(环丙沙星M4) | 93594-39-9

• 物质功能分类: 原料药 - 人工合成抗感染类药 - 喹诺酮类药
• 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: (环丙沙星M4)
• 中文别名: 甲酰基环丙沙星
• 英文名称: 1-cyclopropyl-6-fluoro-7-(4-formylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-cyclopropyl-6-fluoro-7-(4-formylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
• CAS: 93594-39-9
• 化学式: C₁₈H₁₈FN₃O₄
• 分子量: 359.357
• InChiKey: KCXCSXLUYCTARV-UHFFFAOYSA-N

物化性质

• 熔点：
  >280°C (dec.)
• 沸点：
  648.0±55.0 °C(Predicted)
• 密度：
  1.573±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（轻微、加热、超声处理）、甲醇（少量）、水（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 海关编码：
  2933599550
• WGK Germany：
  3
• 储存条件：
  -20°C冷冻库

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  环丙沙星	ciproflaxin	85721-33-1	C17H18FN3O3	331.347
  ——	1-cyclopropyl-6-fluoro-4-oxo-7-(4-((2-(4-fluorobenzoyl)hydrazono)methyl)piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid	1340587-05-4	C25H23F2N5O4	495.486

反应信息

• 作为反应物：
  描述：

  N-(2-氨基苯并噻唑-6-基)-乙酰胺 、 (环丙沙星M4) 在 哌啶 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Discovery of the Highly Potent Fluoroquinolone-Based Benzothiazolyl-4-thiazolidinone Hybrids as Antibacterials

  摘要：

  A new series of fluoroquinolone‐based benzothiazolyl‐4‐thiazolidinone hybrids has been yielded via sulfated tungstate‐promoted highly accelerated N‐formylation at a piperazine residue of ciprofloxacin and norfloxacin entities. The formylated fluoroquinolone moieties were then coupled with substituted 2‐aminobenzothiazoles, which were generated from their respective para‐substituted amines to form corresponding Schiff base intermediates. The Schiff bases were then treated with thioglycolic acid to equip a new class of 4‐thiazolidinones to be analyzed for their antibacterial effects against two Gram‐positive (Staphylococcus aureus and Bacillus subtilis) and two Gram‐negative (Escherichia coli and Pseudomonas aeruginosa) bacterial strains and were found highly potent with lowest Minimum inhibitory concentrations (MIC), 1–2 μg/mL, that is, more potent than control drugs ciprofloxacin (3.12–6.25 μg/mL). Initial outcomes provided for these novel molecular systems will aid researchers to design and develop new antibacterial drugs. The structural assignments of the new products were done on the basis of FT‐IR, 1H NMR and 13C NMR spectroscopy, and elemental analysis.

  DOI：

  10.1111/cbdd.12299
• 作为产物：
  描述：

  1-cyclopropyl-6-fluoro-4-oxo-7-(4-((2-(4-fluorobenzoyl)hydrazono)methyl)piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid 在 水 、 乙酸酐 作用下， 以 二甲基亚砜 为溶剂， 反应 50.83h， 生成 (环丙沙星M4)
  参考文献：
  名称：

  New fluorine-containing hydrazones active against MDR-tuberculosis

  摘要：

  Several new fluorine-containing hydrazones were synthesized and screened for their in vitro anti-mycobacterial activity. Nine of these derivatives have shown a remarkable activity against MDR-TB strain with MIC 0.5 mu g/mL and high value of selectivity index (SI). Compound 3h with the highest SI (1268.58) was used for stability evaluation with putative metabolites (ciprofloxacin and formylciprofloxacin) detection. Compound 3h was stable at pH 7.4 of aqueous buffer and rat plasma, in acidic buffers (at pH 3 and 5) slow decomposition was observed. Interestingly, no formylciprofloxacin was detected in the solution, and only slightly increased concentration of ciprofloxacin was observed instead. Trifluoromethyl hydrazones 3f and 3g exhibited the best activity also against two strains of Mycobacterium kansasii (MIC 1-4 mu mol/L). All evaluated compounds were found to be non-cytotoxic. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.052

文献信息

• Chinoloncarbonsäuren, Verfahren zu ihrer Herstellung sowie diese enthaltende antibakterielle Mittel
  申请人：BAYER AG

  公开号：EP0117473A1

  公开（公告）日：1984-09-05

  Chinoloncarbonsäuren der allgemeinen Formel mit den in der Beschreibung angegebenen Bedeutungen von X und R1-R5 haben gute antibakterielle Wirkung und sollen als Wirkstoffe für Arzneimittel verwendet werden.

  通式中的喹啉羧酸（X 和 R1-R5 的含义见说明）具有良好的抗菌活性，可用作药物的活性成分。
• Bakterizide Mittel auf Chinoloncarbonsäure-Basis
  申请人：BAYER AG

  公开号：EP0121727A1

  公开（公告）日：1984-10-17

  Die Erfindung betrifft die bakterizide Verwendung von neuen 1-Cyclopropyl-1,4-dihydro-4-oxo-3-chinolincarbonsäure-Derivaten der Formel (I) in der R', R2; R3, R", R5 und X die in der Beschreibung gegebene Bedeutung haben.

  本发明涉及式 (I) 的新 1-环丙基-1,4-二氢-4-氧代-3-喹啉羧酸衍生物的杀菌用途 其中 R'、R2；R3、R"、R5 和 X 具有描述中给出的含义。
• Synthesis of ciprofloxacin dimers for evaluation of bacterial permeability in atypical chemical space
  作者：Audrey G. Ross、Bret M. Benton、Donovan Chin、Gianfranco De Pascale、John Fuller、Jennifer A. Leeds、Folkert Reck、Daryl L. Richie、Jason Vo、Matthew J. LaMarche

  DOI：10.1016/j.bmcl.2015.07.010

  日期：2015.9

  We describe the synthesis and evaluation of a library of variably-linked ciprofloxacin dimers. These structures unify and expand on the use of fluoroquinolones as probes throughout the antibiotic literature. A dimeric analog (19) showed enhanced inhibition of its intracellular target (DNA gyrase), and translation to antibacterial activity in whole cells was demonstrated. Overall, cell permeation was governed by physicochemical properties and bacterial type. A principal component analysis demonstrated that the dimers occupy a unique and privileged region of chemical space most similar to the macrolide class of antibiotics. (C) 2015 Elsevier Ltd. All rights reserved.
• Gau; Kurz; Petersen, Arzneimittel-Forschung/Drug Research, 1986, vol. 36, # 10, p. 1545 - 1549
  作者：Gau、Kurz、Petersen、Ploschke、Wuensche

  DOI：——

  日期：——
• Preparation and antibacterial evaluation of decarboxylated fluoroquinolones
  作者：Son T. Nguyen、Xiaoyuan Ding、Michelle M. Butler、Tommy F. Tashjian、Norton P. Peet、Terry L. Bowlin

  DOI：10.1016/j.bmcl.2011.07.060

  日期：2011.10

  Decarboxylated ciprofloxacin (3) has been reported in the literature to have antibacterial activities against Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Bacillus subtilis, Enterobacter cloacae, Serratia marcescens and especially potent activity against Escherichia coli. Herein, we report our syntheses of 3 and five additional decarboxylated fluoroquinolones (FQs). We have re-evaluated the antibacterial activity of these FQs. In contrast to previously reported data, none of these decarboxylated fluoroquinolones showed significant antibacterial activity in our assays using both the broth dilution and agar methods. Our study confirmed that the presence of a carboxylic acid group at the 3-position of the fluoroquinolone scaffold is essential for antibacterial activity. (C) 2011 Elsevier Ltd. All rights reserved.