- Simple one-pot synthesis of 5-(chloromethyl)isoxazoles from aldoximes and 2,3-dichloro-1-propene
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[Figure not available: see fulltext.] A one-pot synthesis of 3-substituted 5-chloromethylisoxazoles from available starting aldoximes and 2,3-dichloro-1-propene, serving both as a solvent and reagent, is proposed. Excess 2,3-dichloro-1-propene is recovered after the reaction. The synthesis is effective for oximes of both aromatic and aliphatic aldehydes.
- Kondrashov, Evgeniy V.,Shatokhina, Nina S.
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p. 1228 - 1232
(2020/01/08)
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- Isoxazole-Derived Amino Acids are Bromodomain-Binding Acetyl-Lysine Mimics: Incorporation into Histone H4 Peptides and Histone H3
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A range of isoxazole-containing amino acids was synthesized that displaced acetyl-lysine-containing peptides from the BAZ2A, BRD4(1), and BRD9 bromodomains. Three of these amino acids were incorporated into a histone H4-mimicking peptide and their affinity for BRD4(1) was assessed. Affinities of the isoxazole-containing peptides are comparable to those of a hyperacetylated histone H4-mimicking cognate peptide, and demonstrated a dependence on the position at which the unnatural residue was incorporated. An isoxazole-based alkylating agent was developed to selectively alkylate cysteine residues in situ. Selective monoalkylation of a histone H4-mimicking peptide, containing a lysine to cysteine residue substitution (K12C), resulted in acetyl-lysine mimic incorporation, with high affinity for the BRD4 bromodomain. The same technology was used to alkylate a K18C mutant of histone H3.
- Sekirnik (née Measures), Angelina R.,Hewings, David S.,Theodoulou, Natalie H.,Jursins, Lukass,Lewendon, Katie R.,Jennings, Laura E.,Rooney, Timothy P. C.,Heightman, Tom D.,Conway, Stuart J.
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supporting information
p. 8353 - 8357
(2016/07/19)
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- Synthesis and biological evaluation of N-heterocyclic indolyl glyoxylamides as orally active anticancer agents
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A series of N-heterocyclic indolyl glyoxylamides were synthesized and evaluated for in vitro and in vivo anticancer activities. They exhibited a broad spectrum of anticancer activity not only in murine leukemic cancer cells but also in human gastric, breast, and uterus cancer cells as well as their multidrug resistant sublines with a wide range of IC50 values. They also induced apoptosis and caused DNA fragmentation in human gastric cancer cells. Among the compounds studied, 7 showed the most potent activity of growth inhibition (IC50 17-1711 nM) in several human cancer cells. Given orally, compounds 7 and 13 dose-dependently prolonged the survival of animals inoculated with P388 leukemic cancer cells. N-Heterocyclic indolyl glyoxylamides may be useful as orally active chemotherapeutic agents against cancer and refractory cancerous diseases of multidrug resistance phenotype.
- Li, Wen-Tai,Hwang, Der-Ren,Chen, Ching-Ping,Shen, Chien-Wei,Huang, Chen-Long,Chen, Tung-Wei,Lin, Chi-Hung,Chang, Yee-Ling,Chang, Ying-Ying,Lo, Yue-Kan,Tseng, Huan-Yi,Lin, Chu-Chung,Song, Jeng-Shin,Chen, Hua-Chien,Chen, Shu-Jen,Wu, Se-Hui,Chen, Chiung-Tong
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p. 1706 - 1715
(2007/10/03)
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- Synthesis and properties of 3-alkyl(aryl)-5-chloromethylisoxazoles
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3-Chloro-2-isothiocyanato-1-propenyl alkyl(aryl) ketones react with hydroxylamine hydrochloride to give 3-alkyl(aryl)-5-chloromethylisoxazole. Treatment of the latter with dimethylamine and ammonium thiocyanate leads to formation of previously unknown 3-alkyl(aryl)-5-dimethylamino(or isothiocyanato)-methylisoxazoles.
- Gadzhily,Aliev
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p. 415 - 418
(2007/10/03)
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- Extractant for selectively extracting strontium from aqueous solution containing the same
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An extractant for selectively extracting strontium from an aqueous solution containing the same, which comprises a 1,2-benzenebis(1,4-dioxanonyl-6,8-dionato)metal complex of the following structural formula: STR1 wherein M represents a metal ion of Cu (II), Zn (II) or Ni (II).
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