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HOME? MEMBERS? CITATIONS? PHOTOS ?LINKS

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RESEARCH

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A brief resume, with selected examples,

over 30 years of research?in Organic Synthesis and

Natural Products Chemistry from the Lobo-Prabhakar Group.

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SYNTHESIZED MOLECULES | ISOLATED COMPOUNDS | PATENTS | SYNTHETIC METHODS | THEORETICAL CHEMISTRY

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2004 - Prof. Ana M. Lobo and Prof. S. Prabhakar awarded with the Estímulo à Excelência Award - Excelence in R&D - from the Portuguese Government (Ministerio da Ciência, Inovação e Ensino Superior).

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SYNTHESIZED MOLECULES

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2003

Staurosporinone (k-252c) ?
2002

Benzazepinones

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diltiazem-related Ca2+ antagonists (antiarrhythmic)

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Benzoxazinones

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potent insecticides in?gramineous plants

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Benzimidazolones?

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activators of chloride secretion: potential therapeutics for Cystic Fibrosis and Chronic Obstructive Pulmonary Disease

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Benzazocinones?

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Oxindoles and Pyrazolones

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2001

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(+/-)-Eseroline

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(-)-eseroline is the major metabolite of

(-)-physostigmine and possess an analgesic effect similar to that of morphine ?

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Calabar beans

(physostigma venenosum seeds)

(-)-Debromoflustramine B

(Flustra foliacea - marine bryozoan, aquatic colonial animal)

2000

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Tryprostatin B

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cell-cycle progression inhibitor?of tsFT210 (a mutant cell line deficient in Cdc2 kinase) at the G2/M phase barrier

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(Aspergillus fumigatus)

1998

Diisocyanate, Diurethanes and Diureides

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prepared from dehydroabietic acid,

(dehydrogenation of rosin or abietic acid) can be used as industrial monomers for polimer production

colophony (rosin)

1997

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Assoanine (Amaryllidacea family)

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Ismine

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Vasconine and Oxoassoanine

(Amaryllidacea family)
1996 Pratosine (Amaryllidacea family)
1995

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Arcyriaflavin-A

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inhibition of protein kinase C, platelet aggregation? and citotoxic activity

(Arcyria denudata)

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(+/-)-Desoxyeseroline ?
1994

N-substituted amino dihydrocarbostyrils ?

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spiro-gamma-lactams ?
1990

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Phenanthridines ?
1989

Benzimidazolinones

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activate?

cystic fibrosis transmembrane conductance regulator ?

(CFTR)

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1987

Hippadine

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antitumour, antiviral and anticholinergic activities

(Amaryllidacea family - crinum spp)

1982

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Cardenolides Sulphates

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Cardiotonic steroids

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1981 (+/-)- Alpinigenine (Papaver Rhoeas)
1977 (+/-)-cis - Alpinigenine

(Papaver Rhoeas)

1975

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Cardenolides?

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Cardiotonic steroids?

allosteric inhibitors of Na+,K+-ATPase

(slide: Dr. Kelly Moule)

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ISOLATED COMPOUNDS

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TOP

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1996

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Ceramides?

(Phellinus pini)

1994

Tetra- and Pentacyclic Triterpenoids

(Euphorbia piscatoria Ait.)

1993

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Triterpenoids

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(Euphorbia mellifera)

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Triterpenoids and Steroids?

(Euphorbia peplus)

1991

Madeiranes? ?
1990

Euferol

and Melliferol?

(Euphorbia mellifera)

1989

Diterpenoids

(Salvia Candelabrum)

1988

Triterpenoids (Pisolithus tinctorius)
1985

Triterpenoids (Pisolithus tinctorius)
1983

Pisolactone

(Pisolithus tinctorius)

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PATENTS

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TOP

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2002

Fases Estacionarias Quirais Baseadas em Terpenoides

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PT 102878, 28-11-02

1992

Diisocyanates, Diurethanes and Diureides from Abietic Acid

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EP 92670001.4, 11-2-92

1991

Processos para a Obtencao de Novos Derivados de Acidos Resinicos: Diisocianatos, Diuretanos e Diureidos

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PT 96748, 11-2-91

1987

Processo para Obtencao de Derivados de Acido Abietico e Composicoes Antimicrobianas desses Derivados

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PT 85433, 28-7-87

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DEVELOPED SYNTHETIC METHODS

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TOP

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19200384

Chemoselective O-desilylation?

using SbCl5–wet acetonitrile

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A new efficient method for deprotection of TBDMS derivatives of phenols, primary alcohols, carboxylic acids and secondary amines, consisting of SbCl5 and MeCN with 0.1% water (w/v). It effects inter alia desilylation of a CH2OTBDMS group in the presence of a ketal function.

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19200184

Synthesis of Aziridines?

using Palladium(II) and Bromamine T

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The palladium(II)-promoted reaction of a variety of olefins and bromamine T, as the nitrogen atom transfer reagent, provide N-tosyl-2-substituted aziridines under mild conditions.

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1997

Synthesis of Benzimidazole Derivatives ?

from 1-Aza-1´,3´-Diaza-3,3´-Sigmatropic Rearrangements?

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1996

Enantioselective Synthesis of N-Arylaziridines?

by Phase-Transfer Catalysis

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1995

Synthesis of N-Aryl and N-Alkyl-O-Methyl Hydroxylamines

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Trifluoroaceto or p-nitrobenzo-N-substituted hydroxamic acids are smoothly methylated with diazomethane and the products cleanly cleaved by hydrazine.

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1994

3,3-Sigmatropic Rearrangements

using Enehydroxylamines

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1993

Synthesis of Aziridines?

using N-Hydroxy-N-pivaloylanilines

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1992

Synthesis of Aminonitrones?

from Hydroxylamines and Ethyl Cyanoformate

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1991

Synthesis 3-Substituted N-Benzoyl Oxindoles?

using N-Aryl-O-Acyl Hydroxamic Acids

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Selective O-Acylation of Aromatic Hydroxylamines?

using 2-Acyl Thiazolium Salts

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1984 Synthesis of N-Hydroxythiobenzamides-(C-Arylhydroxamic Acids)

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THEORETICAL CHEMISTRY

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TOP

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The CIP System:

eliminating ambiguity in the comparison of

diastereomorphic and enantiomorphic ligands

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1994

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Implementation of the Cahn-Ingold-Prelog System for Stereochemical Perception?

in the LHASA Program

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1993

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The CIP Sequence Rules:?

Analysis and Proposal for a Revision

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