1-(4-methoxy-benzyl)-azetidine-3-carboxylic acid | 1127402-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-methoxy-benzyl)-azetidine-3-carboxylic acid
• 英文别名: 1-(4-methoxybenzyl)azetidine-3-carboxylic acid；1-[(4-methoxyphenyl)methyl]azetidine-3-carboxylic acid
• CAS: 1127402-49-6
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: OJLBIKRGQAUMCN-UHFFFAOYSA-N

物化性质

• 沸点：
  369.0±37.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-methoxy-benzyl)-azetidine-3-carboxylic acid 在 叔丁基锂 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 18.0h， 生成 6-(1-(4-methoxybenzyl)azetidine-3-carbonyl)quinolin-2(1H)-one
  参考文献：
  名称：

  [EN] COMPOUNDS FOR THE TREATMENT OF NEUROLOGICAL DISORDERS
  [FR] COMPOSÉS POUR LE TRAITEMENT DE TROUBLES NEUROLOGIQUES

  摘要：

  公开号：

  WO2013170072A3
• 作为产物：
  描述：

  3-吖丁啶羧酸 、 4-甲氧基苯甲醛 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、137.9 kPa 条件下， 以85%的产率得到1-(4-methoxy-benzyl)-azetidine-3-carboxylic acid
  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

文献信息

• 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.
• [EN] COMPOUNDS FOR THE TREATMENT OF NEUROLOGICAL DISORDERS<br/>[FR] COMPOSÉS POUR LE TRAITEMENT DE TROUBLES NEUROLOGIQUES
  申请人：NEUROP INC

  公开号：WO2013170072A3

  公开（公告）日：2014-02-27