Synthesis of Novel, Potentially Biologically Active Dibenzosuberone Derivatives

Abstract

Novel representatives of the important group of biologically active dibenzosuberone derivatives were prepared: 3,7-dibromo-5-(dimethylaminoethyl-oxyimino)-10,11-dihydro-5H-dibenzo[a,d]cyclohepta-1,4-diene (1), 3,7-dibromo-5-(3-dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (2) and 1,7-dibromo-5-(3-dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo-[a,d]-cycloheptene (3). These compounds are potential tricyclic antidepressants (TCAs), which are still the most frequently prescribed antidepressants in many countries.

Synthesis, spectroscopic, and cellular properties of α-pegylated cis-A2B2- and A3B-types ZnPcs

“…ZnPc 9 could also be obtained directly from reaction of phthalonitrile 1 with 4 , in 6.8% yield, as previously reported [19, 42]. The O-alkylation of ZnPc 9 with 3-dimethylaminopropyl chloride afforded ZnPc 10 in 50% yield [48]. N -Demethylation of ZnPc 10 was not observed, even upon prolonged storage at room temperature, as has been reported for other N -methylated ZnPcs [39].…”

“…ZnPc 9 (18.1 mg, 0.024 mmol) and 3-(dimethylamino)propyl chloride hydrochloride (4.7 mg, 0.030 mmol) were dissolved in DMF (5.0 mL) [48]. The solution was heated at 80 °C under argon, and K 2 CO 3 (50.0 mg, 3.6 mmol) was added to the reaction solution.…”

One-pot synthesis of sulfonyl dibenzosuberdiones via In(OTf)3-promoted double Friedel–Crafts reactions of oxygenated arylacetic acids with β-arylvinyl sulfones

“…The compound crystallizes in the triclinic crystal system, space group P1 ˉ, a = 7.8698( 2 8, 185.2, 153.4, 151.8, 148.8, 147.9, 138.8, 137.7, 136.3, 133.5, 129.1 (2×), 128.9, 127.4 (2×), 126.2, 114.3, 111.9, 111.5, 109.7, 102.3, 66.6, 56.4, 56.1, 48.5. 4,186.0,163.5,153.2,148.7,144.6,143.3,136.1,135.8,135.3,129.6 (2×),127.4 (2×),127.1,126.6,114.7,114.2,113.7,112.1,66.2,56.4,56.1,55.7,48.9,3,d] cycloheptene-10,11-dione (6k) 5, 186.0, 163.5, 153.3, 148.8, 143.1, 138.8, 135.9, 135.4, 135.5, 129.1 (2×), 127.4 (2×), 127.2, 126.6, 114.8, 114.4, 113.8, 112.0, 66.1, 56.4, 56.1, 55.7, 49.0. 3,185.9,165.4 (d,J = 255.5 Hz),163.5,153.3,148.9,142.8,135.5,135.4,134.7 (d,J = 3.7 Hz), 130.2 (d, J = 9.8 Hz, 2×), 127.…”

“…1,126.6,116.3 (d,J = 22.8 Hz,2×),114.9,114.2,113.6,112.0,66.1,56.4,56.1,55.7,49.1. 2,3,4,7, 184.9,153.5,152.9,149.7,148.6,146.2,144.5,137.7 (2×),136.0,130.3,129.6 (2×),128.3,127.4 (2×),125.9,114.2,112.4,110.5,66.8,61.8,60.8,56.4,56.0,37.6,21.5. 1,2,3,7, 185.9, 155.8, 154.0, 153.9, 148.9, 144.6, 142.0, 138.0, 135.9, 135.2, 129.6 (2×), 127.5 (2×), 124.2, 123.1, 113.6, 112.3, 108.5, 64.6, 62.5, 60.8, 56.4, 56.3, 56.1, 48.9, 21.5.…”

Stereochemistry – key role in the rearrangements of dibenzo-C8 and -C9 derivatives

“…In fact, the interest for such compounds was generated by the development, since 1950, of a new class of drugs, the tricyclic-antidepressants 1 which have been considered "ion channel blockers". 2 Many other Amitriptyline-related derivatives have been recently synthetized and used as drugs in the treatment of depression 3 or as chelating agents 4 (see Figure 1). A number of these compounds have a 5Hdibenzo[a,d]cycloheptene skeleton [5][6][7][8] or a rearranged one, 9,10 which makes the synthesis of similar structures of great interest.…”