Pyrazolylphenanthroimidazole heterocycles: synthesis, biological and molecular docking studies
The synthesis of a series of novel pyrazolylphenanthroimidazoles 6a-6j has been accomplished utilizing a multi-step synthetic protocol, and characterized through physical and spectral techniques. Among them, the molecules possessing para -bromo ( 6d ), para -methyl ( 6f ) and para -nitro ( 6j ) phen...
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| Veröffentlicht in: | New journal of chemistry 2020-12, Vol.44 (45), p.19612-19622 |
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| container_title | New journal of chemistry |
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| creator | Sivaramakarthikeyan, Ramar Iniyaval, Shunmugam Lim, Wei-Meng Hii, Ling-Wei Mai, Chun-Wai Ramalingan, Chennan |
| description | The synthesis of a series of novel pyrazolylphenanthroimidazoles
6a-6j
has been accomplished utilizing a multi-step synthetic protocol, and characterized through physical and spectral techniques. Among them, the molecules possessing
para
-bromo (
6d
),
para
-methyl (
6f
) and
para
-nitro (
6j
) phenyl substituents on the pyrazole scaffold displayed similar anti-inflammatory activity and the one with no substituents on the aryl unit (
6a
) exhibited the highest anti-inflammatory profile. While investigating the DPPH radical scavenging activity, the synthesized chemical entity with a
para
-methoxyphenyl group attached at the pyrazole structural motif (
6i
) revealed the highest activity when compared to the other synthesized molecules. Furthermore, the evaluation of cytotoxic activity of the synthesized molecule (
6a
) exerted significant activity against both the pancreatic cell lines such as AsPC1 and SW1990. Besides, while performing the molecular docking studies of
6a
with B-cell lymphoma 2, an appreciable binding affinity (−9.04 kcal mol
−1
) has been observed. The results of the present examination imply that these chemical entities could be used as efficient intermediates for the construction of biopertinent molecules.
The synthesis of a series of novel pyrazolylphenanthroimidazoles
6a-6j
has been accomplished utilizing a multi-step synthetic protocol, and characterized through physical and spectral techniques. |
| doi_str_mv | 10.1039/d0nj02214d |
| format | Article |
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6a-6j
has been accomplished utilizing a multi-step synthetic protocol, and characterized through physical and spectral techniques. Among them, the molecules possessing
para
-bromo (
6d
),
para
-methyl (
6f
) and
para
-nitro (
6j
) phenyl substituents on the pyrazole scaffold displayed similar anti-inflammatory activity and the one with no substituents on the aryl unit (
6a
) exhibited the highest anti-inflammatory profile. While investigating the DPPH radical scavenging activity, the synthesized chemical entity with a
para
-methoxyphenyl group attached at the pyrazole structural motif (
6i
) revealed the highest activity when compared to the other synthesized molecules. Furthermore, the evaluation of cytotoxic activity of the synthesized molecule (
6a
) exerted significant activity against both the pancreatic cell lines such as AsPC1 and SW1990. Besides, while performing the molecular docking studies of
6a
with B-cell lymphoma 2, an appreciable binding affinity (−9.04 kcal mol
−1
) has been observed. The results of the present examination imply that these chemical entities could be used as efficient intermediates for the construction of biopertinent molecules.
The synthesis of a series of novel pyrazolylphenanthroimidazoles
6a-6j
has been accomplished utilizing a multi-step synthetic protocol, and characterized through physical and spectral techniques.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/d0nj02214d</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Aromatic compounds ; Chemical activity ; Chemical synthesis ; Molecular docking ; Pyrazole ; Scavenging</subject><ispartof>New journal of chemistry, 2020-12, Vol.44 (45), p.19612-19622</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-357f2cd0fd55ae18cd7777e466052b56b1d9803cd2603017ad0395ad5632cb13</citedby><cites>FETCH-LOGICAL-c281t-357f2cd0fd55ae18cd7777e466052b56b1d9803cd2603017ad0395ad5632cb13</cites><orcidid>0000-0002-1585-9542</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Sivaramakarthikeyan, Ramar</creatorcontrib><creatorcontrib>Iniyaval, Shunmugam</creatorcontrib><creatorcontrib>Lim, Wei-Meng</creatorcontrib><creatorcontrib>Hii, Ling-Wei</creatorcontrib><creatorcontrib>Mai, Chun-Wai</creatorcontrib><creatorcontrib>Ramalingan, Chennan</creatorcontrib><title>Pyrazolylphenanthroimidazole heterocycles: synthesis, biological and molecular docking studies</title><title>New journal of chemistry</title><description>The synthesis of a series of novel pyrazolylphenanthroimidazoles
6a-6j
has been accomplished utilizing a multi-step synthetic protocol, and characterized through physical and spectral techniques. Among them, the molecules possessing
para
-bromo (
6d
),
para
-methyl (
6f
) and
para
-nitro (
6j
) phenyl substituents on the pyrazole scaffold displayed similar anti-inflammatory activity and the one with no substituents on the aryl unit (
6a
) exhibited the highest anti-inflammatory profile. While investigating the DPPH radical scavenging activity, the synthesized chemical entity with a
para
-methoxyphenyl group attached at the pyrazole structural motif (
6i
) revealed the highest activity when compared to the other synthesized molecules. Furthermore, the evaluation of cytotoxic activity of the synthesized molecule (
6a
) exerted significant activity against both the pancreatic cell lines such as AsPC1 and SW1990. Besides, while performing the molecular docking studies of
6a
with B-cell lymphoma 2, an appreciable binding affinity (−9.04 kcal mol
−1
) has been observed. The results of the present examination imply that these chemical entities could be used as efficient intermediates for the construction of biopertinent molecules.
The synthesis of a series of novel pyrazolylphenanthroimidazoles
6a-6j
has been accomplished utilizing a multi-step synthetic protocol, and characterized through physical and spectral techniques.</description><subject>Aromatic compounds</subject><subject>Chemical activity</subject><subject>Chemical synthesis</subject><subject>Molecular docking</subject><subject>Pyrazole</subject><subject>Scavenging</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpFkE1PwzAMQCMEEmNw4Y5UiRui4CRN2nJDG5-agMPOVGmSbhlZM5L2UH49GUPgiy37yZYfQqcYrjDQ8lpBuwJCcKb20AhTXqYl4Xg_1jjLUmAZP0RHIawAMM45HqH3t8GLL2cHu1nqVrTd0juzNmrb08lSd9o7OUirw00ShjjWwYTLpDbOuoWRwiaiVck6wrK3wifKyQ_TLpLQ9crocIwOGmGDPvnNYzS_v5tPHtPZ68PT5HaWSlLgLqUsb4hU0CjGhMaFVHkMnXEOjNSM11iVBVCpCAcKOBcqPsuEYpwSWWM6Rue7tRvvPnsdumrlet_GixXJeEaiGygidbGjpHcheN1UG2_Wwg8Vhmqrr5rCy_OPvmmEz3awD_KP-9dLvwHrMW3U</recordid><startdate>20201207</startdate><enddate>20201207</enddate><creator>Sivaramakarthikeyan, Ramar</creator><creator>Iniyaval, Shunmugam</creator><creator>Lim, Wei-Meng</creator><creator>Hii, Ling-Wei</creator><creator>Mai, Chun-Wai</creator><creator>Ramalingan, Chennan</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0002-1585-9542</orcidid></search><sort><creationdate>20201207</creationdate><title>Pyrazolylphenanthroimidazole heterocycles: synthesis, biological and molecular docking studies</title><author>Sivaramakarthikeyan, Ramar ; Iniyaval, Shunmugam ; Lim, Wei-Meng ; Hii, Ling-Wei ; Mai, Chun-Wai ; Ramalingan, Chennan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-357f2cd0fd55ae18cd7777e466052b56b1d9803cd2603017ad0395ad5632cb13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Aromatic compounds</topic><topic>Chemical activity</topic><topic>Chemical synthesis</topic><topic>Molecular docking</topic><topic>Pyrazole</topic><topic>Scavenging</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sivaramakarthikeyan, Ramar</creatorcontrib><creatorcontrib>Iniyaval, Shunmugam</creatorcontrib><creatorcontrib>Lim, Wei-Meng</creatorcontrib><creatorcontrib>Hii, Ling-Wei</creatorcontrib><creatorcontrib>Mai, Chun-Wai</creatorcontrib><creatorcontrib>Ramalingan, Chennan</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sivaramakarthikeyan, Ramar</au><au>Iniyaval, Shunmugam</au><au>Lim, Wei-Meng</au><au>Hii, Ling-Wei</au><au>Mai, Chun-Wai</au><au>Ramalingan, Chennan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Pyrazolylphenanthroimidazole heterocycles: synthesis, biological and molecular docking studies</atitle><jtitle>New journal of chemistry</jtitle><date>2020-12-07</date><risdate>2020</risdate><volume>44</volume><issue>45</issue><spage>19612</spage><epage>19622</epage><pages>19612-19622</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>The synthesis of a series of novel pyrazolylphenanthroimidazoles
6a-6j
has been accomplished utilizing a multi-step synthetic protocol, and characterized through physical and spectral techniques. Among them, the molecules possessing
para
-bromo (
6d
),
para
-methyl (
6f
) and
para
-nitro (
6j
) phenyl substituents on the pyrazole scaffold displayed similar anti-inflammatory activity and the one with no substituents on the aryl unit (
6a
) exhibited the highest anti-inflammatory profile. While investigating the DPPH radical scavenging activity, the synthesized chemical entity with a
para
-methoxyphenyl group attached at the pyrazole structural motif (
6i
) revealed the highest activity when compared to the other synthesized molecules. Furthermore, the evaluation of cytotoxic activity of the synthesized molecule (
6a
) exerted significant activity against both the pancreatic cell lines such as AsPC1 and SW1990. Besides, while performing the molecular docking studies of
6a
with B-cell lymphoma 2, an appreciable binding affinity (−9.04 kcal mol
−1
) has been observed. The results of the present examination imply that these chemical entities could be used as efficient intermediates for the construction of biopertinent molecules.
The synthesis of a series of novel pyrazolylphenanthroimidazoles
6a-6j
has been accomplished utilizing a multi-step synthetic protocol, and characterized through physical and spectral techniques.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d0nj02214d</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0002-1585-9542</orcidid></addata></record> |
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| issn | 1144-0546 1369-9261 |
| language | eng |
| recordid | cdi_proquest_journals_2464210308 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aromatic compounds Chemical activity Chemical synthesis Molecular docking Pyrazole Scavenging |
| title | Pyrazolylphenanthroimidazole heterocycles: synthesis, biological and molecular docking studies |
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