Synthesis and anticancer activity of long chain substituted 1,3,4-oxadiazol-2-thione, 1,2,4-triazol-3-thione and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives
In this paper, three novel series of 5-long chain alkenyl/hydorxyalkenyl-1,3,4-oxadiazol-2-thiones 2(a–d), 4-amino-5-long chain alkenyl/hydroxyalkenyl-1,2,4-triazol-3-thiones 3(a–d) and 3-long chain alkenyl/hydroxyalkenyl-6-phenyl-(7H)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines 4(a–d) were synthesized...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2017-05-01
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| Series: | Arabian Journal of Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535214000185 |
| _version_ | 1818193925961154560 |
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| author | Aiman Ahmad Himani Varshney Abdul Rauf Asif Sherwani Mohammad Owais |
| author_facet | Aiman Ahmad Himani Varshney Abdul Rauf Asif Sherwani Mohammad Owais |
| author_sort | Aiman Ahmad |
| collection | DOAJ |
| description | In this paper, three novel series of 5-long chain alkenyl/hydorxyalkenyl-1,3,4-oxadiazol-2-thiones 2(a–d), 4-amino-5-long chain alkenyl/hydroxyalkenyl-1,2,4-triazol-3-thiones 3(a–d) and 3-long chain alkenyl/hydroxyalkenyl-6-phenyl-(7H)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines 4(a–d) were synthesized with an aim to produce promising anticancer agents. We describe here the synthesis of compounds 2(a–d), 3(a–d) and 4(a–d) using long chain alkenyl/hydroxyalkenyl hydrazides 1(a–d) as starting material. Our investigation shows that the thione tautomer of 2(a–d) and 3(a–d) dominates. All the synthesized compounds were characterized by IR, 1H NMR, 13C NMR and mass spectral data. After characterization, all compounds were tested for in vitro anticancer activity against PBMCs and three different human cancer cell lines. On the basis of SAR, it may be concluded that the potency of drugs depends on the nature of FA chain and the heterocyclic ring system. Among all the tested compounds, compounds having fused ring system (triazolothiadiazine nucleus) and the hydroxyl group attached to the FA chain (4c and 4d) were found to be the most promising anticancer agents. |
| first_indexed | 2024-12-12T00:54:09Z |
| format | Article |
| id | doaj.art-4bebc9fbc1c8477482eb3838480d499d |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-12T00:54:09Z |
| publishDate | 2017-05-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-4bebc9fbc1c8477482eb3838480d499d2022-12-22T00:43:56ZengElsevierArabian Journal of Chemistry1878-53522017-05-0110S2S3347S335710.1016/j.arabjc.2014.01.015Synthesis and anticancer activity of long chain substituted 1,3,4-oxadiazol-2-thione, 1,2,4-triazol-3-thione and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivativesAiman Ahmad0Himani Varshney1Abdul Rauf2Asif Sherwani3Mohammad Owais4Department of Chemistry, Aligarh Muslim University, Aligarh 202 002, IndiaDepartment of Chemistry, Aligarh Muslim University, Aligarh 202 002, IndiaDepartment of Chemistry, Aligarh Muslim University, Aligarh 202 002, IndiaInterdisciplinary Biotechnology Unit, Aligarh Muslim University, Aligarh 202 002, IndiaInterdisciplinary Biotechnology Unit, Aligarh Muslim University, Aligarh 202 002, IndiaIn this paper, three novel series of 5-long chain alkenyl/hydorxyalkenyl-1,3,4-oxadiazol-2-thiones 2(a–d), 4-amino-5-long chain alkenyl/hydroxyalkenyl-1,2,4-triazol-3-thiones 3(a–d) and 3-long chain alkenyl/hydroxyalkenyl-6-phenyl-(7H)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines 4(a–d) were synthesized with an aim to produce promising anticancer agents. We describe here the synthesis of compounds 2(a–d), 3(a–d) and 4(a–d) using long chain alkenyl/hydroxyalkenyl hydrazides 1(a–d) as starting material. Our investigation shows that the thione tautomer of 2(a–d) and 3(a–d) dominates. All the synthesized compounds were characterized by IR, 1H NMR, 13C NMR and mass spectral data. After characterization, all compounds were tested for in vitro anticancer activity against PBMCs and three different human cancer cell lines. On the basis of SAR, it may be concluded that the potency of drugs depends on the nature of FA chain and the heterocyclic ring system. Among all the tested compounds, compounds having fused ring system (triazolothiadiazine nucleus) and the hydroxyl group attached to the FA chain (4c and 4d) were found to be the most promising anticancer agents.http://www.sciencedirect.com/science/article/pii/S1878535214000185Novel heterocyclic FAsMTT assayAnticancer agentsStructure–activity relationship |
| spellingShingle | Aiman Ahmad Himani Varshney Abdul Rauf Asif Sherwani Mohammad Owais Synthesis and anticancer activity of long chain substituted 1,3,4-oxadiazol-2-thione, 1,2,4-triazol-3-thione and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives Arabian Journal of Chemistry Novel heterocyclic FAs MTT assay Anticancer agents Structure–activity relationship |
| title | Synthesis and anticancer activity of long chain substituted 1,3,4-oxadiazol-2-thione, 1,2,4-triazol-3-thione and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives |
| title_full | Synthesis and anticancer activity of long chain substituted 1,3,4-oxadiazol-2-thione, 1,2,4-triazol-3-thione and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives |
| title_fullStr | Synthesis and anticancer activity of long chain substituted 1,3,4-oxadiazol-2-thione, 1,2,4-triazol-3-thione and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives |
| title_full_unstemmed | Synthesis and anticancer activity of long chain substituted 1,3,4-oxadiazol-2-thione, 1,2,4-triazol-3-thione and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives |
| title_short | Synthesis and anticancer activity of long chain substituted 1,3,4-oxadiazol-2-thione, 1,2,4-triazol-3-thione and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives |
| title_sort | synthesis and anticancer activity of long chain substituted 1 3 4 oxadiazol 2 thione 1 2 4 triazol 3 thione and 1 2 4 triazolo 3 4 b 1 3 4 thiadiazine derivatives |
| topic | Novel heterocyclic FAs MTT assay Anticancer agents Structure–activity relationship |
| url | http://www.sciencedirect.com/science/article/pii/S1878535214000185 |
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