Nagao

  DOI：10.1016/j.bmcl.2006.11.048

  日期：2007.2

  The ring-opening reactions of 1-azabicyclo[1.1.0]butane 3 with thiols 6a-f gave 3-sulfenylazetidine derivatives 7a-fin 50-92% yields. Treatment of 3 with aromatic amines 11a-e and dibenzylamine 11f in the presence of Mg(CIO4)(2) afforded the corresponding 3-aminoazetidine derivatives 12a-f in 24-53% yields. These azetidine derivatives were introduced into the C7 position of a quinolone nucleus 8 to afford the corresponding fluoroquinolones 9a-f and 13a-f in 21-83% yields. Some of them exhibited superior antibacterial activity against quinolone-susceptible MRSA in comparison with clinically used fluoroquinolones, such as levofloxacin, ciprofloxacin, and gatifloxacin. (c) 2006 Elsevier Ltd. All rights reserved.
• NISHIMURA, YOSHIRO;HIROSE, TOHRU;OKADA, HIDETSUGU;SHIBAMORI, KOH-ICHIRO;N+, CHEM. AND PHARM. BULL., 38,(1990) N, C. 2190-2196
  作者：NISHIMURA, YOSHIRO、HIROSE, TOHRU、OKADA, HIDETSUGU、SHIBAMORI, KOH-ICHIRO、N+

  DOI：——

  日期：——
• Synthesis of New Quinolone Antibiotics Utilizing Azetidine Derivatives Obtained from 1-Azabicyclo[1.1.0]butane
  作者：Yoshifumi Ikee、Kana Hashimoto、Mai Kamino、Masaaki Nakashima、Kazuhiko Hayashi、Shigeki Sano、Motoo Shiro、Yoshimitsu Nagao

  DOI：10.1248/cpb.56.346

  日期：——

  N-Benzyl-3-bromoazetidine (13), which was obtained by the reaction of ABB (3) with benzyl bromide, gave 3-aliphatic amino-substituted azetidine derivatives 15a, b. Novel fluoroquinolones 7a-f, 11a-f, 16a, b and 25a-c were obtained by the introduction of these azetidine derivatives into the C7 position of a quinolone nucleus 6 and N1-heterocyclic quinolones 21a-c in 21-83% yields. Some of them exhibited

  通过1-氮杂双环[1.1.0]丁烷（ABB，3）与硫醇4a-f的开环反应以50-92％的产率合成了一系列3-亚磺酰基氮杂环丁烷衍生物5a-f。在Mg（ClO 4）2存在下用芳族胺9a-e和二苄基胺（9f）处理ABB（3）以24-65％的收率得到相应的3-氨基氮杂环丁烷衍生物10a-f。通过ABB（3）与苄基溴反应获得的N-苄基-3-溴氮杂环丁烷（13），得到3-脂族氨基取代的氮杂环丁烷衍生物15a，b。通过将这些氮杂环丁烷衍生物以21-83％的产率引入喹诺酮核6和N1-杂环喹诺酮21a-c的C7位置，获得了新颖的氟喹诺酮类化合物7a-f，11a-f，16a，b和25a-c。