New 1,4-anthracenedione derivatives with fused heterocyclic rings: synthesis and biological evaluation

Abstract

New 1,4-anthracenediones bearing fused-heterocycle rings were synthesized and evaluated as cytotoxics, antifungals and antivirals. Some of them showed GI50 at the μM level.

Combretastatin A-4: The Antitubulin Agent that Inspired the Design and Synthesis of Styrene and Spiroisatin Hybrids as Promising Cytotoxic, Antifungal and Antiviral Compounds

“…Additionally, the flaviviruses use these structures to promote a reconfiguration of the cytoplasmic compartments that are important for the genome replication and translation of viral protein. 22 Considering both the previously described data 23 regarding viral modulation of microtubules and the current need to research on synthesis and biological evaluation of small molecules inspired on the structure of CA-4 1, our screening program for new bioactive heterocycles 23 has focused this research on: (i) design and synthesis of a 20-member library of styrene and spiroisatin hybrids containing the 3,4,5-trimethoxyphenyl and/or the 4-hydroxy-3-methoxyphenyl as pharmacophoric subunits; (ii) evaluation of the cytotoxic activity in tumor cell lines (HeLa (cervix epitheloid adenocarcinoma cell), Jurkat (acute T cell leukemia), U937 (promonocytic cell) and Vero (African green monkey kidney, Cercopithecus aethiops)); (iii) study of the antifungal activities in pathogen dermatophytes (T. mentagrophytes, T. rubrum and F. oxysporum); (iv) determination of the antiviral activity in human herpesvirus 1 and 2 (HHV-1 and HHV-2), and dengue virus serotype 2 (DENV-2) of these molecules and some related tubulin inhibitors, and (v) the study of the possible interactions of these molecules with the active site of the tubulin target through molecular docking studies.…”

Design, synthesis and fungicidal activity of isothiazole–thiazole derivatives

“…6 Heterocyclic compounds are widely used in novel agrochemical researches and developments. [7][8][9][10] Thiazoles have attracted the interest of pharmaceutical and agrochemical anti-fungal research since the development of thiabendazole as a fungicide in 1962 by Merck. 11 Oxathiapiprolin was developed by DuPont in 2007 as a piperidinyl thiazole isoxazoline fungicide targeting at oxysterol binding protein (PcORP1) against Peronospora belbahrii, Phytophthora parasitica var.…”

Synthesis andIn VitroBiological Evaluation of Aminonaphthoquinones and Benzo[b]phenazine-6,11-dione Derivatives as Potential Antibacterial and Antifungal Compounds

“…Quinones are active compounds used widely as raw materials in pharmaceuticals and agrochemical industries. Particularly, (hetero)cyclic quinone moieties not only exist in many natural products and pharmaceutical compounds, but also are well-known and versatile building blocks for the synthesis of quinones derived from benzoquinone, naphthoquinone, or anthracenequinone condensed with five-membered heterocycles [1][2][3] such as isoxazoles [4], six-membered heterocycles [3,5], and seven-membered heterocycles [6,7] such as 1,4-benzodiazepines [8] in order to evaluate their important bioactivities. Therefore, among the bioactive quinones, 1,4naphthoquinones have been extensively studied since those ones contain two ketone groups as a crucial pharmacophore for their bioactivities because of their ability to accept electrons [9].…”