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Keggin-structure heteropolyacid phosphorus-containing organic salt compound as well as preparation method and application

A technology of compound and heteropolyacid, which is applied in chemical synthesis and pharmaceutical application fields, to achieve the effect of high safety, low cytotoxicity and high activity

Active Publication Date: 2016-09-28
BEIJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] So far, in the existing literature, there is no report of Keggin structure heteropolyacid phosphorus-containing organic salt drugs as active ingredients in anti-HIV

Method used

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  • Keggin-structure heteropolyacid phosphorus-containing organic salt compound as well as preparation method and application
  • Keggin-structure heteropolyacid phosphorus-containing organic salt compound as well as preparation method and application
  • Keggin-structure heteropolyacid phosphorus-containing organic salt compound as well as preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0017] Embodiment 1 (preparation of PZ-1)

[0018] Dissolve 91 mmol of sodium tungstate dihydrate and 43 mmol of sodium dihydrogen phosphate in 100 mL of distilled water, add 16 mmol of titanium tetrachloride dropwise, reflux for 30 minutes, filter, add 4.1 mol of solid KCl to the filtrate to obtain a white precipitate, and use Hot water recrystallization gave solid K 7 PTi 2 W 10 o 40 . 10mmol K 7 PTi 2 W 10 o 40 Dissolve in 100mL water, add 100mmol tenofovir, adjust the pH value to 4.0, heat to 60°C, react for 3h, after standing for a while, a white solid (C 9 h 15 N 5 PO 4 ) 7 PTi 2 W 10 o 40 .

[0019] 1 H NMR (400MHz, DMSO-d 6 ):δ H (ppm)1.020(d,3H),3.590(m,2H),3.909(m,1H),4.255(m,2H),8.133(s,1H),8.147(s,1H),9.271(s,3H ), 10.960 (s, 2H). Elemental analysis (4622.24): calcd (%): C, 16.36; N, 10.61; P, 5.36; Ti, 2.07; W, 39.76; found (%): C, 16.43; N ,10.68; P,5.33; Ti,2.02; W,39.69.PTi 2 W 10 o 40 7- X-ray single crystal diffraction structure diagr...

Embodiment 2

[0020] Embodiment 2 (preparation of PZ-2)

[0021] Dissolve 91 mmol of sodium tungstate dihydrate and 43 mmol of sodium dihydrogen phosphate in 100 mL of distilled water, add 16 mmol of titanium tetrachloride dropwise, reflux for 30 minutes, filter, add 4.1 mol of solid KCl to the filtrate to obtain a white precipitate, and use Hot water recrystallization gave solid K 7 PTi 2 W 10 o 40 . 10mmol K 7 PTi 2 W 10 o 40 Dissolve in 100mL water, add 100mmol adefovir, adjust the pH value to 4.0, heat to 60°C, react for 3h, after standing for a while, a white solid (C 8 h 13 N 5 PO 4 ) 7 PTi 2 W 10 o 40 .

[0022] 1 H NMR (400MHz, DMSO-d 6 ):δ H(ppm)3.260(s,2H),3.729(t,2H),4.195(t,2H),7.957(s,1H),8.021(s,1H),9.160(s,3H),10.754(s,2H ). Elemental analysis (4524.10): calcd (%): C, 14.85; N, 10.83; P, 5.48; Ti, 2.12; W, 40.63; found (%): C, 14.95; N, 10.89; Ti, 2.16; W, 40.56.PTi 2 W 10 o 40 7- X-ray single crystal diffraction structure diagram figure 1 , the basi...

Embodiment 3

[0023] Embodiment 3 (preparation of PZ-3)

[0024] Dissolve 91 mmol of sodium tungstate dihydrate and 43 mmol of sodium dihydrogen phosphate in 100 mL of distilled water, add 16 mmol of titanium tetrachloride dropwise, reflux for 30 minutes, filter, add 4.1 mol of solid KCl to the filtrate to obtain a white precipitate, and use Hot water recrystallization gave solid K 7 PTi 2 W 10 o 40 . 10mmol K 7 PTi 2 W 10 o 40 Dissolve in 100mL water, add 100mmol diethyl (α-aminobenzyl) phosphonate hydrochloride, adjust the pH value to 7.0, heat to 60°C, react for 3h, after standing for a while, a white solid (C 11 h 19 NPO 3 ) 7 PTi 2 W 10 o 40 .

[0025] 1 H NMR (400MHz, DMSO-d 6 ):δ H (ppm)1.090(t,3H),1.245(t,3H),3.821-4.116(m,4H),4.939(d,1H),7.412-7.569(m,5H),9.093(s,3H). Analysis (4314.52): calcd (%): C, 21.42; N, 2.27; P, 5.74; Ti, 2.22; W, 42.60; found (%): C, 21.53; N, 2.32; ;W,42.53.PTi 2 W 10 o 40 7- X-ray single crystal diffraction structure diagram figu...

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Abstract

The invention discloses a Keggin-structure heteropolyacid phosphorus-containing organic salt compound as well as a preparation method and application, belonging to the field of chemical synthesis and medicinal application. The general formula of the compound disclosed by the invention is A7PTi2W10O40, wherein A is organic cation containing phosphorus and nitrogen; and the compound is a heteropolyacid compound with a Keggin structure. The preparation method comprises the following steps: dissolving sodium tungstate and sodium dihydrogen phosphate in distilled water; dropwise adding titanium tetrachloride for a reflux reaction; filtering; adding alkali metal salt or amino acid salt into the filtrate to obtain a white precipitate; recrystallizing the precipitate with hot water; adjusting to acidity with a compound containing A group or an A compound; and heating and stirring to obtain the Keggin-structure heteropolyacid phosphorus-containing organic salt compound. The compound can be used for preparing anti-HIV drugs.

Description

technical field [0001] The invention belongs to the fields of chemical synthesis and drug application, and in particular relates to Keggin structure heteropolyacid phosphorus-containing organic salt compounds and their preparation and application of the compounds in the field of preparing anti-HIV drugs. Background technique [0002] AIDS (Acquired Immune Deficiency Syndrom, AIDS) is a fatal infectious disease caused by human immunodeficiency virus (Immunodeficiency Virus, HIV). Since AIDS was first discovered in the United States in 1981, it has now spread widely around the world. At present, there is no effective vaccine or cure drug. In recent years, some promising anti-AIDS drugs have been reported one after another, one is nucleoside drugs targeting HIV reverse transcriptase, the other is protease inhibitors targeting HIV precursor protein cleavage . However, these drugs have disadvantages such as serious toxicity, drug resistance and high price, and the prospect of ...

Claims

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Application Information

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IPC IPC(8): C07F9/11C07F9/165C07F9/6561C07F9/6584A61P31/18C01G41/00C30B29/54
CPCC01G41/006C07B2200/13C07F9/11C07F9/1651C07F9/65616C07F9/65846C30B29/54
Inventor 闫红孙武积高磊胡秦艾萍
Owner BEIJING UNIV OF TECH
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