A new approach to the synthesis of rare thiazino[6,5-b]indol-4-one derivatives. First total synthesis of the indole phytoalexin cyclobrassinon

Synthesis of Thienodolin

“…[6] Additionally, the parent compound 12 has been prepared recently by a palladium promoted reductive cyclization of 3-(2-nitrophenyl)thiophene (13) in the presence of CO. [12] Several attempts to react 12 with hydrogen isocyanate (generated in situ) or chlorosulfonyl isocyanate failed. The desired thienoindoles 1aϪc, were prepared instead by treatment of 11aϪc with 2-mercaptoacetamide in the presence of K 2 CO 3 in methanol at reflux for 16 h.…”

“…Solvents were of analytical grade and were used as received. 2-Chloroindole-3-carboxaldehyde, [9] 1-(tert-butoxycarbonyl)-2-chloroindole-3-carboxaldehyde, [13] 5-chloroxindole, [14] 6-chloroxindole [15] and 2-mercaptoacetamide [16] were prepared as described in the literature.…”

Parallel Synthesis of O‐Phenoxyethyl and O‐Adamantyl N‐acyl Thiocarbamates Endowed with Antiproliferative Activity

“…secondary thiocarbamates bearing an acyl substituent at the thiocarbamic nitrogen, Fig. 1) have been widely studied for their physicochemical properties [1 -4] and biological activities including elastase inhibition [5], anti-inflammatory [6], antiproliferative [7], antibacterial [7], and fungicidal [7] effects ( Fig. 1).…”

Synthesis and biological evaluation of new 5-methyl-N-(3-oxo-1-thia-4-azaspiro[4.5]-dec-4-yl)-3-phenyl-1H-indole-2-carboxamide derivatives

“…Intrinsic or acquired resistance of cancer cells to chemotherapeutics in several malignant tumors decrease the response rate and new therapeutic agents are needed. Indole derivatives have been shown to possess antibacterial, antifungal and anti HIV activities [2][3][4][5][6][7] . There have also been several reports on the anticancer properties of compounds bearing this ring system 8,9 .…”