Biologically Oriented Hybrids of Indole and Hydantoin Derivatives

Indoles and hydantoins are important heterocycles scaffolds which present in numerous bioactive compounds which possess various biological activities. Moreover, they are essential building blocks in organic synthesis, particularly for the preparation of important hybrid molecules. The series of hybrid compounds containing indoles and imidazolidin-2-one moiety with direct C–C bond were synthesized using an amidoalkylation one-pot reaction. All compounds were investigated as a growth regulator for germination, growth and development of wheat seeds (Triticum aestivum L). Their effect on drought resistance at very low concentrations (4 × 10−5 M) was evaluated. The study highlighted identified the leading compounds, 3a and 3e, with higher growth-regulating activity than the indole-auxin analogues

Synthetic Optimizations for Gram-Scale Preparation of 1-O-Methyl d-Glycero-α-d-gluco-heptoside 7-Phosphate from d-Glucose

Heptose phosphates—unique linkers between endotoxic lipid A and O-antigen in the bacterial membrane—are pathogen-associated molecular patterns recognized by the receptors of the innate immune system. Understanding the mechanisms of immune system activation is important for the development of therapeutic agents to combat infectious diseases and overcome antibiotic resistance. However, in practice, it is difficult to obtain a substantial amount of heptose phosphates for biological studies due to the narrow scope of the reported synthetic procedures. We have optimized and developed an inexpensive and convenient synthesis for the first performed gram-scale production of 1-O-methyl d-glycero-α-d-gluco-heptoside 7-phosphate from readily available d-glucose. Scaling up to such amounts of the product, we have increased the efficiency of the synthesis and reduced the number of steps of the classical route through the direct phosphorylation of the O6,O7-unprotected heptose. The refined method could be of practical value for further biological screening of heptose phosphate derivatives

Evaluation of potential and rate of the germination of wheat seeds (Triticum aestivum L) treated with bifunctional growth regulators under water stress

The synthetic cytokinins belonging to the class of bifunctional carbamates and oxamates were tested for a biological activity in a wide concentration range of 10-2 M − 10-6 M along with chlorocholine chloride taken as reference. The compounds have a pronounced growth-regulatory activity for wheat seeds (Triticum aestivum L) at the optimal concentration of 10-5 M, at which the germination potential Gp and the germination rate Gr of seeds, as well as resistance to water stress, determined by RWC values reach their maximum values. It was found that the technique of spraying wheat seeds with solutions of the compounds used is more preferable than soaking.Key words: wheat, plant growth regulators, carbamates, oxamates, water stres

A new synthesis of enantiomerically pure syn-(S)-β-hydroxy-α-amino acids via asymmetric aldol reactions of aldehydes with a homochiral Ni(II)-glycine/(S)-BPB Schiff base complex

syn-(S)-β-Hydroxy-α-amino acids were synthesised stereoselectively via elaboration of the asymmetric aldol reactions of aldehydes with a chiral Ni(II)-(S)-BPB/glycine Schiff base complex in the presence of equimolar NaH in THF. The stereoselectivity of the reaction was studied as a function of time, the reaction conditions, the nature of the carbonyl compounds and the base used. The synthetic potential of this asymmetric method was demonstrated in the preparation of syn-(S)-β-hydroxyleucine on a multi-gram scale.

Evaluation of potential and rate of the germination of wheat seeds (Triticum aestivum L) treated with bifunctional growth regulators under water stress

The synthetic cytokinins belonging to the class of bifunctional carbamates and oxamates were tested for a biological activity in a wide concentration range of 10-2 M − 10-6 M along with chlorocholine chloride taken as reference. The compounds have a pronounced growth-regulatory activity for wheat seeds (Triticum aestivum L) at the optimal concentration of 10-5 M, at which the germination potential Gp and the germination rate Gr of seeds, as well as resistance to water stress, determined by RWC values reach their maximum values. It was found that the technique of spraying wheat seeds with solutions of the compounds used is more preferable than soaking.Key words: wheat, plant growth regulators, carbamates, oxamates, water stres

Synthesis of the Indole-Based Inhibitors of Bacterial Cystathionine γ-Lyase NL1-NL3

Bacterial cystathionine γ-lyase (bCSE) is the main producer of H2S in pathogenic bacteria such as Staphylococcus aureus, Pseudomonas aeruginosa, etc. The suppression of bCSE activity considerably enhances the sensitivity of bacteria to antibiotics. Convenient methods for the efficient synthesis of gram quantities of two selective indole-based bCSE inhibitors, namely (2-(6-bromo-1H-indol-1-yl)acetyl)glycine (NL1), 5-((6-bromo-1H-indol-1-yl)methyl)- 2-methylfuran-3-carboxylic acid (NL2), as well as a synthetic method for preparation 3-((6-(7-chlorobenzo[b]thiophen-2-yl)-1H-indol-1-yl)methyl)- 1H-pyrazole-5-carboxylic acid (NL3), have been developed. The syntheses are based on the use of 6-bromoindole as the main building block for all three inhibitors (NL1, NL2, and NL3), and the designed residues are assembled at the nitrogen atom of the 6-bromoindole core or by the substitution of the bromine atom in the case of NL3 using Pd-catalyzed cross-coupling. The developed and refined synthetic methods would be significant for the further biological screening of NL-series bCSE inhibitors and their derivatives