5,6-Dihydro-1H,4H-1,2,5-thiadiazolo[4,3,2-ij]quinoline-2,2-dioxide: A New N,N'-Cyclic Sulfamide

Abstract

The title compound (la) and its potassium salt (lb) were prepared in two steps, starting from 8-niucquinoline.

Design, synthesis and inhibitory activity against Mycobacterium tuberculosis thymidine monophosphate kinase of acyclic nucleoside analogues with a distal imidazoquinolinone

“…Therefore, it was considered of interest to synthesize a similar analogue where the naphthosultam ring was replaced by the corresponding 5,6-dihydro-1H,4H-1,2,5-thiadiazolo[4,3,2-ij] quinoline-2,2-dioxide (29, Scheme 5). Compound 29 was synthesized following a described procedure [30] by reaction of 8-amino-1,2,3,4-tetrahydroquinoline [31] with sulfamide in diglyme. Reaction of 29 with (Z)-1,4-dichlorobut-2-ene in the presence of NaH in dry DMF afforded the monosubstituted compound 30 in 46% yield (Scheme 5).…”

New indole derivatives as potent and selective serotonin uptake inhibitors

“…In terms of selectivity and potency at the uptake site, the 5-fluoro derivative 14 was better than the 4-fluoro (17) and the 6-fluoro (18) isomers. The binding profile was not affected by incorporation of a double bond in the piperidine ring of 14 (19), and neither did the replacement in 14 of the piperidine by a piperazine (20) or the shift in the chain on the indole ring of 14 from the 3-to the 2-position (21). The indene analog of 14 (22) exhibited about the same binding profile as 14 but was less potent at the uptake site.…”

“…Other structural modifications are shown in Table II (compounds [14][15][16][17][18][19][20][21][22]. It is interesting to note that incorporation of a methylene group between the indole ring and the piperidine moiety led to very selective compounds regarding the ratio of uptake to or to D2.…”

“…(5-Fluoro-l.Ff-indol-3-yl)methyl)-l,2,3,6-tetrahydro-l-pyridinyl]ethyl]-2H-naphth[l,8-c<f|Í80thiazole 1,1-Dioxide (19). This compound was prepared in 12 % yield as an oil (after flash chromatography on silica gel, oxalate salt mp 128 °C) from 2.30 (bs, 2 H, CH2), 3.15 (bs, 2 H, CH2N), 3.3 (bt, 2 H, CH2N), 3.45 (bs, 2 H, CH2), 3.6 (bs, 2 H, CH2N), 4.2 (bt, 2 H, CH2N), 5.5 (bs, 1 H, CH=C), 6.9 (ddd, 1 , H indole), 7.2-7.4 (m, 4 , H arom and indole), 7.7 (m, 2 , H arom), 7.95 (t, 1 H, H arom), 8.9 (2d, 2 , H arom), 11.5 MHz) 2.S-2.6 (bs, 8 H, CH2N piperazine), 2.7 (bt, 2 H, CH2N), 3.6 (bs, 2 H, CH2), 3.9 (t, 2 H, CH2N), 6.9 (ddd, 1 , H indole), 7.1 (dd, 1 , H arom), 7.3 (m, 3 , H indole), 7.6 (m, 2 , H arom), 7.8 (t, 1 , H arom), 8.3 (m, 2 , H arom), 11.0 (bs, 1 H, NH); MS m/z 465 (M+).…”

Sulfamic Acid and Its N- and O-Substituted Derivatives

“…Multiring Heterocycles. A number of bicyclic rings with the sulfamide moiety involved with both such as 539 1126 or more commonly with one ring 540 1127 have been reported. A general route to substituted sulfamides starting from 1,2dianilines with one nitrogen having the p-methoxybenzyl protecting group (PMB) attached is available.…”