1-cyclohexyl-azetidine-3-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: 1-cyclohexyl-azetidine-3-carboxylic acid
• 英文别名: 1-Cyclohexylazetidine-3-carboxylic acid
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: XUZNTJMBNVOKTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-6-fluoro-7-(N-methyl-hydrazino)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 、 1-cyclohexyl-azetidine-3-carboxylic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.08h， 以75%的产率得到7-[N'-(1-cyclohexyl-azetidine-3-carbonyl)-N-methyl-hydrazino]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  New azetidine-3-carbonyl-N-methyl-hydrazino derivatives of fluoroquinolones: synthesis and evaluation of antibacterial and anticancer properties

  摘要：

  A series of nine new N-(substituted azetidine-3-carbonyl)-N-methyl-hydrazino derivatives at C-7 position of fluoroquinolones were designed and synthesized through multistep synthesis. The synthesized compounds were characterized by H-1 NMR, C-13 NMR, ESI-MS and IR. The new compounds were tested for their in vitro antimicrobial and anti-proliferative activity. Out of the nine derivatives, compound 6i exhibited good antibacterial activity by inhibiting the growth of Methicillin-sensitive Staphylococcus aureus, Methicillin-resistant S. aureus and ATCC 35218 Escherichia coli (MIC: 0.25-16.00 mu g/mL). Compounds 6c, 6g-h are displayed good growth inhibition against MCF-7 Breast carcinoma, HCT-116 Colon carcinoma and A549 Lung adenocarcinoma cell lines. Compound 6h is the most active against MCF-7 cell line with superior growth inhibition compared to ciprofloxacin and reference anticancer drug SAHA.

  DOI：

  10.1007/s00044-013-0873-0
• 作为产物：
  描述：

  环己酮 、 3-吖丁啶羧酸 在 palladium on activated charcoal 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以90 %的产率得到1-cyclohexyl-azetidine-3-carboxylic acid
  参考文献：
  名称：

  大环类化合物及其医药用途

  摘要：

  本发明公开了如式(I)所示的大环类化合物或其药学上可接受的盐、互变异构体、内消旋体、外消旋体、立体异构体、代谢产物、代谢前体、前药或溶剂化物。本发明的大环类化合物或其药学上可接受的盐、互变异构体、内消旋体、外消旋体、立体异构体可用于制备预防或治疗MC4R介导的代谢性疾病的药物。本发明还公开了大环类化合物在制备MC4R激动剂中的用途。

  公开号：

  CN116003434A

文献信息

• [EN] NEW TETRACYCLINE DERIVATIVES AS ANTIINFECTIVE AGENTS<br/>[FR] NOUVEAU DÉRIVÉS DE TÉTRACYCLINE EN TANT QU'AGENTS ANTI-INFECTIEUX
  申请人：REDDYS LAB LTD DR

  公开号：WO2009032326A1

  公开（公告）日：2009-03-12

  In accordance with one embodiment, the present invention provides a compound of general formula (I), stereoisomers thereof and/or its pharmaceutically acceptable salts thereof, which have antibacterial activity; with methods of treating infectious diseases in warm blooded animals employing these new compounds.

  根据一种实施例，本发明提供了通式（I）的化合物，其立体异构体和/或其药学上可接受的盐，具有抗菌活性；采用这些新化合物治疗温血动物感染性疾病的方法。
• New azetidine-3-carbonyl-N-methyl-hydrazino derivatives of fluoroquinolones: synthesis and evaluation of antibacterial and anticancer properties
  作者：G. Govinda Rajulu、Halehatty S. Bhojya Naik、G. Charan Kumar、S. Ramaraj、Ganesh Sambasivam、Kesavan Poonimangadu Koppolu

  DOI：10.1007/s00044-013-0873-0

  日期：2014.6

  A series of nine new N-(substituted azetidine-3-carbonyl)-N-methyl-hydrazino derivatives at C-7 position of fluoroquinolones were designed and synthesized through multistep synthesis. The synthesized compounds were characterized by H-1 NMR, C-13 NMR, ESI-MS and IR. The new compounds were tested for their in vitro antimicrobial and anti-proliferative activity. Out of the nine derivatives, compound 6i exhibited good antibacterial activity by inhibiting the growth of Methicillin-sensitive Staphylococcus aureus, Methicillin-resistant S. aureus and ATCC 35218 Escherichia coli (MIC: 0.25-16.00 mu g/mL). Compounds 6c, 6g-h are displayed good growth inhibition against MCF-7 Breast carcinoma, HCT-116 Colon carcinoma and A549 Lung adenocarcinoma cell lines. Compound 6h is the most active against MCF-7 cell line with superior growth inhibition compared to ciprofloxacin and reference anticancer drug SAHA.