Catalyst-free synthesis of substituted pyridin-2-yl, quinolin-2-yl, and isoquinolin-1-yl carbamates from the corresponding hetaryl ureas and alcohols

Kasatkina, Svetlana O.; Geyl, Kirill K.; Baykov, Sergey V.; Boyarskaya, Irina А.; Boyarskiy, Vadim P.

doi:10.1039/d1ob00783a

Cited by 15 publications

(14 citation statements)

References 63 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All 2-pyridyl ureas ( U1–12 ) were synthesized via the acid-catalyzed reaction of corresponding N -oxides with dialkylcyanamides as described in our previous works ( Scheme 1 ) [ 33 , 34 , 37 ]. Briefly, the starting materials were mixed and heated in the presence of methanesulfonic acid (MsOH) in acetonitrile or under solvent-free conditions (depending of the reactivity and solubility of starting N -oxide).…”

Section: Resultsmentioning

confidence: 99%

“…The preparation and characterization of starting pyridine- N -oxides as well as U1–12 are described previously [ 33 , 34 , 37 ]. CuCl 2 , other reactants, and solvents were obtained from commercial sources.…”

Section: Methodsmentioning

confidence: 99%

“…For most of the complexes, noticeable destruction began only at temperatures above 200 • C; for several species, this temperature decreased to 130-150 • C. This indicates not only the thermal stability of the complexes, but also the fact that coordination to the copper metal center stabilizes the ligands. The original ureas themselves begin to decompose already at temperatures slightly above 100 • C [37].…”

Section: Complexmentioning

confidence: 99%

“…The structure and reactivity (including coordination with Pt(II)) of these compounds were studied [ 36 , 37 , 38 ]. In the present study we employed N , N -dialkyl- N ′-(pyridin-2-yl)-ureas, thus obtained, to synthesize novel Cu(II) complexes in the context of the global drug discovery efforts for metal-based tumor-suppressing agents.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis, Structure, and Antiproliferative Action of 2-Pyridyl Urea-Based Cu(II) Complexes

et al. 2022

Self Cite

View full text Add to dashboard Cite

Relying on a recently suggested protocol that furnishes convenient access to variously substituted 2-pyridyl ureas, twelve hitherto unknown Cu(II) complexes have been synthesized in the present work and their structures were evaluated by elemental analysis, HRMS, IR spectroscopy, and X-ray diffraction study. Two structural motifs ([Cu(L)2Cl]+[Cl]− or (Cu(L)2Cl2) depending on the substitution pattern on the 2-pyridine fragment were revealed. In addition, antiproliferative action of the obtained compounds have been investigated against lung cancer cell lines (A549, NCI-H460, NCI-H1975), and healthy WI-26 VA4 cells were used to monitor non-specific cytotoxicity. Two nitro-group substituted complexes Cu(U3)2Cl2 (IC50 = 39.6 ± 4.5 μM) and Cu(U11)2Cl2 (IC50 = 33.4 ± 3.8 μM) demonstrate enhanced activity against the drug resistant NCI-H1975 cells with moderate selectivity toward normal WI-26 VA4 cells. The antiproliferative mechanism of cell death underlying the growth inhibitory effect of the synthesized complexes was studied via additional experiments, including the cell cycle analysis and the apoptosis induction test. Reassuringly, certain 2-pyridyl urea-based Cu(II) complexes exerted cell line-specific antiproliferative effect which renders them valuable starting points for further unveiling the anticancer potential of this class of coordination compounds.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Complexmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis, Structure, and Antiproliferative Action of 2-Pyridyl Urea-Based Cu(II) Complexes

et al. 2022

Self Cite

View full text Add to dashboard Cite

show abstract

“…Therefore, we decided to develop a new strategy based on the ability of urea and alkyl/arylureas to decompose with the formation of ammonia/amines and isocyanates ( Scheme 5 ) [ 20 , 21 ].…”

Section: Resultsmentioning

confidence: 99%

Amination of 5-Spiro-Substituted 3-Hydroxy-1,5-dihydro-2H-pyrrol-2-ones

et al. 2021

View full text Add to dashboard Cite

The 3-hydroxy-1,5-dihydro-2H-pyrrol-2-one motif is a valuable scaffold in drug discovery. The replacement of the 3-oxy fragment in 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones-based compounds with a 3-amino one (3-amino analogs of 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones, 3-amino-1,5-dihydro-2H-pyrrol-2-ones) can play a crucial role in their biological effect. Thus, approaches to 3-amino-1,5-dihydro-2H-pyrrol-2-ones are of significant interest. We developed an approach to 5-spiro-substituted 3-amino-1,5-dihydro-2H-pyrrol-2-ones that could not be obtained using previously reported approaches (reactions of 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones with amines). The developed approach is based on the thermal decomposition of 1,3-disubstituted urea derivatives of 5-spiro-substituted 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones, which were prepared via their reaction with carbodiimides.

show abstract

“Urea to Urea” Approach: Access to Unsymmetrical Ureas Bearing Pyridyl Substituents

et al. 2022

Self Cite

View full text Add to dashboard Cite

A protocol for the synthesis of unsymmetrical ureas substituted by pyridyl/quinolinyl moiety has been developed. This method concluded in metal‐ and base‐free reamination of N,N‐dimethyl‐N‘‐hetaryl ureas with a wide range of aryl and alkyl amines. The isolated yields vary from 40 to 96% depending on the nucleophilicity of the amines. The scope of this method includes more than 50 examples. The reaction is not hindered by either donor or acceptor groups as well as diverse functionalities. The synthesis can be easily scaled to gram quantities. Theoretical calculations supported by experimental data allowed us to propose a plausible mechanism for the process. This reaction takes place through the intermediate formation of hetaryl isocyanate.

show abstract

Catalyst-free synthesis of substituted pyridin-2-yl, quinolin-2-yl, and isoquinolin-1-yl carbamates from the corresponding hetaryl ureas and alcohols

Abstract: A novel catalyst-free synthesis of N-pyridin-2-yl, N-quinolin-2-yl, and N-isoquinolin-1-yl carbamates utilizes easily accessible N-hetaryl ureas and alcohols. The proposed environmentally friendly technique is suitable for the good-to-high yielding synthesis of...

Cited by 15 publications

References 63 publications

Synthesis, Structure, and Antiproliferative Action of 2-Pyridyl Urea-Based Cu(II) Complexes

Synthesis, Structure, and Antiproliferative Action of 2-Pyridyl Urea-Based Cu(II) Complexes

Amination of 5-Spiro-Substituted 3-Hydroxy-1,5-dihydro-2H-pyrrol-2-ones

“Urea to Urea” Approach: Access to Unsymmetrical Ureas Bearing Pyridyl Substituents

Contact Info

Product

Resources

About