Synthesis of N-alkylated benzo- and pyridothienopyrrolo-[1,2a][1,4]diazepin-6-ones acting as antidotes against the herbicide 2,4-D

Строганова, Т. А.; Vasilin, V. K.; Krapivin, G. D.; Стрелков, В. Д.; Dyadyuchenko, L. V.

doi:10.1007/s10593-016-1830-x

Cited by 7 publications

(3 citation statements)

References 6 publications

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“…It is known that some functionalized pyridines are efficient herbicide safeners and plant growth regulators [ 107 , 108 , 109 , 110 , 111 ]. Nicotinamides 16a and 17a,b were studied as 2,4-D antidotes with respect to sunflower seedlings using the reported procedure [ 107 ] (see the Materials and Methods).…”

Section: Resultsmentioning

confidence: 99%

New 6′-Amino-5′-cyano-2-oxo-1,2-dihydro-1′H-spiro[indole-3,4′-pyridine]-3′-carboxamides: Synthesis, Reactions, Molecular Docking Studies and Biological Activity

et al. 2023

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The purpose of this work was to prepare new isatin- and monothiomalondiamide-based indole derivatives, as well as to study the properties of the new compounds. The four-component reaction of 5-R-isatins (R = H, CH3), malononitrile, monothiomalonamide (3-amino-3-thioxo- propanamide) and triethylamine in hot EtOH yields a mixture of isomeric triethylammonium 6′-amino-3′-(aminocarbonyl)-5′-cyano-2-oxo-1,2-dihydro-1′H- and 6′-amino-3′-(aminocarbonyl)- 5′-cyano-2-oxo-1,2-dihydro-3′H-spiro[indole-3,4′-pyridine]-2′-thiolates. The reactivity and structure of the products was studied. We found that oxidation of spiro[indole-3,4′-pyridine]-2′-thiolates with DMSO-HCl system produced only acidification products, diastereomeric 6′-amino-5′-cyano-5-methyl-2-oxo-2′-thioxo-1,2,2′,3′-tetrahydro-1′H-spiro-[indole-3,4′-pyridine]- 3′-carboxamides, instead of the expected isothiazolopyridines. The alkylation of the prepared spiro[indole-3,4′-pyridine]-2′-thiolates upon treatment with N-aryl α-chloroacetamides and α-bromoacetophenones proceeds in a regioselective way at the sulfur atom. In the case of α-bromoacetophenones, ring-chain tautomerism was observed for the S-alkylation products. According to NMR data, the compounds consist of a mixture of stereoisomers of 2′-amino-6′-[(2-aryl- 2-oxoethyl)thio]-3′-cyano-2-oxo-1′H-spiro[indoline-3,4′-pyridine]-5′-carboxamides and 5′-amino- 3′-aryl-6′-cyano-3′-hydroxy-2-oxo-2′,3′-dihydrospiro[indoline-3,7′-thiazolo[3,2-a]pyridine]-8′-carboxamides in various ratios. The structure of the synthesized compounds was confirmed by IR spectroscopy, HRMS, 1H and 13C DEPTQ NMR studies and the results of 2D NMR experiments (1H-13C HSQC, 1H-13C HMBC). Molecular docking studies were performed to investigate suitable binding modes of some new compounds with respect to the transcriptional regulator protein PqsR of Pseudomonas aeruginosa. The docking studies revealed that the compounds have affinity for the bacterial regulator protein PqsR of Pseudomonas aeruginosa with a binding energy in the range of −5.8 to −8.2 kcal/mol. In addition, one of the new compounds, 2′-amino-3′-cyano-5-methyl- 2-oxo-6′-{[2-oxo-2-(p-tolylamino)ethyl]thio}-1′H-spiro-[indoline-3,4′-pyridine]-5′-carboxamide, showed in vitro moderate antibacterial effect against Pseudomonas aeruginosa and good antioxidant properties in a test with 1,1-diphenyl-2-picrylhydrazyl radical. Finally, three of the new compounds were recognized as moderately active herbicide safeners with respect to herbicide 2,4-D in the laboratory experiments on sunflower seedlings.

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Section: Resultsmentioning

confidence: 99%

New 6′-Amino-5′-cyano-2-oxo-1,2-dihydro-1′H-spiro[indole-3,4′-pyridine]-3′-carboxamides: Synthesis, Reactions, Molecular Docking Studies and Biological Activity

et al. 2023

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“…In addition, the ADMET profiles of 5 possible DNA gyrase B inhibitors were predicted by using the pkCSM platform (Table 4). Previous studies of 3-aminothieno[2,3-b]pyridines have revealed among these compounds antidotes that were able to reduce the damaging effects of the herbicide 2,4-D on sunflower plants, 40 as well as compounds that regulated plant growth and mitigated the effects of stressful conditions. 41 We were clearly interested in determining any such possible activity -herbicidal, antidote, or growth regulating, that may be exhibited by our synthesized products -novel thieno[2,3-b]pyridine derivatives 6i,b and 9a,b,e.…”

Section: In Silico Prediction Of Molecular Properties and Admet Profilesmentioning

confidence: 99%

Design, Synthesis, and Screening of Pyridothieno[3,2-b]indole and Pyridothieno[3,2-c]cinnoline Derivatives as Potential Biologically Active Molecules

et al. 2022

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A new pyridothieno[3,2-b]indole and pyridothieno[3,2-c]cinnoline derivatives are designed and prepared form corresponding 3-amino-2-arylthieno[2,3-b]pyridines. By molecular docking method novel potential inhibitors of DNA gyrase B are identified among the thieno[2,3-b]pyridine derivatives. In addition, some of prepared pyridothienoindoles exhibit in vivo antidote activity against the herbicide 2,4-D.

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“…In continuation of our studies on the synthesis and biological properties of thienopyridines, − we wish now to report the synthesis and structures of new polyheterocyclic ensembles prepared by noncatalyzed oxidative dimerization of 3-aminothieno[2,3- b ]pyridine-2-carboxamides.…”

Section: Introductionmentioning

confidence: 99%

Unusual Oxidative Dimerization in the 3-Aminothieno[2,3-b]pyridine-2-carboxamide Series

et al. 2021

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Noncatalyzed, regio-and stereoselective hypochlorite oxidation of 3-aminothieno[2,3-b]pyridine-2-carboxamides is presented. Unexpectedly, the oxidation proceeded by different mechanistic pathways, and different products were formed, depending on the nature of solvents used. A possible mechanism, the structure of products, kinetics and dynamics of intramolecular processes, and biological activity of products are discussed.

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Synthesis of N-alkylated benzo- and pyridothienopyrrolo-[1,2a][1,4]diazepin-6-ones acting as antidotes against the herbicide 2,4-D

Cited by 7 publications

References 6 publications

New 6′-Amino-5′-cyano-2-oxo-1,2-dihydro-1′H-spiro[indole-3,4′-pyridine]-3′-carboxamides: Synthesis, Reactions, Molecular Docking Studies and Biological Activity

New 6′-Amino-5′-cyano-2-oxo-1,2-dihydro-1′H-spiro[indole-3,4′-pyridine]-3′-carboxamides: Synthesis, Reactions, Molecular Docking Studies and Biological Activity

Design, Synthesis, and Screening of Pyridothieno[3,2-b]indole and Pyridothieno[3,2-c]cinnoline Derivatives as Potential Biologically Active Molecules

Unusual Oxidative Dimerization in the 3-Aminothieno[2,3-b]pyridine-2-carboxamide Series

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