Universidade Federal do Rio de Janeiro, Instituto de Química, LABRMN, Rio de Janeiro, Brazil.
Arch Pharm (Weinheim). 2010 Feb;343(2):81-90. doi: 10.1002/ardp.200900162.
A series of alpha- and beta-pyran naphthoquinones (lapachones) have been synthesized and evaluated for their in-vitro antibacterial activity against Mycobacterium tuberculosis strain H37Rv (ATCC 27294) using the Alamar-Blue susceptibility test; the activity was expressed as the minimum inhibitory concentration (MIC) in microg/mL. The synthetic methodology consisted of the formation of methylene and aryl o-quinone methides (o-QMs) generated by Knoevenagel condensation of 2-hydroxy-1,4-naphthoquinone with formaldehyde and arylaldehydes. These o-QMs then undergo facile hetero Diels-Alder reactions with dienophiles in aqueous ethanol media. Some naphthoquinones exhibited inhibition with MIC values of 1.25 microg/mL, similar to that of pharmaceutical concentrations currently used in tuberculosis treatment. These results justify further research into the value of these quinones as part of an original treatment for tuberculosis.
一系列的α-和β-吡喃萘醌（拉帕醌）已被合成，并通过 Alamar-Blue 药敏试验评估其对结核分枝杆菌 H37Rv 株（ATCC 27294）的体外抗菌活性；活性以最小抑菌浓度（MIC）表示，单位为微克/毫升。该合成方法包括通过 2-羟基-1,4-萘醌与甲醛和芳醛的 Knoevenagel 缩合生成亚甲基和芳基邻醌甲醚（o-QMs）。然后，这些 o-QMs 在水乙醇介质中与亲二烯体发生容易的杂 Diels-Alder 反应。一些萘醌具有 1.25 微克/毫升的抑制作用，与目前用于结核病治疗的药物浓度相似。这些结果证明了这些醌类化合物作为结核病原始治疗方法一部分的价值值得进一步研究。
