(4-methoxy-phenyl)-(2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-2-yl)-amine | 64077-23-2

• 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: (4-methoxy-phenyl)-(2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-2-yl)-amine
• 英文别名: N-(4-methoxyphenyl)-2-oxo-1,3,2lambda5-oxazaphosphinan-2-amine；N-(4-methoxyphenyl)-2-oxo-1,3,2λ5-oxazaphosphinan-2-amine
• CAS: 64077-23-2
• 化学式: C₁₀H₁₅N₂O₃P
• 分子量: 242.214
• InChiKey: FCGWGKLTFFRPPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-methoxyphenyl phosphoramidic dichloride 、 3-氨基-1-丙醇 在 三乙胺 作用下， 以 四氯化碳 为溶剂， 反应 10.0h， 以70%的产率得到(4-methoxy-phenyl)-(2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-2-yl)-amine
  参考文献：
  名称：

  Antitumor activities of some new 1,3,2-oxaza- and 1,3,2-diazaphosphorinanes against K562, MDA-MB-231, and HepG2 cells

  摘要：

  New X-substituted 1,3,2-oxazaphosphorinanes, where X = NHC6H5 (1), NHC6H4S(O)(2)NH2-4 (2), NHC6H4OCH3-4 (3), NHC6H4NO2-4 (4), OC6H4CH3-4 (5), NHC(O)C6H4NO2-4 (6), plus one X-substituted 1,3,2-diazaphosphorinane, where X = NHC6H4S(O)(2)NH2-4 (7), were synthesized and characterized by NMR, IR spectroscopy, and elemental analysis. The antitumor activities of these compounds, cyclophosphamide (CP), sulfanilamide (SA), and two X-substituted 5,5-dimethyl-1,3,2-diazaphosphorinanes, where X = NHC6H5 (8) OC6H4CH3-4 (9), were evaluated by cell culture on K562, MDA-MB-231, and HepG2 cell lines using MTT cell proliferation assay. The IC50 values for CP and compounds 1-9 were in the range of 0.06 mu M (for inhibition of HepG2 cells by compound 3) to 3.17 mu M (for inhibition of HepG2 cells by compound 8). It was found that compounds 2 and 7 containing sulfonamide substituent and also SA itself are the best candidates for antitumor activity very close to CP.

  DOI：

  10.1007/s00044-011-9737-7

文献信息

• Potentielle Antineoplastica, 1. Mitt. Cyclophosphamidanaloge 2-Arylamino-tetrahydro-2H-1,3,2-oxazaphosphorin-2-oxide
  作者：Harald Hamacher

  DOI：10.1002/ardp.19773100514

  日期：——

  Die lostgruppenfreien Cyclophosphamidanaloga 7‐‐11 werden dargestellt und durch UV‐, IR‐, 1H‐NMR sowie massenspektroskopische Untersuchungen charakterisiert. 7 zeigt am Walker Carcinom 256 der Ratte keine antineoplastische Wirksamkeit, auch kann bei in vitro Versuchen in Gegenwart des Monooxygenasesystems keine Acroleinfreisetzung nachgewiesen werden.

  介绍了无游离基团的环磷酰胺类似物 7-11，并通过 UV、IR、1H NMR 和质谱研究对其进行了表征。图7显示在大鼠Walker Carcinoma 256中没有抗肿瘤活性，并且在单加氧酶系统存在的体外测试中没有检测到丙烯醛释放。
• Antitumor activities of some new 1,3,2-oxaza- and 1,3,2-diazaphosphorinanes against K562, MDA-MB-231, and HepG2 cells
  作者：Khodayar Gholivand、Fatemeh Ghaziani、Zahra Shariatinia、Nilufar Dorosti、Manouchehr Mirshahi、Sina Sarikhani

  DOI：10.1007/s00044-011-9737-7

  日期：2012.9

  New X-substituted 1,3,2-oxazaphosphorinanes, where X = NHC6H5 (1), NHC6H4S(O)(2)NH2-4 (2), NHC6H4OCH3-4 (3), NHC6H4NO2-4 (4), OC6H4CH3-4 (5), NHC(O)C6H4NO2-4 (6), plus one X-substituted 1,3,2-diazaphosphorinane, where X = NHC6H4S(O)(2)NH2-4 (7), were synthesized and characterized by NMR, IR spectroscopy, and elemental analysis. The antitumor activities of these compounds, cyclophosphamide (CP), sulfanilamide (SA), and two X-substituted 5,5-dimethyl-1,3,2-diazaphosphorinanes, where X = NHC6H5 (8) OC6H4CH3-4 (9), were evaluated by cell culture on K562, MDA-MB-231, and HepG2 cell lines using MTT cell proliferation assay. The IC50 values for CP and compounds 1-9 were in the range of 0.06 mu M (for inhibition of HepG2 cells by compound 3) to 3.17 mu M (for inhibition of HepG2 cells by compound 8). It was found that compounds 2 and 7 containing sulfonamide substituent and also SA itself are the best candidates for antitumor activity very close to CP.