Synthesis, Bioactivity, and the Anion-Binding Property of 2-Sulfydryl-1,3,4-thiodiazole Derivatives

被引:4
作者
Shang, Xuefang [1 ]
Li, Wanli [2 ]
Wei, Xiaofang [3 ]
Zhang, Huanle [3 ]
Fu, Zhiyuan [3 ]
Zhang, Jinlian [3 ]
Xu, Xiufang [4 ]
机构
[1] Xinxiang Med Univ, Dept Chem, Xinxiang 453003, Henan, Peoples R China
[2] Xinxiang Med Univ, Dept Immun, Xinxiang 453003, Henan, Peoples R China
[3] Xinxiang Med Univ, Sch Pharm, Xinxiang 453003, Henan, Peoples R China
[4] Nankai Univ, Dept Chem, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
SELECTIVE RECOGNITION; PHOTOPHYSICAL PROPERTIES; CHEMOSENSORS; RECEPTOR; ACETATE;
D O I
10.1002/hc.21239
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Two new compounds (1 and 2) containing 2-sulfydryl-1,3,4-thiodiazole have been synthesized and optimized. They both showed wide antibacterial activity for colon bacillus, Staphylococcus aureus, S. albus, dysentery bacillus and inferior activity for Bacillus subtilis. In addition, their binding properties were evaluated for biologically important anions (F-, Cl-, Br-, I-, AcO-, and H2PO4-) by theoretical investigation, UV-vis, fluorescence, and H-1 NMR titration experiments, and they displayed strong binding ability for H2PO4- without the interference of other anions tested. Especially the binding ability of compound 2 containing anthracene with H2PO4- was 1000 times stronger than that of compound 1 containing nitrobenzene. Two compounds based on 2-sulfydryl-1,3,4-thiodiazole have both properties of anion recognition and antibacterial activity.
引用
收藏
页码:142 / 149
页数:8
相关论文
共 26 条
[1]   Synthesis and recognition properties of a class of simple colorimetric anion chemosensors containing OH and CONH groups [J].
Bao, Xiaoping ;
Zhou, Yuhui .
SENSORS AND ACTUATORS B-CHEMICAL, 2010, 147 (02) :434-441
[2]   CHEMICALLY MEDIATED FLUORESCENCE YIELD SWITCHING IN NITROXIDE FLUOROPHORE ADDUCTS - OPTICAL SENSORS OF RADICAL REDOX REACTIONS [J].
BLOUGH, NV ;
SIMPSON, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) :1915-1917
[3]   Nature of urea-fluoride interaction:: Incipient and definitive proton transfer [J].
Boiocchi, M ;
Del Boca, L ;
Gómez, DE ;
Fabbrizzi, L ;
Licchelli, M ;
Monzani, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (50) :16507-16514
[4]   ION-RESPONSIVE FLUORESCENT COMPOUNDS .4. EFFECT OF CATION BINDING ON THE PHOTOPHYSICAL PROPERTIES OF A COUMARIN LINKED TO MONOAZA-CROWN AND DIAZA-CROWN ETHERS [J].
BOURSON, J ;
POUGET, J ;
VALEUR, B .
JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (17) :4552-4557
[5]   The synthesis, photophysical properties and fluoride anion recognition of a novel branched organoboron compound [J].
Cao, Duxia ;
Liu, Zhiqiang ;
Zhang, Guohui ;
Li, Guozhong .
DYES AND PIGMENTS, 2009, 81 (03) :193-196
[6]  
Frisch, 2016, GAUSSIAN 16
[7]   DETERMINATION OF PHOSPHATE BASED ON INHIBITION OF CRYSTAL-GROWTH OF CALCITE [J].
GRASES, F ;
MARCH, JG .
ANALYTICA CHIMICA ACTA, 1990, 229 (02) :249-254
[8]   Fluorescent sensing of pyrophosphate and bis-carboxylates with charge neutral PET chemosensors [J].
Gunnlaugsson, T ;
Davis, AP ;
O'Brien, JE ;
Glynn, M .
ORGANIC LETTERS, 2002, 4 (15) :2449-2452
[9]  
Jesus Segui M., 2007, TALANTA, V71, P333
[10]   Benzimidazole-based ratiometric fluorescent receptor for selective recognition of acetate [J].
Joo, Tae Young ;
Singh, Narinder ;
Lee, Gang Woo ;
Jang, Doo Ok .
TETRAHEDRON LETTERS, 2007, 48 (50) :8846-8850