Some Aminodibenzofurans and Derivatives

Abstract

In connection with studies on the correlation of physiological action with chemical constitution the following dibenzofuran derivatives were prepared: 2-and 4-S-aminoethyldibenzofuran, 2and 3-fluorodibenzofuran, 4-dibenzofuryl-N-piperidinomethane, diethyl (3-dibenzofurylamino)ethylmalonate and diethyl (4-dibenzofurylamino)ethylmalonate. The synthesis of 3-and 4-(p-acetamidobenzenesulfonamido)dibenzofuran and of the corresponding amines was also cajrried out. The melting point of the 3-amide differed appreciably from previously recorded values. The interaction of 4-bromodibenzofuran with lithium dimethylamide and lithium diethylamide led to the rearrangement products: 3-dimethylaminodibenzofuran and 3-diethylaminodibenzofuran, respectively.

Dibenzofuranylethylamines as 5-HT2A/2C Receptor Agonists

“…The affinities of all five compounds for both 5-HT 2 receptor subtypes were determined by radioligand displacement assays ([ 3 H]­ketanserin for 5-HT 2A and [ 3 H]­mesulergine for 5-HT 2C ), and the functional activities were assessed by a standard fluorescence assay, as Ca 2+ mobilization. The hydrochlorides of 2-(dibenzo­[ b , d ]­furan-2-yl)­ethanamine ( 1 ) and 2-(dibenzo­[ b , d ]­furan-4-yl)­ethanamine ( 3 ) had been synthesized by another route in the mid-1900s and only said to be “toxic”. , The results are shown in Table .…”

“…The hydrochlorides of 2-(dibenzo[b,d]furan-2-yl)ethanamine (1) and 2-(dibenzo-[b,d]furan-4-yl)ethanamine (3) had been synthesized by another route in the mid-1900s and only said to be "toxic". 12,13 The results are shown in Table 1.…”

“…1 H NMR (400 MHz, CDCl 3 ) δ 8.15 (d, J = 13.4 Hz, 1H), 8.10 (s, 1H), 7.96 (d, J = 7.5 Hz, 1H), 7.69−7.56 (m, 4H), 7.52 (t, J = 7.3 Hz, 1H), 7.41 (t, J = 7.3 Hz, 1H). 13 (20 mmol) in THF at 0 °C. After addition, the solution was refluxed for 16 h. The reaction mixture was then cooled to 0 °C and quenched with a solution of sodium potassium tartrate, and NaOH solution was added to maintain basicity.…”

“…2-(Dibenzo[b,d]furan-2-yl)ethanamine Hydrochloride (1-HCl). 12,13 Yield: 72%; colorless solid; mp 225− 227 °C. 13 H]-ketanserin (47.3 Ci/mL, 1 mCi/mL, PerkinElmer NET791250UC) and HeLa-5-HT 2C cell membranes (cell line was generated in-house) (receptor expression = 150 fmol/mg protein, protein concentration = 2041 μg/mL) against [ 3 H]mesulergine (84.7 Ci/mL, 1 mCi/mL, PerkinElmer NET1148250UC).…”

“…12,13 Yield: 72%; colorless solid; mp 225− 227 °C. 13 H]-ketanserin (47.3 Ci/mL, 1 mCi/mL, PerkinElmer NET791250UC) and HeLa-5-HT 2C cell membranes (cell line was generated in-house) (receptor expression = 150 fmol/mg protein, protein concentration = 2041 μg/mL) against [ 3 H]mesulergine (84.7 Ci/mL, 1 mCi/mL, PerkinElmer NET1148250UC). K D values obtained for [ 3 H]-ketanserin and [ 3 H]-mesulergine at human 5-HT 2A and 5-HT 2C receptors were 1.21 and 0.67 nM, respectively.…”