3-(4-chlorophenyl)-[1, 2, 3] oxadiazol-3-ium-5-olate and its 4-formyl analog-Ultrasound assisted synthesis and in-vitro anticancer evaluation against human tumor cell lines
The title compound, 3-(4-chlorophenyl)-4-formyl-[1, 2, 3] oxadiazol-3-ium-5-olate 5 was synthesized under ultrasonication by formylation of 3-(4-chlorophenyl)-[1, 2, 3] oxadiazol-3-ium-5-olate 4 and characterized by spectral studies. The ultrasonic method of synthesis was found to be simple, ecofrie...
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| Veröffentlicht in: | Pakistan journal of pharmaceutical sciences 2017-03, Vol.30 (2), p.513-520 |
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| creator | Bhosale, Sachin K Deshpande, Shreenivas R Wagh, Rajendra D |
| description | The title compound, 3-(4-chlorophenyl)-4-formyl-[1, 2, 3] oxadiazol-3-ium-5-olate 5 was synthesized under ultrasonication by formylation of 3-(4-chlorophenyl)-[1, 2, 3] oxadiazol-3-ium-5-olate 4 and characterized by spectral studies. The ultrasonic method of synthesis was found to be simple, ecofriendly, economical, reduces reaction time and gave good yield when compared with traditional methods of synthesis. Anticancer activity of the compounds were tested against 60 human tumor cell lines and compared with standard drug vincristine sulphate. Compound 5 was found to be active against CNS (SNB-75, %GI=46.71), renal (UO-31, %GI=31.52), non small cell lung (NCI-H522, %GI=25.65), leukemia (MOLT-4, %GI=23.02) human tumor cell lines whereas, compound 4 against breast (MDA-MB-231/ATCC, %GI=19.90, T-47D %GI=16.50, MCF-7 15.10) and ovarian (IGROV1 %GI=19.30, OVCAR-4 %GI=17.90) human tumor cell lines. Compound 5 showed higher cytotoxicity against NCI-H23 cells (non small lung cancer cell panel) as compared to standard drug vincristine sulphate. Further structural modification of these compounds may lead to potent anticancer activity. |
| format | Article |
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The ultrasonic method of synthesis was found to be simple, ecofriendly, economical, reduces reaction time and gave good yield when compared with traditional methods of synthesis. Anticancer activity of the compounds were tested against 60 human tumor cell lines and compared with standard drug vincristine sulphate. Compound 5 was found to be active against CNS (SNB-75, %GI=46.71), renal (UO-31, %GI=31.52), non small cell lung (NCI-H522, %GI=25.65), leukemia (MOLT-4, %GI=23.02) human tumor cell lines whereas, compound 4 against breast (MDA-MB-231/ATCC, %GI=19.90, T-47D %GI=16.50, MCF-7 15.10) and ovarian (IGROV1 %GI=19.30, OVCAR-4 %GI=17.90) human tumor cell lines. Compound 5 showed higher cytotoxicity against NCI-H23 cells (non small lung cancer cell panel) as compared to standard drug vincristine sulphate. Further structural modification of these compounds may lead to potent anticancer activity.</description><identifier>ISSN: 1011-601X</identifier><identifier>PMID: 28649078</identifier><language>eng</language><publisher>Pakistan: Pakistan Journal of Pharmaceutical Sciences</publisher><subject>Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - pharmacology ; Cancer treatment ; Cell Line, Tumor ; Chemistry Techniques, Synthetic - methods ; Drug Screening Assays, Antitumor ; Health aspects ; Heterocyclic compounds ; Humans ; Methods ; Structure-activity relationships (Pharmacology) ; Ultrasonics</subject><ispartof>Pakistan journal of pharmaceutical sciences, 2017-03, Vol.30 (2), p.513-520</ispartof><rights>COPYRIGHT 2017 Pakistan Journal of Pharmaceutical Sciences</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28649078$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bhosale, Sachin K</creatorcontrib><creatorcontrib>Deshpande, Shreenivas R</creatorcontrib><creatorcontrib>Wagh, Rajendra D</creatorcontrib><title>3-(4-chlorophenyl)-[1, 2, 3] oxadiazol-3-ium-5-olate and its 4-formyl analog-Ultrasound assisted synthesis and in-vitro anticancer evaluation against human tumor cell lines</title><title>Pakistan journal of pharmaceutical sciences</title><addtitle>Pak J Pharm Sci</addtitle><description>The title compound, 3-(4-chlorophenyl)-4-formyl-[1, 2, 3] oxadiazol-3-ium-5-olate 5 was synthesized under ultrasonication by formylation of 3-(4-chlorophenyl)-[1, 2, 3] oxadiazol-3-ium-5-olate 4 and characterized by spectral studies. The ultrasonic method of synthesis was found to be simple, ecofriendly, economical, reduces reaction time and gave good yield when compared with traditional methods of synthesis. Anticancer activity of the compounds were tested against 60 human tumor cell lines and compared with standard drug vincristine sulphate. Compound 5 was found to be active against CNS (SNB-75, %GI=46.71), renal (UO-31, %GI=31.52), non small cell lung (NCI-H522, %GI=25.65), leukemia (MOLT-4, %GI=23.02) human tumor cell lines whereas, compound 4 against breast (MDA-MB-231/ATCC, %GI=19.90, T-47D %GI=16.50, MCF-7 15.10) and ovarian (IGROV1 %GI=19.30, OVCAR-4 %GI=17.90) human tumor cell lines. Compound 5 showed higher cytotoxicity against NCI-H23 cells (non small lung cancer cell panel) as compared to standard drug vincristine sulphate. Further structural modification of these compounds may lead to potent anticancer activity.</description><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Cancer treatment</subject><subject>Cell Line, Tumor</subject><subject>Chemistry Techniques, Synthetic - methods</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Health aspects</subject><subject>Heterocyclic compounds</subject><subject>Humans</subject><subject>Methods</subject><subject>Structure-activity relationships (Pharmacology)</subject><subject>Ultrasonics</subject><issn>1011-601X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc1KHEEQx-eQoGbNK4QGLwrboT9nZ44iMQaEXBSEEIayu2a3Q0_32t0j2TyTD2nLmoMgdaiv378oqj40R5xxTlvG7w6bTzn_YaxVfd8fNIeiqxFbdUfNk6SnipqNjyluNxh2_oz-4ksilkT-JvEvWAf_oqeSunmimkYPBQkES1zJRNExpmnnawF8XNNbXxLkONc25OxyQUvyLpQN1mSvCvTRlRRrUpyBYDARfAQ_Q3ExEFiDC7mQzTxBIGWeYiIGvSfeBczHzccRfMbPr37R3F5-u7m4otc_v_-4OL-ma7HqChVWWW5Gy5gU9wBa695Yy0yre6kk7zoYdYu8k9qibluNqmstRxAKLFpt5aI53c_dpvgwYy7D5PLLGhAwznngPZedFK1QFT3Zo2vwOLgwxnoB84IP56pXSqyEYJX6-g5VzeLkTAw4ulp_I_jyusF8P6EdtslNkHbD_8fJZzOSk9Y</recordid><startdate>201703</startdate><enddate>201703</enddate><creator>Bhosale, Sachin K</creator><creator>Deshpande, Shreenivas R</creator><creator>Wagh, Rajendra D</creator><general>Pakistan Journal of Pharmaceutical Sciences</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>201703</creationdate><title>3-(4-chlorophenyl)-[1, 2, 3] oxadiazol-3-ium-5-olate and its 4-formyl analog-Ultrasound assisted synthesis and in-vitro anticancer evaluation against human tumor cell lines</title><author>Bhosale, Sachin K ; Deshpande, Shreenivas R ; Wagh, Rajendra D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-g278t-2d4d1cfd0032baa5559cdd0c659343188af56e1835de5665e486d1ea24aded5d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Cancer treatment</topic><topic>Cell Line, Tumor</topic><topic>Chemistry Techniques, Synthetic - methods</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Health aspects</topic><topic>Heterocyclic compounds</topic><topic>Humans</topic><topic>Methods</topic><topic>Structure-activity relationships (Pharmacology)</topic><topic>Ultrasonics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bhosale, Sachin K</creatorcontrib><creatorcontrib>Deshpande, Shreenivas R</creatorcontrib><creatorcontrib>Wagh, Rajendra D</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Pakistan journal of pharmaceutical sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bhosale, Sachin K</au><au>Deshpande, Shreenivas R</au><au>Wagh, Rajendra D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>3-(4-chlorophenyl)-[1, 2, 3] oxadiazol-3-ium-5-olate and its 4-formyl analog-Ultrasound assisted synthesis and in-vitro anticancer evaluation against human tumor cell lines</atitle><jtitle>Pakistan journal of pharmaceutical sciences</jtitle><addtitle>Pak J Pharm Sci</addtitle><date>2017-03</date><risdate>2017</risdate><volume>30</volume><issue>2</issue><spage>513</spage><epage>520</epage><pages>513-520</pages><issn>1011-601X</issn><abstract>The title compound, 3-(4-chlorophenyl)-4-formyl-[1, 2, 3] oxadiazol-3-ium-5-olate 5 was synthesized under ultrasonication by formylation of 3-(4-chlorophenyl)-[1, 2, 3] oxadiazol-3-ium-5-olate 4 and characterized by spectral studies. The ultrasonic method of synthesis was found to be simple, ecofriendly, economical, reduces reaction time and gave good yield when compared with traditional methods of synthesis. Anticancer activity of the compounds were tested against 60 human tumor cell lines and compared with standard drug vincristine sulphate. Compound 5 was found to be active against CNS (SNB-75, %GI=46.71), renal (UO-31, %GI=31.52), non small cell lung (NCI-H522, %GI=25.65), leukemia (MOLT-4, %GI=23.02) human tumor cell lines whereas, compound 4 against breast (MDA-MB-231/ATCC, %GI=19.90, T-47D %GI=16.50, MCF-7 15.10) and ovarian (IGROV1 %GI=19.30, OVCAR-4 %GI=17.90) human tumor cell lines. Compound 5 showed higher cytotoxicity against NCI-H23 cells (non small lung cancer cell panel) as compared to standard drug vincristine sulphate. Further structural modification of these compounds may lead to potent anticancer activity.</abstract><cop>Pakistan</cop><pub>Pakistan Journal of Pharmaceutical Sciences</pub><pmid>28649078</pmid><tpages>8</tpages></addata></record> |
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| ispartof | Pakistan journal of pharmaceutical sciences, 2017-03, Vol.30 (2), p.513-520 |
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| subjects | Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Cancer treatment Cell Line, Tumor Chemistry Techniques, Synthetic - methods Drug Screening Assays, Antitumor Health aspects Heterocyclic compounds Humans Methods Structure-activity relationships (Pharmacology) Ultrasonics |
| title | 3-(4-chlorophenyl)-[1, 2, 3] oxadiazol-3-ium-5-olate and its 4-formyl analog-Ultrasound assisted synthesis and in-vitro anticancer evaluation against human tumor cell lines |
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