Synthesis, Antimicrobial, and Anticancer Activities of a New Series of Thieno[2,3-d] Pyrimidine Derivatives

被引:24
|
作者
Saddik, Abdelreheem Abdelfatah [1 ,2 ]
El-Dean, Adel Mohamed Kamal [1 ]
El-Said, Waleed Ahmed [1 ]
Hassan, Khairy Mohamed [1 ]
Abbady, Mohamed Saad [1 ]
机构
[1] Assiut Univ, Dept Chem, Fac Sci, Assiut 71516, Egypt
[2] Natl Chiao Tung Univ, Dept Mat Sci & Engn, Hsinchu 300, Taiwan
关键词
ANTI-VZV NUCLEOSIDES; THIENOPYRIMIDINE DERIVATIVES; ANTIVIRAL ACTIVITY; AGENTS; THIENO; IDENTIFICATION; INHIBITORS;
D O I
10.1002/jhet.3256
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new series from thieno[2,3-d] pyrimidine derivatives have been synthesized based on 2-(ethylmercapto)-4-mercapto-6-phenyl-5-pyrimidine carbonitrile, these compounds used in the synthesis of many pyrimidothienopyrimidine derivatives and triazolo[1,5:1,6]pyrimido[4,5:4,5]thieno[2,3-d] pyrimidine derivatives. The chemical composition of these compounds was confirmed by H-1 NMR, C-13 NMR, and MS techniques. Some of the synthesized compounds were screened for their antimicrobial and anticancer agent. Compound (9b) showed strong effect on Aspergillus Fumigatus (RCMB 2568), Candida albicans (RCMB 05036), Saphylococcus aureus (RCMB 010010), Bacillissubtilis (RCMB 010067), Salmonella sp. (RCMB 010043), and Escherichia coli (RCMB 010052). Compounds (2) and (5a-k) were evaluated for their IC50 values against two cancer cell lines (MCF-7 and HeLa cells) in the presence of Paclitaxel as reference material. Compound (5g) showed the highest cytotoxicity against MCF-7 (IC50 values about 18.87 +/- 0.2g/mL) cells compared with Paclitaxel (IC50 values about 40.37 +/- 1.7g/mL). Also, compound (5d) showed the highest cytotoxicity against HeLa (IC50 values about 40.74 +/- 1.7g/mL) cells compared with Paclitaxel (IC50 values about 45.78 +/- 0.8g/mL).
引用
收藏
页码:2111 / 2122
页数:12
相关论文
共 50 条
  • [31] Synthesis and in vitro antitumor evaluation of some new thiophenes and thieno[2,3-d]pyrimidine derivatives
    Fouad, Mahasen M.
    El-Bendary, Eman R.
    Suddek, Ghada M.
    Shehata, Ihsan A.
    El-Kerdawy, Mohamed M.
    BIOORGANIC CHEMISTRY, 2018, 81 : 587 - 598
  • [32] Design, synthesis, anticancer evaluation, and in silico studies of some thieno[2,3-d]pyrimidine derivatives as EGFR inhibitors
    Sayed, Menna Tallah M.
    Halim, Peter A.
    El-Ansary, Afaf K.
    Hassan, Rasha A.
    DRUG DEVELOPMENT RESEARCH, 2023, 84 (06) : 1299 - 1319
  • [33] Iodine catalysed synthesis and antibacterial evaluation of thieno[2,3-d] pyrimidine derivatives
    Bakavoli, Mehdi
    Bagherzadeh, Ghodsieh
    Vaseghifar, Maryam
    Shiri, Ali
    Pordeli, Parvaneh
    JOURNAL OF CHEMICAL RESEARCH-S, 2009, (11): : 653 - 655
  • [34] Synthesis of polyfunctionally substituted thiophene, thieno[2,3-b]pyridine and thieno[2,3-d]pyrimidine derivatives
    Wardakhan, WW
    Shams, HZ
    Moustafa, HE
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2005, 180 (08) : 1815 - 1827
  • [35] Efficient synthesis and cytotoxic activity of polysubstituted thieno[2,3-d]pyrimidine derivatives
    Wang, Tianshuai
    Wu, Fengxu
    Luo, Lun
    Zhang, Yan
    Ma, Junkai
    Hu, Yanggen
    JOURNAL OF MOLECULAR STRUCTURE, 2022, 1256
  • [36] Facile Syntheses of Some Thieno[2,3-d]Pyrimidine Derivatives
    Aly, A. S.
    Abu-Zied, Kh. M.
    Gaafar, Alaa El-Din M.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (12) : 3063 - 3078
  • [38] Heterocyclic synthesis with nitriles: Synthesis of some new thiophene and thieno[2,3-d]pyrimidine derivatives .4.
    Abdelrazek, FM
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1996, 119 : 271 - 277
  • [39] SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME TETRAMETHYLENETHIENO[2,3-D]PYRIMIDINE DERIVATIVES
    ISMAIL, KA
    ABOULWAFA, OM
    KOREISH, EA
    FARMACO, 1995, 50 (09): : 611 - 616
  • [40] Design, synthesis, in vitro anticancer, molecular docking and SAR studies of new series of pyrrolo[2,3-d]pyrimidine derivatives
    Farid M. Sroor
    Wael M. Tohamy
    Khairy M. A. Zoheir
    Nagwa M. Abdelazeem
    Karima F. Mahrous
    Nada S. Ibrahim
    BMC Chemistry, 17