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Rudys S.,Vilnius University | Rios-Luci C.,University of La Laguna | Perez-Roth E.,University of La Laguna | Cikotiene I.,Vilnius University | And 2 more authors.
Bioorganic and Medicinal Chemistry Letters | Year: 2010

A series of 2-substituted 1,2-dihydro-3-phenyl-1-(trichloromethyl)benzo[b][1,6]naphthyridines were synthesized and their in vitro antiproliferative activities were examined against human solid tumor cell lines and relevant strains of bacteria and Candida. The compounds induced considerably growth inhibition in all cancer cell lines, whilst showed inactive against microbial strains. Furthermore, we found analog 2-ethoxy-1H-pyrano[4,3-b]quinoline as selective inhibitor of microbial strains. © 2010 Elsevier Ltd. All rights reserved. Source


Miguelez J.,CSIC - Institute of Natural Products and Agrobiology | Boto A.,CSIC - Institute of Natural Products and Agrobiology | Marin R.,University of La Laguna | Marin R.,Instituto Canario Of Investigacion Del Cancer Icic | And 2 more authors.
European Journal of Medicinal Chemistry | Year: 2013

Hydroxylated seco-analogs of cytotoxic phenanthroindolizidine alkaloids were prepared in good yields from inexpensive 4-hydroxyproline derivatives, in just two steps. Thus, a sequential oxidative radical scission - oxidation was used for the direct conversion of the proline derivative into a 2-(2-aryl-oxoethyl) pyrrolidine with a variety of aryl and heteroaryl groups. The 4R-stereogenic center allowed ready isomer separation, and stereocontrol in the introduction of new chains (interestingly, the 2,4-cis isomers predominated). In the second step, a cyclization reaction afforded alkaloid analogs with an indolizidinone core; a partial isomerization took place but the isomers were readily purifi ed. Then the cytotoxic activity of the bicyclic indolizidinones and the simpler pyrrolidine derivatives was compared against tumorogenic human neuronal SHSY-5Y and breast cancer MCF7 cells. All the biphenyl derivatives displayed a potent activity (one derivative caused >80% cell death in both tumor lines at micromolar dosis), being comparable in the pyrrolidine and indolizidinone series. © 2013 Elsevier Masson SAS. All rights reserved. Source


Boto A.,CSIC - Institute of Natural Products and Agrobiology | Miguelez J.,CSIC - Institute of Natural Products and Agrobiology | Marin R.,University of La Laguna | Marin R.,Instituto Canario Of Investigacion Del Cancer Icic | And 2 more authors.
Bioorganic and Medicinal Chemistry Letters | Year: 2012

Readily available proline derivatives can be transformed in just two steps into analogues of cytotoxic phenanthroindolizidine alkaloids. The key step uses a sequential radical scission-oxidation-alkylation process, which yields 2-substituted pyrrolidine amides. A second process effects the cyclization to give the desired alkaloid analogues, which possess an indolizidine core. The major and minor isomers (dr 3:2 to 3:1) can be easily separated, allowing their use to study structure-activity relationships (SAR). The process is versatile and allows the introduction of aryl and heteroaryl groups (including biphenyl, halogenated phenyl, and pyrrole rings). Some of these alkaloid analogues displayed a selective cytotoxic activity against tumorogenic human neuronal and mammary cancer cells, and one derivative caused around 80% cell death in both tumor lines at micromolar doses. The cytotoxicity of some monocyclic precursors was also studied, being comparable or superior to the bicyclic derivatives. © 2012 Elsevier Ltd. All rights reserved. Source


Gutierrez-Nicolas F.,University of La Laguna | Gutierrez-Nicolas F.,Instituto Canario Of Investigacion Del Cancer Icic | Gordillo-Roman B.,National Polytechnic Institute of Mexico | Oberti J.C.,University of La Laguna | And 6 more authors.
Journal of Natural Products | Year: 2012

Lupane triterpenoids 2 and 5-12 and oleanene derivatives 13 and 14 were prepared from lupeol (1), betulin (3), and germanicol (4). They were tested for anti-HIV activity, and some structure-activity relationships were outlined. The 20-(S) absolute configuration of epoxylupenone (8) was assessed by comparison of the observed and DFT-calculated vibrational circular dichroism spectra. The CompareVOA algorithm was employed to support the C-20 configuration assignment. The 20,29 double bond in lupenone (2) and 3-epilupeol (15) was stereoselectively epoxidized to produce 20-(S)-8 and 20-(S)-16, respectively, an assignment in agreement with their X-ray diffraction structures. © 2012 The American Chemical Society and American Society of Pharmacognosy. Source


Bonifazi E.L.,University of Buenos Aires | Rios-Luci C.,University of La Laguna | Rios-Luci C.,Instituto Canario Of Investigacion Del Cancer Icic | Leon L.G.,University of La Laguna | And 5 more authors.
Bioorganic and Medicinal Chemistry | Year: 2010

A series of 5-hydroxy-1,4-naphthoquinones analogues was synthesized from juglone (6) and their antiproliferative activity against a representative panel of six human solid tumor cell lines has been investigated. The 2,5-dihydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione (4) and 2,3-dihydro-5-hydroxy-2-(prop-1-en-2-yl)naphtho[2,3-b]furan-4,9-dione (27) were the most potent antiproliferative agents with GI50 values of 0.42-8.1 and 0.80-2.2 μM, respectively. The results provide insight into the correlation between some structural properties of 5-hydroxynaphthoquinones and their antiproliferative activity. © 2010 Elsevier Ltd. All rights reserved. Source

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