Synthesis of new 1-phenyl-3-{4-[(2E)-3-phenylprop-2-enoyl]phenyl}-thiourea and urea derivatives with anti-nociceptive activity

Santos, Lorena dos; Lima, Luíse Azevedo; Cechinel‐Filho, Valdir; Corrêa, Rogério; Buzzi, Fátima de Campos; Nunes, Ricardo José

doi:10.1016/j.bmc.2008.08.019

Cited by 47 publications

(22 citation statements)

References 48 publications

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“…Synthetic procedure for obtaining target compounds ( 7 a‐t ) is depicted in Scheme . As seen in this, the target compounds ( 7 a‐t ) were synthesized by four steps including modified condensation, addition and ring closing reactions …”

Section: Resultsmentioning

confidence: 99%

Synthesis, Biological Activity and Structure‐Activity Relationship of Novel Diphenylurea Derivatives Containing Tetrahydroquinoline as Carbonic Anhydrase I and II Inhibitors

et al. 2018

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A series of novel tetrahydroquinoline derivatives containing urea moiety was synthesized and their in vitro inhibitory effects on the human carbonic anhydrase isoenzymes (hCA−I and hCA‐II) were evaluated by using the CO2 hydration method. All the synthesized compounds exhibited inhibitory activity against both hCA I and hCA II with 1‐(4‐fluorophenyl)‐3‐(4‐(4‐p‐tolyl‐5,6,7,8‐tetrahydroquinolin‐2‐yl)phenyl)urea (7 k, IC50 value of 5.28 μM and 5.51 μM, against hCA I and hCA II, respectively) as the strongest inhibitor in this study. Structure‐activity relationships were also investigated. The results showed that most of synthesized compounds have a higher inhibitory activity against hCA I than hCA II. Also the substituents, containing two or more pairs of non‐bonding electrons, generally increased the hCA I and II inhibitory activity. Furthermore, some electronic parameters such as the highest occupied molecular orbital and the lowest unoccupied molecular orbital (HOMO‐LUMO) energy levels, electron affinity, total energy and dipole moments of the best inhibitors (7 b, 7 h and 7 k) in this study were also calculated by using Gaussian software. The results revealed that HOMO‐LUMO energy differences, total energy, chemical hardness and dipole moment of 7 b, 7 h and 7 k showed a linear relationship with increasing inhibitory activity.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Biological Activity and Structure‐Activity Relationship of Novel Diphenylurea Derivatives Containing Tetrahydroquinoline as Carbonic Anhydrase I and II Inhibitors

et al. 2018

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“…Urea derivatives are important intermediates in medicinal chemistry [3][4][5]. Many convenient processes have been reported for the production of substituted ureas [6][7][8][9][10][11].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 1,1-dimethyl-3-(4-methylphenyl)urea, C₁₀H₁₄N₂O

El‐Hiti

Smith

Hegazy

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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CCDC no.: 1527333The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materialThe title compound was synthesised by reaction of equimolar quantities of 4-methylaniline and dimethylcarbamoyl chloride in dichloromethane at 40°C for 1 h in the presence of excess triethylamine (1.38 mole equivalents). The crude product was recrystallized from a 1:3 mixture (by volume) of ethyl acetate and diethyl ether to give 1,1-dimethyl-3-(4-methylphenyl)urea (92%) as colourless crystals, Mp.

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“…Urea-containing compounds are established as precursors for several biologically active agents [1][2][3][4]. Various efficient procedures have been used for the synthesis of ureas [5][6][7][8][9][10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

A Reversible Single-Crystal to Single-Crystal Thermal Phase Transformation of 3-(2-Bromo-4-(1-methylethyl)phenyl)-1,1-dimethyl urea

Kariuki

El‐Hiti

2017

Crystals

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3-(2-Bromo-4-(1-methylethyl)phenyl)-1,1-dimethylurea was synthesized and structurally characterized at 296 K, 200 K and 140 K. A reversible thermal phase transformation was observed at~170-180 K. On cooling, the structure transforms from a monoclinic to a triclinic crystal system. The isopropyl group is disordered above the phase transition temperature but is ordered below the transition temperature.

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Synthesis of new 1-phenyl-3-{4-[(2E)-3-phenylprop-2-enoyl]phenyl}-thiourea and urea derivatives with anti-nociceptive activity

Cited by 47 publications

References 48 publications

Synthesis, Biological Activity and Structure‐Activity Relationship of Novel Diphenylurea Derivatives Containing Tetrahydroquinoline as Carbonic Anhydrase I and II Inhibitors

Synthesis, Biological Activity and Structure‐Activity Relationship of Novel Diphenylurea Derivatives Containing Tetrahydroquinoline as Carbonic Anhydrase I and II Inhibitors

Crystal structure of 1,1-dimethyl-3-(4-methylphenyl)urea, C₁₀H₁₄N₂O

A Reversible Single-Crystal to Single-Crystal Thermal Phase Transformation of 3-(2-Bromo-4-(1-methylethyl)phenyl)-1,1-dimethyl urea

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Synthesis of new 1-phenyl-3-{4-[(2E)-3-phenylprop-2-enoyl]phenyl}-thiourea and urea derivatives with anti-nociceptive activity

Cited by 47 publications

References 48 publications

Synthesis, Biological Activity and Structure‐Activity Relationship of Novel Diphenylurea Derivatives Containing Tetrahydroquinoline as Carbonic Anhydrase I and II Inhibitors

Synthesis, Biological Activity and Structure‐Activity Relationship of Novel Diphenylurea Derivatives Containing Tetrahydroquinoline as Carbonic Anhydrase I and II Inhibitors

Crystal structure of 1,1-dimethyl-3-(4-methylphenyl)urea, C10H14N2O

A Reversible Single-Crystal to Single-Crystal Thermal Phase Transformation of 3-(2-Bromo-4-(1-methylethyl)phenyl)-1,1-dimethyl urea

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Crystal structure of 1,1-dimethyl-3-(4-methylphenyl)urea, C₁₀H₁₄N₂O