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
  • [21] Synthesis and Antimicrobial Activities of Some Novel Pyrido[2,3-d]pyrimidine Derivatives
    Behalo, M. S.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2009, 184 (01) : 206 - 219
  • [22] Synthesis of thieno[2,3-d] pyrimidine and quinazoline derivatives from monothiooxamides
    Zavarzin, IV
    Smirnova, NG
    Chernoburova, EI
    Yarovenko, VN
    Krayushkin, MM
    RUSSIAN CHEMICAL BULLETIN, 2004, 53 (06) : 1257 - 1260
  • [23] Synthesis of thieno[2,3-d]pyrimidine and quinazoline derivatives from monothiooxamides
    I. V. Zavarzin
    N. G. Smirnova
    E. I. Chernoburova
    V. N. Yarovenko
    M. M. Krayushkin
    Russian Chemical Bulletin, 2004, 53 : 1257 - 1260
  • [24] SYNTHESIS OF THIENO[2,3-D]PYRIMIDINE DERIVATIVES AND THEIR FLUORESCENT AND BIOLOGICAL PROPERTIES
    SABNIS, RW
    RANGNEKAR, DW
    INDIAN JOURNAL OF TECHNOLOGY, 1990, 28 (02): : 54 - 58
  • [25] The utility of isothiocyanato thiophenes in the synthesis of thieno[2,3-d]pyrimidine derivatives as possible radioprotective and anticancer agents
    Ghorab, M. M.
    Osman, A. N.
    Noaman, E.
    Heiba, H. I.
    Zaher, N. H.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2006, 181 (09) : 1983 - 1996
  • [26] Erratum to: Synthesis and Anticancer Activity of Functionalized Thieno[2,3-d]pyrimidine Compounds and Their Triazinyl and Tetrazinyl Derivatives
    Walaa I. El-Sofany
    Dalia Ahmed A. Osman
    Asma M. Mahran
    El-Manawaty A. May
    Wael A. El-Sayed
    Russian Journal of Bioorganic Chemistry, 2020, 46 : 873 - 873
  • [27] SYNTHESIS OF NOVEL THIENO[2,3-D]PYRIMIDINE, THIENO[2,3-B]PYRIDINE AND THIAZOLO[3,2-A]THIENO[2,3-D]PYRIMIDINE DERIVATIVES AND THEIR EFFECT ON THE PRODUCTION OF MYCOTOXINS
    ABDELRAZEK, FM
    SALAH, AM
    ELBAZZA, ZE
    ARCHIV DER PHARMAZIE, 1992, 325 (05) : 301 - 305
  • [28] Synthesis and anticancer activities of diverse furo[2,3-d]pyrimidine and benzofuro[3,2-d]pyrimidine derivatives
    Tang, Xiaoyu
    Zheng, Aihua
    Wu, Fengxu
    Liao, Chujie
    Hu, Yanggen
    Luo, Chao
    SYNTHETIC COMMUNICATIONS, 2022, 52 (07) : 994 - 1003
  • [29] HETEROCYCLIC SYNTHESIS WITH NITRILES - A NEW APPROACH TO THIOPHENE AND THIENO-[2,3-D]-PYRIMIDINE DERIVATIVES
    ABDELRAZEK, FM
    EAD, HA
    JOURNAL FUR PRAKTISCHE CHEMIE, 1988, 330 (04): : 585 - 589
  • [30] Synthesis and antifolate activity of new pyrrolo[2,3-d]pyrimidine and thieno[2,3-d]pyrimidine inhibitors of dihydrofolate reductase
    Vaidya, C
    Wright, JE
    Rosowsky, A
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2004, 41 (05) : 787 - 793