8-Sulfonyl-substituted tetrahydro-1 H -pyrido[4,3- b ]indoles as 5-HT 6 receptor antagonists

γ-Carbolines and their hydrogenated derivatives 3.* Hydrogenated derivatives of γ-carbolines: chemical and biological poperties (Review)

“…Tetrahydro-γ-carbolines add to aryl-and pyridylalkynes with good yields under the conditions of phasetransfer catalysis with the formation of a mixture of the (Z)-and (E)-isomers of the 5-vinyl derivatives 10; they can be reduced to the corresponding 5-(2-arylethyl)tetrahydro-γ-carbolines 11, which cannot be obtained by addition to styrenes [37,43]. Sulfonyl halides react readily with N(5)-unsubstituted γ-carbolines in the presence of NaH in DMF with the formation of the corresponding N-sulfonyl derivatives [2,44].…”

“…This makes it possible to regard the compounds as potential products for the treatment of neurodegenerative illnesses. Such compounds include, for example, 5-(2-hetarylethyl) [28], 5-(2-pyridylvinyl) [37], and 8-sulfonyl [44] derivatives of tetrahydro-γ-carbolines. The drug Dimebon 2 [28,130], which will be discussed in greater detail below, is regarded as an antagonist of serotonin 5-HT 6 -receptors.…”

The synthesis and physiological activity of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles

“…A possibility of the modification of the sulfo group in THPIs 143 with free position 2 have been demonstrated 76 (Scheme 5). The authors synthesized the corresponding sulfonyl chlorides (144), sulfinic acid (145), sulfonamides (146) and sulfones (147).…”

“…), being 5-benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido [4,3-b]indole naphthalene-1,5-disulfonate, nowadays still finds application in medical practice for the treatment of a wide range of allergic diseases. 91 More detailed studies revealed 7,76,88,89 According to Mashkovskii, 91 Dimebon exerts antiserotonergic, anticholinergic, local anaesthetic and sedative effects, prevents the development of anaphylactic shock, reduces itching, the intensity of local exudative manifestations, and vascular permeability. The drug is practiced in the therapy of acute allergic reactions, pollinoses, hives, hay fever, food allergy, cosmetic and drug allergies, Quincke's edema, etc.…”

Ag(I)-Promoted Dehydroxylation and Site-Selective 1,7-Disulfonylation of Diaryl(1H-indol-2-yl)methanols

“…From these wide applications point of view, the synthetic protocol for the access to arylsulfone derivatives was well developed. The conventional methods included the Friedel–Crafts sulfonylation reaction, oxidation of arylsulfides, sulfonyl-radical addition reaction, and later cross-coupling of arenesulfinate salts . Recently, direct sulfonylation of C­(sp 2 )–H bonds comes to be the new pursuit for the arylsulfone synthesis from the consideration of step- and atom-economy .…”