Abstract

A series of 11H-xantheno[2,1-c][1,2,5]selenadiazol-11-one derivatives (Va–m) that incorporate a variety of substituents have been synthesized under both conventional heating and microwave irradiation procedures. All these analogs were evaluated for their antimicrobial activity against the Gram-positive bacteria Bacillus subtilis (BS), Staphylococcus aureus (SA), and Staphylococcus epidermidis (SE), against the Gram-negative bacteria Escherichia coli (EC), Pseudomonas aeruginosa (PA), and Klebsiella pneumonia (KP), and against the fungal species Candida albicans (CA), Candida rugosa (CR), Rhizopus oryzae (RO), and Aspergillus niger (AN) and antitubercular activity against MTB H37Rv. Analog, 7,9-dimethoxy-11H-xantheno[2,1-c][1,2,5]selenadiazol-11-one (Vc) was identified as a potent antibacterial agent (MIC_[BS] = 2.5 µg/mL, MIC_[SA] = 10 µg/mL, MIC_[SE] = 2.5 µg/mL, MIC_[EC] = 5 µg/mL, MIC_[PA] = 10 µg/mL, MIC_[KP] = 2.5 µg/mL), and a potent antifungal agent (MIC_[CA] = 15 µg/mL, MIC_[CR] = 15 µg/mL, MIC_[RO] = 10 µg/mL). Another analog, 7,9-dimethyl-11H-xantheno[2,1-c][1,2,5]selenadiazol-11-one (Vj) was also identified as a potent antibacterial agent (MIC_[BS] = 2.5 µg/mL, MIC_[SA] = 15 µg/mL, MIC_[SE] = 2.5 µg/mL, MIC_[EC] = 10 µg/mL, MIC_[PA] = 15 µg/mL, MIC_[KP] = 20 µg/mL), and a potent antifungal agent (MIC_[CA] = 2.5 g/mL, MIC_[CR] = 10 µg/mL MIC_[RO] = 15 µg/mL and MIC_[AN] = 10 µg/mL). Based on the MIC data analogs, 7,9-dimethoxy-11H-xantheno[2,1-c][1,2,5]selenadiazol-11-one (Vc) and 7,9-dimethyl-11H-xantheno[2,1-c][1,2,5]selena-diazol-11-one (Vj) were identified as the most potent antimicrobial agents in the series. All these 11H-xantheno[2,1-c][1,2,5]selenadiazol-11-one derivatives (Va–m) were also evaluated for their antitubercular activity against MTB H37Rv. Analogs, 7,9-dimethoxy-11H-xantheno[2,1-c][1,2,5]selenadiazol-11-one (Vc) and 7,9-dimethyl-11H-xantheno[2,1-c][1,2,5]selenadiazol-11-one (Vj) showed MIC of 3.12 µg/mL. These results suggest that analogs, 7,9-dimethoxy-11H-xantheno[2,1-c][1,2,5]selenadiazol-11-one (Vc) and 7,9-dimethyl-11H-xantheno[2,1-c][1,2,5]selenadiazol-11-one (Vj) may be a potential multifunctional ligands for the development of highly effective antimicrobial and antitubercular activity.

中文翻译：

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11 H-黄嘌呤[2,1-c] [1,2,5]硒二氮杂十一一衍生物作为强效抗菌剂和抗结核药的设计与合成

摘要

一系列11的ħ -xantheno [2,1- c ^ ] [1,2,5] selenadiazol -11-酮衍生物（VA-米掺入各种取代基的已根据常规加热和微波辐射的方法合成）。评估了所有这些类似物对革兰氏阳性细菌枯草芽孢杆菌（BS），金黄色葡萄球菌（SA）和表皮葡萄球菌（SE）对革兰氏阴性细菌大肠杆菌（EC），铜绿假单胞菌（PA ）的抗菌活性），肺炎克雷伯氏菌（KP）和针对白色念珠菌（CA）的真菌物种，皱纹假丝酵母（CR），米根霉（RO）和黑曲霉（AN）以及针对MTB H37Rv的抗结核活性。鉴定出类似的7,9-二甲氧基-11 H-黄嘌呤[2,1- c ] [1,2,5]硒二氮杂-11-one（Vc）是有效的抗菌剂（MIC _[BS] = 2.5 µg / mL，MIC _[SA] = 10μg/ mL，MIC _[SE] = 2.5μg/ mL，MIC _[EC] = 5μg/ mL，MIC _[PA] = 10μg/ mL，MIC _[KP] = 2.5μg / mL毫升）和有效的抗真菌剂（MIC _[CA] = 15 µg / mL，MIC _[CR] = 15 µg / mL，MIC _[RO]= 10 µg / mL）。另一模拟，7,9-二甲基-11- ħ -xantheno [2,1- c ^ ] [1,2,5] selenadiazol-11-酮（VJ）也被确定为一个有效的抗菌剂（MIC _[BS] = 2.5 µg / mL，MIC _[SA] = 15 µg / mL，MIC _[SE] = 2.5 µg / mL，MIC _[EC] = 10 µg / mL，MIC _[PA] = 15 µg / mL，MIC _[KP] = 20 µg / mL）和有效的抗真菌剂（MIC _[CA]  = 2.5 g / mL，MIC _[CR] = 10 µg / mL MIC _[RO] = 15 µg / mL，MIC _[AN] = 10 µg / mL） 。基于MIC数据类似物7,9-dimethoxy-11 H -xantheno [2,1- c] [1,2,5] selenadiazol-11-酮（Vc的）和7,9-二甲基-11- ħ -xantheno [2,1- c ^ ] [1,2,5] selenadiazol-11-酮（VJ被确认为该系列中最有效的抗菌剂。所有这些11 ħ -xantheno [2,1- c ^ ] [1,2,5] selenadiazol -11-酮衍生物（VA-米）也进行了评价它们对MTB H37Rv的抗结核活性。类似物7,9-二甲氧基-11 H-黄嘌呤[2,1- c ] [1,2,5]硒二氮杂-11-one（Vc）和7,9-二甲基-11 H-黄嘌呤[2,1- c ] [1,2,5] selenadiazol-11-one（Vj）的MIC为3.12 µg / mL。这些结果表明，类似物，7,9-二甲氧基- 11 ħ -xantheno [2,1- c ^ ] [1,2,5] selenadiazol-11-酮（Vc的）和7,9-二甲基-11- ħ -xantheno [ 2,1- c ] [1,2,5] selenadiazol-11-one（Vj）可能是开发高效抗菌和抗结核活性的潜在多功能配体。