153333-22-3Relevant academic research and scientific papers
Synthesis and evaluation of 3-hydroxy-3-phenylpropanoate ester-AZT conjugates as potential dual-action HIV-1 Integrase and Reverse Transcriptase inhibitors
Manyeruke, Meloddy H.,Olomola, Temitope O.,Majumder, Swarup,Abrahams, Shaakira,Isaacs, Michelle,Mautsa, Nicodemus,Mosebi, Salerwe,Mnkandhla, Dumisani,Hewer, Raymond,Hoppe, Heinrich C.,Klein, Rosalyn,Kaye, Perry T.
, p. 7521 - 7528 (2015/12/18)
Novel 3-hydroxy-3-phenylpropanoate ester-azidothymidine (AZT) conjugates have been prepared using Baylis-Hillman methodology, and their potential as dual-action HIV-1 Integrase and Reverse Transcriptase inhibitors has been explored using enzyme inhibition
A novel series of 6-substituted 3-(pyrrolidin-1-ylmethyl)chromen-2-ones as selective monoamine oxidase (MAO) A inhibitors
Mattsson, Cecilia,Svensson, Peder,Sonesson, Clas
, p. 177 - 186 (2014/01/23)
A series of 6-substituted 3-(pyrrolidin-1-ylmethyl)chromen-2-ones (coumarins) have been synthesized and their inhibitory activity to human monoamine oxidase A (MAO A) and B (MAO B) determined. Incorporation of a basic amino function in the C3 position together with substitution at the C6 position produced novel coumarin compounds with selectivity for the MAO A subtype. Substitution in the C6 position with small hydrophilic groups such as hydroxy (19, IC50 = 1.46 μM) or amino (18, IC50 = 3.77 μM) gave the most potent and selective compounds for MAO A. These compounds also showed excellent aqueous solubility properties. Compound 18 [6-amino-3- (pyrrolidin-1-ylmethyl)chromen-2-one] administrated in vivo induced in rat brain a neurotransmitter metabolite profile typical of MAO A inhibition: decreased 3,4-dihydroxyphenylacetic acid (DOPAC) and 5-hydroxyindoleacetic acid (5-HIAA) but increased 3-methoxytyramine (3-MT) levels.
Evaluation of Baylis-Hillman Routes to 3-(Aminomethyl)coumarin Derivatives
Olasupo, Idris,Rose, Nathan R.,Klein, Rosalyn,Adams, Luqman A.,Familoni, Oluwole B.,Kaye, Perry T.
, p. 251 - 258 (2013/12/04)
The relative merits of two different Baylis-Hillman approaches toward the preparation of coumarin derivatives, containing peptide-like side chains, have been explored. In one approach, use of methyl acrylate as the activated alkene requires a protecting group strategy, an approach that is not necessary when using tert-butyl acrylate. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
Synthesis of cinnamate ester-AZT conjugates as potential dual-action HIV-1 integrase and reverse transcriptase inhibitors
Olomola, Temitope O.,Klein, Rosalyn,Kaye, Perry T.
, p. 9449 - 9455 (2015/03/03)
Synthetic approaches to a series of novel cinnamate ester-AZT conjugates have been explored and a successful pathway has finally been developed. α-(Halomethyl)cinnamate esters, obtained in high yield by treating benzyl-protected salicylaldehde-derived Bay
Regio-Controlled Michaelis-Arbuzov reactions of 3-(halomethyl)-coumarins
Rashamuse, Thompo J.,Musa, Musiliyu A.,Klein, Rosalyn,Kaye, Perry T.
scheme or table, p. 302 - 305 (2009/12/25)
3-(Iodomethyl)coumarins and 3-(chloromethyl)coumarins, obtained chemoselectively via Baylis-Hillman reactions of salicylaldehyde derivatives with t-butyl acrylate, can be reacted with triethyl phosphite to afford regioisomeric Michaelis-Arbuzov products.
Application of Baylis-Hillman methodology in the synthesis of coumarin derivatives
Kaye, Perry T.,Musa
, p. 1755 - 1770 (2007/10/03)
A general, chemoselective approach to 3-substituted coumarins via Baylis-Hillman reactions of O-benzylated salicylaldehyde precursors has been demonstrated. Competitive cyclization to chromene derivatives is inhibited by conjugate addition of benzylamine or piperidine to the α,β-unsaturated ester intermediates.
A convenient and improved Baylis-Hillman synthesis of 3-substututed 2H-1-benzopyran-2-ones
Kaye, Perry T.,Musa, Musiliyu A.
, p. 2701 - 2706 (2007/10/03)
Halogen acid-catalysed deprotection and cyclisation of Baylis-Hillman products obtained using O-benzylated salicylaldehyde precursors has been shown to afford 3-(halomethyl)coumarins (3-halomethyl-2H-1-benzopyran-2-ones) chemoselectively and in good yield.
Intramolecular Baylis-Hillman reaction: A pathway to substituted coumarins
Drewes,Njamela,Emslie,Ramesar,Field
, p. 2807 - 2815 (2007/10/02)
The acrylate ester of salicylaldehyde, in the presence of DABCO, affords a crystalline coumarin salt. Formation of this derivative confirms a vital intermediate in the mechanism of the reaction. Salicylaldehyde, suitably protected, reacts with methyl acry
