1-cyclopropyl-6-fluoro-4-oxo-4,10-dihydro-1H-thieno-[2',3':4,5]pyrrolo[3,2-h]quinoline-3-carboxylic acid | 1247019-51-7

• 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-fluoro-4-oxo-4,10-dihydro-1H-thieno-[2',3':4,5]pyrrolo[3,2-h]quinoline-3-carboxylic acid
• 英文别名: 3-Cyclopropyl-9-fluoro-6-oxo-12-thia-3,16-diazatetracyclo[8.6.0.02,7.011,15]hexadeca-1,4,7,9,11(15),13-hexaene-5-carboxylic acid
• CAS: 1247019-51-7
• 化学式: C₁₇H₁₁FN₂O₃S
• 分子量: 342.35
• InChiKey: PHOLFMMCGGYQBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl 1-cyclopropyl-6-fluoro-4-oxo-4,10-dihydro-1H-thieno[2',3':4,5]pyrrolo[3,2-h]quinoline-3-carboxylate 在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 以91%的产率得到1-cyclopropyl-6-fluoro-4-oxo-4,10-dihydro-1H-thieno-[2',3':4,5]pyrrolo[3,2-h]quinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of tetracyclic fluoroquinolones as antibacterial and anticancer agents

  摘要：

  A simple and efficient synthesis of 6-fluoro-4-oxopyrido[2,3-a] carbazole-3-carboxylic acids (13a-e) and a structurally related 6-fluoro-4-oxothieno[2 ',3 ': 4,5] pyrrolo[3,2-h] quinoline (13f) was achieved via Stille arylation of 7-chloro-6-fluoro-8-nitro-4-oxoquinoline-3-carboxylate and a subsequent microwave-assisted phosphite-mediated Cadogan reaction. The new compounds were tested for their in vitro antimicrobial and antiproliferative activity. The ability of 13a-f to inhibit the activity of DNA gyrase and topoisomerase IV was also investigated. The thieno isostere (13f) emerged as the most active antibacterial, while the 9-fluoro derivative (13e) was the most potent against multidrug-resistant staphylococci. Compounds 13a, 13c-f displayed growth inhibition against MCF-7 breast tumor and A549 non-small cell lung cancer cells coupled with an absence of cytotoxicity toward normal human-derm fibroblasts (HuDe). Compound 13e was the most active anticancer against MCF-7 cells, with greater potency than ellipticine (IC50 0.8 and 1.6 mu M, respectively). The most active compounds in this series show promise as dual acting anticancer and antibacterial chemotherapeutics. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.098

文献信息

• Synthesis and biological evaluation of tetracyclic fluoroquinolones as antibacterial and anticancer agents
  作者：Salah A. Al-Trawneh、Jalal A. Zahra、Marwan R. Kamal、Mustafa M. El-Abadelah、Franca Zani、Matteo Incerti、Andrea Cavazzoni、Roberta R. Alfieri、Pier G. Petronini、Paola Vicini

  DOI：10.1016/j.bmc.2010.06.098

  日期：2010.8

  A simple and efficient synthesis of 6-fluoro-4-oxopyrido[2,3-a] carbazole-3-carboxylic acids (13a-e) and a structurally related 6-fluoro-4-oxothieno[2 ',3 ': 4,5] pyrrolo[3,2-h] quinoline (13f) was achieved via Stille arylation of 7-chloro-6-fluoro-8-nitro-4-oxoquinoline-3-carboxylate and a subsequent microwave-assisted phosphite-mediated Cadogan reaction. The new compounds were tested for their in vitro antimicrobial and antiproliferative activity. The ability of 13a-f to inhibit the activity of DNA gyrase and topoisomerase IV was also investigated. The thieno isostere (13f) emerged as the most active antibacterial, while the 9-fluoro derivative (13e) was the most potent against multidrug-resistant staphylococci. Compounds 13a, 13c-f displayed growth inhibition against MCF-7 breast tumor and A549 non-small cell lung cancer cells coupled with an absence of cytotoxicity toward normal human-derm fibroblasts (HuDe). Compound 13e was the most active anticancer against MCF-7 cells, with greater potency than ellipticine (IC50 0.8 and 1.6 mu M, respectively). The most active compounds in this series show promise as dual acting anticancer and antibacterial chemotherapeutics. (C) 2010 Elsevier Ltd. All rights reserved.