Synthesis of 4,4,6-trimethyl-8-R-4H-pyrrolo [3,2,1-ij] quinoline-1,2-diones

Lescheva, E. V.; Медведева, С. М.; Шихалиев, Х. С.

doi:10.24959/ophcj.14.798

Cited by 12 publications

(11 citation statements)

References 3 publications

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“…In the 1 H NMR spectra of all 1,3-oxazinoquinolines 10, the proton signals of the gem-dimethyl groups and other substituents at positions 7 and 9 of the hydroquinoline fragments appear in the corresponding regions. 39,41,42 . It should be noted that in the aromatic areas of the spectra, the signals of some protons of the hydroquinoline cycles were shifted quite downfield -up to 8.0 ppm, which we observed earlier in previous research.…”

Section: Resultsmentioning

confidence: 99%

“…In order to obtain new oxazinohydroquinolines, and to establish their structure, in this work we carried out the oxidation of 4,4,6-trimethyl-4H-pyrrolo[3,2,1-ij]quinoline-1,2-diones 9 and their hydrogenated analogs, 4,4,6-trimethyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-diones 8, with m-chloroperbenzoic acid. -e) were prepared according to the Stolle method, 40 which we had previously modified 41,42 by reacting the hydrochlorides of the corresponding starting substituted hydroquinolines with oxalyl chloride (without using Lewis acids as catalysts, which are required for cyclization in the classical version of the reaction). In a previous paper 38 we developed optimal conditions for the selective oxidation of pyrrolo[3,2,1-ij]quinoline-1,2-dione 5 in THF, leading to the formation of 1,3-oxazinoquinolinedione 6.…”

Section: R Nmentioning

confidence: 99%

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Synthesis of substituted 1,3-oxazino[5,4,3-ij]quinolin-1,3-diones by the oxidation of various pyrrolo[3,2,1-ij]quinoline-1,2-diones with m-chloroperbenzoic acid

Медведева¹,

Movchan²,

Заварзин³

et al. 2022

Arkivoc

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When various pyrrolo[3,2,1-ij]quinoline-1,2-diones were oxidized with m-chloroperbenzoic acid, 1,3oxazino [5,4,3-ij]quinolin-1,3-diones were obtained in good yields (64-86%) and characterized by spectral methods. Recyclization/rearrangement of the pyrroldione fragment of pyrrolo[3,2,1-ij]quinoline-1,2-diones, regardless of the presence and electronic nature of the substituent in the aromatic part, the presence of a bulky phenyl group or a multiple bond in the heterocyclic fragment, proceeds selectively with the formation of a 1,3oxazine cycle, rather than an isomeric 1,4-oxazine ring. This outcome corresponds to the data acquired from quantum mechanical calculations.

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Section: Resultsmentioning

confidence: 99%

Section: R Nmentioning

confidence: 99%

Synthesis of substituted 1,3-oxazino[5,4,3-ij]quinolin-1,3-diones by the oxidation of various pyrrolo[3,2,1-ij]quinoline-1,2-diones with m-chloroperbenzoic acid

Медведева¹,

Movchan²,

Заварзин³

et al. 2022

Arkivoc

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“…The compound 17f (4,4,6-trimethyl-2-oxo-1-(4-oxo-2-thioxo-1,3-thiazolidin-5-ylidene)-1,2-dihydro-4 H -pyrrolo[3,2,1- ij ]quinolin-8-yl-3-[3,4-bis(methyloxy)phenyl]prop-2-enoate) was synthesized by known methods from 6-hydroxy-2,2,4-trimethyl-1,2-dihydroquinoline [ 47 ] consistently carrying out the acylation reaction at the hydroxyl group by 3,4-dimethoxy-cinnamic acid chloride [ 48 ] annelation of pyrrole-1,2-dione fragment on the Stolle reaction by the action of oxalyl chloride [ 49 ] and subsequent condensation on the β -carbonyl group of annelated fragment with rhodanine [ 50 ] ( Scheme 1 ).…”

Section: Materials and Methods Of The Researchmentioning

confidence: 99%

“…The starting compound was synthesized according to a published method [ 47 – 49 ]. Commercially available reagents from Lancaster also were used in the syntheses.…”

Section: Materials and Methods Of The Researchmentioning

confidence: 99%

Application of Molecular Modeling to Development of New Factor Xa Inhibitors

Сулимов

Gribkova

Kochugaeva

et al. 2015

BioMed Research International

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In consequence of the key role of factor Xa in the clotting cascade and absence of its activity in the processes that do not affect coagulation, this protein is an attractive target for development of new blood coagulation inhibitors. Factor Xa is more effective and convenient target for creation of anticoagulants than thrombin, inhibition of which may cause some side effects. This study is aimed at finding new inhibitors of factor Xa by molecular computer modeling including docking SOL and postdocking optimization DISCORE programs. After validation of molecular modeling methods on well-known factor Xa inhibitors the virtual screening of NCI Diversity and Voronezh State University databases of ready-made low molecular weight species has been carried out. Seventeen compounds selected on the basis of modeling results have been tested experimentally in vitro. It has been found that 12 of them showed activity against factor Xa (IC50 = 1.8–40 μM). Based on analysis of the results, the new original compound was synthesized and experimentally verified. It shows activity against factor Xa with IC50 value of 0.7 μM.

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“…The starting compound Ia,b, II was synthesized according to a published method [46,47]. Commercially available reagents from Lancaster were also used in the syntheses.…”

Section: Chemicalsmentioning

confidence: 99%

New Blood Coagulation Factor XIIa Inhibitors: Molecular Modeling, Synthesis, and Experimental Confirmation

et al. 2022

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In the modern world, complications caused by disorders in the blood coagulation system are found in almost all areas of medicine. Thus, the development of new, more advanced drugs that can prevent pathological conditions without disrupting normal hemostasis is an urgent task. The blood coagulation factor XIIa is one of the most promising therapeutic targets for the development of anticoagulants based on its inhibitors. The initial stage of drug development is directly related to computational methods of searching for a lead compound. In this study, docking followed by quantum chemical calculations was used to search for noncovalent low-molecular-weight factor XIIa inhibitors in a focused library of druglike compounds. As a result of the study, four low-molecular-weight compounds were experimentally confirmed as factor XIIa inhibitors. Selectivity testing revealed that two of the identified factor XIIa inhibitors were selective over the coagulation factors Xa and XIa.

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Synthesis of 4,4,6-trimethyl-8-R-4H-pyrrolo [3,2,1-ij] quinoline-1,2-diones

Cited by 12 publications

References 3 publications

Synthesis of substituted 1,3-oxazino[5,4,3-ij]quinolin-1,3-diones by the oxidation of various pyrrolo[3,2,1-ij]quinoline-1,2-diones with m-chloroperbenzoic acid

Synthesis of substituted 1,3-oxazino[5,4,3-ij]quinolin-1,3-diones by the oxidation of various pyrrolo[3,2,1-ij]quinoline-1,2-diones with m-chloroperbenzoic acid

Application of Molecular Modeling to Development of New Factor Xa Inhibitors

New Blood Coagulation Factor XIIa Inhibitors: Molecular Modeling, Synthesis, and Experimental Confirmation

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