Palladium-Catalyzed Aryl CH Activation and Tandem ortho-Hydroxylation/Alkoxylation of 2-Aryl Benzimidazoles: Cytotoxicity and DNA-Binding Studies
An efficient regio‐selective aryl CH activation and tandem o‐hydroxylation method for 2‐arylbenzimidazoles has been developed by using a Pd(OAc)2/oxone/Cs2CO3 catalytic system. This reaction was successfully optimized by using various catalysts, oxidants, bases, and solvents to achieve the desired...
Gespeichert in:
Veröffentlicht in: | Asian journal of organic chemistry 2014-01, Vol.3 (1), p.68-76 |
---|---|
Hauptverfasser: | , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 76 |
---|---|
container_issue | 1 |
container_start_page | 68 |
container_title | Asian journal of organic chemistry |
container_volume | 3 |
creator | Kamal, Ahmed Srinivasulu, Vunnam Sathish, Manda Tangella, Yellaiah Nayak, V. Lakshma Rao, M. P. Narasimha Shankaraiah, Nagula Nagesh, Narayana |
description | An efficient regio‐selective aryl CH activation and tandem o‐hydroxylation method for 2‐arylbenzimidazoles has been developed by using a Pd(OAc)2/oxone/Cs2CO3 catalytic system. This reaction was successfully optimized by using various catalysts, oxidants, bases, and solvents to achieve the desired products in good yields. Further, preliminary mechanistic studies were conducted to examine the source of oxygen for this transformation. Gratifyingly, this catalytic system is also suitable for the introduction of various alkoxy groups, and delivered the products in good yields. The synthesized compounds were evaluated for their cytotoxic activity in selected human cancer cell lines. Some of the representative compounds (1 f, 2 f, 3 f and 4 f) have significant IC50 values ranging from 1–10 μM. Structure‐activity relationship studies indicate that in these compounds the ethoxy substituent is probably responsible for the improved activity. In addition, the DNA‐binding potential of these compounds was also investigated by UV/vis, fluorescence, and circular dichroism spectroscopy.
Do it in tandem: An efficient regioselective aryl CH activation and tandem o‐hydroxylation/alkoxylation method for 2‐aryl benzimidazoles has been developed using a Pd(OAc)2/oxone/Cs2CO3 catalytic system. Some of the compounds have significant IC50 values ranging from 1–10 μM in selected human cancer cell lines. The DNA‐binding potential of the compounds was also investigated by UV/vis, fluorescence, and circular dichroism spectroscopy. |
doi_str_mv | 10.1002/ajoc.201300214 |
format | Article |
fullrecord | <record><control><sourceid>istex_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_ajoc_201300214</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>ark_67375_WNG_JWW0X67P_V</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3274-b7a13275cc0392932b968dc60ce11bc900b306a1eb9fa44453358432d93cfc413</originalsourceid><addsrcrecordid>eNqFkE1OwzAQhSMEEqiwZe0LuPVPfmp2IUALQi0ShbKzHNsBgxujxIWm5-AGHIQjcQXSFlXsmMXMG818b_GC4BijLkaI9MSzk12CMG0XHO4EBwQzCqM-jna3GiX7wVFdP6O2koRhwg6CjxthrVBmPoOZ8MI2S61AWjUWZN-fX0OQSm_ehDeuBKJUYNI2PQOu8k8ODhtVuUVj1-deal-2C3AFIHBtc6rLpZkZJZbO6voEZI133i2MNL5ZW56NUnhqSmXKR3Dr58ro-jDYK4St9dHv7AR3F-eTbAivx4PLLL2GkpIkhHkicCsiKRFlhFGSs7ivZIykxjiXDKGcolhgnbNChGEYURr1Q0oUo7KQIaadoLvxlZWr60oX_LUyM1E1HCO-ipWvYuXbWFuAbYB3Y3XzzzdPr8bZXxZuWFN7vdiyonrhcUKTiE9HA341naKHOLnh9_QH8AWOPw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Palladium-Catalyzed Aryl CH Activation and Tandem ortho-Hydroxylation/Alkoxylation of 2-Aryl Benzimidazoles: Cytotoxicity and DNA-Binding Studies</title><source>Wiley Journals</source><creator>Kamal, Ahmed ; Srinivasulu, Vunnam ; Sathish, Manda ; Tangella, Yellaiah ; Nayak, V. Lakshma ; Rao, M. P. Narasimha ; Shankaraiah, Nagula ; Nagesh, Narayana</creator><creatorcontrib>Kamal, Ahmed ; Srinivasulu, Vunnam ; Sathish, Manda ; Tangella, Yellaiah ; Nayak, V. Lakshma ; Rao, M. P. Narasimha ; Shankaraiah, Nagula ; Nagesh, Narayana</creatorcontrib><description>An efficient regio‐selective aryl CH activation and tandem o‐hydroxylation method for 2‐arylbenzimidazoles has been developed by using a Pd(OAc)2/oxone/Cs2CO3 catalytic system. This reaction was successfully optimized by using various catalysts, oxidants, bases, and solvents to achieve the desired products in good yields. Further, preliminary mechanistic studies were conducted to examine the source of oxygen for this transformation. Gratifyingly, this catalytic system is also suitable for the introduction of various alkoxy groups, and delivered the products in good yields. The synthesized compounds were evaluated for their cytotoxic activity in selected human cancer cell lines. Some of the representative compounds (1 f, 2 f, 3 f and 4 f) have significant IC50 values ranging from 1–10 μM. Structure‐activity relationship studies indicate that in these compounds the ethoxy substituent is probably responsible for the improved activity. In addition, the DNA‐binding potential of these compounds was also investigated by UV/vis, fluorescence, and circular dichroism spectroscopy.
Do it in tandem: An efficient regioselective aryl CH activation and tandem o‐hydroxylation/alkoxylation method for 2‐aryl benzimidazoles has been developed using a Pd(OAc)2/oxone/Cs2CO3 catalytic system. Some of the compounds have significant IC50 values ranging from 1–10 μM in selected human cancer cell lines. The DNA‐binding potential of the compounds was also investigated by UV/vis, fluorescence, and circular dichroism spectroscopy.</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.201300214</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>2-aryl benzimidazoles ; cytotoxicity ; CH activation ; DNA-binding affinity ; o-hydroxylation/alkoxylation</subject><ispartof>Asian journal of organic chemistry, 2014-01, Vol.3 (1), p.68-76</ispartof><rights>Copyright © 2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3274-b7a13275cc0392932b968dc60ce11bc900b306a1eb9fa44453358432d93cfc413</citedby><cites>FETCH-LOGICAL-c3274-b7a13275cc0392932b968dc60ce11bc900b306a1eb9fa44453358432d93cfc413</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fajoc.201300214$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fajoc.201300214$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Kamal, Ahmed</creatorcontrib><creatorcontrib>Srinivasulu, Vunnam</creatorcontrib><creatorcontrib>Sathish, Manda</creatorcontrib><creatorcontrib>Tangella, Yellaiah</creatorcontrib><creatorcontrib>Nayak, V. Lakshma</creatorcontrib><creatorcontrib>Rao, M. P. Narasimha</creatorcontrib><creatorcontrib>Shankaraiah, Nagula</creatorcontrib><creatorcontrib>Nagesh, Narayana</creatorcontrib><title>Palladium-Catalyzed Aryl CH Activation and Tandem ortho-Hydroxylation/Alkoxylation of 2-Aryl Benzimidazoles: Cytotoxicity and DNA-Binding Studies</title><title>Asian journal of organic chemistry</title><addtitle>Asian Journal of Organic Chemistry</addtitle><description>An efficient regio‐selective aryl CH activation and tandem o‐hydroxylation method for 2‐arylbenzimidazoles has been developed by using a Pd(OAc)2/oxone/Cs2CO3 catalytic system. This reaction was successfully optimized by using various catalysts, oxidants, bases, and solvents to achieve the desired products in good yields. Further, preliminary mechanistic studies were conducted to examine the source of oxygen for this transformation. Gratifyingly, this catalytic system is also suitable for the introduction of various alkoxy groups, and delivered the products in good yields. The synthesized compounds were evaluated for their cytotoxic activity in selected human cancer cell lines. Some of the representative compounds (1 f, 2 f, 3 f and 4 f) have significant IC50 values ranging from 1–10 μM. Structure‐activity relationship studies indicate that in these compounds the ethoxy substituent is probably responsible for the improved activity. In addition, the DNA‐binding potential of these compounds was also investigated by UV/vis, fluorescence, and circular dichroism spectroscopy.
Do it in tandem: An efficient regioselective aryl CH activation and tandem o‐hydroxylation/alkoxylation method for 2‐aryl benzimidazoles has been developed using a Pd(OAc)2/oxone/Cs2CO3 catalytic system. Some of the compounds have significant IC50 values ranging from 1–10 μM in selected human cancer cell lines. The DNA‐binding potential of the compounds was also investigated by UV/vis, fluorescence, and circular dichroism spectroscopy.</description><subject>2-aryl benzimidazoles</subject><subject>cytotoxicity</subject><subject>CH activation</subject><subject>DNA-binding affinity</subject><subject>o-hydroxylation/alkoxylation</subject><issn>2193-5807</issn><issn>2193-5815</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkE1OwzAQhSMEEqiwZe0LuPVPfmp2IUALQi0ShbKzHNsBgxujxIWm5-AGHIQjcQXSFlXsmMXMG818b_GC4BijLkaI9MSzk12CMG0XHO4EBwQzCqM-jna3GiX7wVFdP6O2koRhwg6CjxthrVBmPoOZ8MI2S61AWjUWZN-fX0OQSm_ehDeuBKJUYNI2PQOu8k8ODhtVuUVj1-deal-2C3AFIHBtc6rLpZkZJZbO6voEZI133i2MNL5ZW56NUnhqSmXKR3Dr58ro-jDYK4St9dHv7AR3F-eTbAivx4PLLL2GkpIkhHkicCsiKRFlhFGSs7ivZIykxjiXDKGcolhgnbNChGEYURr1Q0oUo7KQIaadoLvxlZWr60oX_LUyM1E1HCO-ipWvYuXbWFuAbYB3Y3XzzzdPr8bZXxZuWFN7vdiyonrhcUKTiE9HA341naKHOLnh9_QH8AWOPw</recordid><startdate>201401</startdate><enddate>201401</enddate><creator>Kamal, Ahmed</creator><creator>Srinivasulu, Vunnam</creator><creator>Sathish, Manda</creator><creator>Tangella, Yellaiah</creator><creator>Nayak, V. Lakshma</creator><creator>Rao, M. P. Narasimha</creator><creator>Shankaraiah, Nagula</creator><creator>Nagesh, Narayana</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201401</creationdate><title>Palladium-Catalyzed Aryl CH Activation and Tandem ortho-Hydroxylation/Alkoxylation of 2-Aryl Benzimidazoles: Cytotoxicity and DNA-Binding Studies</title><author>Kamal, Ahmed ; Srinivasulu, Vunnam ; Sathish, Manda ; Tangella, Yellaiah ; Nayak, V. Lakshma ; Rao, M. P. Narasimha ; Shankaraiah, Nagula ; Nagesh, Narayana</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3274-b7a13275cc0392932b968dc60ce11bc900b306a1eb9fa44453358432d93cfc413</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>2-aryl benzimidazoles</topic><topic>cytotoxicity</topic><topic>CH activation</topic><topic>DNA-binding affinity</topic><topic>o-hydroxylation/alkoxylation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kamal, Ahmed</creatorcontrib><creatorcontrib>Srinivasulu, Vunnam</creatorcontrib><creatorcontrib>Sathish, Manda</creatorcontrib><creatorcontrib>Tangella, Yellaiah</creatorcontrib><creatorcontrib>Nayak, V. Lakshma</creatorcontrib><creatorcontrib>Rao, M. P. Narasimha</creatorcontrib><creatorcontrib>Shankaraiah, Nagula</creatorcontrib><creatorcontrib>Nagesh, Narayana</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Asian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kamal, Ahmed</au><au>Srinivasulu, Vunnam</au><au>Sathish, Manda</au><au>Tangella, Yellaiah</au><au>Nayak, V. Lakshma</au><au>Rao, M. P. Narasimha</au><au>Shankaraiah, Nagula</au><au>Nagesh, Narayana</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium-Catalyzed Aryl CH Activation and Tandem ortho-Hydroxylation/Alkoxylation of 2-Aryl Benzimidazoles: Cytotoxicity and DNA-Binding Studies</atitle><jtitle>Asian journal of organic chemistry</jtitle><addtitle>Asian Journal of Organic Chemistry</addtitle><date>2014-01</date><risdate>2014</risdate><volume>3</volume><issue>1</issue><spage>68</spage><epage>76</epage><pages>68-76</pages><issn>2193-5807</issn><eissn>2193-5815</eissn><abstract>An efficient regio‐selective aryl CH activation and tandem o‐hydroxylation method for 2‐arylbenzimidazoles has been developed by using a Pd(OAc)2/oxone/Cs2CO3 catalytic system. This reaction was successfully optimized by using various catalysts, oxidants, bases, and solvents to achieve the desired products in good yields. Further, preliminary mechanistic studies were conducted to examine the source of oxygen for this transformation. Gratifyingly, this catalytic system is also suitable for the introduction of various alkoxy groups, and delivered the products in good yields. The synthesized compounds were evaluated for their cytotoxic activity in selected human cancer cell lines. Some of the representative compounds (1 f, 2 f, 3 f and 4 f) have significant IC50 values ranging from 1–10 μM. Structure‐activity relationship studies indicate that in these compounds the ethoxy substituent is probably responsible for the improved activity. In addition, the DNA‐binding potential of these compounds was also investigated by UV/vis, fluorescence, and circular dichroism spectroscopy.
Do it in tandem: An efficient regioselective aryl CH activation and tandem o‐hydroxylation/alkoxylation method for 2‐aryl benzimidazoles has been developed using a Pd(OAc)2/oxone/Cs2CO3 catalytic system. Some of the compounds have significant IC50 values ranging from 1–10 μM in selected human cancer cell lines. The DNA‐binding potential of the compounds was also investigated by UV/vis, fluorescence, and circular dichroism spectroscopy.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ajoc.201300214</doi><tpages>9</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 2193-5807 |
ispartof | Asian journal of organic chemistry, 2014-01, Vol.3 (1), p.68-76 |
issn | 2193-5807 2193-5815 |
language | eng |
recordid | cdi_crossref_primary_10_1002_ajoc_201300214 |
source | Wiley Journals |
subjects | 2-aryl benzimidazoles cytotoxicity CH activation DNA-binding affinity o-hydroxylation/alkoxylation |
title | Palladium-Catalyzed Aryl CH Activation and Tandem ortho-Hydroxylation/Alkoxylation of 2-Aryl Benzimidazoles: Cytotoxicity and DNA-Binding Studies |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-24T02%3A39%3A29IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-istex_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Palladium-Catalyzed%20Aryl%20C%EF%A3%BFH%20Activation%20and%20Tandem%20ortho-Hydroxylation/Alkoxylation%20of%202-Aryl%20Benzimidazoles:%20Cytotoxicity%20and%20DNA-Binding%20Studies&rft.jtitle=Asian%20journal%20of%20organic%20chemistry&rft.au=Kamal,%20Ahmed&rft.date=2014-01&rft.volume=3&rft.issue=1&rft.spage=68&rft.epage=76&rft.pages=68-76&rft.issn=2193-5807&rft.eissn=2193-5815&rft_id=info:doi/10.1002/ajoc.201300214&rft_dat=%3Cistex_cross%3Eark_67375_WNG_JWW0X67P_V%3C/istex_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |