title: Selective synthesis and utility of one tripyrrolic compound and its intermediates.
abstract: Highly selective syntheses of tri(2,4-dimethyl-3-carbethoxypyrrolyl)-methane 8 and its dipyrrolic intermediate 6 and pyrrolic one 1 are described based on the successful correction of the wrong process for 1 in literature. Tripyrrolic compounds have attracted much attention recently and been developed in diverse fields. 1 was the key intermediate for some tyrosine kinase inhibitors, including newly-launched Sutent, and most recently we have found 6 was also synthetically useful in the synthesis of 11 that has been discovered as a novel histone deacetylases (HDAC) inhibitor with an IC(50) value of about 1 microM in our assessments and represents a promising lead for the development of more potent histone deacetylase inhibitors (HDACIs).
authors.affiliation: Department of Medicinal Chemistry, Beijing Institute of Radiation Medicine, China.
authors.forename: Haiyong
authors.initials: H
authors.lastname: Wang
authors.forename: Min
authors.initials: M
authors.lastname: Chen
authors.forename: Lin
authors.initials: L
authors.lastname: Wang
mesh_terms: D002460:Cell Line; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology*; D056572:Histone Deacetylase Inhibitors; D006801:Humans; D020128:Inhibitory Concentration 50; D011505:Protein-Tyrosine Kinases / Q000037:antagonists & inhibitors*; D011758:Pyrroles / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013696:Temperature; D013997:Time Factors
chemical_list: D004791:Enzyme Inhibitors; D056572:Histone Deacetylase Inhibitors; D011758:Pyrroles; D011505:Protein-Tyrosine Kinases