The synthesis of polisubstituted thienylpyrroles and the study of their activity as plant growth stimulators
Journal Title: Журнал органічної та фармацевтичної хімії; Журнал органической и фармацевтической химии - Year 2019, Vol 17, Issue 2
Abstract
Aim. To develop the optimal method for the synthesis of new polysubstituted thienylpyrroles and study them as cereal growth stimulants. Results and discussion. Preparative methods for the synthesis of 4-(5-carboxythiophen-2-yl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid, 5-(5-carboxythiophen-2-yl)-2,4-dimethyl-1H-pyrrol-3-carboxylic acid and ethyl 4-(4-amino-5)-ethoxycarbonyl (thiophen-2-yl)-3,5-dimethyl-1H-pyrrole-2-carboxylate have been developed by step reactions. 4-(5-Carboxythiophen-2-yl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid is the most promising for the study of the growth-stimulating activity on grain seeds. Experimental part. Using ethyl 4-acyl-3,5-dimethyl-1H-pyrrole-2-carboxylate and ethyl 5-acetyl-2,4-dimethyl-1H-pyrrole-3-carboxylate as starting compounds 4-(5-carboxythiophen-2-yl)-3,5-dimethyl-1H-pyrrole-2-carboxylic and 5-(5-carboxythiophen-2-yl) 2,4-dimethyl-1H-pyrrol-3-carboxylic acid were obtained. By the action of the Wilsmeier-Haack reagent on the latter the corresponding pyrroles with the chlorvinylcarbaldehyde fragment were isolated; their post-cyclization with ethyl ester of thioglycolic acid and the subsequent hydrolysis leads to the formation of thienylpyroldicarboxylic acids. The study of the physiological activity of the compounds synthesized was performed on seeds of different varieties of wheat and barley. Conclusions. By means of sequential reactions the polysubstituted thienylpyrrolcarboxylic acids previously unknown and their esters have been synthesized. The features of the study of these compounds as plant growth stimulants have been revealed.
Authors and Affiliations
O. I. Mikhedkina, O. S. Pelipets, I. V. Peretiatko, D. T. Kozhich, I. I. Melnik, O. V. Tsygankov, M. V. Vasyleiko
Keywords
Related Articles
- EP ID EP659279
- DOI 10.24959/ophcj.19.972
- Views 70
- Downloads 0
The synthesis and biological assessment of [[1,2,4]triazolo[4,3-a]pyridine-3-yl]acetamides with an 1,2,4-oxadiazol cycle in positions 6, 7 and 8
Fused heterocyclic 1,2,4-triazoles have provided much attention due to variety of their interesting biological properties. Aim. To develop the method for the synthesis of novel 2-[(1,2,4-oxadiazol-5-yl)-[1,2,4]triazolo[4...
Синтез полизамещённых тиенилпирролов и их исследование в качестве регуляторов роста растений
Цель работы – разработка оптимального метода синтеза новых полизамещенных тиенилпирролов и их исследование в качестве стимуляторов роста зерновых культур. Результаты и их обсуждение. Путем ступенчатых реакций были разраб...
Development and validation of the enzymatic kinetic photometric procedure for determination of residual quantities of dequalinium chloride on the surface of the pharmaceutical equipment
Aim. To develop and validate the new enzymatic kinetic photometric procedure for analysis of dequalinium chloride based on application of enzymatic acetylcholine hydrolysis to determine the residual quantities of dequali...
Acetylcholinesterase inhibitors with a thiazolium scaffold: structural features and binding modes
Aim. To assess the structural features of substituents and the role of a thiazolium scaffold in mechanisms of acetylcholinesterase inhibition by thiazolium salts. Results and discussion. On the basis of activities of mo...
Synthesis and antioxidant properties of novel thiazolo[4,5-b]pyridine-2-ones
Aim. To expand the synthetic potential of thiazolo[4,5-b]pyridines, study the reactivity and perform the pharmacological screening of the antioxidant activity of the novel compounds synthesized. Results and discussion. A...