New triazinoindole bearing thiazole/oxazole analogues: Synthesis, α-amylase inhibitory potential and molecular docking study
[Display omitted] •Synthesis of triazinoindole bearing thiazole/oxazole analogues.•In vitro α-amylase activity.•Identification of a new class of α-amylase activity.•Structure Activity Relationship established.•Molecular docking. New triazinoindole bearing thiazole/oxazole analogues (1–21) were synth...
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| Veröffentlicht in: | Bioorganic chemistry 2019-11, Vol.92, p.103284-103284, Article 103284 |
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| container_title | Bioorganic chemistry |
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| creator | Rahim, Fazal Tariq, Sundas Taha, Muhammad Ullah, Hayat Zaman, Khalid Uddin, Imad Wadood, Abdul Khan, Aftab Ahmad Rehman, Ashfaq Ur Uddin, Nizam Zafar, Salman Shah, Syed Adnan Ali |
| description | [Display omitted]
•Synthesis of triazinoindole bearing thiazole/oxazole analogues.•In vitro α-amylase activity.•Identification of a new class of α-amylase activity.•Structure Activity Relationship established.•Molecular docking.
New triazinoindole bearing thiazole/oxazole analogues (1–21) were synthesized and characterized through spectroscopic techniques such as HREI-MS, 1H and 13C NMR. The configuration of compound 2i and 2k was confirmed through NOESY. All analogues were evaluated against α-amylase inhibitory potential. Among the synthesized analogues, compound 1h, 1i, 1j, 2a and 2f having IC50 values 1.80 ± 0.20, 1.90 ± 0.30, 1.2 ± 0.30, 1.2 ± 0.01 and 1.30 ± 0.20 μM respectively, showed excellent α-amylase inhibitory potential when compared with acarbose as standard (IC50 = 0.91 ± 0.20 µM). All other analogues showed good to moderate inhibitory potential. Structural activity relationship (SAR) has been established and binding interactions were confirmed through docking studies. |
| doi_str_mv | 10.1016/j.bioorg.2019.103284 |
| format | Article |
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•Synthesis of triazinoindole bearing thiazole/oxazole analogues.•In vitro α-amylase activity.•Identification of a new class of α-amylase activity.•Structure Activity Relationship established.•Molecular docking.
New triazinoindole bearing thiazole/oxazole analogues (1–21) were synthesized and characterized through spectroscopic techniques such as HREI-MS, 1H and 13C NMR. The configuration of compound 2i and 2k was confirmed through NOESY. All analogues were evaluated against α-amylase inhibitory potential. Among the synthesized analogues, compound 1h, 1i, 1j, 2a and 2f having IC50 values 1.80 ± 0.20, 1.90 ± 0.30, 1.2 ± 0.30, 1.2 ± 0.01 and 1.30 ± 0.20 μM respectively, showed excellent α-amylase inhibitory potential when compared with acarbose as standard (IC50 = 0.91 ± 0.20 µM). All other analogues showed good to moderate inhibitory potential. Structural activity relationship (SAR) has been established and binding interactions were confirmed through docking studies.</description><identifier>ISSN: 0045-2068</identifier><identifier>EISSN: 1090-2120</identifier><identifier>DOI: 10.1016/j.bioorg.2019.103284</identifier><language>eng</language><publisher>Elsevier Inc</publisher><subject>Molecular docking ; Oxazole ; SAR ; Synthesis ; Thiazole ; Triazinoindole ; α-amylase</subject><ispartof>Bioorganic chemistry, 2019-11, Vol.92, p.103284-103284, Article 103284</ispartof><rights>2019 Elsevier Inc.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c339t-5c15e197dffd0aff5a5dc1927a1c84887f65304c1c7d030cff5cc3728067bd173</citedby><cites>FETCH-LOGICAL-c339t-5c15e197dffd0aff5a5dc1927a1c84887f65304c1c7d030cff5cc3728067bd173</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bioorg.2019.103284$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27929,27930,46000</link.rule.ids></links><search><creatorcontrib>Rahim, Fazal</creatorcontrib><creatorcontrib>Tariq, Sundas</creatorcontrib><creatorcontrib>Taha, Muhammad</creatorcontrib><creatorcontrib>Ullah, Hayat</creatorcontrib><creatorcontrib>Zaman, Khalid</creatorcontrib><creatorcontrib>Uddin, Imad</creatorcontrib><creatorcontrib>Wadood, Abdul</creatorcontrib><creatorcontrib>Khan, Aftab Ahmad</creatorcontrib><creatorcontrib>Rehman, Ashfaq Ur</creatorcontrib><creatorcontrib>Uddin, Nizam</creatorcontrib><creatorcontrib>Zafar, Salman</creatorcontrib><creatorcontrib>Shah, Syed Adnan Ali</creatorcontrib><title>New triazinoindole bearing thiazole/oxazole analogues: Synthesis, α-amylase inhibitory potential and molecular docking study</title><title>Bioorganic chemistry</title><description>[Display omitted]
•Synthesis of triazinoindole bearing thiazole/oxazole analogues.•In vitro α-amylase activity.•Identification of a new class of α-amylase activity.•Structure Activity Relationship established.•Molecular docking.
New triazinoindole bearing thiazole/oxazole analogues (1–21) were synthesized and characterized through spectroscopic techniques such as HREI-MS, 1H and 13C NMR. The configuration of compound 2i and 2k was confirmed through NOESY. All analogues were evaluated against α-amylase inhibitory potential. Among the synthesized analogues, compound 1h, 1i, 1j, 2a and 2f having IC50 values 1.80 ± 0.20, 1.90 ± 0.30, 1.2 ± 0.30, 1.2 ± 0.01 and 1.30 ± 0.20 μM respectively, showed excellent α-amylase inhibitory potential when compared with acarbose as standard (IC50 = 0.91 ± 0.20 µM). All other analogues showed good to moderate inhibitory potential. Structural activity relationship (SAR) has been established and binding interactions were confirmed through docking studies.</description><subject>Molecular docking</subject><subject>Oxazole</subject><subject>SAR</subject><subject>Synthesis</subject><subject>Thiazole</subject><subject>Triazinoindole</subject><subject>α-amylase</subject><issn>0045-2068</issn><issn>1090-2120</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kM1qGzEUhUVJoY7TN-hCyywy9pXmP4tAMPkpmHbRdi1k6Y4tdyw5kpxmAnmovEifqXIm664OHM53uPcQ8oXBjAGr5tvZyjjn1zMOrE1WzpviA5kwaCHjjMMJmQAUZcahaj6R0xC2AIwVdTUhL9_wD43eyGdjnbHa9UhXKL2xaxo3yU7G3D29KZVW9m59wHBJfww2bjCYcEH_vmZyN_QyIDV2Y1YmOj_QvYtoo5F9ojTdJVwdeumpdur3sTzEgx7OyMdO9gE_v-uU_Lq9-bm4z5bf774urpeZyvM2ZqViJbK21l2nQXZdKUutWMtryVRTNE3dVWUOhWKq1pCDSgml8po3UNUrzep8Ss7H3r13D-n-KHYmKOx7adEdguC8raqKF8UxWoxR5V0IHjux92Yn_SAYiOPaYivGtcVxbTGunbCrEcP0xqNBL4IyaBVq41FFoZ35f8E_SEeOdw</recordid><startdate>201911</startdate><enddate>201911</enddate><creator>Rahim, Fazal</creator><creator>Tariq, Sundas</creator><creator>Taha, Muhammad</creator><creator>Ullah, Hayat</creator><creator>Zaman, Khalid</creator><creator>Uddin, Imad</creator><creator>Wadood, Abdul</creator><creator>Khan, Aftab Ahmad</creator><creator>Rehman, Ashfaq Ur</creator><creator>Uddin, Nizam</creator><creator>Zafar, Salman</creator><creator>Shah, Syed Adnan Ali</creator><general>Elsevier Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>201911</creationdate><title>New triazinoindole bearing thiazole/oxazole analogues: Synthesis, α-amylase inhibitory potential and molecular docking study</title><author>Rahim, Fazal ; Tariq, Sundas ; Taha, Muhammad ; Ullah, Hayat ; Zaman, Khalid ; Uddin, Imad ; Wadood, Abdul ; Khan, Aftab Ahmad ; Rehman, Ashfaq Ur ; Uddin, Nizam ; Zafar, Salman ; Shah, Syed Adnan Ali</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c339t-5c15e197dffd0aff5a5dc1927a1c84887f65304c1c7d030cff5cc3728067bd173</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Molecular docking</topic><topic>Oxazole</topic><topic>SAR</topic><topic>Synthesis</topic><topic>Thiazole</topic><topic>Triazinoindole</topic><topic>α-amylase</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rahim, Fazal</creatorcontrib><creatorcontrib>Tariq, Sundas</creatorcontrib><creatorcontrib>Taha, Muhammad</creatorcontrib><creatorcontrib>Ullah, Hayat</creatorcontrib><creatorcontrib>Zaman, Khalid</creatorcontrib><creatorcontrib>Uddin, Imad</creatorcontrib><creatorcontrib>Wadood, Abdul</creatorcontrib><creatorcontrib>Khan, Aftab Ahmad</creatorcontrib><creatorcontrib>Rehman, Ashfaq Ur</creatorcontrib><creatorcontrib>Uddin, Nizam</creatorcontrib><creatorcontrib>Zafar, Salman</creatorcontrib><creatorcontrib>Shah, Syed Adnan Ali</creatorcontrib><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rahim, Fazal</au><au>Tariq, Sundas</au><au>Taha, Muhammad</au><au>Ullah, Hayat</au><au>Zaman, Khalid</au><au>Uddin, Imad</au><au>Wadood, Abdul</au><au>Khan, Aftab Ahmad</au><au>Rehman, Ashfaq Ur</au><au>Uddin, Nizam</au><au>Zafar, Salman</au><au>Shah, Syed Adnan Ali</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New triazinoindole bearing thiazole/oxazole analogues: Synthesis, α-amylase inhibitory potential and molecular docking study</atitle><jtitle>Bioorganic chemistry</jtitle><date>2019-11</date><risdate>2019</risdate><volume>92</volume><spage>103284</spage><epage>103284</epage><pages>103284-103284</pages><artnum>103284</artnum><issn>0045-2068</issn><eissn>1090-2120</eissn><abstract>[Display omitted]
•Synthesis of triazinoindole bearing thiazole/oxazole analogues.•In vitro α-amylase activity.•Identification of a new class of α-amylase activity.•Structure Activity Relationship established.•Molecular docking.
New triazinoindole bearing thiazole/oxazole analogues (1–21) were synthesized and characterized through spectroscopic techniques such as HREI-MS, 1H and 13C NMR. The configuration of compound 2i and 2k was confirmed through NOESY. All analogues were evaluated against α-amylase inhibitory potential. Among the synthesized analogues, compound 1h, 1i, 1j, 2a and 2f having IC50 values 1.80 ± 0.20, 1.90 ± 0.30, 1.2 ± 0.30, 1.2 ± 0.01 and 1.30 ± 0.20 μM respectively, showed excellent α-amylase inhibitory potential when compared with acarbose as standard (IC50 = 0.91 ± 0.20 µM). All other analogues showed good to moderate inhibitory potential. Structural activity relationship (SAR) has been established and binding interactions were confirmed through docking studies.</abstract><pub>Elsevier Inc</pub><doi>10.1016/j.bioorg.2019.103284</doi><tpages>1</tpages></addata></record> |
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| source | ScienceDirect Journals (5 years ago - present) |
| subjects | Molecular docking Oxazole SAR Synthesis Thiazole Triazinoindole α-amylase |
| title | New triazinoindole bearing thiazole/oxazole analogues: Synthesis, α-amylase inhibitory potential and molecular docking study |
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