Acetylcholinesterase inhibition and antimicrobial activity of hydroxyl amides synthesized from natural products derivatives
ABSTRACT Thirteen natural products derivatives of hydroxyl amide class, three described for the first time, were synthesized by reaction of three indole acids and 3,4,5-trimethoxybenzoic acid with six different amino alcohols in the presence of triphenylphosphine and N-bromosuccinimide. The derivati...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Academia Brasileira de Ciências
2018-06-01
|
| Series: | Anais da Academia Brasileira de Ciências |
| Subjects: | |
| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0001-37652018000501945&lng=en&tlng=en |
| _version_ | 1819087408201728000 |
|---|---|
| author | MARIA AMÉLIA D. BOAVENTURA LAURA F.W. XAVIER HENRIETE S. VIEIRA JACQUELINE A. TAKAHASHI WILTON J.D. NASCIMENTO JUNIOR TAMIRES P. ARAUJO AMANDA C.S. COELHO |
| author_facet | MARIA AMÉLIA D. BOAVENTURA LAURA F.W. XAVIER HENRIETE S. VIEIRA JACQUELINE A. TAKAHASHI WILTON J.D. NASCIMENTO JUNIOR TAMIRES P. ARAUJO AMANDA C.S. COELHO |
| author_sort | MARIA AMÉLIA D. BOAVENTURA |
| collection | DOAJ |
| description | ABSTRACT Thirteen natural products derivatives of hydroxyl amide class, three described for the first time, were synthesized by reaction of three indole acids and 3,4,5-trimethoxybenzoic acid with six different amino alcohols in the presence of triphenylphosphine and N-bromosuccinimide. The derivatives were tested against the Gram (+) bacteria Staphylococcus aureus and Bacillus cereus, Gram (-) Pseudomonas aeruginosa and Escherichia coli, besides the yeast Candida albicans. One of the compounds (7) was selectively active against C. albicans (91.3 ± 0.49% inhibition) showing a great potential as a new drug lead, since it was more active than the positive control, miconazole (88.7 ± 2.41% inhibition). Regarding bacterial inhibition, compounds demonstrated mild activity, but inhibition of compounds 9, 10 and 13 towards E. coli is of interest since it is difficult to find drugs selectively active against Gram (-) bacteria. Most of the compounds were very active in the acetylcholinesterase inhibition assay. Compound 7 was again the most active (93.2 ± 4.47%), being more potent than the control galantamine (90.3 ± 0.45%). The most active gallic acid derivatives, compounds 3, 7 and 8 have in common, besides gallic acid skeleton, a (CH2)2OH group, which may be one of the structural requirements for AChE inhibition. |
| first_indexed | 2024-12-21T21:35:40Z |
| format | Article |
| id | doaj.art-a75bafb342ba426bb9a8795feb9de837 |
| institution | Directory Open Access Journal |
| issn | 1678-2690 |
| language | English |
| last_indexed | 2024-12-21T21:35:40Z |
| publishDate | 2018-06-01 |
| publisher | Academia Brasileira de Ciências |
| record_format | Article |
| series | Anais da Academia Brasileira de Ciências |
| spelling | doaj.art-a75bafb342ba426bb9a8795feb9de8372022-12-21T18:49:30ZengAcademia Brasileira de CiênciasAnais da Academia Brasileira de Ciências1678-26902018-06-01902 suppl 11945195410.1590/0001-3765201820170451S0001-37652018000501945Acetylcholinesterase inhibition and antimicrobial activity of hydroxyl amides synthesized from natural products derivativesMARIA AMÉLIA D. BOAVENTURALAURA F.W. XAVIERHENRIETE S. VIEIRAJACQUELINE A. TAKAHASHIWILTON J.D. NASCIMENTO JUNIORTAMIRES P. ARAUJOAMANDA C.S. COELHOABSTRACT Thirteen natural products derivatives of hydroxyl amide class, three described for the first time, were synthesized by reaction of three indole acids and 3,4,5-trimethoxybenzoic acid with six different amino alcohols in the presence of triphenylphosphine and N-bromosuccinimide. The derivatives were tested against the Gram (+) bacteria Staphylococcus aureus and Bacillus cereus, Gram (-) Pseudomonas aeruginosa and Escherichia coli, besides the yeast Candida albicans. One of the compounds (7) was selectively active against C. albicans (91.3 ± 0.49% inhibition) showing a great potential as a new drug lead, since it was more active than the positive control, miconazole (88.7 ± 2.41% inhibition). Regarding bacterial inhibition, compounds demonstrated mild activity, but inhibition of compounds 9, 10 and 13 towards E. coli is of interest since it is difficult to find drugs selectively active against Gram (-) bacteria. Most of the compounds were very active in the acetylcholinesterase inhibition assay. Compound 7 was again the most active (93.2 ± 4.47%), being more potent than the control galantamine (90.3 ± 0.45%). The most active gallic acid derivatives, compounds 3, 7 and 8 have in common, besides gallic acid skeleton, a (CH2)2OH group, which may be one of the structural requirements for AChE inhibition.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0001-37652018000501945&lng=en&tlng=enacetylcholinesterase inhibitionantimicrobial activityindole acid derivatives3,4,5-trimethoxybenzoic acid derivatives |
| spellingShingle | MARIA AMÉLIA D. BOAVENTURA LAURA F.W. XAVIER HENRIETE S. VIEIRA JACQUELINE A. TAKAHASHI WILTON J.D. NASCIMENTO JUNIOR TAMIRES P. ARAUJO AMANDA C.S. COELHO Acetylcholinesterase inhibition and antimicrobial activity of hydroxyl amides synthesized from natural products derivatives Anais da Academia Brasileira de Ciências acetylcholinesterase inhibition antimicrobial activity indole acid derivatives 3,4,5-trimethoxybenzoic acid derivatives |
| title | Acetylcholinesterase inhibition and antimicrobial activity of hydroxyl amides synthesized from natural products derivatives |
| title_full | Acetylcholinesterase inhibition and antimicrobial activity of hydroxyl amides synthesized from natural products derivatives |
| title_fullStr | Acetylcholinesterase inhibition and antimicrobial activity of hydroxyl amides synthesized from natural products derivatives |
| title_full_unstemmed | Acetylcholinesterase inhibition and antimicrobial activity of hydroxyl amides synthesized from natural products derivatives |
| title_short | Acetylcholinesterase inhibition and antimicrobial activity of hydroxyl amides synthesized from natural products derivatives |
| title_sort | acetylcholinesterase inhibition and antimicrobial activity of hydroxyl amides synthesized from natural products derivatives |
| topic | acetylcholinesterase inhibition antimicrobial activity indole acid derivatives 3,4,5-trimethoxybenzoic acid derivatives |
| url | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0001-37652018000501945&lng=en&tlng=en |
| work_keys_str_mv | AT mariaameliadboaventura acetylcholinesteraseinhibitionandantimicrobialactivityofhydroxylamidessynthesizedfromnaturalproductsderivatives AT laurafwxavier acetylcholinesteraseinhibitionandantimicrobialactivityofhydroxylamidessynthesizedfromnaturalproductsderivatives AT henrietesvieira acetylcholinesteraseinhibitionandantimicrobialactivityofhydroxylamidessynthesizedfromnaturalproductsderivatives AT jacquelineatakahashi acetylcholinesteraseinhibitionandantimicrobialactivityofhydroxylamidessynthesizedfromnaturalproductsderivatives AT wiltonjdnascimentojunior acetylcholinesteraseinhibitionandantimicrobialactivityofhydroxylamidessynthesizedfromnaturalproductsderivatives AT tamiresparaujo acetylcholinesteraseinhibitionandantimicrobialactivityofhydroxylamidessynthesizedfromnaturalproductsderivatives AT amandacscoelho acetylcholinesteraseinhibitionandantimicrobialactivityofhydroxylamidessynthesizedfromnaturalproductsderivatives |