Chiral oxazolidine moiety is an important core in asymmetric synthesis due to its ability to participate in various stereoselective chemical reactions and because forms a part of more complex important active compounds. Therefore, in this letter we report a convenient diastereoselective and practical strategy for the synthesis of chiral methyl 2-((4R)-3-acryloyl-4-phenyloxazolidin-2-yl)acetates starting from (R)-(–)-2-phenylglycinol and methyl propiolate which were obtained via simple two chemical and stereoselective reactions.

We synthesized a small series of five 3-[4-arylmethoxy)phenyl]propanoic acids using an easy and short step synthetic route. All compounds were tested in vitro against a set of four protein targets identified as key elements in diabetes: GPR40, aldose reductase (AKR1B1), PPARγ and GLUT-4. Compound 1 displayed an EC₅₀ value of 0.075 μM against GPR40 and was an AKR1B1 inhibitor, showing IC₅₀ = 7.4 μM. Compounds 2 and 3 behave as AKR1B1 inhibitors, GPR40 agonists and showed an increase of 2 to 4-times in the mRNA expression of PPARγ, as well as the GLUT-4 levels. Docking studies were conducted in order to explain the polypharmacological mode of action and the interaction binding mode of the most active compounds on these targets. Compounds 1-3 were tested in vivo at 100 mg/kg dose, being 2 and 3 orally actives, reducing glucose levels in a non insulin-dependent diabetes mellitus mice model. Compounds 2 and 3 showed robust in vitro and in vivo efficacy, and could be considered as promising multitarget antidiabetic drug candidates. This is the first report of a single molecule with these four polypharmacological target action.

Benzazoles, such as benzoxazoles and benzothiazoles, are compounds with important biological and pharmacological activities and important intermediaries in synthesis. This report presents the synthesis of a butanamide derived from linking 5-chloro-2-aminobenzoxazole and 2-aminobenzothiazole via 4-chlorobutanoyl chloride. The corresponding compound N-(benzothiazol-2-yl)-4-((5-chlorobenzoxazol-2-yl)aminobutanamide was obtained 76 % yield global using accessible starting materials and methodology in two reaction steps. Furthermore, we made docking studies of this compound on 3-TOP protein to explore its potential as an antidiabetic agent.

Lipopeptides are bioactive compounds produced by Bacillus spp. This work provides insight into de antifungal activity of lipopeptides through a meta-analysis of published studies, in addition following PCR (polymerase chain reaction) technique, the presence of lipopeptides genes in 20 Bacillus strains were also analyzed. The meta-analysis of published studies showed that iturin, fengycin and surfactin significantly reduced the growth of phytopathogenic fungi. Similarly, when applied to plant tissues, the lipopeptides reduced the severity of damage in plant tissues caused by phytopathogenic fungi. As for the lipopeptides genes detection, we used 20 Bacillus strains reported to have antagonistic activity against various fungal plant pathogens. The PCR amplification study was carried out to detect the genes involved in the synthesis of lipopeptides: ituA for iturin A, fenD for fengycin and srfA for surfactin. Comparative sequence analysis showed a range of 98 to 100% identity with the corresponding genes in several Bacillus species. We observed at least one Bacillus gene in the strains: CBRF5, CBRF15, CBSN67, and CBRM9. In the strain CBRF6, we detected the presence of the fabD and srfAD genes. For the development of natural fungicides to control phytopathogenic fungi, lipopeptides produced by Bacillus spp. could be a useful tool.