Page 124 - 201901

·110· 精细化工 FINE CHEMICALS 第 36 卷

球菌（S. aureus A209）和大肠杆菌（E. coli ATCC [4] Supuran C T. Carbonic anhydrases: Novel therapeutic applications
for inhibitors and activators[J]. Nature Reviews Drug Discovery,
25922）的最低抑菌浓度（MIC），结果见表 4。
2008, 7(2): 168-181.

表 4 化合物Ⅲa~j 的最低抑菌浓度（MIC） [5] Dragostin O M, Lupascu F, Vasile C, et al. Synthesis and biological
evaluation of new 2-azetidinones with sulfonamide structures[J].
Table 4 MIC of compounds Ⅲa~j against bacteria Molecules, 2013, 18(4): 4140-4157.
最低抑菌浓度/(mg/L) [6] Krátký M, Vinšová J, Volková M, et al. Antimicrobial activity of
化合物
金黄色葡萄球菌 A209 大肠杆菌 ATCC25922 sulfonamides containing 5-chloro-2-hydroxybenzaldehyde and
5-chloro-2-hydroxybenzoic acid scaffold.[J]. European Journal of
Ⅲa 16 8
Medicinal Chemistry, 2012, 50(6): 433-440.
Ⅲb 8 64
Ⅲc >64 16 [7] Ibrahim H S, Eldehna W M, Abdelaziz H A, et al. Improvement of
antibacterial activity of some sulfa drugs through linkage to certain
Ⅲd 16 8 phthalazin-1(2H)-one scaffolds[J]. European Journal of Medicinal
Ⅲe 8 8
Chemistry, 2014, 85(15): 480-486.
Ⅲf 32 16 [8] Aufort M, Herscovici J, Bouhours P, et al. Synthesis and antibiotic
Ⅲg 8 4 activity of a small molecules library of 1, 2, 3-triazole derivatives[J].
Ⅲh 32 0.25 Bioorganic & Medicinal Chemistry Letters, 2008, 18(3): 1195-1198.
Ⅲi 4 1 [9] Maračić S, Kraljević T G, Paljetak H Č, et al. 1, 2, 3-Triazole
Ⅲj 16 2 pharmacophore-based benzofused nitrogen/sulfur heterocycles with
环丙沙星 3.2 0.25 potential anti-Moraxella catarrhalis activity[J]. Bioorganic &Medicinal
Chemistry, 2015, 23(23): 7448-7463.
表 4 结果表明，大部分化合物对阳性菌和阴性 [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
菌均表现出不同程度的抗菌活性，尤其是化合物Ⅲi
conjugates: Synthesis and antimalarial evaluation[J]. Bioorganic &
对金黄色葡萄球菌（S. aureus A209）的 MIC 达到 Medicinal Chemistry Letters, 2014, 24(3): 756-759.
4 mg/L，接近阳性对照药环丙沙星。化合物Ⅲh 对 [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
大肠杆菌（E. coli ATCC25922）的 MIC 与阳性对照
biological evaluation[J]. Organic & Biomolecular Chemistry, 2015,
药环丙沙星相当（0.25 mg/L）。构效关系分析发现， 13(5): 1507-1514.
三唑环上有脂肪烃基取代时，抗菌活性较弱，苯基 [12] Boechat F D, Sacramento C Q, Cunha A C, et al. 1, 2, 3-Triazolyl-
4-oxoquinolines: A feasible beginning for promising chemical
取代时，活性较强。苯环上有氟取代时对大肠杆菌 structures to inhibit oseltamivir-resistant influenza A and B viruses[J].
抗菌活性最佳。 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
3 结论 incorporated coumarin derivatives as potential antifungal and
antioxidant agents[J]. Chinese Chemical Letters, 2016, 27(2): 295-
301.
通过点击化学和拼合原理设计合成了一系列 1, [14] Reck F, Zhou F, Girardot M, et al. Identification of 4-substituted 1, 2,
2, 3-三唑类磺胺化合物，具有反应时间短、后处理 3-triazoles as novel oxazolidinone antibacterial agents with reduced
activity against monoamine oxidase A[J]. Journal of Medicinal
13
1
简便和收率高的优点。利用 FTIR、HNMR、 CNMR Chemistry, 2005, 48(2): 499-506.
和 ESI-MS 等分析手段对目标化合物的结构进行了 [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
表征。该类化合物的抗菌活性测试结果表明，大部
antimicrobial activity[J]. Bioorganic & Medicinal Chemistry Letters,
分化合物普遍具有抗菌活性，尤其是化合物Ⅲi 对金 2008, 18(17): 4868-4871.
黄色葡萄球菌（S. aureus A209）的抑制活性接近阳 [16] Wang X L, Wan K, Zhou C H. Synthesis of novel sulfanilamide-
derived 1, 2, 3-triazoles and their evaluation for antibacterial and
性对照药环丙沙星。化合物Ⅲh 对大肠杆菌（E. coli
antifungal activities[J]. European Journal of Medicinal Chemistry,
ATCC25922）的抑制活性与阳性对照药环丙沙星活 2010, 45(10): 4631-4639.
性相当（0.25 mg/L），值得进一步深入研究。 [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,
参考文献：
2010, 20(9): 2859-2863.
[1] Isik S, Kockar F, Aydin M, et al. Carbonic anhydrase inhibitors: [18] Yu S, Chai X, Hu H, et al. Synthesis and antifungal evaluation of
Inhibition of the β-class enzyme from the yeast saccharomyces novel triazole derivatives as inhibitors of cytochrome P450 14-alpha-
cerevisiae with sulfonamides and sulfamates[J]. Bioorganic & demethylase[J]. European Journal of Medicinal Chemistry, 2011,
Medicinal Chemistry, 2009, 17: 1158-1163. 42(10): 4435-4445.
[2] Gawin R, De C E, Naesens L, et al. Synthesis and antiviral [19] Alafeefy A M, Ceruso M, Al-Tamimi A M S, et al. Quinazoline–
evaluation of acyclic azanucleosides developed from sulfanilamide as sulfonamides with potent inhibitory activity against the α-carbonic
a lead structure[J]. Bioorganic & Medicinal Chemistry, 2008, 16(18): anhydrase from vibrio cholerae[J]. Bioorganic & Medicinal Chemistry,
8379-8389. 2014, 22(19): 5133-5140.
[3] Bouissane L, Kazzouli S E, Léonce S, et al. Synthesis and biological [20] Ni Yuxing (倪语星), Wang Jinliang (王金良), Xu Yingchun (徐英
evaluation of N-(7-indazolyl) benzenesulfonamide derivatives as 春). et al. Antimicrobial susceptibility testing(second edition)[M].
potent cell cycle inhibitors[J]. Bioorganic & Medicinal Chemistry, Shanghai :Shanghai Science and Technology Press(上海科技出版
2006, 14(4): 1078-1088. 社), 2009: 27-35.