scholarly journals Genetically encoded fluorophenylalanines enable insights into the recognition of lysine trimethylation by an epigenetic reader

2016 ◽  
Vol 52 (85) ◽  
pp. 12606-12609 ◽  
Author(s):  
Yan-Jiun Lee ◽  
M. J. Schmidt ◽  
Jeffery M. Tharp ◽  
Annemarie Weber ◽  
Amber L. Koenig ◽  
...  
Keyword(s):  
Phenyl Ring ◽  
Amber Codon

Fluorophenylalanines bearing 2–5 fluorine atoms at the phenyl ring have been genetically encoded by amber codon.

New Amine and Aromatic Substituted Analogues of Phencyclidine: Synthesis and Determination of Acute and Chronic Pain Activities

2019 ◽  
Vol 22 (8) ◽  
pp. 570-576
Author(s):  
Maryam Shokrollahi ◽  
Marjaneh Samadizadeh ◽  
Mohsen Khalili ◽  
Seyed A. Sobhanian ◽  
Abbas Ahmadi
Keyword(s):  
Nmda Receptors ◽  
Phenyl Ring ◽  
Piperidine Ring ◽  
Methyl Group ◽  
Physiological Properties ◽  
Antinociceptive Effects ◽  
The Central Nervous System ◽  
Analgesic Activities ◽  
Compound Ii ◽  
New Compounds

Background: Phencyclidine (PCP, I) is a synthetic drug with remarkable physiological properties. PCP and its analogues exert many pharmacological activities and interact with some neurotransmitter systems in the central nervous system like particular affinity for PCP sites in NMDA receptors or dopamine uptake blocking or even both. Aim and Objective: The following research, methyl group with electron-donating and dipole moment characters was added in different positions of phenyl ring along with the substitution of benzylamine (with many pharmacological effects) instead of piperidine ring of I to produce new compounds (II-V) of this family with more analgesic activities. Materials and Methods: Analgesic activities of these new compounds were measured by tail immersion and formalin tests for acute and chronic pains, respectively. Also, the outcomes were compared with control and PCP (10 mg/kg) groups. Results: The results indicate that compounds III, IV, and V have more acute and chronic antinociceptive effects than PCP and compound II which may be concerned with more antagonizing activities of these new painkillers for the blockage of dopamine reuptake as well as high affinity for NMDA receptors PCP binding site. Conclusion: It can be concluded that the benzylamine derivative of phencyclidine with a methyl group on the benzyl position on phenyl ring (V) is a more appropriate candidate to reduce acute and chronic (thermal and chemical) pains compared to other substituted phenyl analogs (II-IV) and PCP.

Oxidation of (1-hydroxybenzyl)ferrocene and its derivatives substituted in phenyl ring with bis(triphenylsilyl) chromate

1982 ◽  
Vol 47 (12) ◽  
pp. 3375-3380 ◽  
Author(s):  
Jaroslav Holeček ◽  
Karel Handlíř ◽  
Milan Nádvorník ◽  
Milan Vlček
Keyword(s):  
Linear Dependence ◽  
Rate Constants ◽  
Oxidation Rate ◽  
Phenyl Ring ◽  
Equilibrium Constants ◽  
Aprotic Solvents ◽  
Protonation Equilibrium ◽  
Oxidation Of Alcohols ◽  
Hammett Σ Constants ◽  
Sulphuric Acid Medium

Kinetics have been studied of oxidation of (1-hydroxybenzyl)ferrocenes substituted in phenyl ring with bis(triphenylsilyl) chromate in benzene solutions as well as protonation of these alcohols in sulphuric acid medium. Logarithms of the oxidation rate constants (kobs, 20-40 °C) and those of the protonation equilibrium constants (KR+, 25 °C) show linear dependence on the Hammett σ constants, the ρ constant values being -0.86 to -0.40 and -2.50, respectively. These negative values suggest that the both processes are influenced by the same effects and confirm the mechanism proposed earlier for oxidation of alcohols with ferrocenyl substituent by action of bis(triphenylsilyl) chromate in aprotic solvents.

scholarly journals Computational Investigations on the Binding Mode of Ligands for the Cannabinoid-Activated G Protein-Coupled Receptor GPR18

Biomolecules ◽  
2020 ◽  
Vol 10 (5) ◽  
pp. 686 ◽  
Author(s):  
Alexander Neumann ◽  
Viktor Engel ◽  
Andhika B. Mahardhika ◽  
Clara T. Schoeder ◽  
Vigneshwaran Namasivayam ◽  
...  
Keyword(s):  
Molecular Dynamics ◽  
Molecular Dynamics Simulation ◽  
G Protein ◽  
Phenyl Ring ◽  
Binding Mode ◽  
Dynamics Simulation ◽  
Simulation Studies ◽  
Binding Modes ◽  
G Protein Coupled Receptor ◽  
G Protein Coupled

GPR18 is an orphan G protein-coupled receptor (GPCR) expressed in cells of the immune system. It is activated by the cannabinoid receptor (CB) agonist ∆9-tetrahydrocannabinol (THC). Several further lipids have been proposed to act as GPR18 agonists, but these results still require unambiguous confirmation. In the present study, we constructed a homology model of the human GPR18 based on an ensemble of three GPCR crystal structures to investigate the binding modes of the agonist THC and the recently reported antagonists which feature an imidazothiazinone core to which a (substituted) phenyl ring is connected via a lipophilic linker. Docking and molecular dynamics simulation studies were performed. As a result, a hydrophobic binding pocket is predicted to accommodate the imidazothiazinone core, while the terminal phenyl ring projects towards an aromatic pocket. Hydrophobic interaction of Cys251 with substituents on the phenyl ring could explain the high potency of the most potent derivatives. Molecular dynamics simulation studies suggest that the binding of imidazothiazinone antagonists stabilizes transmembrane regions TM1, TM6 and TM7 of the receptor through a salt bridge between Asp118 and Lys133. The agonist THC is presumed to bind differently to GPR18 than to the distantly related CB receptors. This study provides insights into the binding mode of GPR18 agonists and antagonists which will facilitate future drug design for this promising potential drug target.

Cyanoacrylate Inhibitors of the Hill Reaction V. The Effect of Chirality on Inhibitor Binding

1987 ◽  
Vol 42 (6) ◽  
pp. 684-689 ◽  
Author(s):  
John L. Huppatz ◽  
John N. Phillips
Keyword(s):  
Phenyl Ring ◽  
Alkyl Substituent ◽  
Receptor Site ◽  
Optically Active ◽  
Hill Reaction ◽  
Inhibitor Binding ◽  
Level Of Activity ◽  
The Difference ◽  
The Hill

Optically active α-methylbenzylamino 2-cyanoacrylic esters were synthesized and assayed as inhibitors of the Hill reaction in isolated pea chloroplast fragments. The 5-isomers were more potent inhibitors than the S-isomers with discriminations of from ten to greater than 100-fold being observed. A β-alkyl substituent in the cyanoacrylate molecule affected both the level of activity and the difference in activity between the isomers. An α,α-dimethylbenzylamino derivative was also active at about the same level as the corresponding α-methylbenzylamino racemate. This result could be explained in terms of the orientation of the phenyl ring in the receptor site. Replacement of the α-methylbenzylamino group by other α-alkyl and α-phenyl substituents had little effect on activity. However, an α-benzyl group was beneficial.

XXI.—The Synthesis of Some Methyl- and Dimethylfluoranthenes

1972 ◽  
Vol 69 (4) ◽  
pp. 281-286
Author(s):  
H. F. Andrew ◽  
Neil Campbell ◽  
E. M. Swan ◽  
N. H. Wilson
Keyword(s):  
Benzene Ring ◽  
Propionic Acid ◽  
Hydrofluoric Acid ◽  
Phenyl Ring ◽  
Ring Closure ◽  
Methyl Group ◽  
Image Position

3-Methylfluorene-9-propionic acid (1) with hydrofluoric acid undergoes ring-closure on the substituted ring to give 1,2,3,10b-tetrahydro-5-methylfluoranthen-3-one (II).Wolff-Kishner reduction of the ketone yielded l,2,3,10b-tetrahydro-5-methylfluoranthene which on dehydrogenation gave 2-methylfluoranthene (III, R=H) identical with a sample prepared according to the method of Tucker (1952) and differing from 8-methylfluoranthene. This proved that ring-closure of (I) had occurred as expected on the methyl-bearing benzene ring. In this instance ring-closure occurs in the position meta to the methyl group and is reminiscent of the similar ring-closure of 2-phenyl-2-p-tolylpropionic acid to give 6-methyl-3-phenylindanone (Pfeiffer and Roos 1941). It thus provided a further example of the limitations of von Braun's statement that Friedel-Crafts ring-closure occurs much less readily at the position meta to a methyl group than on a phenyl ring (von Braun, Manz and Reinsch 1928).

scholarly journals 3-(2,4-Dichlorophenyl)-5-(4-fluorophenyl)-2-phenyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

2012 ◽  
Vol 68 (6) ◽  
pp. o1923-o1923
Author(s):  
Ju Liu ◽  
Zhi-Qiang Cai ◽  
Yang Wang ◽  
Yu-Li Sang ◽  
Li-Feng Xu
Keyword(s):  
Dihedral Angle ◽  
Title Compound ◽  
Phenyl Ring ◽  
Crystal Packing ◽  
Van Der Waals ◽  
Van Der Waals Interactions ◽  
Compound C ◽  
Benzene Rings ◽  
Planar Systems

In the title compound, C25H13Cl2F4N3, there are four planar systems, viz. three benzene rings and a pyrazolo[1,5-a]pyrimidine system [r.m.s. deviation = 0.002 Å]. The dihedral angle between the dichlorophenyl ring and the unsubstituted phenyl ring is 69.95 (5)°, while that between the fluorophenyl ring and the unsubstituted phenyl ring is 7.97 (10)°. The crystal packing is dominated by van der Waals interactions. A Cl...Cl interaction of 3.475 (3) Å also occurs.

The Bond N -Cl. A Spectroscopic (35Cl-NQR, IR) Investigation

1994 ◽  
Vol 49 (6) ◽  
pp. 695-702 ◽  
Author(s):  
B. Thimme Gowda ◽  
Alarich Weiss
Keyword(s):  
Phenyl Ring ◽  
Electron Distribution ◽  
Inductive Effect ◽  
Aqueous Media ◽  
Phenyl Group ◽  
Vibration Frequencies ◽  
Resonance Frequencies ◽  
35Cl Nqr ◽  
Cl Atoms ◽  
Cl Atom

Abstract Chlorine bound to nitrogen is an interesting oxidizing agent in aqueous, partial aqueous and non-aqueous media. One can assume that the oxidizing action of the chlorine depends on the polarization of the Cl atom in the bond N -Cl which will depend on the electron distribution in the ligands R and R″ of the configuration R -NCl -CO -R″. 17 compounds were synthesized with R = substituted phenyl radical C6H5-y Xy, X = Cl, NO2, R″ = CH2Cl. The 35Cl NQR frequencies are observed in the range 52 to 54 MHz (T = 77 K) for the Cl(N) 34 to 37 MHz for the phenyl chlorines and the CH2Cl group. Their temperature dependence was followed up to 300 K. Therefrom the assignment of the resonance to certain Cl-atoms in the molecules is possible. Generally, the substitution of a negative substituent X (Cl, NO2) in the phenyl ring raises the resonance frequencies; the influence of the CH2Cl group on the N -Cl bond is weak. Strong is the influence of the carbonyl group on the N -C l bond. The IR group frequencies ν(C = O) are found in the range 1680 ≤ ν (C = O)/ cm−1≤ 1717, shifted up by ≤ 20 cm−1 compared to the corresponding acetamide R ⎯ NH ⎯CO ⎯ R″. Influence of the phenyl ring substitution on ν (C = O) does not follow a simple law of inductive effect. Also a correlation between the vibration frequencies of the N ⎯ Cl group and the phenyl group substitution is not found.

scholarly journals Crystal structure of (3E)-3-(2,4-dinitrophenoxymethyl)-4-phenylbut-3-en-2-one

2014 ◽  
Vol 70 (9) ◽  
pp. o1051-o1052 ◽  
Author(s):  
Ignez Caracelli ◽  
Stella H. Maganhi ◽  
Paulo J. S. Moran ◽  
Bruno R. S. de Paula ◽  
Felix N. Delling ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Double Bond ◽  
Nitro Group ◽  
Benzene Ring ◽  
Torsion Angle ◽  
Title Compound ◽  
Phenyl Ring ◽  
Aromatic Rings ◽  
Compound C ◽  
The One

In the title compound, C17H14N2O6, the conformation about the C=C double bond [1.345 (2) Å] isE, with the ketone moiety almost coplanar [C—C—C—C torsion angle = 9.5 (2)°] along with the phenyl ring [C—C—C—C = 5.9 (2)°]. The aromatic rings are almost perpendicular to each other [dihedral angle = 86.66 (7)°]. The 4-nitro moiety is approximately coplanar with the benzene ring to which it is attached [O—N—C—C = 4.2 (2)°], whereas the one in theorthoposition is twisted [O—N—C—C = 138.28 (13)°]. The molecules associateviaC—H...O interactions, involving both O atoms from the 2-nitro group, to form a helical supramolecular chain along [010]. Nitro–nitro N...O interactions [2.8461 (19) Å] connect the chains into layers that stack along [001].

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