Ionic liquid promoted synthesis, antibacterial and in vitro antiproliferative activity of novel α-aminophosphonate derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 8, 2011, Pages 2527-2532

  Dake, Satish A ^a   Raut, Dnyaneshwar S ^a   Kharat, Kiran R ^b   Mhaske, Rooth S ^b   Deshmukh, Satish U ^b   Pawar, Rajendra P ^b  

^a DNYANOPASAK COLLEGE   (India)

^b DEOGIRI COLLEGE   (India)

Author keywords

Aminophosphonates; Antibacterial agents; Antiproliferative agent; Ethyl ammonium nitrate; Ionic liquid

Indexed keywords

ALDEHYDE; ALPHA AMINOPHOSPHONATE DERIVATIVE; AMINE; DIETHYL (4 IODO 2 NITROPHENYLAMINO)(2 HYDROXYPHENYL) METHYLPHOSPHONATE; DIETHYL (4 IODO 2 NITROPHENYLAMINO)(3 NITROPHENYL) METHYLPHOSPHONATE; DIETHYL (4 IODO 2 NITROPHENYLAMINO)(4 HYDROXY 3 METHOXYPHENYL) METHYLPHOSPHONATE; DIETHYL (4 IODO 2 NITROPHENYLAMINO)(4 HYDROXYPHENYL) METHYLPHOSPHONATE; ETHYL AMMONIUM NITRATE; IONIC LIQUID; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYST; CONTROLLED STUDY; COST EFFECTIVENESS ANALYSIS; DRUG SYNTHESIS; ESCHERICHIA COLI; HUMAN; HUMAN CELL; IN VITRO STUDY; NONHUMAN; ONE POT SYNTHESIS; ROOM TEMPERATURE; SALMONELLA TYPHI;

ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS; CATALYSIS; CELL LINE, TUMOR; HUMANS; IONIC LIQUIDS; MICROBIAL SENSITIVITY TESTS; NITRATES; PHOSPHONIC ACIDS;

ESCHERICHIA COLI; SALMONELLA TYPHI;

EID: 79953280899     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.02.039     Document Type: Article

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34. Experimental section: melting points were measured in open glass capillaries on a Perfit Electrothermal melting-point apparatus and are not very accurate. Preparation of ethyl ammonium nitrate as catalyst To an aqueous solution of ethyl amine (70%, 100 ml), nitric acid (30%, 330 ml) was added drop-wise with external cooling under stirring at the temperature below 10 °C. As soon as the pH of the mixture attained the value of 7.3, the addition was stopped and the mixture was stirred further for 0.5 h. The water from a mixture was removed in a rotary evaporator in a boiling water bath at a pressure of 200 mm of Hg. Final traces of water were removed at 100 °C and 1 mmHg pressure to afford the ionic liquid in quantitative yield (170 g). The ionic liquid obtained was used as catalyst in this reaction. General procedure for synthesis of α-aminophosphonates To a mixture of aldehyde (1 mmol), amine (1 mmol), diethylphosphite (1 mmol) and ethyl ammonium nitrate (2 ml) was added in 50 ml round bottom flask and stirred at room temperature for the appropriate time (Tables 1 and 2 ). The progress of reaction was monitored by thin layer chromatography. After completion of the reaction 50 ml ice cold water was added to the reaction mixture. The separated solid was filtered off, dried and purified, unreacted aromatic amines separated by column chromatography using petroleum ether/ethyl acetate (7:3 ml) as an eluent.