Synthesis and Cytotoxic Activity of New 1,3,4-Thiadiazole Thioglycosides and 1,2,3-Triazolyl-1,3,4-Thiadiazole N-glycosides

被引:47
作者
Alminderej, Fahad M. [1 ]
Elganzory, Hussein H. [1 ]
El-Bayaa, Mohamed N. [2 ]
Awad, Hanem M. [3 ]
El-Sayed, Wael A. [1 ,2 ]
机构
[1] Qassim Univ, Chem Dept, Coll Sci, Buraydah 51452, Saudi Arabia
[2] Natl Res Ctr, Photochem Dept, Cairo 12311, Egypt
[3] Natl Res Ctr, Tanning Mat & Leather Technol Dept, El Behouth St, Cairo 12311, Egypt
关键词
click chemistry; 1; 3; 4-thiadiazoles; 2; 3-triazoles; glycosides; cytotoxic; HCT-116; MCF-7; ANTICANCER ACTIVITY; CLICK CHEMISTRY; ANTIMICROBIAL ACTIVITY; ANTIVIRAL EVALUATION; NUCLEOSIDE; DERIVATIVES; 1,3,4-OXADIAZOLE; 1,2,3-TRIAZOLES; ANALOGS;
D O I
10.3390/molecules24203738
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
070307 [化学生物学]; 071010 [生物化学与分子生物学];
摘要
New 1,3,4-thiadiazole thioglycosides linked to substituted arylidine systems were synthesized via glycosylation of the prepared 1,3,4-thiadiazole thiol compounds. Click strategy was also used for the synthesis of new 1,3,4-thiadiazole and 1,2,3-triazole hybrid glycosides by reaction of the acetylenic derivatives with different glycosyl azids followed by deacetylation process. The cytotoxic activities of the prepared compounds were studied against HCT-116 (human colorectal carcinoma) and MCF-7 (human breast adenocarcinoma) cell lines using the MTT assay. The results showed that the key thiadiazolethione compounds 2 and 3, the triazole glycosides linked to p-methoxyarylidine derivatives 14 and 15 in addition to the free hydroxyl glycoside 20 were found potent in activity comparable to the reference drug doxorubicin against MCF-7 human cancer cells. The acetylenic derivative 2 and glycoside 20 were also found highly active against HCT-116 cell lines.
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页数:14
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