Abstract

Unique 2,6-diiodophenylboronic acid and 2,3-diiodophenylboronic acid derivatives have been synthesized via regioselective metal–iodine exchange (MIE) of 5-substituted 1,2,3-triiodoarenes. The regio­selectivity of the reaction per se is remarkably controlled by the nature of the C5 substituent providing the desired diiodophenylboronic acids in moderate to good yields and with high site selectivity. The diiodophenylboronic acids were then examined for in vitro antimicrobial activity against four strains of bacteria Micrococcus luteus (ATCC 9341), Bacillus cereus (ATCC 11778), Escherichia coli (ATCC 25922), and Serratia marcescens (ATCC 27117) and one fungal strain Candida albicans using well diffusion assay and dilution method. It indicated that 5-fluoro-2,3-diiodophenylboronic acid possesses the most potent antibacterial and antifungal activity with MIC of 2.6 mg/mL for M. luteus and C. albicans. This report discloses a one-step protocol to access hitherto unknowns 2,6-diiodophenylboronic acid and 2,3-diiodophenylboronic acid derivatives that is scalable, good in scope, no chromatography is needed, and these compounds are difficult to prepare by other means.

Unique 2,6-diiodophenylboronic acid and 2,3-diiodophenylboronic acid derivatives have been synthesized via regioselective metal–iodine exchange (MIE) of 5-substituted 1,2,3-triiodoarenes. The regio­selectivity of the reaction per se is remarkably controlled by the nature of the C5 substituent providing the desired diiodophenylboronic acids in moderate to good yields and with high site selectivity. The diiodophenylboronic acids were then examined for in vitro antimicrobial activity against four strains of bacteria Micrococcus luteus (ATCC 9341), Bacillus cereus (ATCC 11778), Escherichia coli (ATCC 25922), and Serratia marcescens (ATCC 27117) and one fungal strain Candida albicans using well diffusion assay and dilution method. It indicated that 5-fluoro-2,3-diiodophenylboronic acid possesses the most potent antibacterial and antifungal activity with MIC of 2.6 mg/mL for M. luteus and C. albicans. This report discloses a one-step protocol to access hitherto unknowns 2,6-diiodophenylboronic acid and 2,3-diiodophenylboronic acid derivatives that is scalable, good in scope, no chromatography is needed, and these compounds are difficult to prepare by other means.

中文翻译：

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通过5-取代的1,2,3-三碘芳烃的金属-碘交换轻度，高效且区域选择性地合成二碘苯基硼酸衍生物

摘要

通过5-取代的1,2,3-三碘代芳烃的区域选择性金属-碘交换（MIE）合成了独特的2,6-二碘苯基硼酸和2,3-二碘苯基硼酸衍生物。反应本身的区域选择性由C 5取代基的性质显着控制，该C 5取代基以中等至良好的收率和高的位点选择性提供了所需的二碘苯基硼酸。然后检查二碘苯基硼酸对四种细菌黄腐微球菌（ATCC 9341），蜡状芽孢杆菌（ATCC 11778），大肠杆菌（ATCC 25922）和粘质沙雷氏菌（ATCC 27117）和一株白色念珠菌的体外抗菌活性。使用孔扩散测定法和稀释法。它指出，5-氟-2,3- diiodophenylboronic酸具有与2.6毫克/毫升的MIC为最有效的抗菌和抗真菌活性藤黄微球菌和白色念珠菌。该报告公开了访问迄今未知的2,6-二碘代苯基硼酸和2,3-二碘代苯基硼酸衍生物的一步式方法，该方法具有可扩展性，适用范围广，不需要色谱法，并且这些化合物很难通过其他方式制备。

通过5-取代的1,2,3-三碘代芳烃的区域选择性金属-碘交换（MIE）合成了独特的2,6-二碘苯基硼酸和2,3-二碘苯基硼酸衍生物。反应本身的区域选择性由C 5取代基的性质显着控制，该C 5取代基以中等至良好的收率和高的位点选择性提供了所需的二碘苯基硼酸。然后检查二碘苯基硼酸对四种细菌黄腐微球菌（ATCC 9341），蜡状芽孢杆菌（ATCC 11778），大肠杆菌（ATCC 25922）和粘质沙雷氏菌（ATCC 27117）和一株白色念珠菌的体外抗菌活性。使用孔扩散测定法和稀释法。它指出，5-氟-2,3- diiodophenylboronic酸具有与2.6毫克/毫升的MIC为最有效的抗菌和抗真菌活性藤黄微球菌和白色念珠菌。该报告公开了访问迄今未知的2,6-二碘代苯基硼酸和2,3-二碘代苯基硼酸衍生物的一步式方法，该方法具有可扩展性，适用范围广，不需要色谱法，并且这些化合物很难通过其他方式制备。