Synthesis and Biological Screening of Pyrano[3,2‑c]quinoline Analogues as Anti-inflammatory and Anticancer Agents
A series of pyrano[3,2-c]quinoline based structural analogues was synthesized using one-pot multicomponent condensation between 2,4-dihydroxy-1-methylquinoline, malononitrile, and diverse un(substituted) aromatic aldehydes. The synthesized compounds were evaluated for their anti-inflammatory and...
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| Published in | ACS medicinal chemistry letters Vol. 9; no. 3; pp. 283 - 288 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
08.03.2018
Amer Chemical Soc |
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| Online Access | Get full text |
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| Abstract | A series of pyrano[3,2-c]quinoline based structural analogues was synthesized using one-pot multicomponent condensation between 2,4-dihydroxy-1-methylquinoline, malononitrile, and diverse un(substituted) aromatic aldehydes. The synthesized compounds were evaluated for their anti-inflammatory and cytotoxicity activity. Initially, all the compounds were evaluated for the percent inhibition of cytokine release, and cytotoxicity activity and 50% inhibitory concentrations (IC50) were also determined. Based on the primary results, it was further studied for their ability to inhibit TNF-α production in the human peripheral blood mononuclear cells (hPBMC) assay. The screening results revealed that compound 4c, 4f, 4i, and 4j were found most active candidates of the series against both anti-inflammatory and anticancer activity. The structure–activity relationship is discussed and suggested that 3-substitution on the aryl ring at C4 position of the pyrano[3,2-c]quinolone structural motif seems to be an important position for both TNF-α and IL-6 inhibition and anticancer activity as well. However, structural diversity with electron withdrawing, electron donating, sterically hindered, and heteroaryl substitution sincerely affected both the inflammation and anticancer activities. |
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| AbstractList | A series of pyrano[3,2-c]quinoline based structural analogues was synthesized using one-pot multicomponent condensation between 2,4-dihydroxy-1-methylquinoline, malononitrile, and diverse un(substituted) aromatic aldehydes. The synthesized compounds were evaluated for their anti-inflammatory and cytotoxicity activity. Initially, all the compounds were evaluated for the percent inhibition of cytokine release, and cytotoxicity activity and 50% inhibitory concentrations (IC50) were also determined. Based on the primary results, it was further studied for their ability to inhibit TNF-α production in the human peripheral blood mononuclear cells (hPBMC) assay. The screening results revealed that compound 4c, 4f, 4i, and 4j were found most active candidates of the series against both anti-inflammatory and anticancer activity. The structure–activity relationship is discussed and suggested that 3-substitution on the aryl ring at C4 position of the pyrano[3,2-c]quinolone structural motif seems to be an important position for both TNF-α and IL-6 inhibition and anticancer activity as well. However, structural diversity with electron withdrawing, electron donating, sterically hindered, and heteroaryl substitution sincerely affected both the inflammation and anticancer activities. A series of pyrano[3,2- ]quinoline based structural analogues was synthesized using one-pot multicomponent condensation between 2,4-dihydroxy-1-methylquinoline, malononitrile, and diverse un(substituted) aromatic aldehydes. The synthesized compounds were evaluated for their anti-inflammatory and cytotoxicity activity. Initially, all the compounds were evaluated for the percent inhibition of cytokine release, and cytotoxicity activity and 50% inhibitory concentrations (IC ) were also determined. Based on the primary results, it was further studied for their ability to inhibit TNF-α production in the human peripheral blood mononuclear cells (hPBMC) assay. The screening results revealed that compound , , , and were found most active candidates of the series against both anti-inflammatory and anticancer activity. The structure-activity relationship is discussed and suggested that 3-substitution on the aryl ring at C4 position of the pyrano[3,2- ]quinolone structural motif seems to be an important position for both TNF-α and IL-6 inhibition and anticancer activity as well. However, structural diversity with electron withdrawing, electron donating, sterically hindered, and heteroaryl substitution sincerely affected both the inflammation and anticancer activities. A series of pyrano[3,2-c]quinoline based structural analogues was synthesized using one-pot multicomponent condensation between 2,4-dihydroxy-1-methylquinoline, malononitrile, and diverse un(substituted) aromatic aldehydes. The synthesized compounds were evaluated for their anti-inflammatory and cytotoxicity activity. Initially, all the compounds were evaluated for the percent inhibition of cytokine release, and cytotoxicity activity and 50% inhibitory concentrations (IC50) were also determined. Based on the primary results, it was further studied for their ability to inhibit TNF-alpha production in the human peripheral blood mononuclear cells (hPBMC) assay. The screening results revealed that compound 4c, 4f, 4i, and 4j were found most active candidates of the series against both anti-inflammatory and anticancer activity. The structure activity relationship is discussed and suggested that 3-substitution on the aryl ring at C4 position of the pyrano[3,2-c]quinolone structural motif seems to be an important position for both TNF-alpha and IL-6 inhibition and anticancer activity as well. However, structural diversity with electron withdrawing, electron donating, sterically hindered, and heteroaryl substitution sincerely affected both the inflammation and anticancer activities. A series of pyrano[3,2- c ]quinoline based structural analogues was synthesized using one-pot multicomponent condensation between 2,4-dihydroxy-1-methylquinoline, malononitrile, and diverse un(substituted) aromatic aldehydes. The synthesized compounds were evaluated for their anti-inflammatory and cytotoxicity activity. Initially, all the compounds were evaluated for the percent inhibition of cytokine release, and cytotoxicity activity and 50% inhibitory concentrations (IC 50 ) were also determined. Based on the primary results, it was further studied for their ability to inhibit TNF-α production in the human peripheral blood mononuclear cells (hPBMC) assay. The screening results revealed that compound 4c , 4f , 4i , and 4j were found most active candidates of the series against both anti-inflammatory and anticancer activity. The structure–activity relationship is discussed and suggested that 3-substitution on the aryl ring at C4 position of the pyrano[3,2- c ]quinolone structural motif seems to be an important position for both TNF-α and IL-6 inhibition and anticancer activity as well. However, structural diversity with electron withdrawing, electron donating, sterically hindered, and heteroaryl substitution sincerely affected both the inflammation and anticancer activities. |
| Author | Upadhyay, Kuldip D Khunt, Rupesh C Chaniara, Ravi S Dodia, Narsinh M Shah, Anamik K |
| AuthorAffiliation | Department of Chemistry Saurashtra University ICMR-National Institute of Occupational Health Wockhardt Research Centre National Facility for Drug Discovery (NFDD) |
| AuthorAffiliation_xml | – name: Department of Chemistry – name: National Facility for Drug Discovery (NFDD) – name: Saurashtra University – name: Wockhardt Research Centre – name: ICMR-National Institute of Occupational Health |
| Author_xml | – sequence: 1 givenname: Kuldip D orcidid: 0000-0002-0416-1923 surname: Upadhyay fullname: Upadhyay, Kuldip D email: drkuldip_upadhyay@rediffmail.com organization: ICMR-National Institute of Occupational Health – sequence: 2 givenname: Narsinh M surname: Dodia fullname: Dodia, Narsinh M organization: Saurashtra University – sequence: 3 givenname: Rupesh C surname: Khunt fullname: Khunt, Rupesh C organization: Saurashtra University – sequence: 4 givenname: Ravi S surname: Chaniara fullname: Chaniara, Ravi S organization: Wockhardt Research Centre – sequence: 5 givenname: Anamik K surname: Shah fullname: Shah, Anamik K organization: Saurashtra University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29541375$$D View this record in MEDLINE/PubMed |
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| Keywords | anti-inflammatory TNF-α IL-6 anticancer Pyrano[3,2-c]quinoline SERIES ASSAY MECHANISM TNF-alpha 4-ARYL-4H-CHROMENES APOPTOSIS INDUCERS DISCOVERY TUMOR-NECROSIS-FACTOR MULTICOMPONENT SYNTHESIS |
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| Snippet | A series of pyrano[3,2-c]quinoline based structural analogues was synthesized using one-pot multicomponent condensation between... A series of pyrano[3,2-c]quinoline based structural analogues was synthesized using one-pot multicomponent condensation between... A series of pyrano[3,2- ]quinoline based structural analogues was synthesized using one-pot multicomponent condensation between... A series of pyrano[3,2- c ]quinoline based structural analogues was synthesized using one-pot multicomponent condensation between... |
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| Title | Synthesis and Biological Screening of Pyrano[3,2‑c]quinoline Analogues as Anti-inflammatory and Anticancer Agents |
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