1,2,3-三唑磺胺类化合物的合成及抗菌活性
|
摘要
以4-氨基苯磺酰胺为原料,其与氯乙酰氯反应得到中间体2-氯-N-(4-氨磺酰基苯基)乙酰胺(Ⅱ),然后Ⅱ与叠氮钠和端基炔"一锅法"反应合成了10个1, 2, 3-三唑类磺胺化合物(Ⅲa～j)。利用FTIR、1HNMR、13CNMR和ESI-MS对产物结构进行了表征。采用二倍稀释法测定了目标化合物的抗菌活性。结果表明:产物对金黄色葡萄球菌和大肠杆菌表现出一定的抗菌活性,特别是2-[4-(3-氟苯基)-1H-1,2,3-三唑-1-基]-N-(4-氨磺酰基苯基)乙酰胺(Ⅲh)对大肠杆菌的最低抑菌浓度MIC为0.25 mg/L,与阳性对照药环丙沙星相当。
2-Chloro-N-(4-sulfamoylphenyl)acetamide(Ⅱ) was prepared from p-amino benzene sulfonamide with chloroacetyl chloride.Then,ten 1,2,3-triazolyl sulfonamides(Ⅲa～j) were prepared using a known one-pot procedure starting from intermediate Ⅱ,sodium azide and terminal alkynes.The target compounds were characterized by FTIR,1 HNMR,13 CNMR,ESI-MS and elemental analysis and their antibacterial activities were determined by using double broth dilution method.The results showed that all the tested compounds exhibited antibacterial activities against S.aureus and E.coli to a certain extent.In particular,the compound 2-[4-(3-fluorophenyl)-1 H-1,2,3-triazol-1-yl]-N-(4-sulfamoylphenyl)acetamide(Ⅲh) with a minimal inhibitory concentration(MIC) value of 0.25 mg/L against E.coli was similar to the positive control drug(ciprofloxacin).
2-Chloro-N-(4-sulfamoylphenyl)acetamide(Ⅱ) was prepared from p-amino benzene sulfonamide with chloroacetyl chloride.Then,ten 1,2,3-triazolyl sulfonamides(Ⅲa～j) were prepared using a known one-pot procedure starting from intermediate Ⅱ,sodium azide and terminal alkynes.The target compounds were characterized by FTIR,1 HNMR,13 CNMR,ESI-MS and elemental analysis and their antibacterial activities were determined by using double broth dilution method.The results showed that all the tested compounds exhibited antibacterial activities against S.aureus and E.coli to a certain extent.In particular,the compound 2-[4-(3-fluorophenyl)-1 H-1,2,3-triazol-1-yl]-N-(4-sulfamoylphenyl)acetamide(Ⅲh) with a minimal inhibitory concentration(MIC) value of 0.25 mg/L against E.coli was similar to the positive control drug(ciprofloxacin).
引文
[1]Isik S,Kockar F,Aydin M,et al.Carbonic anhydrase inhibitors:Inhibition of theβ-class enzyme from the yeast saccharomyces cerevisiae with sulfonamides and sulfamates[J].Bioorganic&Medicinal Chemistry,2009,17:1158-1163.
[2]Gawin R,De C E,Naesens L,et al.Synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure[J].Bioorganic&Medicinal Chemistry,2008,16(18):8379-8389.
[3]Bouissane L,Kazzouli S E,Léonce S,et al.Synthesis and biological evaluation of N-(7-indazolyl)benzenesulfonamide derivatives as potent cell cycle inhibitors[J].Bioorganic&Medicinal Chemistry,2006,14(4):1078-1088.
[4]Supuran C T.Carbonic anhydrases:Novel therapeutic applications for inhibitors and activators[J].Nature Reviews Drug Discovery,2008,7(2):168-181.
[5]Dragostin O M,Lupascu F,Vasile C,et al.Synthesis and biological evaluation of new 2-azetidinones with sulfonamide structures[J].Molecules,2013,18(4):4140-4157.
[6]KrátkyM,Vin?ováJ,VolkováM,et al.Antimicrobial activity of sulfonamides containing 5-chloro-2-hydroxybenzaldehyde and5-chloro-2-hydroxybenzoic acid scaffold.[J].European Journal of Medicinal Chemistry,2012,50(6):433-440.
[7]Ibrahim H S,Eldehna W M,Abdelaziz H A,et al.Improvement of antibacterial activity of some sulfa drugs through linkage to certain phthalazin-1(2H)-one scaffolds[J].European Journal of Medicinal Chemistry,2014,85(15):480-486.
[8]Aufort M,Herscovici J,Bouhours P,et al.Synthesis and antibiotic activity of a small molecules library of 1,2,3-triazole derivatives[J].Bioorganic&Medicinal Chemistry Letters,2008,18(3):1195-1198.
[9]Mara?i?S,Kraljevi?T G,Paljetak H?,et al.1,2,3-Triazole pharmacophore-based benzofused nitrogen/sulfur heterocycles with potential anti-Moraxella catarrhalis activity[J].Bioorganic&Medicinal Chemistry,2015,23(23):7448-7463.
[10]Raj R,Gut J,Rosenthal P J,et al.1H-1,2,3-triazole-tethered isatin-7-chloroquinoline and 3-hydroxy-indole-7-chloroquinoline conjugates:Synthesis and antimalarial evaluation[J].Bioorganic&Medicinal Chemistry Letters,2014,24(3):756-759.
[11]Wei G,Luan W,Wang S,et al.A library of 1,2,3-triazole-substituted oleanolic acid derivatives as anticancer agents:Design,synthesis and biological evaluation[J].Organic&Biomolecular Chemistry,2015,13(5):1507-1514.
[12]Boechat F D,Sacramento C Q,Cunha A C,et al.1,2,3-Triazolyl-4-oxoquinolines:A feasible beginning for promising chemical structures to inhibit oseltamivir-resistant influenza A and B viruses[J].Bioorganic&Medicinal Chemistry,2015,23(24):7777-7784.
[13]Shaikh M H,Subhedar D D,Khan F A K,et al.1,2,3-Triazole incorporated coumarin derivatives as potential antifungal and antioxidant agents[J].Chinese Chemical Letters,2016,27(2):295-301.
[14]Reck F,Zhou F,Girardot M,et al.Identification of 4-substituted 1,2,3-triazoles as novel oxazolidinone antibacterial agents with reduced activity against monoamine oxidase A[J].Journal of Medicinal Chemistry,2005,48(2):499-506.
[15]Demaray J A,Thuener J E,Dawson M N,et al.Synthesis of triazole-oxazolidinones via a one-pot reaction and evaluation of their antimicrobial activity[J].Bioorganic&Medicinal Chemistry Letters,2008,18(17):4868-4871.
[16]Wang X L,Wan K,Zhou C H.Synthesis of novel sulfanilamidederived 1,2,3-triazoles and their evaluation for antibacterial and antifungal activities[J].European Journal of Medicinal Chemistry,2010,45(10):4631-4639.
[17]Huang X G,Zhang A Q,Chen D L.et al.4-Substituted 4-(1H-1,2,3-triazol-1-yl)piperidine:Novel C7 moieties of fluoroquinolones as antibacterial agents[J].Bioorganic&Medicinal Chemistry Letters,2010,20(9):2859-2863.
[18]Yu S,Chai X,Hu H,et al.Synthesis and antifungal evaluation of novel triazole derivatives as inhibitors of cytochrome P450 14-alphademethylase[J].European Journal of Medicinal Chemistry,2011,42(10):4435-4445.
[19]Alafeefy A M,Ceruso M,Al-Tamimi A M S,et al.Quinazolinesulfonamides with potent inhibitory activity against theα-carbonic anhydrase from vibrio cholerae[J].Bioorganic&Medicinal Chemistry,2014,22(19):5133-5140.
[20]Ni Yuxing(倪语星),Wang Jinliang(王金良),Xu Yingchun(徐英春).et al.Antimicrobial susceptibility testing(second edition)[M].Shanghai:Shanghai Science and Technology Press(上海科技出版社),2009:27-35.
[2]Gawin R,De C E,Naesens L,et al.Synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure[J].Bioorganic&Medicinal Chemistry,2008,16(18):8379-8389.
[3]Bouissane L,Kazzouli S E,Léonce S,et al.Synthesis and biological evaluation of N-(7-indazolyl)benzenesulfonamide derivatives as potent cell cycle inhibitors[J].Bioorganic&Medicinal Chemistry,2006,14(4):1078-1088.
[4]Supuran C T.Carbonic anhydrases:Novel therapeutic applications for inhibitors and activators[J].Nature Reviews Drug Discovery,2008,7(2):168-181.
[5]Dragostin O M,Lupascu F,Vasile C,et al.Synthesis and biological evaluation of new 2-azetidinones with sulfonamide structures[J].Molecules,2013,18(4):4140-4157.
[6]KrátkyM,Vin?ováJ,VolkováM,et al.Antimicrobial activity of sulfonamides containing 5-chloro-2-hydroxybenzaldehyde and5-chloro-2-hydroxybenzoic acid scaffold.[J].European Journal of Medicinal Chemistry,2012,50(6):433-440.
[7]Ibrahim H S,Eldehna W M,Abdelaziz H A,et al.Improvement of antibacterial activity of some sulfa drugs through linkage to certain phthalazin-1(2H)-one scaffolds[J].European Journal of Medicinal Chemistry,2014,85(15):480-486.
[8]Aufort M,Herscovici J,Bouhours P,et al.Synthesis and antibiotic activity of a small molecules library of 1,2,3-triazole derivatives[J].Bioorganic&Medicinal Chemistry Letters,2008,18(3):1195-1198.
[9]Mara?i?S,Kraljevi?T G,Paljetak H?,et al.1,2,3-Triazole pharmacophore-based benzofused nitrogen/sulfur heterocycles with potential anti-Moraxella catarrhalis activity[J].Bioorganic&Medicinal Chemistry,2015,23(23):7448-7463.
[10]Raj R,Gut J,Rosenthal P J,et al.1H-1,2,3-triazole-tethered isatin-7-chloroquinoline and 3-hydroxy-indole-7-chloroquinoline conjugates:Synthesis and antimalarial evaluation[J].Bioorganic&Medicinal Chemistry Letters,2014,24(3):756-759.
[11]Wei G,Luan W,Wang S,et al.A library of 1,2,3-triazole-substituted oleanolic acid derivatives as anticancer agents:Design,synthesis and biological evaluation[J].Organic&Biomolecular Chemistry,2015,13(5):1507-1514.
[12]Boechat F D,Sacramento C Q,Cunha A C,et al.1,2,3-Triazolyl-4-oxoquinolines:A feasible beginning for promising chemical structures to inhibit oseltamivir-resistant influenza A and B viruses[J].Bioorganic&Medicinal Chemistry,2015,23(24):7777-7784.
[13]Shaikh M H,Subhedar D D,Khan F A K,et al.1,2,3-Triazole incorporated coumarin derivatives as potential antifungal and antioxidant agents[J].Chinese Chemical Letters,2016,27(2):295-301.
[14]Reck F,Zhou F,Girardot M,et al.Identification of 4-substituted 1,2,3-triazoles as novel oxazolidinone antibacterial agents with reduced activity against monoamine oxidase A[J].Journal of Medicinal Chemistry,2005,48(2):499-506.
[15]Demaray J A,Thuener J E,Dawson M N,et al.Synthesis of triazole-oxazolidinones via a one-pot reaction and evaluation of their antimicrobial activity[J].Bioorganic&Medicinal Chemistry Letters,2008,18(17):4868-4871.
[16]Wang X L,Wan K,Zhou C H.Synthesis of novel sulfanilamidederived 1,2,3-triazoles and their evaluation for antibacterial and antifungal activities[J].European Journal of Medicinal Chemistry,2010,45(10):4631-4639.
[17]Huang X G,Zhang A Q,Chen D L.et al.4-Substituted 4-(1H-1,2,3-triazol-1-yl)piperidine:Novel C7 moieties of fluoroquinolones as antibacterial agents[J].Bioorganic&Medicinal Chemistry Letters,2010,20(9):2859-2863.
[18]Yu S,Chai X,Hu H,et al.Synthesis and antifungal evaluation of novel triazole derivatives as inhibitors of cytochrome P450 14-alphademethylase[J].European Journal of Medicinal Chemistry,2011,42(10):4435-4445.
[19]Alafeefy A M,Ceruso M,Al-Tamimi A M S,et al.Quinazolinesulfonamides with potent inhibitory activity against theα-carbonic anhydrase from vibrio cholerae[J].Bioorganic&Medicinal Chemistry,2014,22(19):5133-5140.
[20]Ni Yuxing(倪语星),Wang Jinliang(王金良),Xu Yingchun(徐英春).et al.Antimicrobial susceptibility testing(second edition)[M].Shanghai:Shanghai Science and Technology Press(上海科技出版社),2009:27-35.
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |