tetraethyl ((4-isopropylphenylamino)methylene)bisphosphonate | 1361336-04-0

• 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: tetraethyl ((4-isopropylphenylamino)methylene)bisphosphonate
• CAS: 1361336-04-0
• 化学式: C₁₈H₃₃NO₆P₂
• 分子量: 421.411
• InChiKey: HFHJULAJTCHXKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  27.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  83.09
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tetraethyl ((4-isopropylphenylamino)methylene)bisphosphonate 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 生成 N-(4-isopropylphenyl)aminomethylenebisphosphonic acid
  参考文献：
  名称：

  Bisphosphonic acids as effective inhibitors ofMycobacterium tuberculosisglutamine synthetase

  摘要：

  Inhibition of glutamine synthetase (GS) is one of the most promising strategies for the discovery of novel drugs against tuberculosis. Forty-three bisphosphonic and bis-H-phosphinic acids of various scaffolds, bearing aromatic substituents, were screened against recombinant GS from Mycobacterium tuberculosis. Most of the studied compounds exhibited activities in micromolar range, with N-(3,5-dichlorophenyl)-2-aminoethylidenebisphoshonic acid, N-(3,5difluorophenyl)-2-aminoethylidene-bisphoshonic acid and N-(3,4-dichlorophenyl)-1-hydroxy1,1-ethanebisphosphonic acid showing the highest potency with kinetic parameters similar to the reference compound - L-methionine-S-sulfoximine. Moreover, these inhibitors were found to be much more effective against pathogen enzyme than against the human ortholog. Thus, with the bone-targeting properties of the bisphosphonate compounds in mind, this activity/selectivity profile makes these compounds attractive agents for the treatment of bone tuberculosis.

  DOI：

  10.3109/14756366.2015.1070846
• 作为产物：
  描述：

  4-异丙基苯胺 、 亚磷酸二乙酯 在 ytterbium perfluorooctanoate 、 原甲酸三乙酯 作用下， 反应 0.3h， 以89%的产率得到tetraethyl ((4-isopropylphenylamino)methylene)bisphosphonate
  参考文献：
  名称：

  A facile synthesis of aminomethylene bisphosphonates catalyzed by ytterbium perfluorooctanoate under ionic liquid condition

  摘要：

  Three-component reactions of amines, triethylorthoformate and diethyl phosphite are efficiently catalyzed by ytterbium perfiuorooctanoate [Yb(PFO)(3)] in 1-butyl-3-methylimidazolium chloride ([bmim][Cl]) ionic liquid, giving the corresponding aminomethylene bisphosphonates in good yields. The catalyst can be recovered and reused for several times without any significant loss of activity. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.10.005

文献信息

• Sulfonic acid functionalized hyper-cross-linked polymer: An efficient heterogeneous acid catalyst for the synthesis of N-containing bisphosphonates
  作者：Sirigireddy Sudharsan Reddy、Reddi Mohan Naidu Kalla、Anuraj Varyambath、Il Kim

  DOI：10.1016/j.catcom.2019.04.009

  日期：2019.6

  then functionalized by chlorosulfonic acid to obtain sulfonated HCBP (HCBP-SO3H) having surface area of 452 m2/g. The synthesized HCBP and HCBP-SO3H were characterized systematically by spectroscopic techniques. Further, the catalytic potential was evaluated towards the one-pot synthesis of N-containing bisphosphonates (N-BPs). To the delight, catalyst showed excellent activity in the synthesis of various

  一种新的微多孔超交联2,2'-联苯酚聚合物（氯代联苯）与770微米的良好的比表面积2 / g的合成，然后通过氯磺酸官能化以获得磺化氯代联苯（氯代联苯-SO 3 1H）具有表面积为452m 2 / g。用光谱技术对合成的HCBP和HCBP-SO 3 H进行了系统表征。此外，催化电位朝向一锅合成的评价Ñ含双膦酸盐（Ñ -bps）。令人高兴的是，催化剂在合成各种具有生物活性的芳族和杂芳族N时表现出出色的活性。-血压。值得注意的是，它可以循环使用七个周期，而其酸官能度没有任何重大损失。