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Creativity and Knowledge

Medicinal chemistry in cancer and neurodegenerative diseases 

Semisynthetic natural product derivatives

Computer assisted drug discovery

Selected publications and patents

SALVADOR, J.A.R.; PINTO, R.M.A.; SILVESTRE, S.M.

Pharmaceutical green chemistry applied to the chemical synthesis of steroid compounds;

Current Green Chemistry, 2015, DOI:10.2174/2213346101666140915212312.

 

SOUSA, M. C.; VARANDAS, R.; SANTOS, R.C.; SANTOS-ROSA, M.; ALVES, V.; SALVADOR, J.A.R.

Antileishmanial Acivity of Semisynthetic Lupane Triterpenoids, Betulin, and Betulinic Acid Derivatives: Synergistic Effects with Miltefosine,

PLOS ONE, 2014, 9, e89939.

 

RAMOS, S.S, ALMEIDA, S.S, LEIRA, P.M., BOTO, R.E.F., SILVESTRE, S., ALMEIDA, P.

VT-NMR and cytotoxic evaluation of some new ortho-(alkylchalcogen)acetanilides.

Tetrahedron, 2014, 70, 46, 8930–8937. doi:10.1016/j.tet.2014.09.055

 

SALVADOR, J.A.R.; SANTOS, R.C.; FIGUEIREDO, S.A.C.; JING, Y.

Antitumor effects of celastrol and semi-synthetic derivatives,

Mini Review in Organic Chemistry, 2014, 11, 400-407.

 

FERREIRA, A., RODRIGUES, M., SILVESTRE, S., FALCÃO, A., ALVES, G.

HepaRG cell line as an in vitro model for screening drug–drug interactions mediated by metabolic induction: Amiodarone used as a model substance.

Toxicology in Vitro, 2014, 28, 8, 1531–1535. doi:10.1016/j.tiv.2014.08.004

 

SALVADOR, J.A.R.; CARVALHO, J.F.S.; LEITÃO, A.J.; NEVES, M.A.C.; SILVA, M.M.C.; SILVESTRE, S.M.; SÁ E MELO, M.L.

Anticancer Steroids: Linking natural and semi-synthetic compounds,

Nat. Prod. Rep., 2013, 30, 324-374.

 

LEAL, A.S.M.; WANG, R.; SALVADOR, J.A.R.; JING, Y.

Synthesis of novel heterocyclic oleanolic acid derivatives with improved antiproliferative activity in solid tumor cells,

Org. & Biomol. Chem, 2013, 11, 1726-1738.

 

MOREIRA, V.M.; SALVADOR, J.A.R.; SIMÕES, S.; DESTRO, F.; GAVIOLI, R.

Novel oleanolic vinyl boronates: synthesis and antitumor activity,

Eur. J. Med. Chem., 2013, 63, 46-56.

 

SALVADOR, J.A.R.; PINTO, R.M.A.; SILVESTRE, S.M.

Steroidal 5α-reductase and 17α-hydroxylase/17,20-lyase(CYP17) inhibitors useful in treatment of prostatic diseases,

J. Steroid Biochem. Mol. Biol., 2013, 137,199-222.

 

SALVADOR, J.A.R.; SILVESTRE, S.M.; PINTO, R.M.A.; Le ROUX, C.

New Bismuth(III) Salts Applications in Organic Synthesis: From Bulk Chemicals to Steroid and Terpenoid Chemistry,

Topics in Current Chemistry, 2012, 311, 143-178.

 

SALVADOR, J.A.R.; SILVESTRE, S.M.; MOREIRA, V.M.

Recent Developments in Oxidative Processes in Steroid Chemistry,

Curr. Org. Chem., 2012, 16, 1243-1276.

 

SALVADOR , J.A.R.; MOREIRA V.M.; PINTO, R.M.A.; LEAL, A. S.; PAIXÃO, J.A.

Efficient oxidation of oleanolic acid derivatives using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP). Convenient 2-step procedure towards 12-oxo-28-carboxylic acid derivatives,

Beilstein J. Org. Chem., 2012, 8, 164-169.

 

SALVADOR, J.A.R.; MOREIRA, V.M.; GONÇALVES B. M. F.; LEAL, A.S.M.; JING, Y.

Ursane-type Pentacyclic Triterpenoids as Useful Platforms to Discovery Anticancer Drugs,

Nat. Prod. Rep., 2012, 29, 1463-1479.

 

SALVADOR, J.A.R.; FIGUEIREDO, S.A.C.; PINTO, R.M.A.; SILVESTRE, S.M.

Bismuth Compounds in Medicinal Chemistry,

Future Med. Chem., 2012, 4, (11), 1495-1523.

 

LEAL, A.S.M.; WANG, R.; SALVADOR, J.A.R.; JING, Y.

Semisynthetic ursolic acid fluorolactone derivatives inhibit growth with induction of p21waf1 and induce apoptosis with upregulation of NOXA and downregulation of c-FLIP in pancreatic cancer cells,

ChemMedChem, 2012, 7, 1635-1646.

 

LEAL, A.S.M.; SALVADOR, J.A.R.; JING, Y.

Synthesis of novel ursolic acid heterocyclic derivatives with improved abilities of antiproliferation and induction of p53, p21waf1 and NOXA in pancreatic cancer cells,

Bioorg. & Med. Chem. 2012, 5774-5786.

 

CARVALHO, J.F.S.; SILVA, M.M.C.; MOREIRA, J.N.; SIMÕES, S.; SÁ e MELO, M.L.

Selective Cytotoxicity of Oxysterols through Structural Modulation on Rings A and B. Synthesis, in Vitro Evaluation, and SAR.

J. Med. Chem., 2011, 54, 6375–6393. DOI: 10.1021/jm200803d

 

SALVADOR, J.A.R.; SILVESTRE, S.M.; PINTO, R.M.A.

Bismuth(III) Reagents in Steroid and Terpene Chemistry,

Molecules, 2011, 16, 2884-2913.

 

CRUZ, C., CAIRRÃO, E., SILVESTRE, S., BREITENFELD, L., ALMEIDA, P., QUEIROZ, J.A.

Targeting of Mitochondria-Endoplasmic Reticulum by Fluorescent Macrocyclic Compounds.

PLOS ONE, 2011, 6, 11, e27078. DOI: 10.1371/journal.pone.0027078

 

MOREIRA, V. M.; SALVADOR, J.A.R.; MATOS BEJA, A.; PAIXÃO, J. A.

The Reaction of Azoles with 17-Chloro-16-formylandrosta-5,16-dien-3β-yl-acetate: Synthesis and Structural Elucidation of Novel 16-Azolylmethylene-17-oxoandrostanes,

Steroids, 2011, 76, 582–587.

 

SANTOS, R.C.; SALVADOR, J.A.R.; CORTÉS, R.; PACHÓN, G.; MARÍN, S.; CASCANTE, M.

New Betulinic Acid Derivatives Induce Potent and Selective Antiproliferative Activity Through Cell Cycle Arrest at the S Phase and Caspase Dependent Apoptosis in Human Cancer Cells,

Biochimie, 2011, 93, 1065-1075.

 

SALVADOR, J.A.R.; MOREIRA, V.M.; PINTO, R.M.A.; LEAL A. S.; Le ROUX, C.

Bismuth(III) triflate Catalyzed Direct Opening of Oleanolic Hydroxy-g-lactones to Afford 12-Oxo-28-carboxylic acids,

Adv. Synth.& Catal., 2011, 353, 2637-2642.

 

SILVA, M.M.C.; CARVALHO, J.F.S.; RIVA, S.; SÁ E MELO, M.L.

Biocatalytic Transformations of Steroids: Focus on Hydrolase-Catalyzed Reactions.

Curr. Org. Chemistry, 2011, 15, 6, 928-941. DOI: 10.2174/138527211794518871

 

CARVALHO, J.F.S.; SILVA, M.M.C.; MOREIRA, J.N.; SIMÕES, S.; SÁ e MELO, M.L.

Sterols as Anticancer Agents: Synthesis of Ring-B Oxygenated Steroids, Cytotoxic Profile, and Comprehensive SAR Analysis.

J. Med. Chem., 2010, 53 (21), pp 7632–7638. DOI: 10.1021/jm1007769

 

SANTOS R.C, SALVADOR, J.A.R.; MARIN S.; CASCANTE, M.; MOREIRA, J.N.; DINIS, T.P.C.

Synthesis and Structure-activity Relationship Study of Novel Cytotoxic Carbamate and N-Acylheterocyclic Bearing Derivatives of Betulin and Betulinic acid,

Bioorg. Med. Chem., 2010, 18, 4385-4396.

 

CARVALHO, J.F.S.; SILVA, M.M.C.; MOREIRA, J.N.; SIMÕES, S.; SÁ e MELO, M.L.

Efficient Chemoenzymatic Synthesis, Cytotoxic Evaluation, and SAR of Epoxysterols.

J. Med. Chem., 2009, 52 (13), pp 4007–4019. DOI: 10.1021/jm9003973

 

SALVADOR, J.A.R.; PINTO, R.M.A; SANTOS, R. C.; Le ROUX, C.; MATOS BEJA, A.; PAIXÃO, J. A.

Bismuth triflate-catalyzed Wagner-Meerwein rearrangement in terpenes. Application to the synthesis of the 18α-core and A-neo-18α-oleanene compounds from lupanes,

Org. & Biomol. Chem., 2009, 7, 508-517.

 

PINTO, R.M.A; SALVADOR, J.A.R.; Le ROUX, C.; CARVALHO, R.A.; MATOS BEJA, A.; PAIXÃO, J. A.

Bismuth(III) Triflate-Catalyzed Rearrangement of 16α,17α-Epoxy-20-oxosteroids, Synthesis and Structural Elucidation of New 16α-Substituted 17α-Alkyl-17β-methyl-Δ13-18-norsteroids,

Tetrahedron, 2009, 65, 6169-6178.

 

SANTOS, R.C.; SALVADOR, J.A.R.; MARÍN, S.; CASCANTE, M.

Novel Semisynthetic Derivatives of Betulin and Betulinic acid with Cytotoxic Activity,

Bioorg. Med. Chem., 2009, 17, 6241-6250.

 

SALVADOR, J.A.R.; PINTO, R.M.A.; SILVESTRE, S.M.

Recent Advances of Bismuth(III) Salts in Organic Chemistry: Application to the Synthesis of Heterocycles of Pharmaceutical Interest,

Curr. Org. Synthesis, 2009, 6, 426-470.

 

PINTO, R.M.A; SALVADOR, J.A.R.; Le ROUX, C.; PAIXÃO, J. A.

Bismuth(III) Triflate-Catalyzed Direct Conversion of Corticosteroids into Highly Functionalized 17-Ketosteroids by Cleavage of the C17-Dihydroxyacetone Side Chain,

J. Org. Chem., 2009, 74, 8488-8491.

 

SALVADOR, J.A.R.; PINTO, R.M.A.; SILVESTRE, S.M.

Recent Advances of Bismuth(III) Salts in Organic Chemistry: Application to the Synthesis of Aliphatics, Alicyclics, Aromatics, Amino acids and Peptides, Terpenes and Steroids of Pharmaceutical Interest,

Mini Reviews in Organic Chemistry, 2009, 6, 241-274.

 

PINTO, R.M.A.; SALVADOR, J.A.R.; Le ROUX, C.

Metal Triflates Combined with Caffeine Based Imidazolium Salts: a New Family of Highly Efficient and Reusable Catalysts,

Catalysis Communications, 2008, 9, 465-469.

 

LEITÃO A.J.L.; SALVADOR, J.A.R.; PINTO , R.M.A.; SÁ E MELO, M.L.

Hydrazine sulphate: a cheap and efficient catalyst for the regioselective ring-opening of epoxides. A metal-free procedure for the preparation of b-alkoxy alcohols, Tetrahedron Lett., 2008, 49, 1694-1697.

 

SALVADOR, J.A.R.; SILVESTRE, S.M.; MOREIRA, V.M.

Catalytic Epoxidation and syn-Dihydroxylation Reactions in Steroid Chemistry,

Curr. Org. Chem., 2008, 12, 492-522.

 

MOREIRA, V.M.; SALVADOR, J.A.R.; VASAITIS T.S.; NJAR, V.C.O.

CYP17 Inhibitors for Prostate Cancer Treatment. An Update.

Curr. Med. Chem., 2008, 15, 868-899.

 

PINTO, R.M.A.; SALVADOR, J.A.R.; Le ROUX, C; CARVALHO, R.A.; SILVA, M.R.; BEJA, A.M.; PAIXÃO, J.A.

Bismuth(III) Salt-Catalyzed Westphalen and “Backbone” Rearrangements of 5b-6b-Epoxysteroids. Synthesis and Structural Elucidation of New Olefinic 19-Nor and 18,19-Dinorsteroids,

Steroids, 2008, 73, 549-561.

 

SILVESTRE, S.M.; SALVADOR, J.A.R.

Allylic and benzylic oxidation reactions with sodium chlorite,

Tetrahedron, 2007, 63, 2439-2445.

 

PINTO, R.M.A.; SALVADOR J.A.R.; Le ROUX, C.

Bismuth(III) salts mediated regioselective ring opening of epoxides: an easy route to halohydrins and b-hydroxy nitrates.

Tetrahedron, 2007, 63, 9221-9228.

 

MOREIRA, V.M.; VASAITIS T.S.; NJAR, V.C.O.; SALVADOR, J.A.R.

Synthesis and Evaluation of Novel 17-Indazole Androstene Derivatives Designed as CYP17 Inhibitors,

Steroids, 2007, 72, 939-948.

 

SALVADOR, J.A.R.; MOREIRA, V.M.; HANSON, J.R.; CARVALHO, R.

One-pot, high yield synthesis of alpha-ketols from ∆5-steroids,

Steroids, 2006, 71, 266-272.

 

SALVADOR, J.A.R.; SILVESTRE, S.M.; MOREIRA, V.M.

Catalytic oxidative processes in steroid chemistry: allylic oxidation, β-selective epoxidation, alcohol oxidation and remote functionalization reactions,

Curr. Org. Chem., 2006, 10, 2227-2257.

 

PINTO, R.M.; SALVADOR J.A.R; Le ROUX, C.

Ritter Reaction Mediated by Bismuth (III) Salts. One-Step Conversion of Epoxides into Acylamino-hydroxy Compounds,

Synlett, 2006, 13, 2047-2050.

 

SALVADOR, J.A.R.; LEITÃO A.J.L.; SÁ E MELO M.L.; HANSON J.R.

Hydrazine hydrate induced reductive cleavage of a,b-epoxy-ketones: an efficient procedure for the preparation of b-hydroxy ketones,

Tetrahedron Lett., 2005, 46, 7, 1067-1070.

 

SALVADOR, J.A.R.; SILVESTRE, S.M.

Bismuth-catalysed allylic oxidation using t-butylhydroperoxide,

Tetrahedron Lett., 2005, 46, 2581-2584.

       

SILVESTRE, S.M.; SALVADOR, J.A.R.; CLARK, J.H.

β-Selective Epoxidation of ∆5-Steroids by O2 Using Surface Functionalised Silica Supported Cobalt Catalysts,

J.Mol.Catal. A. Chemical, 2004, 219, 143-147.

 

SALVADOR, J.A.R.; CLARK, J.H.

The Allylic Oxidation of Unsaturated Steroids by tert-Butyl Hydroperoxide using Surface Functionalised Silica Supported Metal Catalysts,

Green Chem., 2002, 4, 352-356.

 

SALVADOR, J.A.R.; CLARK, J.H.

The Allylic Oxidation of Unsaturated Steroids by tert-Butyl Hydroperoxide using Homogeneous and Heterogeneous Cobalt Acetate,

Chem.Commun., 2001, (1), 33-34.

 

FREIXA, Z.; PEREIRA, M.M.; BAYON, J.C.; SILVA, A.M.S.; SALVADOR, J.A.R.; MATOS BEJA, A.; PAIXÃO, J.A.; RAMOS SILVA, M.

Diastereoselective Hydroformylation of ∆4-Steroids with Rhodium-Phosphite Catalysts.,

Tetrahedron Asymmetry, 2001, 12,1083-1087.

 

CAMPOS NEVES, A.S.; SÁ E MELO, M.L.; MORENO, M.J.S.M.; TAVARES da SILVA , E.J.; SALVADOR, J.A.R.; PEREIRA DA COSTA, S.C.; MARTINS, R.M.L.M.

Improved Synthesis of Aromatase Inhibitors and Neuroactive Steroids. Efficient Oxidations and Reductions at Key Positions for Bioactivity,

Tetrahedron, 1999, 55, 3255-3264.

 

SALVADOR, J.A.R.; SÁ E MELO, M.L.; CAMPOS NEVES, A.S.

Copper-Catalysed Allylic Oxidation of ∆5-Steroids by t-Butyl Hydroperoxide,

Tetrahedron Lett., 1997, 38, (1), 119-122.

 

SALVADOR, J.A.R.; SÁ E MELO, M.L.; CAMPOS NEVES, A.S.

Oxidations with Potassium Permanganate-Metal Sulphates and Nitrates. ∆-Selective Epoxidation of ∆5-Unsaturated Steroids,

Tetrahedron Lett., 1996, 37, (5), 687-690.

 

SÁ E MELO, M.L.; MORENO, M.J.S.M.; PEREIRA DA COSTA, S.C.; SALVADOR, J.A.R.; CAMPOS NEVES, A.S.

Ultrasound Assisted Oxidations and Reductions in Steroid Synthesis,

Ultrasonics Sonochemistry, 1994, 1, (1), S37-S40.

 

SALVADOR, J.A.R.; SÁ e MELO, M.L.; CAMPOS NEVES, A.S.

Ultrasound Assisted Zinc Reactions in Synthesis 1. Efficient Reduction of Enones,

Tetrahedron Lett., 1993, 34, (2), 357-360.

 

SALVADOR, J.A.R.; SÁ E MELO, M.L.; CAMPOS NEVES, A.S.

Ultrasound Assisted Zinc Reactions in Synthesis 2. A New Clemmensen-type Reduction,

Tetrahedron Lett., 1993, 34, (2), 361-362.

 

 

SELECTED PATENTS:

 

 

SALVADOR, J.A.R.; SANTOS, R.C.; SERRATOSA, M.C.

Triterpenoid Derivatives Usefull as Antiproliferative Agents, US Patent. US 8,969,395 B2, 2015.

 

SALVADOR, J.A.R.; SANTOS, R.C.; SERRATOSA, M.C.

Derivados Triterpenóides úteis como agentes Antiproliferativos, Patente Portuguesa, PT Patent 104607B, 2011.

 

SALVADOR, J.A.R.; SANTOS, R.C.; SERRATOSA, M.C.

Triterpenoid Derivatives and Their Use as Antiproliferative Agents, PCT/PT2010/000021, WO 2010/134830 A1, 2010.

 

SALVADOR, J.A.R.; SILVESTRE, S.M.

Processo para a Oxidação Alílica de Compostos Insaturados, Patente Portuguesa, PT Patent 104193B, 2009.

 

SALVADOR, J.A.R.; SILVESTRE, S.M.

Processo para a Oxidação Alílica de Compostos Insaturados, Patente Portuguesa, PT Patent 103592B, 2008.

 

SALVADOR, J.A.R.; SILVESTRE, S.M.

Processo para a Oxidação Alílica de Compostos Insaturados Usando Hidroperóxido de t-Butilo e Catalisadores de Bismuto, Patente Portuguesa, PT Patent 103211B, 2006.

 

SALVADOR, J.A.R.; SÁ E MELO, M.L.; CAMPOS NEVES, A.S.

Copper-Catalysed Allylic Oxidation Using Alkyl Hydroperoxide, US Patent, US 6,252,119 B1, 2001.