1-(4-fluoro-benzyl)-azetidine-3-carboxylic acid | 1127402-43-0

• 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-fluoro-benzyl)-azetidine-3-carboxylic acid
• 英文别名: 1-(4-fluorobenzyl)azetidine-3-carboxylic acid；1-[(4-Fluorophenyl)methyl]azetidine-3-carboxylic acid
• CAS: 1127402-43-0
• 化学式: C₁₁H₁₂FNO₂
• 分子量: 209.22
• InChiKey: IHHYEODYOHUZKG-UHFFFAOYSA-N

物化性质

• 沸点：
  333.0±37.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-fluoro-benzyl)-azetidine-3-carboxylic acid 、 1-cyclopropyl-6-fluoro-7-(N-methyl-hydrazino)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 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 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.08h， 生成 1-cyclopropyl-6-fluoro-7-{N'-[1-(4-fluoro-benzyl)-azetidine-3-carbonyl]-N-methyl-hydrazino}-4-oxo-1,4-dihydro-quinoline-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
• 作为产物：
  描述：

  对氟苯甲醛 、 3-吖丁啶羧酸 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81%的产率得到1-(4-fluoro-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

• PYRROLOPYRIDINE INHIBITORS OF KINASES
  申请人：Florjancic Alan S.

  公开号：US20110015173A1

  公开（公告）日：2011-01-20

  The present invention relates to compounds of formula (I) or pharmaceutical acceptable salts, wherein R 1a , R 1b , R 1c , X, and Y are defined in the description. The present invention relates also to compositions containing said compounds which are useful for inhibiting kinases such as Cdc7 and methods of treating diseases such as cancer.

  本发明涉及公式（I）的化合物或药用可接受的盐，其中R1a、R1b、R1c、X和Y在描述中有定义。本发明还涉及含有上述化合物的组合物，该组合物对抑制Cdc7等激酶以及治疗癌症等疾病有用。
• US8435980B2
  申请人：——

  公开号：US8435980B2

  公开（公告）日：2013-05-07
• US8822446B2
  申请人：——

  公开号：US8822446B2

  公开（公告）日：2014-09-02
• US9181246B2
  申请人：——

  公开号：US9181246B2

  公开（公告）日：2015-11-10
• [EN] PYRROLOPYRIDINE INHIBITORS OF KINASES<br/>[FR] PYRROLOPYRIDINES INHIBITEURS DE KINASES
  申请人：ABBOTT LAB

  公开号：WO2011008915A1

  公开（公告）日：2011-01-20

  The present invention relates to compounds of formula (I) or pharmaceutical acceptable salts, formula (I) wherein R1a, R1b, R1c, X, and Y are defined in the description. The present invention relates also to compositions containing said compounds which are useful for inhibiting kinases such as Cdc7 and methods of treating diseases such as cancer.