2-(4'-羧基苯基)-1,2-苯并异硒唑-3(H)-酮的合成与晶体结构及抑菌活性
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摘要
以邻氨基苯甲酸为原料,通过重氮化、二硒醚化、氯化和缩合反应,合成得到2-(4'-羧基苯基)-1,2-苯并异硒唑-3(H)-酮,化合物结构经HR-MS、~1H NMR、~(13)C NMR表征,采用XRD测定其单晶结构,该晶体属于单斜晶系,P21/c空间群,晶胞参数a=2.0641(3)nm,b=0.5000(17)nm,c=1.2046(1)nm,β=97.495(3)°,V=1.2326(6)nm~3,Dc=1.715 g·cm~3,Z=4,F(000)=632.0。初步抑菌试验发现该化合物对金黄色葡萄球菌和大肠杆菌有一定的抑菌活性(CCDC:1576226)。
Anthranilic acid was used as raw material.2-(4'-carboxyl phenyl)-1,2-benzoisoselenazole-3(H)-ketone was synthesized by the diazo-reaction,the disselenenylation,the chlorination and followed by the condensation reaction.The crystal structure was determined by HR-MS,~1H NMR,~(13)C NMR spectra and XRD.The crystal belongs to monoclinic,P2_1/c space group,lattice parameter of a = 2.0641(3) nm,b = 0.5000(17) nm,c = 1.2046(1) nm,β = 97.495(3) °,V = 1.2326(6) nm~3,Dc= 1.715 g·cm~3,Z = 4,F(000) = 632.0.Preliminary bacteriostatic test showed that the compound had the inhibition activity on Staphylococcus aureus and Escherichia coli(CCDC:1576226).
Anthranilic acid was used as raw material.2-(4'-carboxyl phenyl)-1,2-benzoisoselenazole-3(H)-ketone was synthesized by the diazo-reaction,the disselenenylation,the chlorination and followed by the condensation reaction.The crystal structure was determined by HR-MS,~1H NMR,~(13)C NMR spectra and XRD.The crystal belongs to monoclinic,P2_1/c space group,lattice parameter of a = 2.0641(3) nm,b = 0.5000(17) nm,c = 1.2046(1) nm,β = 97.495(3) °,V = 1.2326(6) nm~3,Dc= 1.715 g·cm~3,Z = 4,F(000) = 632.0.Preliminary bacteriostatic test showed that the compound had the inhibition activity on Staphylococcus aureus and Escherichia coli(CCDC:1576226).
引文
[1]Rayman M P.The importance of selenium to human health[J].Lancet,2000,356(9225):233.
[2]Whanger P D.Selenium and its relationship to cancer:an update[J].Brit J Nutr,2004,91(1):11.
[3]Duffieldlillico A J,Slate E H,Reid M E,et al.Selenium supplementation and secondary prevention of nonmelanoma skin cancer in a randomized trial[J].J Natl Cancer I,2003,95(19):1477-1481.
[4]Thomson C D.Assessment of requirements for selenium and adequacy of selenium status:a review[J].Eur J Clin Nutr,2004,58(3):391-402.
[5]Mossa A T H,Heikal T M,Mohafrash S M M.Lipid peroxidation and oxidative stress in rat erythrocytes induced by aspirin and diazinon:the protective role of selenium[J].Asian Pac Trop Biomed,2014,4(2):603-609.
[6]Li Y,Lin Z,Guo M,et al.Inhibitory activity of selenium nanoparticles functionalized with oseltamivir on H1N1 influenza virus[J].Int J Nanomed,2017,12:5733-5743.
[7]Hema Vunta,Faith Davis,Umamaheswari D.Palempalli,et al.The anti-inflammatory effects of selenium are mediated through 15-deoxy-Δ12,14-prostaglandin J2 in macrophages[J].J Bio Chem,2007,282(25):17964-17973.
[8]Zakrzewski J,Krawczyk M.Reactions of nitroxides.Part X:antifungal activity of selected sulfur and selenium derivatives of 2,2,6,6-tetramethylpiperidine[J].Bioorg Med Chem Lett,2011,21(1):514-516.
[9]Lu J,Jin L,Ge H,et al.Synthesis,crystal,computational study and biological activity of N-(1-(2,4-Dichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-4-(N,N-dipropylsulfamoyl)benzamide[J].Chin J Struct Chem,2017,36(11):1810-1816.
[10]Papp L V,Lu J,Holmgren A,et al.From selenium to selenoproteins:synthesis,identity,and their role in human health[J].Antioxid Redox Sign,2007,9(7):775-806.
[11]Ninomiya M,Garud D R,Koketsu M.Biologically significant selenium-containing heterocycles[J].Coordin Chem Rev,2011,255(23-24):2968-2990.
[12]徐汉生,肖颖歆,刘秀芳.苯并异硒唑酮氨基酸衍生物的合成及其抗脂质过氧化作用[J].有机化学,1995,15:252-258.
[13]肖颖歆,刘秀芳,徐汉生,等.Ebselen氨基酸衍生物的合成及其抗脂质过氧化作用[J].高等学校化学学报,1996,17(6):914-916.
[14]肖颖歆,黄祖云,刘秀芳,等.苯并异硒唑酮氨基酸衍生物的谷胱甘肽过氧化物酶样活性[J].应用化学,1997,14(3):66-69.
[15]Selvakumar K,Shah P,Singh H B,et al.Synthesis,structure,and glutathione peroxidase-like activity of amino acid containing ebselen analogues and diaryl diselenides.[J].Chem Eur J,2011,17(45):12741-12755.
[16]Sheldrick G M.A short history of SHELX[J].Acta Cryst,2008,64(1):112-122.
[17]Sheldrick G M.Crystal structure refinement with SHELXL[J].Acta Cryst,2015,C71:3-8.
[18]Li Z,Liu G,Meng L,et al.K1K8:an Hp1404-derived antibacterial peptide[J].Appl Microbio Biot,2016,100(11):5069-5077.
[19]Dupont L,Dideberg O,Jacquemin P.Structures de l'ebselen(phényl-2 2 H-benzisosélénazole-1,2 one-3)(I)et de l'acétonylséléno-2 benzanilide(II)[J].Acta Cryst,1990,46(3):484-486.
[20]Chan G,Hardej D,Santoro M,et al.Evaluation of the antimicrobial activity of ebselen:Role of the yeast plasma membrane H+‐ATPase[J].J Biochem Mol Toxic,2007,21(5):252-264.
[2]Whanger P D.Selenium and its relationship to cancer:an update[J].Brit J Nutr,2004,91(1):11.
[3]Duffieldlillico A J,Slate E H,Reid M E,et al.Selenium supplementation and secondary prevention of nonmelanoma skin cancer in a randomized trial[J].J Natl Cancer I,2003,95(19):1477-1481.
[4]Thomson C D.Assessment of requirements for selenium and adequacy of selenium status:a review[J].Eur J Clin Nutr,2004,58(3):391-402.
[5]Mossa A T H,Heikal T M,Mohafrash S M M.Lipid peroxidation and oxidative stress in rat erythrocytes induced by aspirin and diazinon:the protective role of selenium[J].Asian Pac Trop Biomed,2014,4(2):603-609.
[6]Li Y,Lin Z,Guo M,et al.Inhibitory activity of selenium nanoparticles functionalized with oseltamivir on H1N1 influenza virus[J].Int J Nanomed,2017,12:5733-5743.
[7]Hema Vunta,Faith Davis,Umamaheswari D.Palempalli,et al.The anti-inflammatory effects of selenium are mediated through 15-deoxy-Δ12,14-prostaglandin J2 in macrophages[J].J Bio Chem,2007,282(25):17964-17973.
[8]Zakrzewski J,Krawczyk M.Reactions of nitroxides.Part X:antifungal activity of selected sulfur and selenium derivatives of 2,2,6,6-tetramethylpiperidine[J].Bioorg Med Chem Lett,2011,21(1):514-516.
[9]Lu J,Jin L,Ge H,et al.Synthesis,crystal,computational study and biological activity of N-(1-(2,4-Dichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-4-(N,N-dipropylsulfamoyl)benzamide[J].Chin J Struct Chem,2017,36(11):1810-1816.
[10]Papp L V,Lu J,Holmgren A,et al.From selenium to selenoproteins:synthesis,identity,and their role in human health[J].Antioxid Redox Sign,2007,9(7):775-806.
[11]Ninomiya M,Garud D R,Koketsu M.Biologically significant selenium-containing heterocycles[J].Coordin Chem Rev,2011,255(23-24):2968-2990.
[12]徐汉生,肖颖歆,刘秀芳.苯并异硒唑酮氨基酸衍生物的合成及其抗脂质过氧化作用[J].有机化学,1995,15:252-258.
[13]肖颖歆,刘秀芳,徐汉生,等.Ebselen氨基酸衍生物的合成及其抗脂质过氧化作用[J].高等学校化学学报,1996,17(6):914-916.
[14]肖颖歆,黄祖云,刘秀芳,等.苯并异硒唑酮氨基酸衍生物的谷胱甘肽过氧化物酶样活性[J].应用化学,1997,14(3):66-69.
[15]Selvakumar K,Shah P,Singh H B,et al.Synthesis,structure,and glutathione peroxidase-like activity of amino acid containing ebselen analogues and diaryl diselenides.[J].Chem Eur J,2011,17(45):12741-12755.
[16]Sheldrick G M.A short history of SHELX[J].Acta Cryst,2008,64(1):112-122.
[17]Sheldrick G M.Crystal structure refinement with SHELXL[J].Acta Cryst,2015,C71:3-8.
[18]Li Z,Liu G,Meng L,et al.K1K8:an Hp1404-derived antibacterial peptide[J].Appl Microbio Biot,2016,100(11):5069-5077.
[19]Dupont L,Dideberg O,Jacquemin P.Structures de l'ebselen(phényl-2 2 H-benzisosélénazole-1,2 one-3)(I)et de l'acétonylséléno-2 benzanilide(II)[J].Acta Cryst,1990,46(3):484-486.
[20]Chan G,Hardej D,Santoro M,et al.Evaluation of the antimicrobial activity of ebselen:Role of the yeast plasma membrane H+‐ATPase[J].J Biochem Mol Toxic,2007,21(5):252-264.