Synthesis and biological activity of new thiazole isosteres of goniofufurone and 7-epi-goniofufurone

Herein we report a total synthesis of two novel (7-epi-)goniofufurone isosteres bearing a 2-thiazolyl-4-carboxylic acid ethyl ester moiety instead of the aromatic ring at C-7

Synthesis and antiprol iferative activity of (+)-muricatacin and two novel conformationally constrained analogues

Herein we describe a modified total synthesis of (+)-Muricatacin starting from D-xylose, as well as synthesis of two new conformationally constrained (+)-muricatacin mimics from D-glucose

Synthesis and antitumour activity of two dephenilated (-)-goniofufurone analogues

(-)-Goniofufurone (1) is a synthetic styryl lactone that exhibits significant antitumor activity. In the search for new and more potent antitumor agents the synthesis of lactones 5 and 6 was planned from D-glucose. Compounds 5 and 6 are designed as dephenylated analogues of 1 (Figure 1). The results of the evaluation of antiproliferative activity of 5 and 6 against a number of human tumor cell lines, as well as the structure-activity relationship (SAR), will be presented and discussed in details

Design, synthesis, and biological evaluation of thiazole bioisosteres of goniofufurone through in vitro antiproliferative activity and in vivo toxicity (vol 121, 105691, 2022)

The contribution corrects an equation from the paper: Delasoie, J., Radakovic, N., Pavic, A., & Zobi, F. (2020). Neovascularization Effects of Carbon Monoxide Releasing Drugs Chemisorbed on Coscinodiscus Diatoms Carriers Characterized by Spectromicroscopy Imaging. Applied Sciences, 10(20), 7380. [https://doi.org/10.3390/app10207380

Synthesis and in vitro antitumour activity of new goniofufurone mimics with thiophene ring at the C-7 position

Ostvarena je višefazna sinteza novih mimetika (+)-goniofufurona (1) sa tiofenskim prstenom umesto fenil grupe u položaju C-7 polazeći iz D-glukoze (Shema 1). Ispitana je in vitro citotoksična aktivnost novosintetizovanih mimetika prema odabranim tumorskim ćelijskim linijama, kao i prema jednoj normalnoj ćelijskoj liniji (fetalni fibroblasti pluća, MRC-5).Multiphase synthesis of (+)-goniofufurone (1) mimetics with thiofene ring instead of phenyl group at the C-7 position is completed using D-glucose as a starting compound (Scheme 1). In vitro cytotoxicity of newly synthetized analogues against eleven human tumour cell lines and against a single normal cell line (MRC-5) was evaluated

Fractionation of complex mixtures of naphthenic acids, their characterization and biological activity

Naphthenic acids (NAs) are complex mixtures of cycloaliphatic and alkyl-substituted acyclic carboxylic acids whose overall characteristics are determined by the composition of the mixture. A complex mixture of NAs from a commercial fraction of atmospheric oil of the Vojvodina naphthenic crude "Velebit" (Serbia) was separated into narrower fractions on the basis of their acidity. Electrospray ionization mass spectrometry analysis of the fractions showed the occurrence of structural differentiation of acids. By extraction at pH 3-5, about 50% of the total mass of acids was separated, consisting predominantly of tricyclic and bicyclic structures. Acids of lower acidity, (about 22%), separated at pH 9 and 10, and their dominant constituents were acids with three, four and five rings. A correlation was found between the dominant structure and the biological activity of NAs of the fractions. The fraction extracted at pH 8, also with dominant bicyclic and tricyclic structures, showed the highest auxin and gibberellin activities

Eco-friendly microwave-assisted synthesis of biologically active naphthenic acid n-cyclohexyl amides

Inside the framework of green chemistry, a noticeable results were obtained in microwaveassisted solvent-free synthesis of biologically active N-cyclohexyl amides of naphthenic acids (NAs). Naphthenic acid amides were synthesized directly from free carboxylic acids in the absence of solvent and catalyst. Synthesized N-cyclohexyl amides of naphthenic acid were evaluated for their auxin activity

S-O acetyl rearrangement in 6-thio-D-glucose derivatives

The solvolytic reaction of 1,2-O-isopropylidene-3,6-di-O-(p-toluenesulphonyl)- α-D-glucofuranose (2), as well as that of 6-chloro-6-deoxy-1,2-O-isopropylidene-3-O-(p-toluenesulphonyl)-α-D-glucofuranose (3), in the presence of potassium thioacetate unexpectedly gave the 6-S-acetyl-5-O-acetyl derivative 5 as the main reaction product. A possible mechanism of these transformations was postulated whereby the main role was ascribed to a neighbouring group participation process, involving hydrogen thio-orthoester formation as an intermediate. The regiospecific monosubstitution of the 6-tosyloxy group in compound 2 was successfully achieved with potassium thioacetate, in presence of 2,3-benzo-15-crown-5 as a catalyst. The corresponding 6-S-acetyl derivative 7 was obtained representing a possible intermediate in the mentioned solvolytic reactions. Compound 7 was shown to be very reactive, since it fully transformed into the corresponding mercaptan 8 in the presence of silica gel. This transformation occurred via the same thio-orthoester 7a as in the mentioned solvolytic reactions of furanoses 2 and 3. The synthesized compounds are key intermediates in the planned synthesis of selected natural products and their analogues. [Project of the Serbian Ministry of Education, Science and Technological Development, Grant no. OI 172006

An efficient de novo synthesis of 3-deoxythymidine from D-xylose

An efficient stereospecific synthesis of 3-deoxythymidine has been achieved, starting from D-xylose. The key step of the synthesis involved the NBS promoted conversion of 5-O-benzoyl-2,3-di-S-ethyl-2,3-dithio-D-ribose diethyl dithioacetal (4) into the 1-O-acetyl-5-O-benzoyl-2,3-di-S-ethyl-2,3-dithio-b-D-ribofuranose (5), followed by the stereospecific coupling of the intermediate 5 with silylated thymine, in the presence of ethylaluminium dichloride as the catalyst