Polyethylene glycol (PEG-400): An efficient one-pot green synthesis and anti-viral activity of novel α-diaminophosphonates

被引:10
作者
Patnala, Harika [1 ]
Abbo, Hanna S. [2 ,3 ]
Potla, Krishna Murthy [4 ]
Titinchi, Salam J. J. [2 ,3 ]
Chinnam, Sampath [5 ]
机构
[1] Andhra Loyola Inst Engn & Technol, Dept Chem, Vijayawada, Andhra Pradesh, India
[2] Univ Basrah, Dept Chem, Basrah, Iraq
[3] Univ Western Cape, Dept Chem, Cape Town, South Africa
[4] Acharya Nagarjuna Univ, Post Grad Res Ctr, Bapatla Engn Coll, Dept Chem, Bapatla, Andhra Pradesh, India
[5] BMS Coll Engn, Dept Chem, Bengaluru, Karnataka, India
关键词
Green synthesis; alpha-diaminophosphonates; anti-viral activity; Kabachnik-Fields reaction; AMINO-PHOSPHONATES; 3-COMPONENT SYNTHESIS; ACID-DERIVATIVES; CATALYST; SOLVENT; AMINOPHOSPHONATES; INHIBITION; CHLORIDE; FACILE; KETONES;
D O I
10.1080/10426507.2019.1597365
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An efficient and eco-friendly protocol has been accomplished for a series of novel alpha-diaminophosphonates by a one-pot, three-component system via Kabachnik-Fields reaction of 4,4 '-methylenedianiline, a variety of aryl/heteroaryl aldehydes and diphenylphosphite employing polyethylene glycol (PEG-400) as a green solvent at 80 degrees C. All products were obtained in good to excellent yields (80-95%). The identity of the new synthesized compounds was confirmed by IR, H-1, 13C, and 31P NMR, LC-MS and elemental analysis. In vivo anti-viral activity was evaluated against tobacco mosaic virus (TMV). Compounds 4b, 4c, 4j and 4k exhibited the highest anti-viral activities against tobacco mosaic virus (TMV) when compared with the standard drug ningnanmycin. [GRAPHICS] .
引用
收藏
页码:1035 / 1039
页数:5
相关论文
共 38 条
[1]  
Abbas A.J., 2010, HETEROATOM CHEM, V21, P397, DOI [DOI 10.1002/HC.20635, 10.1002/hc.20635]
[2]   RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND [J].
ALLEN, MC ;
FUHRER, W ;
TUCK, B ;
WADE, R ;
WOOD, JM .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1652-1661
[3]  
[Anonymous], 1982, CHEM ORGANOPHOSPHORU
[4]   Lithium perchlorate-catalyzed three-component coupling:: A facile and general method for the synthesis of α-aminophosphonates under solvent-free conditions [J].
Azizi, N ;
Saidi, MR .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (23) :4630-4633
[5]   POTENT INHIBITION OF PEPSIN AND PENICILLOPEPSIN BY PHOSPHORUS-CONTAINING PEPTIDE ANALOGS [J].
BARTLETT, PA ;
HANSON, JE ;
GIANNOUSIS, PP .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6268-6274
[6]   PHOSPHORUS-CONTAINING HETEROCYCLES AS FUNGICIDES - SYNTHESIS OF 2,2'-DIPHENYLENE CHLOROPHOSPHONATE AND 2,2'-DIPHENYLENE CHLOROTHIOPHOSPHONATE [J].
BHATIA, MS ;
PAWANJIT .
EXPERIENTIA, 1976, 32 (09) :1111-1111
[7]   Amberlite-IR 120 catalyzed three-component synthesis of α-amino phosphonates in one-pot [J].
Bhattacharya, Asish K. ;
Rana, Kalpeshkumar C. .
TETRAHEDRON LETTERS, 2008, 49 (16) :2598-2601
[8]   REACTIONS OF CHIRAL PHOSPHORUS-ACID DIAMIDES - THE ASYMMETRIC-SYNTHESIS OF CHIRAL ALPHA-HYDROXY PHOSPHONAMIDES, PHOSPHONATES, AND PHOSPHONIC-ACIDS [J].
BLAZIS, VJ ;
KOELLER, KJ ;
SPILLING, CD .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) :931-940
[9]   Solvent and catalyst free three-component coupling of carbonyl compounds, amines and triethylphosphite;: a new synthesis of α-aminophosphonates [J].
Chandrasekhar, S ;
Narsihmulu, C ;
Sultana, SS ;
Saritha, B ;
Prakash, SJ .
SYNLETT, 2003, (04) :505-506
[10]   Three component coupling catalyzed by TaCl5-SiO2:: synthesis of α-amino phosphonates [J].
Chandrasekhar, S ;
Prakash, SJ ;
Jagadeshwar, V ;
Narsihmulu, C .
TETRAHEDRON LETTERS, 2001, 42 (32) :5561-5563