Synthesis and antiviral activity of camphor-based 1,3-thiazolidin-4-one and thiazole derivatives as Orthopoxvirus-reproduction inhibitors

Abstract

Camphor based heterocyclic systems containing 1,3-thiazolidin-4-one and thiazole rings showed promising antiviral activity towards Orthopoxviruses.

(+)‐Camphor and (−)‐borneol derivatives as potential anti‐orthopoxvirus agents

“…The chemical compounds library contains 18 agents (1-18) that were screened against OPVs including VARV and four agents (19-22) that were tested against VV. The synthesis of compounds 1 and 2, [17] 3, 5-8, [11] 4, [18] 9-14, [12] and 15-18 [13] was previously described. For the synthesis of derivatives 19, 21, and 22, camphorquinone [19] and camphor hydrazine [13] were prepared according to the procedure reported in the literature from (+)-camphor.…”

“…This virus is similar to the VARV but can be studied at BSL-2 facilities. Over 300 monoterpenoid derivatives were screened, among which esters 1-4 based on (−)-borneol, amides 5-8 with N-containing heterocycles, [11] the (+)-camphor thiosemicarbazone derivatives 9-14, [12] and (+)-camphor-based N-acylhydrazones 15-18 [13] were found as good inhibitors of the VV (Figure 2). Derivatives 1-18 had IC 50 (the 50% inhibitory concentration) values in the range of 2.5-70 µM against VV and CC 50 (the 50% cytotoxic concentration) values in the range of 120-1430 μM.…”

Synthesis ofd-(+)-camphor-basedN-acylhydrazones and their antiviral activity

“…20 A series of nitrogen-sulphur-containing heterocycles, such as 1,3-thiazolidin-4-one and other thia-zoles, and a 1,7,7-trimethylbicycloij2.2.1]heptane scaffold were synthesized on (+)-camphor and screened for their antiviral activity. 21 The bioassay results showed that thiazole 3, which contained a substituted benzene ring, was able to inhibit VV with IC 50 values in the micromolar range whilst exhibiting moderate cytotoxicity. The aim of this work was to synthesize N-acylhydrazones based on (+)-camphor bearing also some alkaloid nitrogen heterocycles as privileged fragments 22 and to study their antiviral properties.…”

Novel synthesis of pyran, thiophene, and pyridine derivatives incorporating thiazole ring and their antitumor evaluation

“…In nature, thiazoles play an important role where thiazolium ring present in vitamin B1. Many pendant and fused thiazole systems exhibit various applications in different fields, such as in medicinal chemistry as antibacterial, anti‐fungal, anti‐inflammatory, anticonvulsant, antiviral, antioxidants, skin whitening agent (KHG22394), and anticancer . In addition, thiazoles are applied in agriculture as agrochemicals.…”