Synthesis of Apicidin-Derived Quinolone Derivatives:  Parasite-Selective Histone Deacetylase Inhibitors and Antiproliferative Agents

Journal of Medicinal Chemistry
2000.0

Abstract

Apicidin's indole was efficiently converted into a series of N-substituted quinolone derivatives by indole N-alkylation followed by a two-step, one-pot, ozonolysis/aldol condensation protocol. The new quinolones exhibited good parasite selectivity and potency both at the level of their molecular target, histone deacetylase, and in their whole cell antiproliferative activity in vitro.

Knowledge Graph

Similar Paper

Synthesis of Apicidin-Derived Quinolone Derivatives:  Parasite-Selective Histone Deacetylase Inhibitors and Antiproliferative Agents
Journal of Medicinal Chemistry 2000.0
Broad spectrum antiprotozoal agents that inhibit histone deacetylase: structure–activity relationships of apicidin. Part 2
Bioorganic & Medicinal Chemistry Letters 2001.0
Broad spectrum antiprotozoal agents that inhibit histone deacetylase: structure–activity relationships of apicidin. Part 1
Bioorganic & Medicinal Chemistry Letters 2001.0
Structure and Chemistry of Apicidins, a Class of Novel Cyclic Tetrapeptides without a Terminal α-Keto Epoxide as Inhibitors of Histone Deacetylase with Potent Antiprotozoal Activities
The Journal of Organic Chemistry 2002.0
Apicidins: Novel cyclic tetrapeptides as coccidiostats and antimalarial agents from Fusarium pallidoroseum
Tetrahedron Letters 1996.0
A series of novel, potent, and selective histone deacetylase inhibitors
Bioorganic & Medicinal Chemistry Letters 2006.0
Design, synthesis and preliminary bioactivity evaluations of substituted quinoline hydroxamic acid derivatives as novel histone deacetylase (HDAC) inhibitors
Bioorganic & Medicinal Chemistry 2015.0
Design, synthesis and bioactivity evaluations of 8-substituted-quinoline-2-carboxamide derivatives as novel histone deacetylase (HDAC) inhibitors
Bioorganic & Medicinal Chemistry 2023.0
The synthesis of cyclic tetrapeptoid analogues of the antiprotozoal natural product apicidin
Bioorganic & Medicinal Chemistry Letters 2001.0
Design, synthesis and biological evaluation of 3-[4-(7-chloro-quinolin-4-yl)-piperazin-1-yl]-propionic acid hydrazones as antiprotozoal agents
European Journal of Medicinal Chemistry 2014.0