A series of novel N‐triazolo‐benzene sulfonamides‐1,5‐benzodiazepines 9a–d and 10d were designed and prepared through the copper‐catalyzed azide alkyne cycloaddition click chemistry procedure, ...reacting the N1‐propargyl‐1,5‐benzodiazepine 2 and the N1,N5‐dipropargyl analog 6 with various benzene sulfonamide azides 8a–d. The synthesized compounds were found to show nanomolar affinity toward relevant isoforms of human carbonic anhydrase such as hCA I, II, IV, VII, IX, and XII. The divalent derivative 10d showed a particularly high inhibitory activity against all hCA isoforms when compared with acetazolamide, and showed potent multivalent effects, better than reported previously for divalent CA inhibitors.
Novel N‐triazolo‐benzene sulfonamides‐1,5‐benzodiazepines 9a–d and 10d were designed and prepared through copper‐catalyzed azide alkyne cycloaddition click chemistry. The synthesized compounds show nanomolar affinity toward the human carbonic anhydrase (hCA) isoforms I, II, IV, VII, IX, and XII. The divalent derivative 10d showed a particularly high inhibitory activity against all hCA isoforms.
The reaction of 4‐methyl‐(A) and 3‐methyl‐1H‐2,3,4,5‐tetrahydro‐1,5‐benzodiazepin‐2‐one (B) with selected α,β‐unsaturated acid chlorides: crotonoyl, cinnamoyl, and 4‐nitrocinnamoyl is described. We ...have also characterized immunotropic activities of these compounds in the proliferative response of human lymphocytes to phytohemagglutinin A (PHA) or to allogeneic cells in one‐way mixed lymphocyte reaction (MLR), as well as their action on tumor necrosis factor alpha (TNF‐α) and interleukin 6 (IL‐6) production in peripheral blood mononuclear cells (PBMC) and mixed lymphocyte cultures (MLC). Some of the compounds exhibited regulatory activities in the proliferative response of cells to PHA depending on the reactivity of cells to PHA. The MLR induced proliferation of lymphocytes was moderately inhibited by two selected compounds. The compounds showed also inhibitory properties with regard to lipopolysaccharide (LPS)‐ and MLR‐induced TNF‐α production. Structure‐activity relationship was discussed.
Sa1513C NMR spectral data for nine tetrahydro‐1,5‐benzodiazepin‐2‐ones are reported and the chemical shift assignments are discussed. The steric energies of the E and Z isomers of formyl derivatives ...were estimated by computer molecular modeling
Starting from 3,6-dichloro-N-(2-chloro-5-nitrophenyl)-pyridazine-4-carboxamide (7) a series of 6,11-dialkylated pyridazino- 3,4-b1,5benzodiazepin-5-ones with a 3-chloro-8-nitro, 8-amino, ...8-acetylamino, or 8-chloro substitution pattern was prepared via N-alkyl-3-alkylamino-6-chloro-N-(2-chloro-5-nitrophenyl) -pyridazine-4-carboxamides. The new compounds were screened as non-nucleoside reverse transcriptase inhibitors. The influence of the substitution pattern in compounds 10-13 on inhibitory potency is discussed.
