Synthesis and molecular docking of new hydrazones derived from ethyl isonipecotate and their biological activities
Purpose: To investigate the antibacterial and α-glucosidase inhibitory activities of hydrazone derivatives (8a-h) of ethyl isonipecotate. Methods: The reaction of ethyl isonipecotate (2) with 3,5-dichloro-2-hydroxybenzenesulfonyl chloride (1) in an aqueous basic medium yielded ethyl 1-[(3,5-dichloro...
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| Veröffentlicht in: | Tropical journal of pharmaceutical research 2019-11, Vol.16 (5) |
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| creator | Munir, A Aziz-ur-Rehman Abbasi, MA Siddiqui, SZ Nasir, A Khan, SG Rasool, S Shah, SAA |
| description | Purpose: To investigate the antibacterial and α-glucosidase
inhibitory activities of hydrazone derivatives (8a-h) of ethyl
isonipecotate. Methods: The reaction of ethyl isonipecotate (2) with
3,5-dichloro-2-hydroxybenzenesulfonyl chloride (1) in an aqueous basic
medium yielded ethyl
1-[(3,5-dichloro-2-hydroxyphenyl)sulfonyl]piperidin-4-carboxylate (3).
Compound 3 was subsequently converted to ethyl
1-[(3,5-dichloro-2-ethoxyphenyl)sulfonyl]piperidin-4-carboxylate (5)
via O-alkylation. Compound 5 on reaction with hydrated hydrazine
yielded
1-[(3,5-dichloro-2-ethoxyphenyl)sulfonyl]piperidin-4-carbohyrazide (6)
in MeOH. Target compounds 8a-h were synthesized by stirring 6 with
different aromatic aldehydes (7a-h) in MeOH. All the synthesized
compounds were structurally elucidated by proton nuclear magnetic
resonance (1H-NMR), electron impact mass spectrometry (EI-MS) and
infrared (IR) spectroscopy. For antibacterial activity, solutions of
the synthesized compounds were mixed with bacterial strains, and the
change in absorbance before and after incubation was determined. For
enzyme inhibitory activity, change in the absorbance of mixtures of
synthesized compounds and enzyme before and after incubation with
substrate was determined. Results: The target compounds were
synthesized in appreciable yields and well characterized by spectral
data analysis. Salmonella typhi was inhibited by 8e (MIC 8.00 ±
0.54 μM), Escherichia coli by 8f (8.21 ± 0.83 μM),
Bacillus subtilis by 8c (8.56 ± 0.63 μM) and Staphylococcus
aureus by 8c (8.86 ± 0.29 μM). Two compounds, 8e and 8d,
were very effective inhibitors of α-glucosidase with IC50 values
of 40.62 ± 0.07 and 48.64 ± 0.08 μM, respectively.
Conclusion: Low IC50 values of the synthesized compounds against
α-glucosidase demonstrates their potential in type-2 diabetes
treatment. Furthermore, these compounds exhibit substantial
antibacterial activity against the bacterial strains tested. |
| format | Article |
| fullrecord | <record><control><sourceid>bioline</sourceid><recordid>TN_cdi_bioline_primary_cria_bioline_pr_pr17148</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>cria_bioline_pr_pr17148</sourcerecordid><originalsourceid>FETCH-bioline_primary_cria_bioline_pr_pr171483</originalsourceid><addsrcrecordid>eNqVjMFqAkEQROdgQJP4D_0Dikuyq3MWg3dzXzozvbuts9PSMxrWr1dDwLNQUFC8eiMzKUpbzUprq7F5TWm_WJSVtcXE6G6IuaPECTB66CWQOwVU8OIOHFuQBiL9Qjd4xYtESuBJ-UweGpUeKHdDAE4S-UhOMmb6E92crPDDEqRlhwHQZT5zZkrv5qXBkGj6329m_rX5Xm9nd5oj1UflHnWonTLWj_GWYll8rj6ePlwBS7NXIA</addsrcrecordid><sourcetype>Publisher</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Synthesis and molecular docking of new hydrazones derived from ethyl isonipecotate and their biological activities</title><source>DOAJ Directory of Open Access Journals</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>African Journals Online (Open Access)</source><source>Bioline International</source><source>Free Full-Text Journals in Chemistry</source><creator>Munir, A ; Aziz-ur-Rehman ; Abbasi, MA ; Siddiqui, SZ ; Nasir, A ; Khan, SG ; Rasool, S ; Shah, SAA</creator><creatorcontrib>Munir, A ; Aziz-ur-Rehman ; Abbasi, MA ; Siddiqui, SZ ; Nasir, A ; Khan, SG ; Rasool, S ; Shah, SAA</creatorcontrib><description>Purpose: To investigate the antibacterial and α-glucosidase
inhibitory activities of hydrazone derivatives (8a-h) of ethyl
isonipecotate. Methods: The reaction of ethyl isonipecotate (2) with
3,5-dichloro-2-hydroxybenzenesulfonyl chloride (1) in an aqueous basic
medium yielded ethyl
1-[(3,5-dichloro-2-hydroxyphenyl)sulfonyl]piperidin-4-carboxylate (3).
Compound 3 was subsequently converted to ethyl
1-[(3,5-dichloro-2-ethoxyphenyl)sulfonyl]piperidin-4-carboxylate (5)
via O-alkylation. Compound 5 on reaction with hydrated hydrazine
yielded
1-[(3,5-dichloro-2-ethoxyphenyl)sulfonyl]piperidin-4-carbohyrazide (6)
in MeOH. Target compounds 8a-h were synthesized by stirring 6 with
different aromatic aldehydes (7a-h) in MeOH. All the synthesized
compounds were structurally elucidated by proton nuclear magnetic
resonance (1H-NMR), electron impact mass spectrometry (EI-MS) and
infrared (IR) spectroscopy. For antibacterial activity, solutions of
the synthesized compounds were mixed with bacterial strains, and the
change in absorbance before and after incubation was determined. For
enzyme inhibitory activity, change in the absorbance of mixtures of
synthesized compounds and enzyme before and after incubation with
substrate was determined. Results: The target compounds were
synthesized in appreciable yields and well characterized by spectral
data analysis. Salmonella typhi was inhibited by 8e (MIC 8.00 ±
0.54 μM), Escherichia coli by 8f (8.21 ± 0.83 μM),
Bacillus subtilis by 8c (8.56 ± 0.63 μM) and Staphylococcus
aureus by 8c (8.86 ± 0.29 μM). Two compounds, 8e and 8d,
were very effective inhibitors of α-glucosidase with IC50 values
of 40.62 ± 0.07 and 48.64 ± 0.08 μM, respectively.
Conclusion: Low IC50 values of the synthesized compounds against
α-glucosidase demonstrates their potential in type-2 diabetes
treatment. Furthermore, these compounds exhibit substantial
antibacterial activity against the bacterial strains tested.</description><identifier>ISSN: 1596-5996</identifier><language>eng</language><publisher>Pharmacotherapy Group, Faculty of Pharmacy, University of Benin, Benin City, Nigeria</publisher><subject>Antibacterial activity ; Ethyl isonipecotate ; Hydrazones ; α-Glucosidase inhibition</subject><ispartof>Tropical journal of pharmaceutical research, 2019-11, Vol.16 (5)</ispartof><rights>Copyright 2017 - Pharmacotherapy Group, Faculty of Pharmacy, University of Benin, Benin City, 300001 Nigeria.</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>314,780,784,79196</link.rule.ids></links><search><creatorcontrib>Munir, A</creatorcontrib><creatorcontrib>Aziz-ur-Rehman</creatorcontrib><creatorcontrib>Abbasi, MA</creatorcontrib><creatorcontrib>Siddiqui, SZ</creatorcontrib><creatorcontrib>Nasir, A</creatorcontrib><creatorcontrib>Khan, SG</creatorcontrib><creatorcontrib>Rasool, S</creatorcontrib><creatorcontrib>Shah, SAA</creatorcontrib><title>Synthesis and molecular docking of new hydrazones derived from ethyl isonipecotate and their biological activities</title><title>Tropical journal of pharmaceutical research</title><description>Purpose: To investigate the antibacterial and α-glucosidase
inhibitory activities of hydrazone derivatives (8a-h) of ethyl
isonipecotate. Methods: The reaction of ethyl isonipecotate (2) with
3,5-dichloro-2-hydroxybenzenesulfonyl chloride (1) in an aqueous basic
medium yielded ethyl
1-[(3,5-dichloro-2-hydroxyphenyl)sulfonyl]piperidin-4-carboxylate (3).
Compound 3 was subsequently converted to ethyl
1-[(3,5-dichloro-2-ethoxyphenyl)sulfonyl]piperidin-4-carboxylate (5)
via O-alkylation. Compound 5 on reaction with hydrated hydrazine
yielded
1-[(3,5-dichloro-2-ethoxyphenyl)sulfonyl]piperidin-4-carbohyrazide (6)
in MeOH. Target compounds 8a-h were synthesized by stirring 6 with
different aromatic aldehydes (7a-h) in MeOH. All the synthesized
compounds were structurally elucidated by proton nuclear magnetic
resonance (1H-NMR), electron impact mass spectrometry (EI-MS) and
infrared (IR) spectroscopy. For antibacterial activity, solutions of
the synthesized compounds were mixed with bacterial strains, and the
change in absorbance before and after incubation was determined. For
enzyme inhibitory activity, change in the absorbance of mixtures of
synthesized compounds and enzyme before and after incubation with
substrate was determined. Results: The target compounds were
synthesized in appreciable yields and well characterized by spectral
data analysis. Salmonella typhi was inhibited by 8e (MIC 8.00 ±
0.54 μM), Escherichia coli by 8f (8.21 ± 0.83 μM),
Bacillus subtilis by 8c (8.56 ± 0.63 μM) and Staphylococcus
aureus by 8c (8.86 ± 0.29 μM). Two compounds, 8e and 8d,
were very effective inhibitors of α-glucosidase with IC50 values
of 40.62 ± 0.07 and 48.64 ± 0.08 μM, respectively.
Conclusion: Low IC50 values of the synthesized compounds against
α-glucosidase demonstrates their potential in type-2 diabetes
treatment. Furthermore, these compounds exhibit substantial
antibacterial activity against the bacterial strains tested.</description><subject>Antibacterial activity</subject><subject>Ethyl isonipecotate</subject><subject>Hydrazones</subject><subject>α-Glucosidase inhibition</subject><issn>1596-5996</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>RBI</sourceid><recordid>eNqVjMFqAkEQROdgQJP4D_0Dikuyq3MWg3dzXzozvbuts9PSMxrWr1dDwLNQUFC8eiMzKUpbzUprq7F5TWm_WJSVtcXE6G6IuaPECTB66CWQOwVU8OIOHFuQBiL9Qjd4xYtESuBJ-UweGpUeKHdDAE4S-UhOMmb6E92crPDDEqRlhwHQZT5zZkrv5qXBkGj6329m_rX5Xm9nd5oj1UflHnWonTLWj_GWYll8rj6ePlwBS7NXIA</recordid><startdate>20191129</startdate><enddate>20191129</enddate><creator>Munir, A</creator><creator>Aziz-ur-Rehman</creator><creator>Abbasi, MA</creator><creator>Siddiqui, SZ</creator><creator>Nasir, A</creator><creator>Khan, SG</creator><creator>Rasool, S</creator><creator>Shah, SAA</creator><general>Pharmacotherapy Group, Faculty of Pharmacy, University of Benin, Benin City, Nigeria</general><scope>RBI</scope></search><sort><creationdate>20191129</creationdate><title>Synthesis and molecular docking of new hydrazones derived from ethyl isonipecotate and their biological activities</title><author>Munir, A ; Aziz-ur-Rehman ; Abbasi, MA ; Siddiqui, SZ ; Nasir, A ; Khan, SG ; Rasool, S ; Shah, SAA</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-bioline_primary_cria_bioline_pr_pr171483</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Antibacterial activity</topic><topic>Ethyl isonipecotate</topic><topic>Hydrazones</topic><topic>α-Glucosidase inhibition</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Munir, A</creatorcontrib><creatorcontrib>Aziz-ur-Rehman</creatorcontrib><creatorcontrib>Abbasi, MA</creatorcontrib><creatorcontrib>Siddiqui, SZ</creatorcontrib><creatorcontrib>Nasir, A</creatorcontrib><creatorcontrib>Khan, SG</creatorcontrib><creatorcontrib>Rasool, S</creatorcontrib><creatorcontrib>Shah, SAA</creatorcontrib><collection>Bioline International</collection><jtitle>Tropical journal of pharmaceutical research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Munir, A</au><au>Aziz-ur-Rehman</au><au>Abbasi, MA</au><au>Siddiqui, SZ</au><au>Nasir, A</au><au>Khan, SG</au><au>Rasool, S</au><au>Shah, SAA</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and molecular docking of new hydrazones derived from ethyl isonipecotate and their biological activities</atitle><jtitle>Tropical journal of pharmaceutical research</jtitle><date>2019-11-29</date><risdate>2019</risdate><volume>16</volume><issue>5</issue><issn>1596-5996</issn><abstract>Purpose: To investigate the antibacterial and α-glucosidase
inhibitory activities of hydrazone derivatives (8a-h) of ethyl
isonipecotate. Methods: The reaction of ethyl isonipecotate (2) with
3,5-dichloro-2-hydroxybenzenesulfonyl chloride (1) in an aqueous basic
medium yielded ethyl
1-[(3,5-dichloro-2-hydroxyphenyl)sulfonyl]piperidin-4-carboxylate (3).
Compound 3 was subsequently converted to ethyl
1-[(3,5-dichloro-2-ethoxyphenyl)sulfonyl]piperidin-4-carboxylate (5)
via O-alkylation. Compound 5 on reaction with hydrated hydrazine
yielded
1-[(3,5-dichloro-2-ethoxyphenyl)sulfonyl]piperidin-4-carbohyrazide (6)
in MeOH. Target compounds 8a-h were synthesized by stirring 6 with
different aromatic aldehydes (7a-h) in MeOH. All the synthesized
compounds were structurally elucidated by proton nuclear magnetic
resonance (1H-NMR), electron impact mass spectrometry (EI-MS) and
infrared (IR) spectroscopy. For antibacterial activity, solutions of
the synthesized compounds were mixed with bacterial strains, and the
change in absorbance before and after incubation was determined. For
enzyme inhibitory activity, change in the absorbance of mixtures of
synthesized compounds and enzyme before and after incubation with
substrate was determined. Results: The target compounds were
synthesized in appreciable yields and well characterized by spectral
data analysis. Salmonella typhi was inhibited by 8e (MIC 8.00 ±
0.54 μM), Escherichia coli by 8f (8.21 ± 0.83 μM),
Bacillus subtilis by 8c (8.56 ± 0.63 μM) and Staphylococcus
aureus by 8c (8.86 ± 0.29 μM). Two compounds, 8e and 8d,
were very effective inhibitors of α-glucosidase with IC50 values
of 40.62 ± 0.07 and 48.64 ± 0.08 μM, respectively.
Conclusion: Low IC50 values of the synthesized compounds against
α-glucosidase demonstrates their potential in type-2 diabetes
treatment. Furthermore, these compounds exhibit substantial
antibacterial activity against the bacterial strains tested.</abstract><pub>Pharmacotherapy Group, Faculty of Pharmacy, University of Benin, Benin City, Nigeria</pub></addata></record> |
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; African Journals Online (Open Access); Bioline International; Free Full-Text Journals in Chemistry |
| subjects | Antibacterial activity Ethyl isonipecotate Hydrazones α-Glucosidase inhibition |
| title | Synthesis and molecular docking of new hydrazones derived from ethyl isonipecotate and their biological activities |
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