Synthesis and characterisation of some novel fused thiazolo[3,2-a] pyrimidinones and pyrimido[2,1-b][1,3]thiazinones

被引:11
作者
Abbas, Ikhlass M. [1 ]
Gomha, Sobhi M. [1 ]
Elaasser, Mahmoud M. [2 ]
Mabrouk, Bazada K. A. [1 ]
机构
[1] Cairo Univ, Dept Chem, Fac Sci, Giza 12613, Egypt
[2] Al Azhar Univ, Reg Ctr Mycol & Biotechnol, Cairo, Egypt
关键词
thiazolo[3,2-a]pyrimidinones; pyrimido[2,1-b][1,3]thiazinones; thiones; cytotoxic activity; ANTICANCER ACTIVITY; DERIVATIVES; HETEROCYCLES; THIAZOLOPYRIMIDINE; ANTITUMOR; BEARING; ANTIOXIDANT; MOIETIES;
D O I
10.3184/174751915X14474391581067
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reactions of 7,9-bis(4-methoxyphenyl)-2-thioxo-2,3-dihydropyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4(1H)-one with alpha-haloketones, chloroacetonitrile and DMAD, afforded the corresponding fused thiazolo[3,2-a]pyrimidinone derivatives. The reaction of the thione with chloroacetic acid and an appropriate aromatic aldehyde yielded the respective 2-arylidene-2H-pyrido[3',2':4,5]thieno[3,2-d]thiazolo[3,2-a]pyrimidine-3,5-diones. Also, the treatment of thione with arylidenemalononitriles gave the fused pyrimido[2,1-b][1,3]thiazine derivatives, respectively. The structures of the synthesised products were confirmed by IR, H-1 NMR and mass spectral techniques. The cytotoxic activity of the new products against breast carcinoma (MCF-7) and hepatocellular carcinoma (HepG2) cell lines were determined and the results revealed promising activity.
引用
收藏
页码:719 / 723
页数:5
相关论文
共 39 条
[11]   Synthesis of Novel Highly Functionalized 4-Thiazolidinone Derivatives from 4-Phenyl-3-thiosemicarbazones [J].
Benmohammed, Abdelmadjid ;
Khoumeri, Omar ;
Djafri, Ayada ;
Terme, Thierry ;
Vanelle, Patrice .
MOLECULES, 2014, 19 (03) :3068-3083
[12]  
Chandrahas N. K., 2010, J ENZYM INHIB MED CH, V25, P615
[13]   Synthesis and antimicrobial activity of some new 1,3-diphenylpyrazoles bearing pyrimidine, pyrimidinethione, thiazolopyrimidine, triazolopyrimidine, thio- and alkylthiotriazolop-yrimidinone moieties at the 4-position [J].
El-Emary, T. I. ;
Abdel-Mohsen, Sh. A. .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2006, 181 (11) :2459-2474
[14]   Synthesis and reactions of polynuclear heterocycles: Azolothienopyrimidines and thienothiazolopyrimidines [J].
El-Gazzar, A. B. A. ;
Hussein, H. A. R. ;
Aly, A. S. .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2006, 181 (12) :2771-2784
[15]   Synthesis, analgesic, anti-inflammatory, and antimicrobial activity of some novel pyrimido[4,5-b]quinolin-4-ones [J].
El-Gazzar, Abdel-Rahman B. A. ;
El-Enany, Mervat M. ;
Mahmoud, N. Mahmoud .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (06) :3261-3273
[16]   Synthesis and reactions of some tetrahydrobenzothieno[2,3-d]pyrimidine derivatives with biological interest [J].
El-Sharief, AMS ;
Micky, JAA ;
Shmeiss, NAMM ;
El-Gharieb, G .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2003, 178 (03) :439-451
[17]  
Fadi M. A., 2008, SCI PHARM, V76, P415
[18]   Synthesis and antitumor activity of pyrido [2,3-d]pyrimidine and pyrido[2,3-d] [1,2,4]triazolo[4,3-a]pyrimidine derivatives that induce apoptosis through G1 cell-cycle arrest [J].
Fares, Mohamed ;
Abou-Seri, Sahar Mahmoud ;
Abdel-Aziz, Hatem A. ;
Abbas, Safinaz E. -S. ;
Youssef, Mohieldin Magdy ;
Eladwy, Radwa Ahmed .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 83 :155-166
[19]   A novel synthesis of some new pyrimidine and thiazolopyrimidine derivatives for anticancer evaluation [J].
Flefel, E. E. ;
Salama, M. A. ;
El-Shahat, M. ;
El-Hashash, M. A. ;
El-Farargy, A. F. .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (08) :1739-1756
[20]   Synthesis of new functionalised derivatives of [1,2,4]triazolo[4,3-a]pyrimidine and pyrimido[2,1-b][1,3,5]thiadiazine as aromatase inhibitors [J].
Gomha, Sobhi M. ;
Abdelrazek, Fathy M. ;
Abdulla, Mohamed M. .
JOURNAL OF CHEMICAL RESEARCH, 2015, (07) :425-429