Biological evaluation of glycosyl-isoindigo derivatives against the pathogenic agents of tropical diseases (malaria, Chagas disease, leishmaniasis and human African trypanosomiasis)

Recent Advances in the Discovery of Novel Antiprotozoal Agents

“…In another series of imidazole compounds synthesized by Trunz et al [218], compounds 115a and 115b demonstrated good potency against T.b.rhodesiense and their reported IC 50 values were 0.16 and 0.10 µM, respectively. Bouchikhi et al [219] designed a series of compounds based on glycosyl-isoindigo conjugates, and an evaluation of their antitrypanosomal activities revealed that among the compounds synthesized, compounds 116a–c expressed significant biological activity against T. b. brucei strains with IC 50 values between 0.51 and 0.84 µM. Among the several halonitrobenzamides derivatives synthesized by Hwang et al [220], and evaluated against a T. b. brucei culture compounds, compound 117 was found to be the most potent inhibitor (IC 50 = 1.5 µM).…”

A Convenient Deoxygenation-Dimerization-[1+2]-Cycloaddition Synthetic Sequence from ω-Bromoalkylisatins to Indolin-2-onemethanofullerenes Bearing Isoindigo Moiety

“…1 H NMR (400 MHz, CDCl 3 ): δ = 1.44-1.52 (m, 4 H, 2 CH 2 ), 1.71-1.78 (m, 2 H, CH 2 ), 1.83-1.90 (m, 2 H, CH 2 ), 3.40 (t, J = 6.7 Hz, 2 H, CH 2 Br), 3.80 (t, J = 7.1 Hz, 2 H, NCH 2 ), 6.80 (d, J = 7.7 Hz, 1 H, ArH), 7.06 (dt, J = 8.0, 1.0 Hz, 1 H, ArH), 7.37 (dt, J = 7.7, 1.2 Hz, 1 H, ArH), 9.19 (dd, J = 8.0, 0.8 Hz, 1 H, ArH). 13…”

“…The temperature was gradually increased to 20°C during 8 h. The solvent was removed in vacuo, and the residue was column chromatographed on silica gel using PE-EtOAc (10:1) as eluent to give the desired product as a maroon solid. {3-[1-(2-Bromoethyl) 13 C NMR: Due to the very low solubility of this compound in a wide range of organic solvents, the 13 {3-[1-(5-Bromopentyl)-2-oxoindolin-3-ylidene]-2-oxoindolin-1-yl}pentyl)indoline-2,3-dione (3c) Yield: 16.60 g (78%); dark-red solid; mp 110°C; R f = 0.80 (PE-EtOAc, 1:1). 2924, 2854, 1743, 1724, 1684, 1607, 1464, 1353, 1092, 740 cm -1 .…”

“…Isatin derivatives are also used as starting materials in the synthesis of bis-indoles, such as indigo, indirubin, and isoindigo. [12][13][14] Isoindigo [1H,1′Hbis(indolin-3-ylidene)-2,2′-dione] derivatives attract great attention as substances, which show a specific biological activity (anti-leukemia, antiproliferative, anti-inflammatory, etc.). [15][16][17][18][19] Recently, the syntheses of isoindigo-based oligothiophenes and polyfluorenes and their utilization as electron acceptors in molecular bulk-heterojunction solar cells and organic semiconductor memory devices have been reported.…”

Advances in the synthesis and application of isoindigo derivatives

“…Thus, compound (42) possessed high activity against L. donovani (leishmaniasis), whereas structures (43, 44) and (45, 46) were effective against P. falciparum (malaria) and T. cruzi (trypanosomiasis) respectively (Scheme 22). 81 …”