Synthesis, Antiviral and Cytostatic Activity of New Series of Naphthalimide Derivatives

Katarzyna Gawron, D. Piotrowska, G. Andrei, D. Schols, R. Snoeck, I. Głowacka
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Abstract

A new series of N-(diethylphosphonoalkyl)-1,8-naphthalimides were synthesized via direct reaction of 1,8-naphthalic anhydride or its 3-nitro- and 4-bromo- derivatives with selected ɷ-aminoalkylphosphonates and evaluated against a broad-spectrum of viruses as well as for their cytostatic properties toward selected cell lines. N-(diethylphosphonomethyl)-3-nitro-1,8-naphthalimide 15a exhibited inhibitory activity toward coxsackie virus B4 in Vero cells (EC50 = 9.45 μM), whereas 3-nitro-1,8-naphthalimides 15b and 15d containing short 2-carbon linker showed moderate activity against herpes simplex virus-2 (G) and herpes simplex virus-1 TK– KOS ACVr. Furthermore, compounds 15a, 15b and 15d showed antiviral potency against human coronavirus. Several naphthalimides exhibited cytostatic activity toward tested cancerous cell lines as well as normal retina cells. Transformation of selected diethyl phosphonates 13, 14 and 15 into ammonium phosphonates 21, 22 and 23 improved the solubility, however, did not result in the enhancement of antiviral and cytostatic potency of the compounds.
新系列萘啶酰亚胺衍生物的合成、抗病毒和细胞抑制活性
通过 1,8-萘二甲酸酐或其 3-硝基和 4-溴衍生物与选定的ɷ-氨基烷基膦酸盐直接反应,合成了一系列新的 N-(二乙基膦酰基)-1,8-萘二甲酰亚胺,并评估了它们对广谱病毒的抑制作用以及对选定细胞系的细胞抑制特性。N-(二乙基膦酰甲基)-3-硝基-1,8-萘二甲酰亚胺 15a 在 Vero 细胞中对柯萨奇病毒 B4 具有抑制活性(EC50 = 9.45 μM),而含有短 2 碳连接体的 3-硝基-1,8-萘二甲酰亚胺 15b 和 15d 对单纯疱疹病毒-2(G)和单纯疱疹病毒-1 TK- KOS ACVr 具有中等程度的活性。此外,化合物 15a、15b 和 15d 对人类冠状病毒具有抗病毒效力。一些萘二甲酰亚胺化合物对测试的癌细胞系和正常视网膜细胞具有细胞抑制活性。将选定的膦酸二乙酯 13、14 和 15 转化为膦酸铵 21、22 和 23 可以提高溶解度,但并不能增强化合物的抗病毒和细胞抑制效力。
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