Synthesis, in vitro anticancer and antimycobacterial evaluation of new 5-(2,5-dimethoxyphenyl)-1,3,4-thiadiazole-2-amino derivatives
Design strategy for new 2,5-disubstituted-1,3,4-thiadiazole derivatives. [Display omitted] A series of 2,5-disubstituted-1,3,4-thiadiazole derivatives 5a–5l, 7a–7e and 9 have been synthesised and screened for in vitro antimycobacterial activity against Mycobacterium smegmatis MC-155. In addition the...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2015-04, Vol.25 (7), p.1398-1402 |
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| creator | Polkam, Naveen Rayam, Parsharamulu Anireddy, Jaya Shree Yennam, Satyanarayana Anantaraju, Hasitha Shilpa Dharmarajan, Sriram Perumal, Yogeeswari Kotapalli, Sudha Sravanti Ummanni, Ramesh Balasubramanian, Sridhar |
| description | Design strategy for new 2,5-disubstituted-1,3,4-thiadiazole derivatives. [Display omitted]
A series of 2,5-disubstituted-1,3,4-thiadiazole derivatives 5a–5l, 7a–7e and 9 have been synthesised and screened for in vitro antimycobacterial activity against Mycobacterium smegmatis MC-155. In addition these compounds have also been screened for cytotoxic activity against cancer cell lines HT-29, MDA-MB-231 by MTT colorimetric assay. The compounds are well characterized by spectral analysis viz. 1H NMR, 13C NMR, FT-IR, mass and HRMS. Screening results indicate that compounds 5g, 7a possess good antitubercular activity with MIC value 65.74 and 40.86, respectively, compounds 5g, 7a, 7b, 7d, 7e and 9 displayed promising cytotoxic activity against the cell lines tested. 5g and 7a stand out to be potent antimycobacterial and anticancer agents among the tested series. Further the title compounds were also tested on human normal cells HEK293T and are found to be safer with lesser cytotoxicity. It is interesting to observe that compound 5g has come out to be safer, potent anticancer and antimycobacterial agent. |
| doi_str_mv | 10.1016/j.bmcl.2015.02.052 |
| format | Article |
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A series of 2,5-disubstituted-1,3,4-thiadiazole derivatives 5a–5l, 7a–7e and 9 have been synthesised and screened for in vitro antimycobacterial activity against Mycobacterium smegmatis MC-155. In addition these compounds have also been screened for cytotoxic activity against cancer cell lines HT-29, MDA-MB-231 by MTT colorimetric assay. The compounds are well characterized by spectral analysis viz. 1H NMR, 13C NMR, FT-IR, mass and HRMS. Screening results indicate that compounds 5g, 7a possess good antitubercular activity with MIC value 65.74 and 40.86, respectively, compounds 5g, 7a, 7b, 7d, 7e and 9 displayed promising cytotoxic activity against the cell lines tested. 5g and 7a stand out to be potent antimycobacterial and anticancer agents among the tested series. Further the title compounds were also tested on human normal cells HEK293T and are found to be safer with lesser cytotoxicity. It is interesting to observe that compound 5g has come out to be safer, potent anticancer and antimycobacterial agent.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2015.02.052</identifier><identifier>PMID: 25765907</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>2,5-Disubstitued-1,3,4-thiadiazole ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Anti-mycobacterial activity ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Crystallography, X-Ray ; Cytotoxic activity ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; HEK293 Cells ; HT29 Cells ; Humans ; In vitro studies ; Microbial Sensitivity Tests ; Models, Molecular ; Molecular Structure ; MTT colorimetric assay ; Mycobacterium smegmatis - drug effects ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2015-04, Vol.25 (7), p.1398-1402</ispartof><rights>2015 Elsevier Ltd</rights><rights>Copyright © 2015 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-7491dc15b9c73973bd0ef8fd6f99fa6aa2e2dc30b153310176c755ecfa37fb053</citedby><cites>FETCH-LOGICAL-c356t-7491dc15b9c73973bd0ef8fd6f99fa6aa2e2dc30b153310176c755ecfa37fb053</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2015.02.052$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25765907$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Polkam, Naveen</creatorcontrib><creatorcontrib>Rayam, Parsharamulu</creatorcontrib><creatorcontrib>Anireddy, Jaya Shree</creatorcontrib><creatorcontrib>Yennam, Satyanarayana</creatorcontrib><creatorcontrib>Anantaraju, Hasitha Shilpa</creatorcontrib><creatorcontrib>Dharmarajan, Sriram</creatorcontrib><creatorcontrib>Perumal, Yogeeswari</creatorcontrib><creatorcontrib>Kotapalli, Sudha Sravanti</creatorcontrib><creatorcontrib>Ummanni, Ramesh</creatorcontrib><creatorcontrib>Balasubramanian, Sridhar</creatorcontrib><title>Synthesis, in vitro anticancer and antimycobacterial evaluation of new 5-(2,5-dimethoxyphenyl)-1,3,4-thiadiazole-2-amino derivatives</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Design strategy for new 2,5-disubstituted-1,3,4-thiadiazole derivatives. [Display omitted]
A series of 2,5-disubstituted-1,3,4-thiadiazole derivatives 5a–5l, 7a–7e and 9 have been synthesised and screened for in vitro antimycobacterial activity against Mycobacterium smegmatis MC-155. In addition these compounds have also been screened for cytotoxic activity against cancer cell lines HT-29, MDA-MB-231 by MTT colorimetric assay. The compounds are well characterized by spectral analysis viz. 1H NMR, 13C NMR, FT-IR, mass and HRMS. Screening results indicate that compounds 5g, 7a possess good antitubercular activity with MIC value 65.74 and 40.86, respectively, compounds 5g, 7a, 7b, 7d, 7e and 9 displayed promising cytotoxic activity against the cell lines tested. 5g and 7a stand out to be potent antimycobacterial and anticancer agents among the tested series. Further the title compounds were also tested on human normal cells HEK293T and are found to be safer with lesser cytotoxicity. It is interesting to observe that compound 5g has come out to be safer, potent anticancer and antimycobacterial agent.</description><subject>2,5-Disubstitued-1,3,4-thiadiazole</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Anti-mycobacterial activity</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Crystallography, X-Ray</subject><subject>Cytotoxic activity</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Screening Assays, Antitumor</subject><subject>HEK293 Cells</subject><subject>HT29 Cells</subject><subject>Humans</subject><subject>In vitro studies</subject><subject>Microbial Sensitivity Tests</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>MTT colorimetric assay</subject><subject>Mycobacterium smegmatis - drug effects</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE2LFDEQhoMo7rj6BzxIH1eYtPnONnhZFr9gwYMK3kI6qWYydHfGJNPanv3hZpzVo6eqgvd9oB6EnlPSUkLVq33bT25sGaGyJawlkj1AGyqUwFwQ-RBtSKcIvu7E1wv0JOc9IVQQIR6jCya1kh3RG_Tr0zqXHeSQt02YmyWUFBs7l-Ds7CDV1f85p9XF3roCKdixgcWOR1tCnJs4NDN8byS-YluJfZig7OKP9bCDeR1fYrrlW4HLLlgf7M84AmbYTmGOja-opTIWyE_Ro8GOGZ7dz0v05e2bz7fv8d3Hdx9ub-6w41IVrEVHvaOy75zmnea9JzBcD14NXTdYZS0D5h0nPZWcV0NaOS0luMFyPfRE8kt0deYeUvx2hFzMFLKDcbQzxGM2VCmlmZRC1Sg7R12KOScYzCGFyabVUGJO9s3enOybk31DmKn2a-nFPf_YT-D_Vf7qroHX5wDUL5cAyWQXoIr2IYErxsfwP_5v9tiXQA</recordid><startdate>20150401</startdate><enddate>20150401</enddate><creator>Polkam, Naveen</creator><creator>Rayam, Parsharamulu</creator><creator>Anireddy, Jaya Shree</creator><creator>Yennam, Satyanarayana</creator><creator>Anantaraju, Hasitha Shilpa</creator><creator>Dharmarajan, Sriram</creator><creator>Perumal, Yogeeswari</creator><creator>Kotapalli, Sudha Sravanti</creator><creator>Ummanni, Ramesh</creator><creator>Balasubramanian, Sridhar</creator><general>Elsevier Ltd</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20150401</creationdate><title>Synthesis, in vitro anticancer and antimycobacterial evaluation of new 5-(2,5-dimethoxyphenyl)-1,3,4-thiadiazole-2-amino derivatives</title><author>Polkam, Naveen ; Rayam, Parsharamulu ; Anireddy, Jaya Shree ; Yennam, Satyanarayana ; Anantaraju, Hasitha Shilpa ; Dharmarajan, Sriram ; Perumal, Yogeeswari ; Kotapalli, Sudha Sravanti ; Ummanni, Ramesh ; Balasubramanian, Sridhar</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-7491dc15b9c73973bd0ef8fd6f99fa6aa2e2dc30b153310176c755ecfa37fb053</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>2,5-Disubstitued-1,3,4-thiadiazole</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Anti-mycobacterial activity</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Crystallography, X-Ray</topic><topic>Cytotoxic activity</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Screening Assays, Antitumor</topic><topic>HEK293 Cells</topic><topic>HT29 Cells</topic><topic>Humans</topic><topic>In vitro studies</topic><topic>Microbial Sensitivity Tests</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>MTT colorimetric assay</topic><topic>Mycobacterium smegmatis - drug effects</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Polkam, Naveen</creatorcontrib><creatorcontrib>Rayam, Parsharamulu</creatorcontrib><creatorcontrib>Anireddy, Jaya Shree</creatorcontrib><creatorcontrib>Yennam, Satyanarayana</creatorcontrib><creatorcontrib>Anantaraju, Hasitha Shilpa</creatorcontrib><creatorcontrib>Dharmarajan, Sriram</creatorcontrib><creatorcontrib>Perumal, Yogeeswari</creatorcontrib><creatorcontrib>Kotapalli, Sudha Sravanti</creatorcontrib><creatorcontrib>Ummanni, Ramesh</creatorcontrib><creatorcontrib>Balasubramanian, Sridhar</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Polkam, Naveen</au><au>Rayam, Parsharamulu</au><au>Anireddy, Jaya Shree</au><au>Yennam, Satyanarayana</au><au>Anantaraju, Hasitha Shilpa</au><au>Dharmarajan, Sriram</au><au>Perumal, Yogeeswari</au><au>Kotapalli, Sudha Sravanti</au><au>Ummanni, Ramesh</au><au>Balasubramanian, Sridhar</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, in vitro anticancer and antimycobacterial evaluation of new 5-(2,5-dimethoxyphenyl)-1,3,4-thiadiazole-2-amino derivatives</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2015-04-01</date><risdate>2015</risdate><volume>25</volume><issue>7</issue><spage>1398</spage><epage>1402</epage><pages>1398-1402</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Design strategy for new 2,5-disubstituted-1,3,4-thiadiazole derivatives. [Display omitted]
A series of 2,5-disubstituted-1,3,4-thiadiazole derivatives 5a–5l, 7a–7e and 9 have been synthesised and screened for in vitro antimycobacterial activity against Mycobacterium smegmatis MC-155. In addition these compounds have also been screened for cytotoxic activity against cancer cell lines HT-29, MDA-MB-231 by MTT colorimetric assay. The compounds are well characterized by spectral analysis viz. 1H NMR, 13C NMR, FT-IR, mass and HRMS. Screening results indicate that compounds 5g, 7a possess good antitubercular activity with MIC value 65.74 and 40.86, respectively, compounds 5g, 7a, 7b, 7d, 7e and 9 displayed promising cytotoxic activity against the cell lines tested. 5g and 7a stand out to be potent antimycobacterial and anticancer agents among the tested series. Further the title compounds were also tested on human normal cells HEK293T and are found to be safer with lesser cytotoxicity. It is interesting to observe that compound 5g has come out to be safer, potent anticancer and antimycobacterial agent.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>25765907</pmid><doi>10.1016/j.bmcl.2015.02.052</doi><tpages>5</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2015-04, Vol.25 (7), p.1398-1402 |
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| subjects | 2,5-Disubstitued-1,3,4-thiadiazole Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Anti-mycobacterial activity Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Cell Line, Tumor Cell Proliferation - drug effects Crystallography, X-Ray Cytotoxic activity Dose-Response Relationship, Drug Drug Screening Assays, Antitumor HEK293 Cells HT29 Cells Humans In vitro studies Microbial Sensitivity Tests Models, Molecular Molecular Structure MTT colorimetric assay Mycobacterium smegmatis - drug effects Structure-Activity Relationship |
| title | Synthesis, in vitro anticancer and antimycobacterial evaluation of new 5-(2,5-dimethoxyphenyl)-1,3,4-thiadiazole-2-amino derivatives |
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