Design, synthesis and biological evaluation of novel nitrogen and sulfur containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents
Design, synthesis and biological evaluation of novel nitrogen and sulfur containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents
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DOI：
10.1016/j.ejmech.2009.03.006
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发表时间：
2009-08-01
影响因子：
6.7
通讯作者：
Shukia, Praveen K.
中科院分区：
文献类型：
--
作者：
Tandon, Vishnu K.;Maurya, Hardesh K.;Shukia, Praveen K.
一系列2-芳氨基-3-氯-1,4-萘醌 (3)、2-氨基-3-芳硫基-1,4-萘醌 (5)、2-芳氨基-3-芳基硫基-1,4-萘醌 (6)、二氢苯并[f]萘并[2,3-b][1,4]硫氮平-6,11-二酮(9)（通过 Pictet-Spengler 环化），1,4-萘醌的异吲哚啉-1,3-二酮衍生物 (13)、2,2'-(1,4-二氧代-1,4-二氢萘-2,3-二基)双(亚甲基)二苯甲腈 (14)、13-氨基-12-取代-6H-苯并[e]萘基合成了[2,3-b][1,4]二氮杂-6,11(12H)-二酮(15-16)、2-氯-3-阿基硫基-1,4-萘醌(17-18)和3-甲基-6H-苯并[b]吩噻嗪-6,11(12H)-二酮(19)并研究了它们的抗真菌和抗菌作用活动。结果表明化合物3b、5a和5b具有有效的抗真菌活性。在最有前途的抗真菌化合物中，3b对申克孢子丝菌（MIC50 = 1.56 μg/mL）表现出比临床流行的抗真菌药物氟康唑（MIC50 = 2.0 μg/mL）更好的抗真菌活性，对白色念珠菌（MIC50 = 1.56 μg/mL）、新型隐球菌（MIC50 = 0.78 mu g/mL) 和毛癣菌 (MIC50 = 1.56 mu g/mL)，与两性霉素-B 相比，对新型毛癣菌 (MIC50 = 0.78 mu g/mL) 具有相同的抗真菌活性。化合物 3b、5a 和 5b 也显示出有希望的抗菌活性。 (C) 2009 Elsevier Masson SAS。版权所有。
A series of 2-Arylamino-3-chloro-1,4-naphthoquinones (3), 2-Amino-3-aryisulfanyl-1,4-naphthoquinones (5), 2-Arylamino-3-arylsulfanyl-1,4-naphthoquinones (6), Dihydrobenzo[f]naphtho[2,3-b][1,4]thiazelpine-6,11-diones (9) (via Pictet-Spengler cyclization), Isoindoline-1,3-dione derivatives of 1,4- naphthoquinone (13), 2,2'-(1,4-Dioxo-1,4-dihydronaphthalene-2,3-diyl)bis(methylene)dibenzonitrile (14), 13-Amino-12-substituted-6H-benzo[e]naphtho [2,3-b][1,4]diazepine-6,11(12H)-diones (15-16), 2-Chloro-3-atylsulfanyl-1,4-naphthoquinones (17-18) and 3-Methyl-6H-benzo[b]phenothiazine-6,11(12H)-dione (19) were synthesized and studied for their antifungal and antibacterial activities. The results indicate that compounds 3b, 5a and 5b have potent antifungal activity. Amongst the most promising antifungal compounds, 3b showed better antifungal activity than clinically prevalent antifungal drug Fluconazole (MIC50 = 2.0 mu g/mL) against Sporothrix schenckii (MIC50 = 1.56 mu g/mL), significant profile against Candida albicans (MIC50 = 1.56 mu g/mL), Cryptococcus neoformans (MIC50 = 0.78 mu g/mL) and Trichophyton mentagraphytes (MIC50 = 1.56 mu g/mL) and same antifungal activity when compared with Amphotericin-B against C. neoformans (MIC50 = 0.78 mu g/mL). Compounds 3b, 5a and 5b also showed promising antibacterial activity. (C) 2009 Elsevier Masson SAS. All rights reserved.