Chemoenzymatic synthesis with lipase catalyzed resolution and evaluation of antitumor activity of (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one
Synthesis, characterization, resolution and evaluation of novel (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one derivatives are described. Enantiomerically pure compounds were isolated in good to excellent yield with high enantiomeric excess under mild reacti...
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| Veröffentlicht in: | European journal of medicinal chemistry 2011-06, Vol.46 (6), p.2152-2156 |
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| creator | Nagarapu, Lingaiah Gaikwad, Hanmant K. Bantu, Rajashaker Manikonda, Sheeba Rani |
| description | Synthesis, characterization, resolution and evaluation of novel (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one derivatives are described. Enantiomerically pure compounds were isolated in good to excellent yield with high enantiomeric excess under mild reaction conditions by using Candida antarctica B (CAL-B) and Candida rugosa (CRL) Lipases. Newly synthesized and resolved compounds were screened for their antitumor activity against cancer cells such as human neuroblastoma SK–N–SH and human lung carcinoma A549 cell line in vitro. The results have shown that the compound 1 S-(−) alcohol was more effective in inhibiting the tumor cell growth.
Synthesis and resolution of (±)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3, 4-b]quinolin-3(2H)-one (1) in good to excellent yield. Newly isolated compounds were evaluated for their antitumor activity against the human cancer cell lines. [Display omitted]
► Synthesized and characterized the novel derivatives of (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl) propyl]-1H-pyrrolo [3,4-b] quinolin-3(2H)-one in good to excellent yields. ► Synthesized racemic derivatives were resolved by using Candida antarctica B (CAL-B) and Candida rugosa (CRL) Lipases. ► All newly synthesized and resolved isomers were evaluated for their antitumor activity against cancer cells such as human neuroblastoma SK–N–SH and human lung carcinoma A549 cell lines. ► The results have shown that the compound 1 S-(−) alcohol was more effective in inhibiting the tumor cell growth. |
| doi_str_mv | 10.1016/j.ejmech.2011.02.069 |
| format | Article |
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Synthesis and resolution of (±)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3, 4-b]quinolin-3(2H)-one (1) in good to excellent yield. Newly isolated compounds were evaluated for their antitumor activity against the human cancer cell lines. [Display omitted]
► Synthesized and characterized the novel derivatives of (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl) propyl]-1H-pyrrolo [3,4-b] quinolin-3(2H)-one in good to excellent yields. ► Synthesized racemic derivatives were resolved by using Candida antarctica B (CAL-B) and Candida rugosa (CRL) Lipases. ► All newly synthesized and resolved isomers were evaluated for their antitumor activity against cancer cells such as human neuroblastoma SK–N–SH and human lung carcinoma A549 cell lines. ► The results have shown that the compound 1 S-(−) alcohol was more effective in inhibiting the tumor cell growth.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2011.02.069</identifier><identifier>PMID: 21440337</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Kidlington: Elsevier Masson SAS</publisher><subject>Antineoplastic agents ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - metabolism ; Antineoplastic Agents - pharmacology ; Biocatalysis ; Biological and medical sciences ; Candida - enzymology ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Cytotoxicity ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; General aspects ; Humans ; Lipase ; Lipase - metabolism ; Lung carcinoma A549 cell line ; Medical sciences ; Molecular Structure ; Neuroblastoma cell line (SK–N–SH) ; Pharmacology. Drug treatments ; Piperazines - chemistry ; Piperazines - metabolism ; Piperazines - pharmacology ; Quinolines - chemistry ; Quinolines - metabolism ; Quinolines - pharmacology ; Stereoisomerism ; Structure-Activity Relationship</subject><ispartof>European journal of medicinal chemistry, 2011-06, Vol.46 (6), p.2152-2156</ispartof><rights>2011 Elsevier Masson SAS</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c391t-214020251b02e3d570f3d164a94cfd01fdc1759547fafb4e4d6c60ec1daf60843</citedby><cites>FETCH-LOGICAL-c391t-214020251b02e3d570f3d164a94cfd01fdc1759547fafb4e4d6c60ec1daf60843</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0223523411001978$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24170597$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21440337$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nagarapu, Lingaiah</creatorcontrib><creatorcontrib>Gaikwad, Hanmant K.</creatorcontrib><creatorcontrib>Bantu, Rajashaker</creatorcontrib><creatorcontrib>Manikonda, Sheeba Rani</creatorcontrib><title>Chemoenzymatic synthesis with lipase catalyzed resolution and evaluation of antitumor activity of (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>Synthesis, characterization, resolution and evaluation of novel (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one derivatives are described. Enantiomerically pure compounds were isolated in good to excellent yield with high enantiomeric excess under mild reaction conditions by using Candida antarctica B (CAL-B) and Candida rugosa (CRL) Lipases. Newly synthesized and resolved compounds were screened for their antitumor activity against cancer cells such as human neuroblastoma SK–N–SH and human lung carcinoma A549 cell line in vitro. The results have shown that the compound 1 S-(−) alcohol was more effective in inhibiting the tumor cell growth.
Synthesis and resolution of (±)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3, 4-b]quinolin-3(2H)-one (1) in good to excellent yield. Newly isolated compounds were evaluated for their antitumor activity against the human cancer cell lines. [Display omitted]
► Synthesized and characterized the novel derivatives of (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl) propyl]-1H-pyrrolo [3,4-b] quinolin-3(2H)-one in good to excellent yields. ► Synthesized racemic derivatives were resolved by using Candida antarctica B (CAL-B) and Candida rugosa (CRL) Lipases. ► All newly synthesized and resolved isomers were evaluated for their antitumor activity against cancer cells such as human neuroblastoma SK–N–SH and human lung carcinoma A549 cell lines. ► The results have shown that the compound 1 S-(−) alcohol was more effective in inhibiting the tumor cell growth.</description><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - metabolism</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biocatalysis</subject><subject>Biological and medical sciences</subject><subject>Candida - enzymology</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Cytotoxicity</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General aspects</subject><subject>Humans</subject><subject>Lipase</subject><subject>Lipase - metabolism</subject><subject>Lung carcinoma A549 cell line</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Neuroblastoma cell line (SK–N–SH)</subject><subject>Pharmacology. Drug treatments</subject><subject>Piperazines - chemistry</subject><subject>Piperazines - metabolism</subject><subject>Piperazines - pharmacology</subject><subject>Quinolines - chemistry</subject><subject>Quinolines - metabolism</subject><subject>Quinolines - pharmacology</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kV2LEzEUhgdR3HX1H4jMjdiC6eZrZtobQYpaYUHw42pZQpqcYVIyyWySqaY_zV_n1Fa98yqcw_OenOQpiucELwgm9fVuAbseVLegmJAFpgtcrx4Ul6Spl4jRij8sLjGlDFWU8YviSYw7jHFVY_y4uKCEc8xYc1n8XHfQe3CH3MtkVBmzSx1EE8vvJnWlNYOMUCqZpM0H0GWA6O2YjHeldLqEvbSj_F36duokk8beh1KqZPYm5WN39vn6yxxRdEtRl3XwPzJiaMbR0IHLdjADBHkwDhGU7XwIfsj2DpENGnII3vpb9pqj7d39aJy3E8ZmdDNH3sHT4lErbYRn5_Oq-Pb-3df1Bt18-vBx_fYGKbYiCU1vxRTTimwxBaarBrdMk5rLFVetxqTVijTVquJNK9stB65rVWNQRMu2xkvOropXp7nTbvcjxCR6ExVYKx34MYplzZvmmJ9IfiJV8DEGaMUQTC9DFgSLozSxEydp4ihNYComaVPsxfmCcduD_hv6Y2kCXp4BGZW0bZBOmfiP46TB1erIvTlxMH3H3kAQURlwCrQJoJLQ3vx_k1-Rf7kJ</recordid><startdate>20110601</startdate><enddate>20110601</enddate><creator>Nagarapu, Lingaiah</creator><creator>Gaikwad, Hanmant K.</creator><creator>Bantu, Rajashaker</creator><creator>Manikonda, Sheeba Rani</creator><general>Elsevier Masson SAS</general><general>Elsevier</general><scope>IQODW</scope><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>20110601</creationdate><title>Chemoenzymatic synthesis with lipase catalyzed resolution and evaluation of antitumor activity of (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one</title><author>Nagarapu, Lingaiah ; Gaikwad, Hanmant K. ; Bantu, Rajashaker ; Manikonda, Sheeba Rani</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c391t-214020251b02e3d570f3d164a94cfd01fdc1759547fafb4e4d6c60ec1daf60843</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - metabolism</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biocatalysis</topic><topic>Biological and medical sciences</topic><topic>Candida - enzymology</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Cytotoxicity</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General aspects</topic><topic>Humans</topic><topic>Lipase</topic><topic>Lipase - metabolism</topic><topic>Lung carcinoma A549 cell line</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Neuroblastoma cell line (SK–N–SH)</topic><topic>Pharmacology. Drug treatments</topic><topic>Piperazines - chemistry</topic><topic>Piperazines - metabolism</topic><topic>Piperazines - pharmacology</topic><topic>Quinolines - chemistry</topic><topic>Quinolines - metabolism</topic><topic>Quinolines - pharmacology</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nagarapu, Lingaiah</creatorcontrib><creatorcontrib>Gaikwad, Hanmant K.</creatorcontrib><creatorcontrib>Bantu, Rajashaker</creatorcontrib><creatorcontrib>Manikonda, Sheeba Rani</creatorcontrib><collection>Pascal-Francis</collection><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>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nagarapu, Lingaiah</au><au>Gaikwad, Hanmant K.</au><au>Bantu, Rajashaker</au><au>Manikonda, Sheeba Rani</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemoenzymatic synthesis with lipase catalyzed resolution and evaluation of antitumor activity of (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2011-06-01</date><risdate>2011</risdate><volume>46</volume><issue>6</issue><spage>2152</spage><epage>2156</epage><pages>2152-2156</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>Synthesis, characterization, resolution and evaluation of novel (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one derivatives are described. Enantiomerically pure compounds were isolated in good to excellent yield with high enantiomeric excess under mild reaction conditions by using Candida antarctica B (CAL-B) and Candida rugosa (CRL) Lipases. Newly synthesized and resolved compounds were screened for their antitumor activity against cancer cells such as human neuroblastoma SK–N–SH and human lung carcinoma A549 cell line in vitro. The results have shown that the compound 1 S-(−) alcohol was more effective in inhibiting the tumor cell growth.
Synthesis and resolution of (±)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3, 4-b]quinolin-3(2H)-one (1) in good to excellent yield. Newly isolated compounds were evaluated for their antitumor activity against the human cancer cell lines. [Display omitted]
► Synthesized and characterized the novel derivatives of (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl) propyl]-1H-pyrrolo [3,4-b] quinolin-3(2H)-one in good to excellent yields. ► Synthesized racemic derivatives were resolved by using Candida antarctica B (CAL-B) and Candida rugosa (CRL) Lipases. ► All newly synthesized and resolved isomers were evaluated for their antitumor activity against cancer cells such as human neuroblastoma SK–N–SH and human lung carcinoma A549 cell lines. ► The results have shown that the compound 1 S-(−) alcohol was more effective in inhibiting the tumor cell growth.</abstract><cop>Kidlington</cop><pub>Elsevier Masson SAS</pub><pmid>21440337</pmid><doi>10.1016/j.ejmech.2011.02.069</doi><tpages>5</tpages></addata></record> |
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| ispartof | European journal of medicinal chemistry, 2011-06, Vol.46 (6), p.2152-2156 |
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| subjects | Antineoplastic agents Antineoplastic Agents - chemistry Antineoplastic Agents - metabolism Antineoplastic Agents - pharmacology Biocatalysis Biological and medical sciences Candida - enzymology Cell Line, Tumor Cell Proliferation - drug effects Cytotoxicity Dose-Response Relationship, Drug Drug Screening Assays, Antitumor General aspects Humans Lipase Lipase - metabolism Lung carcinoma A549 cell line Medical sciences Molecular Structure Neuroblastoma cell line (SK–N–SH) Pharmacology. Drug treatments Piperazines - chemistry Piperazines - metabolism Piperazines - pharmacology Quinolines - chemistry Quinolines - metabolism Quinolines - pharmacology Stereoisomerism Structure-Activity Relationship |
| title | Chemoenzymatic synthesis with lipase catalyzed resolution and evaluation of antitumor activity of (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one |
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