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Synthesis of Some Novel Thiazole, Thiadiazole and 1,4-phenylene-bis-thiazole Derivatives as Potent Antitumor Agents
| Content Provider | Semantic Scholar |
|---|---|
| Author | Gomha, Sobhi M. Abdelrazek, Fathy Mohamed Abdelrahman, Aly H. Metz, Peter |
| Copyright Year | 2016 |
| Abstract | A novel series of 2-ethylidenehydrazono-5-arylazothiazoles 5a-h and 2-ethylidenehydrazono-5-arylazothiazolones 9a-d were prepared by cyclocondensation of hydrazonyl halides 3a-h and 7a-d with ethylidenethiosemicarbazide 2. In addition, reaction of 2 with N-phenylcarbohydrazonyl chloride (14), afforded 1,3,4-thiadiazole derivative 17 as the end product. Moreover, the thiosemicarbazide derivative 2 was reacted with various bromoacetyl compounds 19a-d and 1,1'-(1,4-phenylene)bis(2-bromoethanone) (21) furnished the respective thiazole derivatives 20a-d and 1,4-phenylene-bisthiazole derivative 22. The structures of the newly synthesized compounds were established on the basis of spectroscopic evidences and their alternative syntheses. The newly synthesized compounds were evaluated for their antitumor activities against hepatocellular carcinoma (HepG2) cell line and the results revealed promising activities of compounds 5h, 5d, 5g, 5f and 5e with IC50 equal 2.23 ± 0.28, 2.48 ± 0.34, 2.49 ± 0.24, 4.03 ± 0.11, and 5.32 ± 0.27 μM, respectively. Functionalized thiazole derivatives have received much attention due to their diverse biological activities such as antimicrobial,1 antiviral,2 cytotoxic and antitumor,3-6 and HIV-protease inhibitory agents.7 Compounds incorporating two thiazole rings either directly connected as in bisthiazoles or through a linker unit as in bisthiazolyl compounds, show pronounced biological activity as DNA replication inhibitors in the tumor cells8 and HIV-protease inhibitors.7-9 Pyridine deivatives also play a key role catalyzing both biological and chemical systems. In many enzymes of living organisms it is the prosthetic pyridine nucleotide (NADP) that is involved in various 954 HETEROCYCLES, Vol. 92, No. 5, 2016 |
| Starting Page | 954 |
| Ending Page | 967 |
| Page Count | 14 |
| File Format | PDF HTM / HTML |
| DOI | 10.3987/COM-16-13443 |
| Volume Number | 92 |
| Alternate Webpage(s) | https://scholar.cu.edu.eg/sites/default/files/photo/files/heterocycles.pdf |
| Alternate Webpage(s) | https://doi.org/10.3987/COM-16-13443 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
