Synthesis and biological evaluation of some new polyfluorinated 4-thiazolidinone and α-aminophosphonic acid derivatives

被引：32

作者：

Abdel-Rahman, Reda M. ^{[1
]}

Ali, Tarik E. ^{[2
]}

机构：

[1] King Abdulaziz Univ, Fac Sci, Dept Chem, Jeddah, Saudi Arabia

[2] Ain Shams Univ, Fac Educ, Dept Chem, Cairo 11711, Egypt

来源：

MONATSHEFTE FUR CHEMIE | 2013年 / 144卷 / 08期

关键词：

Synthesis; Antifungal; Fluorine; 4-thiazolidinone; alpha-Aminophosphonic acids and their esters; LEUCINE AMINOPEPTIDASE; FLUORINE CHEMISTRY; MICROWAVE; DESIGN;

D O I：

10.1007/s00706-013-0934-6

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple route for the synthesis of new polyfluorinated 4-thiazolidinones and 1,4-bis(4-thiazolidinone)phenylenes was achieved from one-pot three-component reaction of fluorinated aniline, mono- and dialdehyde and thioglycolic acid followed by fluorination with trifluoroacetamide and 4-fluorobenzaldehyde. Also, some new fluorinated alpha-aminophosphonates, 1,4-bis(alpha-aminophosphonate)phenylenes and their corresponding acids were synthesized via one-pot three-component reaction of fluorinated aniline, mono- and dialdehyde and diethyl phosphite followed by fluorination with trifluoroacetic anhydride. All the synthesized compounds were screened for their antifungal activity against Alternaria alternate and Fusarium oxysporium. Also, their effects on the enzymatic effect of cellobiase produced from Alternaria alternate and Fusarium oxysporium were estimated. Compounds that have trifluoromethyl groups recorded good inhibition against the fungal strains and also enhanced the enzymatic effect of cellobiase. .

引用

页码：1243 / 1252

页数：10

共 42 条

[1]

Abdel-Rahman R.M., 2010, Eur. J. Chem., V1, P236, DOI [10.5155/eurjchem.1.3.236-245.54, DOI 10.5155/EURJCHEM.1.3.236-245.54]

[2] Chemical composition, antibacterial and antifungal activities of the essential oil of Haplophyllum tuberculatum from Oman [J].

Al-Burtamani, SKS ;

Fatope, MO ;

Marwah, RG ;

Onifade, AK ;

Al-Saidi, SH .

JOURNAL OF ETHNOPHARMACOLOGY, 2005, 96 (1-2) :107-112

[3] Synthesis and molluscicidal activity of phosphorus-containing heterocyclic compounds derived from 5,6-bis (4-bromophenyl)-3-hydrazino-1,2,4-triazine [J].

Ali, T. E. ;

Abdel-Rahman, R. M. ;

Hanafy, F. I. ;

El-Edfawy, S. M. .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (10) :2565-2577

[4] Synthesis and antibacterial activity of some new thiadiaza/triazaphospholes, thiadiaza/triaza/tetrazaphosphinines and thiadiaza/tetrazaphosphepines containing 1,2,4-triazinone moiety [J].

Ali, Tarik El-Sayed .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (11) :4539-4546

[5]

Bakhotmah DA, 2011, INT J CHEM RES, V2, P65

[6] Computer-aided analysis and design of phosphonic and phosphinic enzyme inhibitors as potential drugs and agrochemicals [J].

Berlicki, L ;

Kafarski, P .

CURRENT ORGANIC CHEMISTRY, 2005, 9 (18) :1829-1850

[7] The polar hydrophobicity of fluorinated compounds [J].

Biffinger, JC ;

Kim, HW ;

DiMagno, SG .

CHEMBIOCHEM, 2004, 5 (05) :622-627

[8] Thiazolidin-4-one formation. Mechanistic and synthetic aspects of the reaction of imines and mercaptoacetic acid under microwave and conventional heating [J].

Bolognese, A ;

Correale, G ;

Manfra, M ;

Lavecchia, A ;

Novellino, E ;

Barone, V .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (19) :2809-2813

[9] Enzymatic hydrolysis of corncob and ethanol production from cellulosic hydrolysate [J].

Chen, Ming ;

Xia, Liming ;

Xue, Peijian .

INTERNATIONAL BIODETERIORATION & BIODEGRADATION, 2007, 59 (02) :85-89

[10] Synthesis of the first stable phosphonamide transition state analogue [J].

de Medina, P ;

Ingrassia, LS ;

Mulliez, ME .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (22) :8424-8430

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