On the Reaction of 2-Alkanoylnaphthohydroquinones with Hydroxylamine: Access to Cytotoxic 2-(Hydroxyamino)-1,4-naphthoquinone and Their 3-(Hydroxyimino)alkyl Analogous
Oximes are known for their anti-inflammatory, antimicrobial, antioxidant, and anticancer activities. Frequently, modification of biologically active carbonyl compounds into oximes leads to increased activity. The present study reports the reactivity of 2-alkanoylnaphthohydroquinones against hydroxyl...
Saved in:
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Wiley
2022-01-01
|
| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2022/7664037 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1832551125810675712 |
|---|---|
| author | Jaime A. Valderrama Andrea Pérez-Herrera Giulio G. Muccioli Edmundo A. Venegas-Casanova Rafael Jara-Aguilar Pedro Buc Calderon Julio Benites |
| author_facet | Jaime A. Valderrama Andrea Pérez-Herrera Giulio G. Muccioli Edmundo A. Venegas-Casanova Rafael Jara-Aguilar Pedro Buc Calderon Julio Benites |
| author_sort | Jaime A. Valderrama |
| collection | DOAJ |
| description | Oximes are known for their anti-inflammatory, antimicrobial, antioxidant, and anticancer activities. Frequently, modification of biologically active carbonyl compounds into oximes leads to increased activity. The present study reports the reactivity of 2-alkanoylnaphthohydroquinones against hydroxylamine under aerial conditions. Results show that, depending on the structure of the hydroquinones, the reaction proceeds through two different chemical pathways to produce 2-(hydroxyamino)-1,4-naphthoquinone and their C-3 (hydroxyimino)alkyl derivatives. Both the formation of the quinoid compounds under aerial oxidation and C-C cleavage reactions of hemiaminal intermediates are discussed. In vitro screening of the substituted 1,4-naphthoquinones on a panel of cancer cells reveals moderate cytotoxic activities. Compound 19, 2-(hydroxyamino)-1,4-naphthoquinone, stands out by its anticancer potency against prostate cancer cells as shown by the lowest IC50 value (8.08 μM) and the best selectivity index (3.90). |
| format | Article |
| id | doaj-art-896959ef273b400cb700e199f407e506 |
| institution | Kabale University |
| issn | 2090-9071 |
| language | English |
| publishDate | 2022-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-896959ef273b400cb700e199f407e5062025-02-03T06:04:53ZengWileyJournal of Chemistry2090-90712022-01-01202210.1155/2022/7664037On the Reaction of 2-Alkanoylnaphthohydroquinones with Hydroxylamine: Access to Cytotoxic 2-(Hydroxyamino)-1,4-naphthoquinone and Their 3-(Hydroxyimino)alkyl AnalogousJaime A. Valderrama0Andrea Pérez-Herrera1Giulio G. Muccioli2Edmundo A. Venegas-Casanova3Rafael Jara-Aguilar4Pedro Buc Calderon5Julio Benites6Química y FarmaciaQuímica y FarmaciaBioanalysis and Pharmacology of Bioactive Lipids (BPBL)Facultad de Farmacia y BioquímicaFacultad de Farmacia y BioquímicaQuímica y FarmaciaQuímica y FarmaciaOximes are known for their anti-inflammatory, antimicrobial, antioxidant, and anticancer activities. Frequently, modification of biologically active carbonyl compounds into oximes leads to increased activity. The present study reports the reactivity of 2-alkanoylnaphthohydroquinones against hydroxylamine under aerial conditions. Results show that, depending on the structure of the hydroquinones, the reaction proceeds through two different chemical pathways to produce 2-(hydroxyamino)-1,4-naphthoquinone and their C-3 (hydroxyimino)alkyl derivatives. Both the formation of the quinoid compounds under aerial oxidation and C-C cleavage reactions of hemiaminal intermediates are discussed. In vitro screening of the substituted 1,4-naphthoquinones on a panel of cancer cells reveals moderate cytotoxic activities. Compound 19, 2-(hydroxyamino)-1,4-naphthoquinone, stands out by its anticancer potency against prostate cancer cells as shown by the lowest IC50 value (8.08 μM) and the best selectivity index (3.90).http://dx.doi.org/10.1155/2022/7664037 |
| spellingShingle | Jaime A. Valderrama Andrea Pérez-Herrera Giulio G. Muccioli Edmundo A. Venegas-Casanova Rafael Jara-Aguilar Pedro Buc Calderon Julio Benites On the Reaction of 2-Alkanoylnaphthohydroquinones with Hydroxylamine: Access to Cytotoxic 2-(Hydroxyamino)-1,4-naphthoquinone and Their 3-(Hydroxyimino)alkyl Analogous Journal of Chemistry |
| title | On the Reaction of 2-Alkanoylnaphthohydroquinones with Hydroxylamine: Access to Cytotoxic 2-(Hydroxyamino)-1,4-naphthoquinone and Their 3-(Hydroxyimino)alkyl Analogous |
| title_full | On the Reaction of 2-Alkanoylnaphthohydroquinones with Hydroxylamine: Access to Cytotoxic 2-(Hydroxyamino)-1,4-naphthoquinone and Their 3-(Hydroxyimino)alkyl Analogous |
| title_fullStr | On the Reaction of 2-Alkanoylnaphthohydroquinones with Hydroxylamine: Access to Cytotoxic 2-(Hydroxyamino)-1,4-naphthoquinone and Their 3-(Hydroxyimino)alkyl Analogous |
| title_full_unstemmed | On the Reaction of 2-Alkanoylnaphthohydroquinones with Hydroxylamine: Access to Cytotoxic 2-(Hydroxyamino)-1,4-naphthoquinone and Their 3-(Hydroxyimino)alkyl Analogous |
| title_short | On the Reaction of 2-Alkanoylnaphthohydroquinones with Hydroxylamine: Access to Cytotoxic 2-(Hydroxyamino)-1,4-naphthoquinone and Their 3-(Hydroxyimino)alkyl Analogous |
| title_sort | on the reaction of 2 alkanoylnaphthohydroquinones with hydroxylamine access to cytotoxic 2 hydroxyamino 1 4 naphthoquinone and their 3 hydroxyimino alkyl analogous |
| url | http://dx.doi.org/10.1155/2022/7664037 |
| work_keys_str_mv | AT jaimeavalderrama onthereactionof2alkanoylnaphthohydroquinoneswithhydroxylamineaccesstocytotoxic2hydroxyamino14naphthoquinoneandtheir3hydroxyiminoalkylanalogous AT andreaperezherrera onthereactionof2alkanoylnaphthohydroquinoneswithhydroxylamineaccesstocytotoxic2hydroxyamino14naphthoquinoneandtheir3hydroxyiminoalkylanalogous AT giuliogmuccioli onthereactionof2alkanoylnaphthohydroquinoneswithhydroxylamineaccesstocytotoxic2hydroxyamino14naphthoquinoneandtheir3hydroxyiminoalkylanalogous AT edmundoavenegascasanova onthereactionof2alkanoylnaphthohydroquinoneswithhydroxylamineaccesstocytotoxic2hydroxyamino14naphthoquinoneandtheir3hydroxyiminoalkylanalogous AT rafaeljaraaguilar onthereactionof2alkanoylnaphthohydroquinoneswithhydroxylamineaccesstocytotoxic2hydroxyamino14naphthoquinoneandtheir3hydroxyiminoalkylanalogous AT pedrobuccalderon onthereactionof2alkanoylnaphthohydroquinoneswithhydroxylamineaccesstocytotoxic2hydroxyamino14naphthoquinoneandtheir3hydroxyiminoalkylanalogous AT juliobenites onthereactionof2alkanoylnaphthohydroquinoneswithhydroxylamineaccesstocytotoxic2hydroxyamino14naphthoquinoneandtheir3hydroxyiminoalkylanalogous |