Design and synthesis of quinazoline-3,4-(4H)-diamine endowed with thiazoline moiety as new class for DPP-4 and DPPH inhibitor
New N3-benzylidene (substituted)-2-phenyl-N4-(thiazol-2-yl)-quinazoline-3,4-(4H)-diamine derivatives were designed and synthesized by a sequence of reactions starting from appropriate 6-methyl anthranilic acid. Hopefully in future, compound 7g could be used as a lead compound for developing new anti...
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| Veröffentlicht in: | Bioorganic chemistry 2017-04, Vol.71, p.181-191 |
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| creator | Ali, Zulphikar Akhtar, Md Jawaid Haider, Md Rafi Khan, Ahsan Ahmed Siddiqui, Anees Ahmad Yar, M. Shahar |
| description | New N3-benzylidene (substituted)-2-phenyl-N4-(thiazol-2-yl)-quinazoline-3,4-(4H)-diamine derivatives were designed and synthesized by a sequence of reactions starting from appropriate 6-methyl anthranilic acid. Hopefully in future, compound 7g could be used as a lead compound for developing new antidiabetic agent with good antioxidant property.
[Display omitted]
•N3-benzylidene (substituted)-2-phenyl-N4-(thiazol-2-yl)-quinazoline-3,4-(4H)-diamine derivatives were design and synthesized.•Title compounds were screening for in vitro dipeptidyl peptidase IV (DPP-4) inhibitory activity and diphenyl-2-picryl-hydrazyl (DPPH) assay.•Docking study was also performed to provide an insight about the binding mode into binding sites of DPP-4 enzyme.•Compound 7g could be used as a lead compound for developing new antidiabetic agent with good antioxidant property.
New N3-benzylidene (substituted)-2-phenyl-N4-(thiazol-2-yl)-quinazoline-3,4-(4H)-diamine derivatives were design and synthesized by a sequence of reactions starting from appropriate 6-methyl anthranilic acid. The title compounds were screened for in vitro dipeptidyl peptidase IV (DPP-4) inhibitory activity and diphenyl-2-picryl-hydrazyl (DPPH) assay and results showed significant to good activity in compared to Linagliptin for antidiabetic activity and Ascorbic acid for antioxidant activity. Compound 7g (IC50=0.76nM) exhibited most promising DPP-4 inhibitory activity and also showed good antioxid and result. Docking study was also performed to provide an insight about the binding mode into binding sites of DPP-4 enzyme. Hopefully in future, compound 7g could be used as a lead compound for developing new antidiabetic agent with good antioxidant property. |
| doi_str_mv | 10.1016/j.bioorg.2017.02.004 |
| format | Article |
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[Display omitted]
•N3-benzylidene (substituted)-2-phenyl-N4-(thiazol-2-yl)-quinazoline-3,4-(4H)-diamine derivatives were design and synthesized.•Title compounds were screening for in vitro dipeptidyl peptidase IV (DPP-4) inhibitory activity and diphenyl-2-picryl-hydrazyl (DPPH) assay.•Docking study was also performed to provide an insight about the binding mode into binding sites of DPP-4 enzyme.•Compound 7g could be used as a lead compound for developing new antidiabetic agent with good antioxidant property.
New N3-benzylidene (substituted)-2-phenyl-N4-(thiazol-2-yl)-quinazoline-3,4-(4H)-diamine derivatives were design and synthesized by a sequence of reactions starting from appropriate 6-methyl anthranilic acid. The title compounds were screened for in vitro dipeptidyl peptidase IV (DPP-4) inhibitory activity and diphenyl-2-picryl-hydrazyl (DPPH) assay and results showed significant to good activity in compared to Linagliptin for antidiabetic activity and Ascorbic acid for antioxidant activity. Compound 7g (IC50=0.76nM) exhibited most promising DPP-4 inhibitory activity and also showed good antioxid and result. Docking study was also performed to provide an insight about the binding mode into binding sites of DPP-4 enzyme. Hopefully in future, compound 7g could be used as a lead compound for developing new antidiabetic agent with good antioxidant property.</description><identifier>ISSN: 0045-2068</identifier><identifier>EISSN: 1090-2120</identifier><identifier>DOI: 10.1016/j.bioorg.2017.02.004</identifier><identifier>PMID: 28215601</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Animals ; Antioxidants - chemical synthesis ; Antioxidants - chemistry ; Antioxidants - pharmacology ; Antioxidants - therapeutic use ; Biphenyl Compounds - antagonists & inhibitors ; Diabetes Mellitus, Experimental - drug therapy ; Diabetes Mellitus, Experimental - enzymology ; Dipeptidyl Peptidase 4 - metabolism ; Dipeptidyl-Peptidase IV Inhibitors - chemical synthesis ; Dipeptidyl-Peptidase IV Inhibitors - chemistry ; Dipeptidyl-Peptidase IV Inhibitors - pharmacology ; Dipeptidyl-Peptidase IV Inhibitors - therapeutic use ; DPP-4 inhibitors ; DPPH ; Drug Design ; Free Radicals - antagonists & inhibitors ; Hypoglycemic Agents - chemical synthesis ; Hypoglycemic Agents - chemistry ; Hypoglycemic Agents - pharmacology ; Hypoglycemic Agents - therapeutic use ; Molecular docking ; Molecular Docking Simulation ; Picrates - antagonists & inhibitors ; Quinazoline ; Quinazolines - chemical synthesis ; Quinazolines - chemistry ; Quinazolines - pharmacology ; Quinazolines - therapeutic use ; Rats, Wistar ; Thiazoles - chemical synthesis ; Thiazoles - chemistry ; Thiazoles - pharmacology ; Thiazoles - therapeutic use ; Thiazoline</subject><ispartof>Bioorganic chemistry, 2017-04, Vol.71, p.181-191</ispartof><rights>2017 Elsevier Inc.</rights><rights>Copyright © 2017 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c362t-c079b9a05ee02e5994891522f2d2728dd99dff8745f75c09dad7a3a5ece3ffce3</citedby><cites>FETCH-LOGICAL-c362t-c079b9a05ee02e5994891522f2d2728dd99dff8745f75c09dad7a3a5ece3ffce3</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.2017.02.004$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,778,782,3539,27911,27912,45982</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28215601$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ali, Zulphikar</creatorcontrib><creatorcontrib>Akhtar, Md Jawaid</creatorcontrib><creatorcontrib>Haider, Md Rafi</creatorcontrib><creatorcontrib>Khan, Ahsan Ahmed</creatorcontrib><creatorcontrib>Siddiqui, Anees Ahmad</creatorcontrib><creatorcontrib>Yar, M. Shahar</creatorcontrib><title>Design and synthesis of quinazoline-3,4-(4H)-diamine endowed with thiazoline moiety as new class for DPP-4 and DPPH inhibitor</title><title>Bioorganic chemistry</title><addtitle>Bioorg Chem</addtitle><description>New N3-benzylidene (substituted)-2-phenyl-N4-(thiazol-2-yl)-quinazoline-3,4-(4H)-diamine derivatives were designed and synthesized by a sequence of reactions starting from appropriate 6-methyl anthranilic acid. Hopefully in future, compound 7g could be used as a lead compound for developing new antidiabetic agent with good antioxidant property.
[Display omitted]
•N3-benzylidene (substituted)-2-phenyl-N4-(thiazol-2-yl)-quinazoline-3,4-(4H)-diamine derivatives were design and synthesized.•Title compounds were screening for in vitro dipeptidyl peptidase IV (DPP-4) inhibitory activity and diphenyl-2-picryl-hydrazyl (DPPH) assay.•Docking study was also performed to provide an insight about the binding mode into binding sites of DPP-4 enzyme.•Compound 7g could be used as a lead compound for developing new antidiabetic agent with good antioxidant property.
New N3-benzylidene (substituted)-2-phenyl-N4-(thiazol-2-yl)-quinazoline-3,4-(4H)-diamine derivatives were design and synthesized by a sequence of reactions starting from appropriate 6-methyl anthranilic acid. The title compounds were screened for in vitro dipeptidyl peptidase IV (DPP-4) inhibitory activity and diphenyl-2-picryl-hydrazyl (DPPH) assay and results showed significant to good activity in compared to Linagliptin for antidiabetic activity and Ascorbic acid for antioxidant activity. Compound 7g (IC50=0.76nM) exhibited most promising DPP-4 inhibitory activity and also showed good antioxid and result. Docking study was also performed to provide an insight about the binding mode into binding sites of DPP-4 enzyme. Hopefully in future, compound 7g could be used as a lead compound for developing new antidiabetic agent with good antioxidant property.</description><subject>Animals</subject><subject>Antioxidants - chemical synthesis</subject><subject>Antioxidants - chemistry</subject><subject>Antioxidants - pharmacology</subject><subject>Antioxidants - therapeutic use</subject><subject>Biphenyl Compounds - antagonists & inhibitors</subject><subject>Diabetes Mellitus, Experimental - drug therapy</subject><subject>Diabetes Mellitus, Experimental - enzymology</subject><subject>Dipeptidyl Peptidase 4 - metabolism</subject><subject>Dipeptidyl-Peptidase IV Inhibitors - chemical synthesis</subject><subject>Dipeptidyl-Peptidase IV Inhibitors - chemistry</subject><subject>Dipeptidyl-Peptidase IV Inhibitors - pharmacology</subject><subject>Dipeptidyl-Peptidase IV Inhibitors - therapeutic use</subject><subject>DPP-4 inhibitors</subject><subject>DPPH</subject><subject>Drug Design</subject><subject>Free Radicals - antagonists & inhibitors</subject><subject>Hypoglycemic Agents - chemical synthesis</subject><subject>Hypoglycemic Agents - chemistry</subject><subject>Hypoglycemic Agents - pharmacology</subject><subject>Hypoglycemic Agents - therapeutic use</subject><subject>Molecular docking</subject><subject>Molecular Docking Simulation</subject><subject>Picrates - antagonists & inhibitors</subject><subject>Quinazoline</subject><subject>Quinazolines - chemical synthesis</subject><subject>Quinazolines - chemistry</subject><subject>Quinazolines - pharmacology</subject><subject>Quinazolines - therapeutic use</subject><subject>Rats, Wistar</subject><subject>Thiazoles - chemical synthesis</subject><subject>Thiazoles - chemistry</subject><subject>Thiazoles - pharmacology</subject><subject>Thiazoles - therapeutic use</subject><subject>Thiazoline</subject><issn>0045-2068</issn><issn>1090-2120</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMFuEzEQhi0EoqHwBgj5WCR2GTve9fqCVLVAkCrRA5wtxx43jnbt1t4QBYl3xyWBIxePPfrGv-Yj5DWDlgHr32_bdUgp37UcmGyBtwDiCVkwUNBwxuEpWdRO13DohzPyopQtAGNC9s_JGR8463pgC_LrGku4i9RER8shzpv6LDR5-rAL0fxMY4jYLN-J5kKs3jYumKk2KEaX9ujoPswbOm_CCaRTCjgfqCk04p7a0ZRCfcr0-va2EX8y6m1FQ9yEdZhTfkmeeTMWfHWq5-T7p4_frlbNzdfPX64ubxq77PncWJBqrQx0iMCxU0oMinWce-645INzSjnvByk6LzsLyhknzdJ0aHHpfT3OycXx3_ucHnZYZj2FYnEcTcS0K5oNEnohJKiKiiNqcyolo9f3OUwmHzQD_Sheb_VRvH4Ur4HrqrmOvTkl7NYTun9Df01X4MMRwLrnj4BZFxswWnQho521S-H_Cb8BRK-WAQ</recordid><startdate>201704</startdate><enddate>201704</enddate><creator>Ali, Zulphikar</creator><creator>Akhtar, Md Jawaid</creator><creator>Haider, Md Rafi</creator><creator>Khan, Ahsan Ahmed</creator><creator>Siddiqui, Anees Ahmad</creator><creator>Yar, M. Shahar</creator><general>Elsevier Inc</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>201704</creationdate><title>Design and synthesis of quinazoline-3,4-(4H)-diamine endowed with thiazoline moiety as new class for DPP-4 and DPPH inhibitor</title><author>Ali, Zulphikar ; Akhtar, Md Jawaid ; Haider, Md Rafi ; Khan, Ahsan Ahmed ; Siddiqui, Anees Ahmad ; Yar, M. Shahar</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c362t-c079b9a05ee02e5994891522f2d2728dd99dff8745f75c09dad7a3a5ece3ffce3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Animals</topic><topic>Antioxidants - chemical synthesis</topic><topic>Antioxidants - chemistry</topic><topic>Antioxidants - pharmacology</topic><topic>Antioxidants - therapeutic use</topic><topic>Biphenyl Compounds - antagonists & inhibitors</topic><topic>Diabetes Mellitus, Experimental - drug therapy</topic><topic>Diabetes Mellitus, Experimental - enzymology</topic><topic>Dipeptidyl Peptidase 4 - metabolism</topic><topic>Dipeptidyl-Peptidase IV Inhibitors - chemical synthesis</topic><topic>Dipeptidyl-Peptidase IV Inhibitors - chemistry</topic><topic>Dipeptidyl-Peptidase IV Inhibitors - pharmacology</topic><topic>Dipeptidyl-Peptidase IV Inhibitors - therapeutic use</topic><topic>DPP-4 inhibitors</topic><topic>DPPH</topic><topic>Drug Design</topic><topic>Free Radicals - antagonists & inhibitors</topic><topic>Hypoglycemic Agents - chemical synthesis</topic><topic>Hypoglycemic Agents - chemistry</topic><topic>Hypoglycemic Agents - pharmacology</topic><topic>Hypoglycemic Agents - therapeutic use</topic><topic>Molecular docking</topic><topic>Molecular Docking Simulation</topic><topic>Picrates - antagonists & inhibitors</topic><topic>Quinazoline</topic><topic>Quinazolines - chemical synthesis</topic><topic>Quinazolines - chemistry</topic><topic>Quinazolines - pharmacology</topic><topic>Quinazolines - therapeutic use</topic><topic>Rats, Wistar</topic><topic>Thiazoles - chemical synthesis</topic><topic>Thiazoles - chemistry</topic><topic>Thiazoles - pharmacology</topic><topic>Thiazoles - therapeutic use</topic><topic>Thiazoline</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ali, Zulphikar</creatorcontrib><creatorcontrib>Akhtar, Md Jawaid</creatorcontrib><creatorcontrib>Haider, Md Rafi</creatorcontrib><creatorcontrib>Khan, Ahsan Ahmed</creatorcontrib><creatorcontrib>Siddiqui, Anees Ahmad</creatorcontrib><creatorcontrib>Yar, M. Shahar</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ali, Zulphikar</au><au>Akhtar, Md Jawaid</au><au>Haider, Md Rafi</au><au>Khan, Ahsan Ahmed</au><au>Siddiqui, Anees Ahmad</au><au>Yar, M. Shahar</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design and synthesis of quinazoline-3,4-(4H)-diamine endowed with thiazoline moiety as new class for DPP-4 and DPPH inhibitor</atitle><jtitle>Bioorganic chemistry</jtitle><addtitle>Bioorg Chem</addtitle><date>2017-04</date><risdate>2017</risdate><volume>71</volume><spage>181</spage><epage>191</epage><pages>181-191</pages><issn>0045-2068</issn><eissn>1090-2120</eissn><abstract>New N3-benzylidene (substituted)-2-phenyl-N4-(thiazol-2-yl)-quinazoline-3,4-(4H)-diamine derivatives were designed and synthesized by a sequence of reactions starting from appropriate 6-methyl anthranilic acid. Hopefully in future, compound 7g could be used as a lead compound for developing new antidiabetic agent with good antioxidant property.
[Display omitted]
•N3-benzylidene (substituted)-2-phenyl-N4-(thiazol-2-yl)-quinazoline-3,4-(4H)-diamine derivatives were design and synthesized.•Title compounds were screening for in vitro dipeptidyl peptidase IV (DPP-4) inhibitory activity and diphenyl-2-picryl-hydrazyl (DPPH) assay.•Docking study was also performed to provide an insight about the binding mode into binding sites of DPP-4 enzyme.•Compound 7g could be used as a lead compound for developing new antidiabetic agent with good antioxidant property.
New N3-benzylidene (substituted)-2-phenyl-N4-(thiazol-2-yl)-quinazoline-3,4-(4H)-diamine derivatives were design and synthesized by a sequence of reactions starting from appropriate 6-methyl anthranilic acid. The title compounds were screened for in vitro dipeptidyl peptidase IV (DPP-4) inhibitory activity and diphenyl-2-picryl-hydrazyl (DPPH) assay and results showed significant to good activity in compared to Linagliptin for antidiabetic activity and Ascorbic acid for antioxidant activity. Compound 7g (IC50=0.76nM) exhibited most promising DPP-4 inhibitory activity and also showed good antioxid and result. Docking study was also performed to provide an insight about the binding mode into binding sites of DPP-4 enzyme. Hopefully in future, compound 7g could be used as a lead compound for developing new antidiabetic agent with good antioxidant property.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>28215601</pmid><doi>10.1016/j.bioorg.2017.02.004</doi><tpages>11</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0045-2068 |
| ispartof | Bioorganic chemistry, 2017-04, Vol.71, p.181-191 |
| issn | 0045-2068 1090-2120 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1870644709 |
| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Animals Antioxidants - chemical synthesis Antioxidants - chemistry Antioxidants - pharmacology Antioxidants - therapeutic use Biphenyl Compounds - antagonists & inhibitors Diabetes Mellitus, Experimental - drug therapy Diabetes Mellitus, Experimental - enzymology Dipeptidyl Peptidase 4 - metabolism Dipeptidyl-Peptidase IV Inhibitors - chemical synthesis Dipeptidyl-Peptidase IV Inhibitors - chemistry Dipeptidyl-Peptidase IV Inhibitors - pharmacology Dipeptidyl-Peptidase IV Inhibitors - therapeutic use DPP-4 inhibitors DPPH Drug Design Free Radicals - antagonists & inhibitors Hypoglycemic Agents - chemical synthesis Hypoglycemic Agents - chemistry Hypoglycemic Agents - pharmacology Hypoglycemic Agents - therapeutic use Molecular docking Molecular Docking Simulation Picrates - antagonists & inhibitors Quinazoline Quinazolines - chemical synthesis Quinazolines - chemistry Quinazolines - pharmacology Quinazolines - therapeutic use Rats, Wistar Thiazoles - chemical synthesis Thiazoles - chemistry Thiazoles - pharmacology Thiazoles - therapeutic use Thiazoline |
| title | Design and synthesis of quinazoline-3,4-(4H)-diamine endowed with thiazoline moiety as new class for DPP-4 and DPPH inhibitor |
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