The application of vinylogous iminium salts and related synthons to the regiocontrolled preparation of 2,3- and 2,5-disubstituted pyrroles

Cytotoxicity of Substituted Alkyl-3,4-bis(4-methoxyphenyl)pyrrole-2-carboxylates in L1210 Lymphoid Leukemia Cells

“…Gupton and co-workers [14] in recent years have been actively involved in developing methods for the regiochemically controlled synthesis of polysubstituted pyrroles from appropriately substituted derivatives of vinylogous iminium salts. Pyrroles, compounds 1 and 2, were prepared as depicted in Scheme 1 from the commercially available 2-(4-methoxyphenyl)-4′-methoxyacetophenone (3).…”

“…The incorporation of 14 C-glycine (53.0 mCi/mmol) into purines [20] and the incorporation of 14 C-formate (53.0 mCi/mmol) into pyrimidines [21] was determined in a similar manner.…”

“…Messenger-, ribosomal-and transfer-RNA polymerase enzymes were isolated with different concentrations of ammonium sulfate; individual RNA polymerase activities were determined using 3 H-UTP [25,26] . Ribonucleoside reductase activity was measured using 14 C-CDP with dithioerythritol [27] . The deoxyribonucleotides 14 C-dCDP were separated from the ribonucleotides by TLC on PEI plates.…”

“…These include 1-acyl-and 1,2-diacyl-4,4-diethyl-3,5-pyrazolidinediones [1] , 1-acyl-and 1,2-diacyl-1,2,4-triazolidinedione-3,5-diones [2] , 3,5-isoxazolidinediones and 2-isoxazoline-5-ones [3] , 2-alkoxycarbonyl-5-aryl-1,3,5-triazine-4,6(1H,5H)diones [4] , 3 -imino-1-oxaisoindolines [5] , 5,6-substituted 1(2)H-indazole-4,7-diones [6] , N-pyridinyl and N-quinolinyl substituted phthalimides and succinimides [7] , diazomethyl ketone and chloromethyl ketone analogues of N-tosyl amino acids [8] , furan derivatives [9] , and vinyl, cyanomethyl and pyranyl activated esters of 2-furoic acid and 2-furylacrylic acids [10] , [(N-alkyl-1,3-dioxo-1H,3H-isoindolin-5-yl)oxy]-alkanoic acids [11] , [ (N-alkyl-1H,3H-1-oxoisoindolin-5-yl-oxyalkanoates [12] , and 5,6-disubstituted 1(2)H-indazole-4,7-diones [13] . Recently, the marine natural product rigidin, which is a pyrrolopyrimidine, has demonstrated several types of biological activity [14] . Lamellarin O and Lukianol A also represent new and related marine natural products which possess a highly functionalized pyrrole nucleus.…”

Synthesis and Cytotoxicity of 2,4-Disubstituted and 2,3,4-Trisubstituted Brominated Pyrroles in Murine and Human Cultured Tumor Cells

“…H-thymine (72 Ci/mmol), 3 H-uracil (12 Ci/mmol) or 3 H-leucine (120 Ci/mmol) into DNA, RNA or protein, respectively, for 10 6 Tmolt4 T cell leukemia cells at 25, 50 and 100 µM was determined for 60 min [12] . The acid insoluble labeled DNA, RNA, or protein was collected on discs [GF/A] which were counted in a Packard beta counter.…”