Photoredox generation of sulfonyl radicals and coupling with electron deficient olefins

Various sulfone tetrazoles were activated via iridium photoredox catalysis in the presence of DMAP to give dialkyl sulfones. The presumed sulfone radical intermediates were trapped by a range of electron deficient olefins in generally good to excel-lent yields.Pfizer for funding the postdoctoral fellowship. COST Action CA18133 ERNEST for funding short term scientific mission (STSM). American Chemical Society through the Arthur C. Cope Fund (award to SVL). H2020-FETOPEN-2016-2017 programe of European commission (SVL; grant agreement number: 737266-ONE FLOW

2-(2,5-Dimeth­oxy­phen­yl)-N-[2-(4-hy­droxy­phen­yl)eth­yl]acetamide

In the title compound, C18H21NO4, the dihedral angles between the acetamide group and the meth­oxy- and hy­droxy-substitured benzene rings are 80.81 (5) and 8.19 (12)°, respectively. The benzene rings are twisted with respect to each other, making a dihedral angle of 72.89 (5)°. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network

Involvement of GPR17 in Neuronal Fibre Outgrowth

Characterization of new pharmacological targets is a promising approach in research of neurorepair mechanisms. The G protein-coupled receptor 17 (GPR17) has recently been proposed as an interesting pharmacological target, e.g., in neuroregenerative processes. Using the well-established ex vivo model of organotypic slice co-cultures of the mesocortical dopaminergic system (prefrontal cortex (PFC) and substantia nigra/ventral tegmental area (SN/VTA) complex), the influence of GPR17 ligands on neurite outgrowth from SN/VTA to the PFC was investigated. The growthpromoting effects of Montelukast (MTK; GPR17- and cysteinyl-leukotriene receptor antagonist), the glial cell line-derived neurotrophic factor (GDNF) and of two potent, selective GPR17 agonists (PSB-16484 and PSB-16282) were characterized. Treatment with MTK resulted in a significant increase in mean neurite density, comparable with the effects of GDNF. The combination of MTK and GPR17 agonist PSB-16484 significantly inhibited neuronal growth. qPCR studies revealed an MTK-induced elevated mRNA-expression of genes relevant for neuronal growth. Immunofluorescence labelling showed a marked expression of GPR17 on NG2-positive glia. Western blot and RT-qPCR analysis of untreated cultures suggest a time-dependent, injury-induced stimulation of GPR17. In conclusion, MTK was identified as a stimulator of neurite fibre outgrowth, mediating its effects through GPR17, highlighting GPR17 as an interesting therapeutic target in neuronal regeneration

1-(4-Hy­droxy­phen­yl)-3-(3,4,5-tri­methoxy­phen­yl)thio­urea

In the title compound, C16H18N2O4S, the dihedral angle between the hy­droxy­phenyl ring and the plane of the thio­urea moiety is 54.53 (8)°. The H atoms of the NH groups of thio­urea are positioned anti to each other. In the crystal, inter­molecular N—H⋯S, N—H⋯O, and O—H⋯S hydrogen bonds link the mol­ecules into a three-dimensional network

1-(2-Hy­droxy­eth­yl)-3-(3-meth­oxy­phen­yl)thio­urea

In the title compound, C10H14N2O3S, the 3-meth­oxy­phenyl unit is almost planar, with an r.m.s. deviation of 0.013 Å. The dihedral angle between the benzene ring and the plane of the thio­urea unit is 62.57 (4)°. In the crystal, N—H⋯O and O—H⋯S hydrogen bonds link the mol­ecules into a three-dimensional network

1-(2,5-Dimeth­oxy­phen­yl)-3-(2-hy­droxy­eth­yl)urea

In the title compound, C11H16N2O4, the 2,5-dimeth­oxy­phenyl moiety is almost planar, with an r.m.s. deviation of 0.026 Å. The dihedral angle between the benzene ring and the plane of the urea moiety is 13.86 (5)°. The mol­ecular structure is stabilized by a short intra­molecular N—H⋯O hydrogen bond. In the crystal, inter­molecular N—H⋯O and O—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network

N-(2,5-Dimeth­oxy­phen­yl)-N′-[4-(2-hy­droxy­eth­yl)phen­yl]urea

In the title compound, C17H20N2O4, the 2,5-dimeth­oxy­phenyl unit is essentially planar, with an r.m.s. deviation of 0.015 Å. The dihedral angle between the benzene rings is 43.66 (4)°. The mol­ecular structure is stabilized by a short intra­molecular N—H⋯O hydrogen bond. In the crystal, inter­molecular N—H⋯O and O—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network