diethyl hydroxy(tetrazolo[1,5-a]quinolin-4-yl)methylphosphonate | 1220960-23-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: diethyl hydroxy(tetrazolo[1,5-a]quinolin-4-yl)methylphosphonate
• 英文别名: Diethoxyphosphoryl(tetrazolo[1,5-a]quinolin-4-yl)methanol
• CAS: 1220960-23-5
• 化学式: C₁₄H₁₇N₄O₄P
• 分子量: 336.287
• InChiKey: GCDJZFWJHRQUSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  98.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl hydroxy(tetrazolo[1,5-a]quinolin-4-yl)methylphosphonate 、 乙酸酐 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 C₁₆H₁₉N₄O₅P
  参考文献：
  名称：

  Synthesis, in vitro antibacterial and antifungal evaluations of new α-hydroxyphosphonate and new α-acetoxyphosphonate derivatives of tetrazolo [1, 5-a] quinoline

  摘要：

  A series of new alpha-hydroxyphosphonate and alpha-acetoxyphosphonate derivatives have been synthesized for the first time of tetrazolo [1, 5-a] quinoline derivatives. Elemental analysis, IR, H-1 NMR, C-13 NMR and mass spectral data elucidated the structures of the all newly synthesized compounds. In vitro antimicrobial activities of the synthesized compounds were investigated against Gram-positive Bacillus subtilis, Gram-negative Escherichia coli and fungi Candida albicans and Aspergillus niger. Some of the tested compounds showed significant antimicrobial activity. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.013
• 作为产物：
  描述：

  2-氯-3-喹啉甲醛 在 sodium azide 、 三乙胺 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 4.0h， 生成 diethyl hydroxy(tetrazolo[1,5-a]quinolin-4-yl)methylphosphonate
  参考文献：
  名称：

  基于四氮杂唑啉的单和双膦酸酯酯类作为有效的消炎剂的合成

  摘要：

  由2-叠氮喹啉3-甲醛1a，b与亚磷酸三烷基酯和亚磷酸二烷基酯的反应合成了四唑-喹啉的几种新的α-烷氧基和α-羟基膦酸酯衍生物。另一方面，通过用三（二甲基氨基）膦处理1a，b获得氮杂磷酯12a，b。此外，1a，b和亚甲基双膦酸四乙酯的Perkin型缩合反应提供了相应的基于四唑并喹啉的双膦酸酯14a，b。根据预测结果（PASS程序），在体内确定了所制备化合物的抗炎活性由急性角叉菜胶诱导的大鼠足水肿引起。许多新化合物以50 mg / kg体重的剂量表现出显着的抗炎特性。与吲哚美辛相比，尤其是14a和14b表现出显着的活性，吲哚美辛在本研究中用作参考标准。

  DOI：

  10.1002/jhet.968

文献信息

• An organocatalyzed facile and rapid access to α-hydroxy and α-amino phosphonates under conventional/ultrasound technique
  作者：Pravin V. Shinde、Amol H. Kategaonkar、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.1016/j.tetlet.2011.03.138

  日期：2011.6

  irradiation for the rapid synthesis of α-hydroxy and α-amino phosphonates under solvent-free conditions is demonstrated. Use of a novel catalyst (i.e., camphor sulfonic acid) in combination with ultrasound technique is reported for the first time. Comparative study for the synthesis of α-hydroxy and α-amino phosphonates using conventional as well as ultrasonication method is discussed.

  在本工作中，证明了在无溶剂条件下成功实施超声辐射以快速合成α-羟基和α-氨基膦酸酯的方法。首次报道了将新型催化剂（樟脑磺酸）与超声技术结合使用。讨论了使用常规方法和超声方法合成α-羟基和α-氨基膦酸酯的比较研究。
• Synthesis, in vitro antibacterial and antifungal evaluations of new α-hydroxyphosphonate and new α-acetoxyphosphonate derivatives of tetrazolo [1, 5-a] quinoline
  作者：Amol H. Kategaonkar、Rajkumar U. Pokalwar、Swapnil S. Sonar、Vaibhav U. Gawali、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.1016/j.ejmech.2009.12.013

  日期：2010.3

  A series of new alpha-hydroxyphosphonate and alpha-acetoxyphosphonate derivatives have been synthesized for the first time of tetrazolo [1, 5-a] quinoline derivatives. Elemental analysis, IR, H-1 NMR, C-13 NMR and mass spectral data elucidated the structures of the all newly synthesized compounds. In vitro antimicrobial activities of the synthesized compounds were investigated against Gram-positive Bacillus subtilis, Gram-negative Escherichia coli and fungi Candida albicans and Aspergillus niger. Some of the tested compounds showed significant antimicrobial activity. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Synthesis of Tetrazoloquinoline-Based Mono- and Bisphosphonate Esters as Potent Anti-Inflammatory Agents
  作者：Wafaa M. Abdou、Rizk E. Khidre、Abeer A. Shaddy

  DOI：10.1002/jhet.968

  日期：2013.1

  Several new α‐alkoxy‐ and α‐hydroxyphosphonate derivatives of tetrazole‐quinolines were synthesized from the reaction of 2‐azidoquinolines 3‐carboxaldehyde 1a,b with trialkyl phosphites and dialkyl phosphites. On the other hand, azaphospholes 12a,b were obtained by treating 1a,b with tris(dimethylamino)phosphine. Furthermore, Perkin‐type condensation of 1a,b and tetraethyl methylenebisphosphonate provided

  由2-叠氮喹啉3-甲醛1a，b与亚磷酸三烷基酯和亚磷酸二烷基酯的反应合成了四唑-喹啉的几种新的α-烷氧基和α-羟基膦酸酯衍生物。另一方面，通过用三（二甲基氨基）膦处理1a，b获得氮杂磷酯12a，b。此外，1a，b和亚甲基双膦酸四乙酯的Perkin型缩合反应提供了相应的基于四唑并喹啉的双膦酸酯14a，b。根据预测结果（PASS程序），在体内确定了所制备化合物的抗炎活性由急性角叉菜胶诱导的大鼠足水肿引起。许多新化合物以50 mg / kg体重的剂量表现出显着的抗炎特性。与吲哚美辛相比，尤其是14a和14b表现出显着的活性，吲哚美辛在本研究中用作参考标准。