3-Hydroxy-2,6-dinitroacetophenone: an Unusual Substitution Pattern Resulting from Nitration of 3-Hydroxyacetophenone

M. L. S. Cristiano; Johnstone, R. A. W.; Pratt, M. J.; Loureiro, R. M. S.; Pena, Paula C. A.; Johnstone, Robert A. W.; Loureiro, Rui M. S.; Pena, Paula C. A.; M. L. S. Cristiano; O'Neill, Paul M; Rosenthal, Philip J; Gut, Jiri; Guedes, Rita C; Moreira, Rui; Sharma, Raman; Berry, Neil; M. L. S. Cristiano; Shone, Alison E; Ward, Stephen A; O'Neill, Paul M; Biagini, Giancarlo A.; O’Neill, Paul M.; Nixon, Gemma L.

Organic Reactivity and Medicinal Chemistry

Short Title

OrgMedChem

Description

Development of heterocyclic compounds applicable in medicine, environmental remediation or aquaculture. Investigation of structure, reactivity and activity of compounds obtained from synthesis or natural sources.

Coordinator

Maria de Lurdes dos Santos Cristiano

Organiza

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The group applies the methods and tools of Physical Organic Chemistry and Medicinal Chemistry to investigate structure/reactivity/activity relationships of selected compounds from biologically relevant chemotypes: endoperoxydes, quinolones, tetrazoles and saccharins. We aim to contribute to the elucidation of interactions between compounds and their biological targets, thereby gathering instrumental information for rational drug design and optimization.

Topic 1. Development of anti-infective agents comprising quinolone- or peroxide-based heterocycles.

We investigate structural requirements of 4-oxoquinoline-3-esters for inhibition of the bc1 complex (respiratory chain) of Plasmodium falciparum (CQ-sensitive and multiresistant strains). Selected 2-substituted-4-oxoquinolines prepared exhibit potent activity against Mycobacterium tuberculosis.

Inspired in the antimalarial drug Artemisinin, a natural product, we develop synthetic endoperoxides with improved pharmacologic profile. We consider exploring peroxides inspired in Plakortin, a peroxide-based metabolite obtained from the marine sponge Plakortis halichondrioides.

We scrutinize the potencial of endoperoxides against other protozoans: Leishmania donovani, Perkinsus olseni, and Amyloodinium ocellatum the causative agents of Leishmaniases (in mamals), Perkinsosis (in bivalves) and Amyloodinium ocellatum (in fish), respectively.

Topic 2. Synthesis, reactivity and applications of chelants derived from tetrazole and saccharin.

We develop tetrazole-saccharyl conjugates as selective chelants and scrutinise their potential in catalysis, environmental remediation, medicine and in the design of supramolecular frameworks.

We demonstrated their utility as ligands for divalent cations. Selected copper complexes act as effective catalysts for oxidation of secondary alcohols and have shown potent cytotoxicity against adherent cancer cell lines.

We are organizing the 24TH IUPAC INTERNATIONAL CONFERENCE ON PHYSICAL ORGANIC CHEMISTRY (ICPOC 24) this year.

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CCMAR researchers won 1st prize in “Ideias em Caixa “contest

Patrícia Amado won the prize for the best poster at ESOR2021

The toxic effects of microalgae on humans

New Position: Joana F.Leal

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Coordinator	Position
Maria de Lurdes dos Santos Cristiano

Name	Position
Alina Secrieru	PhD Student
Amin Lopes Ismael	Investigador
André Lourenço Fernandes	Investigador
Bruno de Campos Guerreiro	PhD Student
Joana F. Leal	Investigador
Lília Cabral	Research Assistant
Maria de Lurdes dos Santos Cristiano
Patrícia Amado	PhD Student
Pedro Filipe Castela Horta
Valentin Bessergenev

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Alina Secrieru

Position:

PhD Student

Amin Lopes Ismael

Position:

Investigador

André Lourenço Fernandes

Position:

Investigador

Bruno de Campos Guerreiro

Position:

PhD Student

Joana F. Leal

Position:

Investigador

Lília Cabral

Position:

Research Assistant

Maria de Lurdes dos Santos Cristiano

Position:

Patrícia Amado

Position:

PhD Student

Pedro Filipe Castela Horta

Position:

Valentin Bessergenev

Position:

Gallery

Publications

All Publications


W. Hong D, Gibbons PD, Leung SC, et al. Rational Design, Synthesis, and Biological Evaluation of Heterocyclic Quinolones Targeting the Respiratory Chain of Mycobacterium tuberculosis. Journal of Medicinal Chemistry. 2017;60(9):3703 - 3726. doi:10.1021/acs.jmedchem.6b01718 Read more about Rational Design, Synthesis, and Biological Evaluation of Heterocyclic Quinolones Targeting the Respiratory Chain of Mycobacterium tuberculosis Google Scholar DOI
Frija LMT, Kuznetsov ML, Rocha BGM, et al. Organocatalyzed oxidation of benzyl alcohols by a tetrazole-amino-saccharin: A combined experimental and theoretical (DFT) study. Molecular Catalysis. 2017;442:57 - 65. doi:10.1016/j.mcat.2017.09.003 Read more about Organocatalyzed oxidation of benzyl alcohols by a tetrazole-amino-saccharin: A combined experimental and theoretical (DFT) study Google Scholar DOI
Horta P, Henriques MSC, Brás EM, et al. On the ordeal of quinolone preparation via cyclisation of aryl-enamines; synthesis and structure of ethyl 6-methyl-7-iodo-4-(3-iodo-4-methylphenoxy)-quinoline-3-carboxylateAbstract. Pure and Applied Chemistry. 2017;89(6). doi:10.1515/pac-2016-1119 Read more about On the ordeal of quinolone preparation via cyclisation of aryl-enamines; synthesis and structure of ethyl 6-methyl-7-iodo-4-(3-iodo-4-methylphenoxy)-quinoline-3-carboxylateAbstract Google Scholar DOI
Cabral LIL, Henriques MSC, Paixão JA, Cristiano MLS. Synthesis and structure of 2-substituted pyrene-derived scaffolds. Tetrahedron Letters. 2017;58(48):4547 - 4550. doi:10.1016/j.tetlet.2017.10.058 Read more about Synthesis and structure of 2-substituted pyrene-derived scaffolds Google Scholar DOI
Cabral LIL, Brás E, Henriques M, et al. Synthesis, Structure and Cytotoxicity of a Novel Sulphanyl-Bridged Thiadiazolyl-Saccharinate Conjugate. The Relevance of S…N Interaction. Chemistry - A European Journal. 2017. doi:10.1002/chem.201705319 Read more about Synthesis, Structure and Cytotoxicity of a Novel Sulphanyl-Bridged Thiadiazolyl-Saccharinate Conjugate. The Relevance of S…N Interaction Google Scholar DOI
Mestre ALG, Inácio PMC, Elamine Y, et al. Extracellular Electrophysiological Measurements of Cooperative Signals in Astrocytes Populations. Frontiers in Neural Circuits. 2017;11. doi:10.3389/fncir.2017.00080 Read more about Extracellular Electrophysiological Measurements of Cooperative Signals in Astrocytes Populations Google Scholar DOI
Mestre ALG, Cerquido M, Inácio PMC, et al. Ultrasensitive gold micro-structured electrodes enabling the detection of extra-cellular long-lasting potentials in astrocytes populations. Scientific Reports. 2017;7(1). doi:10.1038/s41598-017-14697-y Read more about Ultrasensitive gold micro-structured electrodes enabling the detection of extra-cellular long-lasting potentials in astrocytes populations Google Scholar DOI
Lobo L, de Sousa B, Cabral LIL, Cristiano MLS, Nogueira F. Highly active ozonides selected against drug resistant malaria. Memórias do Instituto Oswaldo Cruz. 2016;111(7):450 - 453. doi:10.1590/0074-02760160077 Read more about Highly active ozonides selected against drug resistant malaria Google Scholar DOI
Frija LMT, Alegria ECBA, Sutradhar M, et al. Copper(II) and cobalt(II) tetrazole-saccharinate complexes as effective catalysts for oxidation of secondary alcohols. Journal of Molecular Catalysis A: Chemical. 2016;425:283 - 290. doi:10.1016/j.molcata.2016.10.023 Read more about Copper(II) and cobalt(II) tetrazole-saccharinate complexes as effective catalysts for oxidation of secondary alcohols Google Scholar DOI
Ismael A, Henriques MSC, Marques C, et al. Exploring saccharinate-tetrazoles as selective Cu(. RSC Adv. 2016;6(75):71628 - 71637. doi:10.1039/C6RA15051A Read more about Exploring saccharinate-tetrazoles as selective Cu( Google Scholar DOI
Ismael A, Fausto R, Cristiano MLS. Photochemistry of 1- and 2-Methyl-5-aminotetrazoles: Structural Effects on Reaction Pathways. The Journal of Organic Chemistry. 2016;81(23):11656 - 11663. doi:10.1021/acs.joc.6b02023 Read more about Photochemistry of 1- and 2-Methyl-5-aminotetrazoles: Structural Effects on Reaction Pathways Google Scholar DOI
Ismael A, Borba A, Henriques MSC, Paixão JA, Fausto R, Cristiano MLS. Structure and photochemistry of a saccharyl thiotetrazole. J Org Chem. 2015;80(1):392-400. doi:10.1021/jo502419u Read more about Structure and photochemistry of a saccharyl thiotetrazole. Google Scholar PubMed DOI
Cortes S, Albuquerque A, Cabral LIL, Lopes L, Campino L, Cristiano MLS. In Vitro Susceptibility of Leishmania infantum to Artemisinin Derivatives and Selected Trioxolanes. Antimicrob Agents Chemother. 2015;59(8):5032-5. doi:10.1128/AAC.00298-15 Read more about In Vitro Susceptibility of Leishmania infantum to Artemisinin Derivatives and Selected Trioxolanes. Google Scholar PubMed DOI
Borba A, Cabral LIL, Fausto R, Cristiano MLS. Structure, vibrational spectroscopy, and photochemistry of 5-phenoxy-1-phenyltetrazole in argon and nitrogen cryomatrices. Canadian Journal of Chemistry. 2015;93(12):1335 - 1344. doi:10.1139/cjc-2015-0025 Read more about Structure, vibrational spectroscopy, and photochemistry of 5-phenoxy-1-phenyltetrazole in argon and nitrogen cryomatrices Google Scholar DOI
Horta PC, Henriques MSC, Kuş N, et al. Synthesis, structural and conformational analysis, and IR spectra of ethyl 4-chloro-7-iodoquinoline-3-carboxylate. Tetrahedron. 2015;71(40):7583 - 7592. doi:10.1016/j.tet.2015.07.076 Read more about Synthesis, structural and conformational analysis, and IR spectra of ethyl 4-chloro-7-iodoquinoline-3-carboxylate Google Scholar DOI
Horta P, Kuş N, Henriques MSofia C, et al. Quinolone-Hydroxyquinoline Tautomerism in Quinolone 3-Esters. Preserving the 4-Oxoquinoline Structure To Retain Antimalarial Activity. J Org Chem. 2015;80(24):12244-57. doi:10.1021/acs.joc.5b02169 Read more about Quinolone-Hydroxyquinoline Tautomerism in Quinolone 3-Esters. Preserving the 4-Oxoquinoline Structure To Retain Antimalarial Activity. Google Scholar PubMed DOI
Frija LMT, Cristiano MLS, Gómez-Zavaglia A, Reva I, Fausto R. Genesis of rare molecules using light-induced reactions of matrix-isolated tetrazoles. Journal of Photochemistry and Photobiology C: Photochemistry Reviews. 2014;18:71 - 90. doi:10.1016/j.jphotochemrev.2013.09.001 Read more about Genesis of rare molecules using light-induced reactions of matrix-isolated tetrazoles Google Scholar DOI
Ismael A, Gago DJP, Cabral LIL, Fausto R, Cristiano MLS. Investigations into the Mechanism of Solvolysis of 3-aryloxybenzisothiazoles. Croatica Chemica Acta. 2014;87(4):363 - 373. doi:10.5562/cca2478 Read more about Investigations into the Mechanism of Solvolysis of 3-aryloxybenzisothiazoles Google Scholar DOI
Ismael A, Gómez-Zavaglia A, Borba A, Cristiano MLS, Fausto R. Amino→imino tautomerization upon in vacuo sublimation of 2-methyltetrazole-saccharinate as probed by matrix isolation infrared spectroscopy. J Phys Chem A. 2013;117(15):3190-7. doi:10.1021/jp401360c Read more about Amino→imino tautomerization upon in vacuo sublimation of 2-methyltetrazole-saccharinate as probed by matrix isolation infrared spectroscopy. Google Scholar PubMed DOI
La Pensée L, Sabbani S, Sharma R, et al. Artemisinin-polypyrrole conjugates: synthesis, DNA binding studies and preliminary antiproliferative evaluation. ChemMedChem. 2013;8(5):709-18. doi:10.1002/cmdc.201200536 Read more about Artemisinin-polypyrrole conjugates: synthesis, DNA binding studies and preliminary antiproliferative evaluation. Google Scholar PubMed DOI
Cabral LIL, Maria TMR, Martelo L, Eusébio MES, Cristiano MLS, Fausto R. The thermal sigmatropic isomerization of pseudosaccharyl crotyl ether. Tetrahedron. 2013;69(2):810 - 815. doi:10.1016/j.tet.2012.10.100 Read more about The thermal sigmatropic isomerization of pseudosaccharyl crotyl ether Google Scholar DOI
Duarte L, Reva I, Cristiano MLS, Fausto R. Photoisomerization of saccharin. J Org Chem. 2013;78(7):3271-5. doi:10.1021/jo400191p Read more about Photoisomerization of saccharin. Google Scholar PubMed DOI
Araujo NCP, Afonso R, Bringela A, M. Cancela L, Cristiano MLS, Leite RB. Peroxides with antiplasmodial activity inhibit proliferation of Perkinsus olseni, the causative agent of Perkinsosis in bivalves. Parasitol Int. 2013;62(6):575-82. doi:10.1016/j.parint.2013.06.010 Read more about Peroxides with antiplasmodial activity inhibit proliferation of Perkinsus olseni, the causative agent of Perkinsosis in bivalves. Google Scholar PubMed DOI
Ismael A, Serpa C, Cristiano MLS. Photochemistry of 1-allyl-4-aryltetrazolones in solution; structural effects on photoproduct selectivity. Photochem Photobiol Sci. 2013;12(2):272-83. doi:10.1039/c2pp25210d Read more about Photochemistry of 1-allyl-4-aryltetrazolones in solution; structural effects on photoproduct selectivity. Google Scholar PubMed DOI
Ismael A, Paixão JAntónio, Fausto R, Cristiano MLS. Molecular structure of nitrogen-linked methyltetrazole-saccharinates. Journal of Molecular Structure. 2012;1023:128 - 142. doi:10.1016/j.molstruc.2012.04.018 Read more about Molecular structure of nitrogen-linked methyltetrazole-saccharinates Google Scholar DOI
Ismael A, Borba A, Duarte L, Giuliano BM, Gómez-Zavaglia A, Cristiano MLS. Structure and photochemistry of a novel tetrazole-saccharyl conjugate isolated in solid argon. Journal of Molecular Structure. 2012;1025:105 - 116. doi:10.1016/j.molstruc.2012.04.081 Read more about Structure and photochemistry of a novel tetrazole-saccharyl conjugate isolated in solid argon Google Scholar DOI
Gómez-Zavaglia A, Ismael A, Cabral LIL, et al. Structural investigation of nitrogen-linked saccharinate–tetrazole. Journal of Molecular Structure. 2011;1003(1-3):103 - 110. doi:10.1016/j.molstruc.2011.07.044 Read more about Structural investigation of nitrogen-linked saccharinate–tetrazole Google Scholar DOI
Frija LMT, Reva I, Ismael A, Coelho DV, Fausto R, Cristiano MLS. Sigmatropic rearrangements in 5-allyloxytetrazoles. Org Biomol Chem. 2011;9(17):6040-54. doi:10.1039/c1ob05460k Read more about Sigmatropic rearrangements in 5-allyloxytetrazoles. Google Scholar PubMed DOI
Gibbons P, Verissimo E, Araujo NC, et al. Endoperoxide carbonyl falcipain 2/3 inhibitor hybrids: toward combination chemotherapy of malaria through a single chemical entity. J Med Chem. 2010;53(22):8202-6. doi:10.1021/jm1009567 Read more about Endoperoxide carbonyl falcipain 2/3 inhibitor hybrids: toward combination chemotherapy of malaria through a single chemical entity. Google Scholar PubMed DOI
Frija LMiguel Teo, Ismael A, Cristiano MLS. Photochemical transformations of tetrazole derivatives: applications in organic synthesis. Molecules. 2010;15(5):3757-74. doi:10.3390/molecules15053757 Read more about Photochemical transformations of tetrazole derivatives: applications in organic synthesis. Google Scholar PubMed DOI
Ismael A, Cristiano MLS, Fausto R, Gómez-Zavaglia A. Tautomer selective photochemistry in 1-(tetrazol-5-yl)ethanol. J Phys Chem A. 2010;114(50):13076-85. doi:10.1021/jp109215q Read more about Tautomer selective photochemistry in 1-(tetrazol-5-yl)ethanol. Google Scholar PubMed DOI
Araújo NCP, Barton V, Jones M, et al. Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates. Bioorg Med Chem Lett. 2009;19(7):2038-43. doi:10.1016/j.bmcl.2009.02.013 Read more about Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates. Google Scholar PubMed DOI
Gómez-Zavaglia A, Kaczor A, Almeida R, et al. Thermally induced sigmatropic isomerization of pseudosaccharyl allylic ether. J Phys Chem A. 2009;113(15):3517-22. doi:10.1021/jp8112254 Read more about Thermally induced sigmatropic isomerization of pseudosaccharyl allylic ether. Google Scholar PubMed DOI
Gómez-Zavaglia A, Kaczor A, Coelho D, Cristiano MLS, Fausto R. Conformational and structural analysis of 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide as probed by matrix-isolation spectroscopy and quantum chemical calculations. Journal of Molecular Structure. 2009;919(1-3):271 - 276. doi:10.1016/j.molstruc.2008.09.013 Read more about Conformational and structural analysis of 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide as probed by matrix-isolation spectroscopy and quantum chemical calculations Google Scholar DOI
Almeida R, Gómez-Zavaglia A, Kaczor A, Ismael A, Cristiano MLS, Fausto R. Matrix-isolation FTIR, theoretical structural analysis and reactivity of amino-saccharins: N-(1,1-dioxo-1,2-benzisothiazol-3-yl)-N-methyl amine and -N,N-dimethyl amine. Journal of Molecular Structure. 2009;938(1-3):198 - 206. doi:10.1016/j.molstruc.2009.09.027 Read more about Matrix-isolation FTIR, theoretical structural analysis and reactivity of amino-saccharins: N-(1,1-dioxo-1,2-benzisothiazol-3-yl)-N-methyl amine and -N,N-dimethyl amine Google Scholar DOI
Frija LMT, Fausto R, Loureiro RMS, Cristiano MLS. Synthesis and structure of novel benzisothiazole-tetrazolyl derivatives for potential application as nitrogen ligands. Journal of Molecular Catalysis A: Chemical. 2009;305(1-2):142 - 146. doi:10.1016/j.molcata.2008.12.007 Read more about Synthesis and structure of novel benzisothiazole-tetrazolyl derivatives for potential application as nitrogen ligands Google Scholar DOI
Frija LMT, Khmelinskii IV, Serpa C, Reva ID, Fausto R, Cristiano MLS. Photochemistry of 5-allyloxy-tetrazoles: steady-state and laser flash photolysis study. Org Biomol Chem. 2008;6(6):1046-55. doi:10.1039/b718104c Read more about Photochemistry of 5-allyloxy-tetrazoles: steady-state and laser flash photolysis study. Google Scholar PubMed DOI
Gómez-Zavaglia A, Kaczor A, Almeida R, Cristiano MLS, Fausto R. Conformational Space of the P seudo saccharin Allyl Ether 3-(Allyloxy)-1,2-benzisothiazole 1,1-Dioxide in Gas Phase and in Rare Gas Matrices. The Journal of Physical Chemistry A. 2008;112(8):1762 - 1772. doi:10.1021/jp0770918 Read more about Conformational Space of the P seudo saccharin Allyl Ether 3-(Allyloxy)-1,2-benzisothiazole 1,1-Dioxide in Gas Phase and in Rare Gas Matrices Google Scholar DOI
Verissimo E, Berry N, Gibbons P, et al. Design and synthesis of novel 2-pyridone peptidomimetic falcipain 2/3 inhibitors. Bioorg Med Chem Lett. 2008;18(14):4210-4. doi:10.1016/j.bmcl.2008.05.068 Read more about Design and synthesis of novel 2-pyridone peptidomimetic falcipain 2/3 inhibitors. Google Scholar PubMed DOI
Frija LMT, Khmelinskii IV, Serpa C, Reva ID, Fausto R, Cristiano MLS. Photochemistry of 5-allyloxy-tetrazoles: steady-state and laser flash photolysis study. Organic & Biomolecular Chemistry. 2008;6(6):1046. doi:10.1039/b718104c Read more about Photochemistry of 5-allyloxy-tetrazoles: steady-state and laser flash photolysis study Google Scholar DOI
Cristiano MLS, Ruasse M-F. Editorial. Journal of Physical Organic Chemistry. 2008;21(7-8):523 - 523. doi:10.1002/poc.1411 Read more about Editorial Google Scholar DOI
Verissimo E, Berry N, Gibbons P, et al. Design and synthesis of novel 2-pyridone peptidomimetic falcipain 2/3 inhibitors. Bioorganic & Medicinal Chemistry Letters. 2008;18(14):4210 - 4214. doi:10.1016/j.bmcl.2008.05.068 Read more about Design and synthesis of novel 2-pyridone peptidomimetic falcipain 2/3 inhibitors Google Scholar DOI
Kaczor A, Proniewicz LM, Almeida R, et al. The Chapman-type rearrangement in pseudosaccharins: The case of 3-(methoxy)-1,2-benzisothiazole 1,1-dioxide. Journal of Molecular Structure. 2008;892(1-3):343 - 352. doi:10.1016/j.molstruc.2008.05.054 Read more about The Chapman-type rearrangement in pseudosaccharins: The case of 3-(methoxy)-1,2-benzisothiazole 1,1-dioxide Google Scholar DOI
Gómez-Zavaglia A, Kaczor A, Almeida R, Cristiano MLS, Fausto R. Conformational space of the Pseudosaccharin allyl ether 3-(allyloxy)-1,2-benzisothiazole 1,1-dioxide in gas phase and in rare gas matrices. J Phys Chem A. 2008;112(8):1762-72. doi:10.1021/jp0770918 Read more about Conformational space of the Pseudosaccharin allyl ether 3-(allyloxy)-1,2-benzisothiazole 1,1-dioxide in gas phase and in rare gas matrices. Google Scholar PubMed DOI
Kaczor A, Almeida R, Gómez-Zavaglia A, Cristiano MLS, Fausto R. Molecular structure and infrared spectra of the monomeric 3-(methoxy)-1,2-benzisothiazole 1,1-dioxide (methyl pseudosaccharyl ether). Journal of Molecular Structure. 2008;876(1-3):77 - 85. doi:10.1016/j.molstruc.2007.06.004 Read more about Molecular structure and infrared spectra of the monomeric 3-(methoxy)-1,2-benzisothiazole 1,1-dioxide (methyl pseudosaccharyl ether) Google Scholar DOI
V.G. B, R.J.F. P, A.M. Bdo Rego. Thin film sulphides and oxides of 3d metals prepared from complex precursors by CVD. Surface and Coatings Technology. 2007;201. Read more about Thin film sulphides and oxides of 3d metals prepared from complex precursors by CVD Google Scholar
Frija LMT, Reva ID, Gómez-Zavaglia A, Cristiano MLS, Fausto R. Photochemistry and vibrational spectra of matrix-isolated 5-ethoxy-1-phenyl-1H-tetrazole. J Phys Chem A. 2007;111(15):2879-88. doi:10.1021/jp068556h Read more about Photochemistry and vibrational spectra of matrix-isolated 5-ethoxy-1-phenyl-1H-tetrazole. Google Scholar PubMed DOI
Frija LMT, Reva ID, Gómez-Zavaglia A, Cristiano MLS, Fausto R. UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone. Photochem Photobiol Sci. 2007;6(11):1170-6. doi:10.1039/b703961a Read more about UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone. Google Scholar PubMed DOI
Frija LMT, Khmelinskii IV, Cristiano MLS. Mechanistic investigations into the photochemistry of 4-allyl-tetrazolones in solution: a new approach to the synthesis of 3,4-dihydro-pyrimidinones. J Org Chem. 2006;71(9):3583-91. doi:10.1021/jo060164j Read more about Mechanistic investigations into the photochemistry of 4-allyl-tetrazolones in solution: a new approach to the synthesis of 3,4-dihydro-pyrimidinones. Google Scholar PubMed DOI
Gómez-Zavaglia A, Reva ID, Frija L, Cristiano MLS, Fausto R. Molecular structure, vibrational spectra and photochemistry of 5-mercapto-1-methyltetrazole. Journal of Molecular Structure. 2006;786(2-3):182 - 192. doi:10.1016/j.molstruc.2005.08.019 Read more about Molecular structure, vibrational spectra and photochemistry of 5-mercapto-1-methyltetrazole Google Scholar DOI
Gómez-Zavaglia A, Reva ID, Frija L, Cristiano MLS, Fausto R. Photochemistry of 1-phenyl-tetrazolone isolated in solid argon. Journal of Photochemistry and Photobiology A: Chemistry. 2006;179(3):243 - 255. doi:10.1016/j.jphotochem.2005.08.021 Read more about Photochemistry of 1-phenyl-tetrazolone isolated in solid argon Google Scholar DOI
Breda S, Reva I, Lapinski L, Cristiano MLS, Frija L, Fausto R. Photochemical Ring-Opening and Intramolecular Hydrogen Shift Reactions in Sulfur Analogues of α-Pyrone. The Journal of Physical Chemistry A. 2006;110(20):6415 - 6425. doi:10.1021/jp061139k Read more about Photochemical Ring-Opening and Intramolecular Hydrogen Shift Reactions in Sulfur Analogues of α-Pyrone Google Scholar DOI
Gómez-Zavaglia A, Reva ID, Frija L, Cristiano MLS, Fausto R. Molecular Structure, Vibrational Spectra and Photochemistry of 2-Methyl-2 H -Tetrazol-5-Amine in Solid Argon. The Journal of Physical Chemistry A. 2005;109(35):7967 - 7976. doi:10.1021/jp0517706 Read more about Molecular Structure, Vibrational Spectra and Photochemistry of 2-Methyl-2 H -Tetrazol-5-Amine in Solid Argon Google Scholar DOI
Frija LMT, Cristiano MLS, Guimarães EMO, Martins NC, Loureiro RMS, Bickley JF. Palladium-catalysed reduction of heteroaromatic naphthyl ethers: Structural effects on reactivity. Journal of Molecular Catalysis A: Chemical. 2005;242(1-2):241 - 250. doi:10.1016/j.molcata.2005.08.022 Read more about Palladium-catalysed reduction of heteroaromatic naphthyl ethers: Structural effects on reactivity Google Scholar DOI
Araújo NCP, Brigas AF, Cristiano MLS, Frija LMT, Guimarães EMO, Loureiro RMS. Heteroaromatic benzyl ethers as intermediates for palladium-catalysed transfer hydrogenolysis of benzyl alcohols. Journal of Molecular Catalysis A: Chemical. 2004;215(1-2):113 - 120. doi:10.1016/j.molcata.2003.12.033 Read more about Heteroaromatic benzyl ethers as intermediates for palladium-catalysed transfer hydrogenolysis of benzyl alcohols Google Scholar DOI
Cristiano MLS, Gago DJP, Gonsalves AM d'ARo, Johnstone RAW, McCarron M, Varejão JMTB. Investigations into the mechanism of action of nitrobenzene as a mild dehydrogenating agent under acid-catalysed conditions. Organic & Biomolecular Chemistry. 2003;1(3):565 - 574. doi:10.1039/b210887a Read more about Investigations into the mechanism of action of nitrobenzene as a mild dehydrogenating agent under acid-catalysed conditions Google Scholar DOI
Araújo NCP, Barroca PMM, Bickley JF, et al. Structural effects on sigmatropic shifts in heteroaromatic allyl ethersElectronic supplementary information (ESI) available: selected crystal data for compound 7. See http://www.rsc.org/suppdata/p1/b1/b102674g/. Journal of the Chemical Society, Perkin Transactions 1. 2002;(9):1213 - 1219. doi:10.1039/b102674g Read more about Structural effects on sigmatropic shifts in heteroaromatic allyl ethersElectronic supplementary information (ESI) available: selected crystal data for compound 7. See http://www.rsc.org/suppdata/p1/b1/b102674g/ Google Scholar DOI
Bugalho SCS, Serra AC, Lapinski L, Cristiano MLS, Fausto R. Low temperature matrix-isolation and solid state vibrational spectra of 5-chlorotetrazoleElectronic supplementary information (ESI) available: Calculated molecular geometries, rotational constants, energies and dipole moments. . Physical Chemistry Chemical Physics. 2002;4(10):1725 - 1731. doi:10.1039/b111329c Read more about Low temperature matrix-isolation and solid state vibrational spectra of 5-chlorotetrazoleElectronic supplementary information (ESI) available: Calculated molecular geometries, rotational constants, energies and dipole moments. Google Scholar DOI
Bugalho SCS, Lapinski L, Cristiano MLS, Frija LMT, Fausto R. Vibrational spectra and structure of 1-phenyltetrazole and 5-chloro-1-phenyltetrazole. Vibrational Spectroscopy. 2002;30(2):213 - 225. doi:10.1016/S0924-2031(02)00028-0 Read more about Vibrational spectra and structure of 1-phenyltetrazole and 5-chloro-1-phenyltetrazole Google Scholar DOI
Bugalho SCS, Maçôas EMS, Cristiano MLS, Fausto R. Low temperature matrix-isolation and solid state vibrational spectra of tetrazole. Physical Chemistry Chemical Physics. 2001;3(17):3541 - 3547. doi:10.1039/b103344c Read more about Low temperature matrix-isolation and solid state vibrational spectra of tetrazole Google Scholar DOI
Cristiano MLS, Brigas AF, Johnstone RAW, Loureiro RMS, Pena PCA. Thermal Rearrangement of 3-Allyloxy-1,2-benzisothiazole 1,1-Dioxides: an Unusual Inversion of Products of Sigmatropic [3,3]-Shift to Give the [1,3]-Isomers. Journal of Chemical Research. 1999;(12):704 - 705. doi:10.1039/a906750g Read more about Thermal Rearrangement of 3-Allyloxy-1,2-benzisothiazole 1,1-Dioxides: an Unusual Inversion of Products of Sigmatropic [3,3]-Shift to Give the [1,3]-Isomers Google Scholar DOI
Lurdes M, Cristiano MLS, Johnstone RAW. A kinetic investigation of the thermal rearrangement of allyloxytetrazoles to N-allyltetrazolones. Journal of the Chemical Society, Perkin Transactions 2. 1997;(3):489 - 494. doi:10.1039/a606376d Read more about A kinetic investigation of the thermal rearrangement of allyloxytetrazoles to N-allyltetrazolones Google Scholar DOI
Cristiano MLS, Johnstone RAW. Intramolecularity of the Thermal Rearrangement of Allyloxytetrazoles to N-Allyltetrazolones†. Journal of Chemical Research. 1997;(5):164 - 165. doi:10.1039/a608333a Read more about Intramolecularity of the Thermal Rearrangement of Allyloxytetrazoles to N-Allyltetrazolones† Google Scholar DOI
Barkley JV, Cristiano MLS, Johnstone RAW, Loureiro RMS. 3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-Dioxide: Unusual C—O—C Ether Bond Lengths and Reactivity. Acta Crystallographica Section C Crystal Structure Communications. 1997;53(3):383 - 386. doi:10.1107/S0108270196014151/bm1104sup2.hkl Read more about 3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-Dioxide: Unusual C—O—C Ether Bond Lengths and Reactivity Google Scholar DOI
Cristiano MLS, Johnstone RAW, Price PJ. Metal-assisted reactions. Part 25. Heterogeneous and homogeneous catalytic transfer hydrogenolysis of allyloxytetrazoles to yield alkenes or alkanes. Journal of the Chemical Society, Perkin Transactions 1. 1996;(12):1453. doi:10.1039/p19960001453 Read more about Metal-assisted reactions. Part 25. Heterogeneous and homogeneous catalytic transfer hydrogenolysis of allyloxytetrazoles to yield alkenes or alkanes Google Scholar DOI
Cristiano MLS, Johnstone RAW, Pratt MJ. 3-Hydroxy-2,6-dinitroacetophenone: an Unusual Substitution Pattern Resulting from Nitration of 3-Hydroxyacetophenone. Acta Crystallographica Section C Crystal Structure Communications. 1995;51(12):2581 - 2583. doi:10.1107/S0108270195007451 Read more about 3-Hydroxy-2,6-dinitroacetophenone: an Unusual Substitution Pattern Resulting from Nitration of 3-Hydroxyacetophenone Google Scholar DOI

Projects

	Title	Coordinator	Time frame	Funding	CCMAR	All
INNOVATE	Implantable Organic Devices For Advanced Therapies (INNOVATE)	Maria de Lurdes dos Santos Cristiano	07/01/2016 to 06/30/2019	FCT	7.92k€
CLAMS	Reversing the pathophysiology of Perkinsosis in clams hatcheries through the use of analogues of Artemisinin	Maria de Lurdes dos Santos Cristiano	06/01/2016 to 05/31/2018	FCT	97.96k€

	Title	Coordinator	Time frame	Funding	CCMAR	All
PTDC 67674	Estudos de reactividade em derivados de tetrazol e isotiazol; derivados isotiazolílicos de tetrazol como potenciais ligandos bidentados e sua aplicação em catálise	Maria de Lurdes dos Santos Cristiano	10/21/2007 to 10/20/2010	FCT	20.40k€

Events

Type of Event

Project Meeting

Apresentação pública dos principais resultados do projeto DEPURATOX

Convidamos os interessados para a apresentação pública dos principais resultados do projeto DEPURATOX - Descontaminação de moluscos bivalves, contaminados com biotoxinas marinhas, durante o processo...

Group

Organic Reactivity and Medicinal Chemistry

February 28, 2023

Sala Polivalente da Biblioteca Municipal de Olhão (Biblioteca José Mariano Gago)