An Efficient Synthesis of Thiazolidine-4-ones with Antitumor and Antioxidant Activities

被引：20

作者：

Aly, Ashraf A. ^{[1
]}

Brown, Alan B. ^{[2
]}

Abdel-Aziz, Mohamed ^{[3
]}

Abuo-Rahma, Gamal El-Din A. A. ^{[3
]}

Radwan, Mohamed F. ^{[3
]}

Ramadan, Mohamed ^{[3
]}

Gamal-Eldeen, Amira M. ^{[4
]}

机构：

[1] Menia Univ, Fac Sci, Chem Dept, El Menia 61519, Egypt

[2] Florida Inst Technol, Chem Dept, Melbourne, FL 32901 USA

[3] Menia Univ, Fac Pharm, Dept Med Chem, El Menia 61519, Egypt

[4] Natl Res Ctr, Dept Biochem, Div Genet Engn & Biotechnol, Cairo, Egypt

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2012年 / 49卷 / 04期

基金：

美国国家科学基金会;

关键词：

DIMETHYL ACETYLENEDICARBOXYLATE; BIOLOGICAL-ACTIVITY; ONE-POT; DERIVATIVES; 4-THIAZOLIDINONES; THIOAMIDES; ESTERS;

D O I：

10.1002/jhe.641

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of 3-aroyl-1-arylthioureas with dimethyl but-2-ynedioate in dichloromethane and catalyzed by triphenylphosphine at -5 degrees C led to (Z)-methyl 2-[(Z)-2-(4-aroylimino)-4-oxo-3-aryl-1,3-thiazolidin-5-ylidene]acetates in good yields. The mechanism is discussed. X-ray structure analysis of one thiazolidine derivative is described. Antitumor and antioxidant activities have been investigated. One derivative of 1,3-thiazolidine showed moderate antiproliferative in vitro activity against hepatocellular carcinoma Hep-G2, whereas another 1,3-thiazolidine introduced effective antioxidant activity compared to ascorbic acid.

引用

页码：726 / 731

页数：6

共 25 条

[1]

Aly A. A., 2006, J SULFUR CHEM, V27, P419, DOI DOI 10.1080/17415990600908714

[2] Update survey on aroyl substituted thioureas and their applications [J].

Chemistry Department, Faculty of Science, El-Minia University, 61519 El-Minia, Egypt ;

不详 .

J. Sulfur Chem., 2007, 1 (73-93) :73-93

[3]

ALY AA, 2007, J SULF CHEM, V28, P285

[4] Reactions of aroylthioureas with acetylenic esters and dibenzoyl ethylene. Selectivity towards the formation of new 1,3-thiazines [J].

Aly, Ashraf A. ;

Ahmed, Essam K. ;

El-Mokadam, Khalad M. .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (06) :1431-1438

[5] The novel one-pot synthesis of functionalized vinyl sulfides using triphenylphosphine catalyzed nucleophilic addition of thiols to acetylenes [J].

Baharfar, Robabeh ;

Baghbanian, Seyed M. ;

Hossein nia, Roghayeh ;

Bijanzadeh, Hamid R. .

LETTERS IN ORGANIC CHEMISTRY, 2007, 4 (08) :567-570

[6] Design, synthesis, structure-activity relationships, and molecular modeling studies of 2,3-diaryl-1,3-thiazolidin-4-ones as potent anti-HIV agents [J].

Barreca, ML ;

Balzarini, J ;

Chimirri, A ;

De Clercq, E ;

De Luca, L ;

Höltje, HD ;

Höltje, M ;

Monforte, AM ;

Monforte, P ;

Pannecouque, C ;

Rao, A ;

Zappalà, M .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (24) :5410-5413

[7] Condensations of thioamides with acetylenecarboxylic acid derivatives [J].

Danilkina, N. A. ;

Mikhailov, L. E. ;

Ivin, B. A. .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 42 (06) :783-814

[8]

Danilkina N.A., 2004, 3 EUR HET M HET ORG

[9] RE-EXAMINATION AND FURTHER DEVELOPMENT OF A PRECISE AND RAPID DYE METHOD FOR MEASURING CELL-GROWTH CELL KILL [J].

HANSEN, MB ;

NIELSEN, SE ;

BERG, K .

JOURNAL OF IMMUNOLOGICAL METHODS, 1989, 119 (02) :203-210

[10] ABOUT THE REVERSIBLE CONVERSION OF 3-DIETHYLAMINO-5-PHENYL-1,2,4-DITHIAZOLIUM-HALOMETALLATES INTO METAL-CHELATES OF 3-(THIO)BENZOYL(THIO)UREAS [J].

HARTUNG, J ;

ROSENBAUM, K ;

BEYER, L ;

LOSADA, J ;

FERNANDEZ, V .

JOURNAL FUR PRAKTISCHE CHEMIE, 1991, 333 (04) :537-544

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