一个基于N′-(3-溴-5-氯-2-羟基苯亚甲基)-3-羟基-4-甲氧基苯甲酰肼的甲基麦芽酚配位的氧钒(Ⅴ)配合物:合成、晶体结构及其胰岛素增强活性（英文）
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摘要
制备了1个芳酰腙化合物:N′-(3-溴-5-氯-2-羟基苯亚甲基)-3-羟基-4-甲氧基苯甲酰肼(H2L),并利用元素分析、红外、紫外、高分辨质谱、核磁共振氢谱和碳谱对其进行了表征。利用H2L与甲基麦芽酚和VO(acac)2在甲醇中反应得到了1个甲基麦芽酚配位的氧钒(Ⅴ)配合物[VO(mat)L]·Me OH。通过元素分析、红外和紫外光谱对其进行了表征,同时还研究了配合物的热稳定性。通过单晶X射线衍射进一步确认了H2L和配合物的结构。通过对C2C12肌细胞的胰岛素模拟实验,表明该配合物能显著促进细胞对葡萄糖的利用,其细胞毒性仅为0.07 g·L-1。
An aroylhydrazone compound, N′-(3-bromo-5-chloro-2-hydroxybenzylidene)-3-hydroxyl-4-methoxybenzohydrazide(H2L), was prepared and characterized by elemental analysis, IR, UV, HRMS,1H NMR and13 C NMR spectrum. Reaction of H2 L, maltol(3-hydroxy-2-methyl-4-pyrone) and VO(acac)2in methanol afforded a maltolatocoordinated oxovanadium (Ⅴ) complex, [VO(mat)L]·Me OH. The complex was characterized by elemental analysis,IR and UV spectra. Thermal analysis was also performed. Structures of H2 L and the complex were further confirmed by single crystal X-ray diffraction. Insulin-mimetic tests on C2C12 muscle cells indicate that the complex significantly stimulated cell glucose utilization with cytotoxicity at 0.07 g·L-1.
An aroylhydrazone compound, N′-(3-bromo-5-chloro-2-hydroxybenzylidene)-3-hydroxyl-4-methoxybenzohydrazide(H2L), was prepared and characterized by elemental analysis, IR, UV, HRMS,1H NMR and13 C NMR spectrum. Reaction of H2 L, maltol(3-hydroxy-2-methyl-4-pyrone) and VO(acac)2in methanol afforded a maltolatocoordinated oxovanadium (Ⅴ) complex, [VO(mat)L]·Me OH. The complex was characterized by elemental analysis,IR and UV spectra. Thermal analysis was also performed. Structures of H2 L and the complex were further confirmed by single crystal X-ray diffraction. Insulin-mimetic tests on C2C12 muscle cells indicate that the complex significantly stimulated cell glucose utilization with cytotoxicity at 0.07 g·L-1.
引文
[1]Pillai S I,Subramanian S P,Kandaswamy M.Eur.J.Med.Chem.,2013,63:109-117
[2]Smee J J,Epps J A,Ooms K,et al.J.Inorg.Biochem.,2009,103:575-584
[3]Sanna D,Micera G,Garribba E.Inorg.Chem.,2013,52:11975-11985
[4]He L,Wang X S,Zhao C,et al.Metallomics,2014,6:1087-1096
[5]Crans D C,Trujillo A M,Pharazyn P S,et al.Coord.Chem.Rev.,2011,255:2178-2192
[6]Sheela A,Roopan S M,Vijayaraghavan R.Eur.J.Med.Chem.,2008,43:2206-2210
[7]Zhang Y,Yang X D,Wang K,et al.J.Inorg.Biochem.,2006,100:80-87
[8]Dornyei A,Marcao S,Pessoa J C,et al.Eur.J.Inorg.Chem.,2006,18:3614-3621
[9]Haratake M,Fukunaga M,Ono M,et al.J.Biol.Inorg.Chem.,2005,10:250-258
[10]Mc Neill J H,Yuen V G,Hoveyda H R,et al.J.Med.Chem.,1992,35:1489-1491
[11]Yuen V G,Orvig C,Mc Neill J H.Can.J.Physiol.Pharmacol.,1993,71:263-269
[12]Yuen V G,Orvig C,Thompson K H,et al.Can.J.Physiol.Pharmacol.,1993,71:270-276
[13]Fujimoto S,Fujii K,Yasui H.J.Clin.Biochem.Nutr.,1997,23:113-129
[14]Nejo A A,Kolawole G A,Opoku A R,et al.J.Coord.Chem.,2009,62:3411-3424
[15]Xie M J,Yang X D,Liu W P,et al.J.Inorg.Biochem.,2010,104:851-857
[16]Amir M,Ali I,Hassan M Z,et al.Arch.Pharm.,2014,347:958-968
[17]Rajitha G,Prasad K V S R G,Umamaheswari A,et al.Med.Chem.Res.,2014,23:5204-5214
[18]El-Sayed M A A,Abdel-Aziz N I,Abdel-Aziz A A M,et al.Bioorg.Med.Chem.,2011,19:3416-3424
[19]Horiuchi T,Chiba J,Uoto K,et al.Bioorg.Med.Chem.Lett.,2009,19:305-308
[20]Zhang M,Xian D M,Li H H,et al.Aust.J.Chem.,2012,65:343-350
[21]SMART and SAINT,Bruker AXS Inc.,Madison,2002.
[22]Sheldrick G M.SADABS,University of G觟ttingen,Germany,1996.
[23]Sheldrick G M.Acta Crystallogr.,2008,A64:112-122
[24]Dinda R,Sengupta P,Ghosh S,et al.J.Chem.Soc.Dalton Trans.,2002:4434-4439
[25]REN Jin-Qi(任晋琦),JIAO Qing-Zhu(焦庆祝),WANG YiNuo(王艺诺),et al.Chinese J.Inorg.Chem.(无机化学学报),2014,30(3):640-648
[26]ZHAO Yue(赵月),HAN Xiao(韩笑),ZHOU Xiao-Xia(周晓霞),et al.Chinese J.Inorg.Chem.(无机化学学报),2013,29(4):867-874
[27]HE Miao(贺淼),JIAO Qing-Zhu(焦庆祝),CHEN Xiang-Fei(陈相飞),et al.Chinese J.Inorg.Chem.(无机化学学报),2015,31(8):1590-1596
[28]You Z L,Xian D M,Zhang M.Cryst Eng Comm,2012,14:7133-7136
[29]Sangeetha N R,Kavita V,Wocadlo S.J.Coord.Chem.,2000,51:55-66
[30]Asgedom G,Sreedhara A,Kivikoski J,et al.J.Chem.Soc.,Dalton Trans.,1996,1:93-97
[2]Smee J J,Epps J A,Ooms K,et al.J.Inorg.Biochem.,2009,103:575-584
[3]Sanna D,Micera G,Garribba E.Inorg.Chem.,2013,52:11975-11985
[4]He L,Wang X S,Zhao C,et al.Metallomics,2014,6:1087-1096
[5]Crans D C,Trujillo A M,Pharazyn P S,et al.Coord.Chem.Rev.,2011,255:2178-2192
[6]Sheela A,Roopan S M,Vijayaraghavan R.Eur.J.Med.Chem.,2008,43:2206-2210
[7]Zhang Y,Yang X D,Wang K,et al.J.Inorg.Biochem.,2006,100:80-87
[8]Dornyei A,Marcao S,Pessoa J C,et al.Eur.J.Inorg.Chem.,2006,18:3614-3621
[9]Haratake M,Fukunaga M,Ono M,et al.J.Biol.Inorg.Chem.,2005,10:250-258
[10]Mc Neill J H,Yuen V G,Hoveyda H R,et al.J.Med.Chem.,1992,35:1489-1491
[11]Yuen V G,Orvig C,Mc Neill J H.Can.J.Physiol.Pharmacol.,1993,71:263-269
[12]Yuen V G,Orvig C,Thompson K H,et al.Can.J.Physiol.Pharmacol.,1993,71:270-276
[13]Fujimoto S,Fujii K,Yasui H.J.Clin.Biochem.Nutr.,1997,23:113-129
[14]Nejo A A,Kolawole G A,Opoku A R,et al.J.Coord.Chem.,2009,62:3411-3424
[15]Xie M J,Yang X D,Liu W P,et al.J.Inorg.Biochem.,2010,104:851-857
[16]Amir M,Ali I,Hassan M Z,et al.Arch.Pharm.,2014,347:958-968
[17]Rajitha G,Prasad K V S R G,Umamaheswari A,et al.Med.Chem.Res.,2014,23:5204-5214
[18]El-Sayed M A A,Abdel-Aziz N I,Abdel-Aziz A A M,et al.Bioorg.Med.Chem.,2011,19:3416-3424
[19]Horiuchi T,Chiba J,Uoto K,et al.Bioorg.Med.Chem.Lett.,2009,19:305-308
[20]Zhang M,Xian D M,Li H H,et al.Aust.J.Chem.,2012,65:343-350
[21]SMART and SAINT,Bruker AXS Inc.,Madison,2002.
[22]Sheldrick G M.SADABS,University of G觟ttingen,Germany,1996.
[23]Sheldrick G M.Acta Crystallogr.,2008,A64:112-122
[24]Dinda R,Sengupta P,Ghosh S,et al.J.Chem.Soc.Dalton Trans.,2002:4434-4439
[25]REN Jin-Qi(任晋琦),JIAO Qing-Zhu(焦庆祝),WANG YiNuo(王艺诺),et al.Chinese J.Inorg.Chem.(无机化学学报),2014,30(3):640-648
[26]ZHAO Yue(赵月),HAN Xiao(韩笑),ZHOU Xiao-Xia(周晓霞),et al.Chinese J.Inorg.Chem.(无机化学学报),2013,29(4):867-874
[27]HE Miao(贺淼),JIAO Qing-Zhu(焦庆祝),CHEN Xiang-Fei(陈相飞),et al.Chinese J.Inorg.Chem.(无机化学学报),2015,31(8):1590-1596
[28]You Z L,Xian D M,Zhang M.Cryst Eng Comm,2012,14:7133-7136
[29]Sangeetha N R,Kavita V,Wocadlo S.J.Coord.Chem.,2000,51:55-66
[30]Asgedom G,Sreedhara A,Kivikoski J,et al.J.Chem.Soc.,Dalton Trans.,1996,1:93-97
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