Synthesis, Theoretical Calculation and α-glucosidase inhibition of new chalcone oximes
A series of eleven hydroxy and methoxy substituted new chalcone oximes (2a-2k) were synthesized by the condensation of chalcone (1a-1k) with hydroxylamine hydrochloride in pyridine. Structures of the synthesized compounds were characterized using NMR (1D; 1H, 13C/APT and 2D 1H- 1H COSY, NOESY and RO...
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| Veröffentlicht in: | Organic communications 2018-01, Vol.11 (1), p.23-34 |
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| creator | Fandaklı, Seda Doğan, İnci Selin Sellitepe, Hasan Erdinç Yaşar, Ahmet Yaylı, Nurettin |
| description | A series of eleven hydroxy and methoxy substituted new chalcone oximes (2a-2k) were synthesized by the condensation of chalcone (1a-1k) with hydroxylamine hydrochloride in pyridine. Structures of the synthesized compounds were characterized using NMR (1D; 1H, 13C/APT and 2D 1H- 1H COSY, NOESY and ROESY), FT-IR, UV, LC-MS/MS spectral data and elemental analysis. These synthetic compounds (2a-k) were screened for their α-glucosidase inhibition. The most α-glucosidase inhibitory activity were observe on compounds 2a and 2b with in the range of 1.61-3.36 µM (IC 50 values) which were more active then acarbose (IC 50, 13,34 µM). IC 50 values of other synthesized compounds 2c-2h are within the range of 7,25-25,55 µM which were more or as active as acarbose, but, IC 50 values for compounds 2j-2k were not observed. The geometric isomers of compounds 2a-2k were calculated theoretically. Experimental and theoretical calculations showed that cisoid 1E,2E is the most stable geometrical isomer of all. |
| doi_str_mv | 10.25135/acg.oc.38.18.02.067 |
| format | Article |
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Structures of the synthesized compounds were characterized using NMR (1D; 1H, 13C/APT and 2D 1H- 1H COSY, NOESY and ROESY), FT-IR, UV, LC-MS/MS spectral data and elemental analysis. These synthetic compounds (2a-k) were screened for their α-glucosidase inhibition. The most α-glucosidase inhibitory activity were observe on compounds 2a and 2b with in the range of 1.61-3.36 µM (IC 50 values) which were more active then acarbose (IC 50, 13,34 µM). IC 50 values of other synthesized compounds 2c-2h are within the range of 7,25-25,55 µM which were more or as active as acarbose, but, IC 50 values for compounds 2j-2k were not observed. The geometric isomers of compounds 2a-2k were calculated theoretically. Experimental and theoretical calculations showed that cisoid 1E,2E is the most stable geometrical isomer of all.</description><identifier>ISSN: 1307-6175</identifier><identifier>EISSN: 1307-6175</identifier><identifier>DOI: 10.25135/acg.oc.38.18.02.067</identifier><language>eng</language><publisher>Gebze: ACG Publications</publisher><subject>Acarbose ; Data processing ; Glucosidase ; Hydroxylamine ; Infrared radiation ; Isomers ; Mathematical analysis ; NMR ; Nuclear magnetic resonance ; Oximes ; Pyridines ; Synthesis ; α-Glucosidase</subject><ispartof>Organic communications, 2018-01, Vol.11 (1), p.23-34</ispartof><rights>2018. 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Experimental and theoretical calculations showed that cisoid 1E,2E is the most stable geometrical isomer of all.</description><subject>Acarbose</subject><subject>Data processing</subject><subject>Glucosidase</subject><subject>Hydroxylamine</subject><subject>Infrared radiation</subject><subject>Isomers</subject><subject>Mathematical analysis</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Oximes</subject><subject>Pyridines</subject><subject>Synthesis</subject><subject>α-Glucosidase</subject><issn>1307-6175</issn><issn>1307-6175</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>8G5</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><sourceid>GUQSH</sourceid><sourceid>M2O</sourceid><recordid>eNpNkE1OwzAQhS0EElXpDVhYYkuC7fFPskQVf1IlFhSxtBzbaVylcYlTQY_FRTgToWXB28yT3psZ6UPokpKcCQrixthVHm0ORU6LnLCcSHWCJhSIyiRV4vSfP0ezlNbkV4ooxSbo7WXfDY1PIV3jZeNj74dgTYvnprW71gwhdth0Dn9_Zat2Z2MKziSPQ9eEKhzSWOPOf2DbjBux8zh-ho1PF-isNm3ys785Ra_3d8v5Y7Z4fnia3y4yC0wMGXW1pww8SA-CKyko5cI5WRkpmOKVcw4soyALwWkJBgpeVd4YZUtrWAUwRVfHu9s-vu98GvQ67vpufKkZ4WVJJWdsbPFjy_Yxpd7XetuHjen3mhJ9oKhHijpaDYWmhSZMjxThBwPeZ8k</recordid><startdate>20180101</startdate><enddate>20180101</enddate><creator>Fandaklı, Seda</creator><creator>Doğan, İnci Selin</creator><creator>Sellitepe, Hasan Erdinç</creator><creator>Yaşar, Ahmet</creator><creator>Yaylı, Nurettin</creator><general>ACG Publications</general><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7XB</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FK</scope><scope>8G5</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>EDSIH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>HCIFZ</scope><scope>L6V</scope><scope>LK8</scope><scope>M2O</scope><scope>M7P</scope><scope>M7S</scope><scope>MBDVC</scope><scope>PADUT</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>PTHSS</scope><scope>Q9U</scope></search><sort><creationdate>20180101</creationdate><title>Synthesis, Theoretical Calculation and α-glucosidase inhibition of new chalcone oximes</title><author>Fandaklı, Seda ; 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Structures of the synthesized compounds were characterized using NMR (1D; 1H, 13C/APT and 2D 1H- 1H COSY, NOESY and ROESY), FT-IR, UV, LC-MS/MS spectral data and elemental analysis. These synthetic compounds (2a-k) were screened for their α-glucosidase inhibition. The most α-glucosidase inhibitory activity were observe on compounds 2a and 2b with in the range of 1.61-3.36 µM (IC 50 values) which were more active then acarbose (IC 50, 13,34 µM). IC 50 values of other synthesized compounds 2c-2h are within the range of 7,25-25,55 µM which were more or as active as acarbose, but, IC 50 values for compounds 2j-2k were not observed. The geometric isomers of compounds 2a-2k were calculated theoretically. Experimental and theoretical calculations showed that cisoid 1E,2E is the most stable geometrical isomer of all.</abstract><cop>Gebze</cop><pub>ACG Publications</pub><doi>10.25135/acg.oc.38.18.02.067</doi><tpages>12</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Acarbose Data processing Glucosidase Hydroxylamine Infrared radiation Isomers Mathematical analysis NMR Nuclear magnetic resonance Oximes Pyridines Synthesis α-Glucosidase |
| title | Synthesis, Theoretical Calculation and α-glucosidase inhibition of new chalcone oximes |
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