Title:
USE OF FLAVONES, COUMARINS AND RELATED COMPOUNDS TO TREAT INFECTIONS
Document Type and Number:
WIPO Patent Application WO2001003681
Kind Code:
A3
Abstract:
The invention provides the use of flavin compounds or coumarins, as well as 2-(3',4'-dibenzyloxy)-4,5,6-trimethoxy acetophenone or 3',4'-dibenzyloxy-2-hydroxy-4,5,6-trimethoxy dibenzoylmethane or derivatives thereof, more particularly cirsiliol, 3'4'-diacetoxy-5,6,7-trimethoxyflavone, naringin, naringenin, tangeretin or gossypetin, in the treatment of viral (e.g. RSV, HIV, SIV, picornavirus, rhinovirus, 'para!myxoviridae or orthomyxoviridae, (para)influenza, retrovirus, hepatitis virus, pneumovirus, herpes (HSV), entero- or coronavirus) or parasitic (e.g., malaria, toxoplasmosis, trypanosoma) infections.
Inventors:
PRENDERGAST PATRICK T (IE)
Application Number:
PCT/IB2000/001039
Publication Date:
May 10, 2002
Filing Date:
July 07, 2000
Export Citation:
Assignee:
PRENDERGAST PATRICK T (IE)
International Classes:
C07H15/26; A61K31/12; A61K31/235; A61K31/352; A61K31/353; A61K31/37; A61K31/7048; A61P31/12; A61P31/14; A61P31/16; A61P31/18; A61P31/20; A61P31/22; A61P33/00; A61P33/02; A61P33/06; C07D311/14; C07D311/18; C07D311/30; C07D311/32; C07D311/36; C07D311/92; C07H17/07; (IPC1-7): A61K31/37; A61K31/35; A61K31/352; A61K31/353; A61P31/12; A61P31/14; A61P31/16; A61P31/18; A61P31/20; A61P31/22; A61P33/02; A61P33/06
Domestic Patent References:
| WO1997047270A2 | 1997-12-18 | |||
| WO1998046238A1 | 1998-10-22 | |||
| WO1992014458A1 | 1992-09-03 | |||
| WO1998042188A1 | 1998-10-01 | |||
| WO1999044578A1 | 1999-09-10 | |||
| WO2000032201A2 | 2000-06-08 | |||
| WO1999049862A1 | 1999-10-07 | |||
| WO2000032177A2 | 2000-06-08 |
Foreign References:
| EP0348509A1 | 1990-01-03 | |||
| EP0019081A1 | 1980-11-26 | |||
| EP0373986A1 | 1990-06-20 | |||
| EP0861662A1 | 1998-09-02 |
Other References:
DATABASE WPI Week 199750, Derwent World Patents Index; AN 1997-539680, XP002183224
DATABASE CAPLUS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002183216
DATABASE CAPLUS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002183217
DATABASE WPI Week 198333, Derwent World Patents Index; AN 1983-739004, XP002183225
PATENT ABSTRACTS OF JAPAN vol. 0, no. 0
DATABASE WPI Week 199108, Derwent World Patents Index; AN 1991-055557, XP002183226
PATENT ABSTRACTS OF JAPAN vol. 0, no. 0
PATENT ABSTRACTS OF JAPAN vol. 0, no. 0
DATABASE CAPLUS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002183218
DATABASE VETU [online] GLINSKI Z ET AL: "The Antimicrobial Activity of Propolis. (Przeciwdrobnoustrojowe Dzialanie Propolisu.))", XP002183219, retrieved from STN Database accession no. 1987-62306
DATABASE BIOSIS [online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; LEE, JI-HYUN (1) ET AL: "Antiherpetic activities of natural naringenin alone and in combinations with acyclovir and vidarabine.", XP002183220, retrieved from STN Database accession no. PREV199900309481
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; LEE, JI-HYUN ET AL: "Antiviral activity of some flavonoids on herpes simplex viruses", XP002183221, retrieved from STN Database accession no. 131:165028
BRINKWORTH R I ET AL: "Flavones are Inhibitors of HIV-1 Proteinase.", BIOCHEM.BIOPHYS.RES.COMMUN. (188, NO. 2, 631-37, 1992) 1 FIG. 2 TAB. 21 REF. CODEN: BBRCA9 ISSN: 0006-291X, XP001031188
CRITCHFIELD J W ET AL: "INHIBITION OF HIV ACTIVATION IN LATENTLY INFECTED CELLS BY FLAONOID COMPOUNDS", AIDS RESEARCH HUMAN RETROVIRUSES (1996) 12 (1) P. 39-46., RETROVIRUS DIS BRANCH, DIV VIRAL RICKETTSIAL, NATL CENT INFECT DIS, ATLANTA GA 30333 USA, XP001031189
PATHAK D ET AL: "Flavonoids as Medicinal Agents - Recent Advances.", FITOTERAPIA (62, NO. 5, 371-89, 1991) 166 REF. CODEN: FTRPAE ISSN: 0367-326X, XP001039766
LIU K C S C ET AL: "Antimalarial Activity of Artemisia Annua Flavonoids from Whole Plants and Cell Cultures.", PLANT CELL REP. (11, NO. 12, 637-40, 1992) 3 TAB. 2 FIG. 16 REF. CODEN: PCRPD8 ISSN: 0721-7714, XP001039836
HU, CHANG QI ET AL: "Anti-aids agents, 10. Acacetin-7-O-.beta.-D-galactopyranoside, an anti-HIV principle from Chrysanthemum morifolium and a structure-activity correlation with some related flavonoids", J. NAT. PROD. (1994), 57(1), 42-51, XP001039690
KHALID S A ET AL: "POTENTIAL ANTIMALARIAL CANDIDATES FROM AFRICAN PLANTS: AN IN VITRO APPROACH USING PLASMODIUM FALCIPARUM", J ETHNOPHARMACOL (1986) 15 (2) P. 201-209., DEPT PHARMACOG, FAC PHARM, UNIV KHARTOUM, KHARTOUM SUDAN, XP001039769
KAIJ A KAMB M ET AL: "Search for New Antiviral Agents of Plant Origin.", PHARM.ACTA HELV. (67, NO. 5-6, 130-47, 1992) 2 TAB. 86 REF. CODEN: PAHEAA ISSN: 0031-6865, XP001039765
WLEKLIK, M. ET AL: "Structural basis for antiviral activity of flavonoids - naturally occurring compounds", ACTA VIROL. (ENGL. ED.) (1988), 32(6), 522-5, XP001039754
TSUCHIYA, YOSHINORI ET AL: "Antiviral activity of natural occurring flavonoids in vitro", CHEM. PHARM. BULL. (1985), 33(9), 3881-6, XP002101665
KUSUMOTO I T ET AL: "A COMPARATIVE STUDY ON THE INHIBITORY EFFECTS OF FLAVONOIDS AND ALKALOIDS ON REVERSE TRANSCRIPTASES OF DIFFERENT RETROVIRUSES", SHOYAKUGAKU ZASSHI (1993) 47 (3) P. 291-294., RES INST ORIENTAL MED, TOYAMA MED & PHARM UNIV, TOYAMA 930-01 JAPAN, XP001039764
KUSUMOTO, INES TOMOCO ET AL: "Effects of flavonoids and alkaloids on reverse transcriptase", SHOYAKUGAKU ZASSHI (1991), 45(3), 240-54, XP000579880
WACKER A ET AL: "Antiviral activity of plant components. Part 1. Flavonoids.", ARZNEIM.-FORSCH, (1978).VOL. 28, NO. 3, PP. 347-50. CODEN: ARZNAD., Zentr. Biol. Chem., Univ. Frankfurt, Frankfurt/Main, Ger., XP002101663
LIN, YUH-MEEI ET AL: "In Vitro Anti-HIV Activity of Biflavanoids Isolated from Rhus succedanea and Garcinia multiflora", J. NAT. PROD. (1997), 60(9), 884-888, XP001039752
GRAEL C F F ET AL: "Trypanocidal activity of crude extracts and compounds from Lychnophora granmongolense (Duarte) semir and leitao filho (vernonieae, asteraceae).", BOLL.CHIM.FARM. (138, NO. 2, LVII, FEB. 1999) 5 REF. CODEN: BCFAAI ISSN: 0006-6648, Univ.Sao-Paulo, XP001039822
SCHINOR E C ET AL: "Biological activity of the crude extracts and some isolated substances from Moquinia kiingi (DC) H. Robinson.", BOLL.CHIM.FARM. (138, NO. 2, LXXIII, FEB. 1999) CODEN: BCFAAI ISSN: 0006-6648, Univ.Sao-Paulo, XP001039842
LOPES N P ET AL: "Flavonoids and lignans from Virola surinasmensis twigs and their in vitro activity against Trypanosoma cruzi.", PLANTA MED. (64, NO. 7, 667-69, 1998) 1 FIG. 1 TAB. 16 REF. CODEN: PLMEAA ISSN: 0032-0943, Univ.Sao-Paulo;Univ.Paulista-State, XP001039767
MAHMOOD N ET AL: "Inhibition of HIV Infection by Flavanoids.", ANTIVIRAL RES. (22, NO. 2-3, 189-99, 1993) 1 FIG. 6 TAB. 23 REF. CODEN: ARSRDR ISSN: 0166-3542, Univ.Naples, XP001039821
KAUL T N ET AL: "INTERACTION OF FLAVONOIDS AND VIRUSES IN-VITRO POTENTIAL ROLE IN ANTI VIRAL THERAPY.", 38TH ANNUAL MEETING OF THE AMERICAN ACADEMY OF ALLERGY, MONTREAL, QUEBEC, CANADA, MARCH 6-10, 1982. J ALLERGY CLIN IMMUNOL. (1982) 69 (1 PART 2), 104., XP001039866
BURNHAM, WELDON S. ET AL: "Synthesis and antiviral activity of 4'-hydroxy-5,6,7,8- tetramethoxyflavone", J. MED. CHEM. (1972), 15(10), 1075-6, XP001031173
RAZ B ET AL: "Phytochemical investigation of the African medicinal plant Ehretia amoena for the identification of trypanocidal molecules.", TROP.MED.INT.HEALTH (1, NO. 6, A30-A31, 1996) CODEN: TMIHFL ISSN: 1360-2276, Swiss-Trop.Inst.;Univ.Lausanne, XP001039869
ZANI C.L. ET AL: "Trypanocidal components of Pluchea quitoc L..", PHYTOTHERAPY RESEARCH, (1994) 8/6 (375-377)., XP001039757
GONZALEZ J ET AL: "IN VITRO ACTIVITY OF NATURAL PRODUCTS AGAINST THE TRYPOMASTIGOTE FORMOF TRYPANOSOMA CRUZI", PHYTOTHER RES (1990) 4 (1) P. 1-4., DEPT PRECLIN SCI, UNIV ANTOFAGASTA, ANTOFAGASTA CHILE, XP001039755
DATABASE DRUGU [online] CASTRILLO J L ET AL: "3-Methylquercetin Is a Potent and Selective Inhibitor of Poliovirus RNA Synthesis.", XP002183222, retrieved from STN Database accession no. 1986-48913
HORIE, TOKUNARU ET AL: "Syntheses of 3',4'-dihydroxy-5,6,7- and 5,7,8-trioxygenated 3',4'-dihydroxy flavones having alkoxy groups and their inhibitory activities against arachidonate 5-lipoxygenase", J. MED. CHEM. (1986), 29(11), 2256-62, XP001031172
LIEN, ERIC J. ET AL: "Epstein-Barr virus DNA polymerase inhibitors from Chinese herbs: use of preliminary screening, physicochemical properties and taxonomy for new lead compounds generation", CHIN. PHARM. J. (TAIPEI) (1998), 50(4), 233-247, XP001039794
RIBEIRO A ET AL: "Trypanocidal flavonoids from Trixis vauthieri.", JOURNAL OF NATURAL PRODUCTS, (1997 AUG) 60 (8) 836-41., XP001039751
KAUL T N ET AL: "ANTIVIRAL EFFECT OF FLAVONOIDS ON HUMAN VIRUSES", JOURNAL OF MEDICAL VIROLOGY, NEW YORK, NY, US, vol. 15, no. 1, January 1985 (1985-01-01), pages 71 - 80, XP000990920
FORMICA J V ET AL: "REVIEW OF THE BIOLOGY OF QUERCETIN AND RELATED BIOFLAVONOIDS", FOOD AND CHEMICAL TOXICOLOGY, XX, XX, vol. 33, no. 12, 1995, pages 1061 - 1080, XP000886722, ISSN: 0278-6915
FESEN M R ET AL: "INHIBITION OF HIV-1 INTEGRASE BY FLAVONES, CAFFEIC ACID PHENETHYL ESTER (CAPE) AND RELATED COMPOUNDS", BIOCHEMICAL PHARMACOLOGY, PERGAMON, OXFORD, GB, vol. 48, no. 3, 1994, pages 595 - 608, XP000911085, ISSN: 0006-2952
ALVES, C. N. ET AL: "A quantum chemical and statistical study of flavonoid compounds with anti-HIV activity", THEOCHEM (1999), 491, 123-131, XP001039687
VLIETINCK A J ET AL: "PLANT-DERIVED LEADING COMPOUNDS FOR CHEMOTHERAPY OF HUMAN IMMUNODEFICIENCY VIRUS (HIV) INFECTION", PLANTA MEDICA, THIEME, STUTTGART, DE, vol. 64, no. 2, March 1998 (1998-03-01), pages 97 - 109, XP001028147, ISSN: 0032-0943
DATABASE CAPLUS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002183223
EGAN D ET AL: "The Pharmacology, Metabolism, Analysis and Applications of Coumarin and Coumarin-Related Compounds.", DRUG METAB.REV. (22, NO. 5, 503-29, 1990) 4 FIG. 2 TAB. 89 REF. CODEN: DMTRAR ISSN: 0360-2532, XP001039763
DATABASE CAPLUS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002183216
DATABASE CAPLUS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002183217
DATABASE WPI Week 198333, Derwent World Patents Index; AN 1983-739004, XP002183225
PATENT ABSTRACTS OF JAPAN vol. 0, no. 0
DATABASE WPI Week 199108, Derwent World Patents Index; AN 1991-055557, XP002183226
PATENT ABSTRACTS OF JAPAN vol. 0, no. 0
PATENT ABSTRACTS OF JAPAN vol. 0, no. 0
DATABASE CAPLUS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002183218
DATABASE VETU [online] GLINSKI Z ET AL: "The Antimicrobial Activity of Propolis. (Przeciwdrobnoustrojowe Dzialanie Propolisu.))", XP002183219, retrieved from STN Database accession no. 1987-62306
DATABASE BIOSIS [online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; LEE, JI-HYUN (1) ET AL: "Antiherpetic activities of natural naringenin alone and in combinations with acyclovir and vidarabine.", XP002183220, retrieved from STN Database accession no. PREV199900309481
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; LEE, JI-HYUN ET AL: "Antiviral activity of some flavonoids on herpes simplex viruses", XP002183221, retrieved from STN Database accession no. 131:165028
BRINKWORTH R I ET AL: "Flavones are Inhibitors of HIV-1 Proteinase.", BIOCHEM.BIOPHYS.RES.COMMUN. (188, NO. 2, 631-37, 1992) 1 FIG. 2 TAB. 21 REF. CODEN: BBRCA9 ISSN: 0006-291X, XP001031188
CRITCHFIELD J W ET AL: "INHIBITION OF HIV ACTIVATION IN LATENTLY INFECTED CELLS BY FLAONOID COMPOUNDS", AIDS RESEARCH HUMAN RETROVIRUSES (1996) 12 (1) P. 39-46., RETROVIRUS DIS BRANCH, DIV VIRAL RICKETTSIAL, NATL CENT INFECT DIS, ATLANTA GA 30333 USA, XP001031189
PATHAK D ET AL: "Flavonoids as Medicinal Agents - Recent Advances.", FITOTERAPIA (62, NO. 5, 371-89, 1991) 166 REF. CODEN: FTRPAE ISSN: 0367-326X, XP001039766
LIU K C S C ET AL: "Antimalarial Activity of Artemisia Annua Flavonoids from Whole Plants and Cell Cultures.", PLANT CELL REP. (11, NO. 12, 637-40, 1992) 3 TAB. 2 FIG. 16 REF. CODEN: PCRPD8 ISSN: 0721-7714, XP001039836
HU, CHANG QI ET AL: "Anti-aids agents, 10. Acacetin-7-O-.beta.-D-galactopyranoside, an anti-HIV principle from Chrysanthemum morifolium and a structure-activity correlation with some related flavonoids", J. NAT. PROD. (1994), 57(1), 42-51, XP001039690
KHALID S A ET AL: "POTENTIAL ANTIMALARIAL CANDIDATES FROM AFRICAN PLANTS: AN IN VITRO APPROACH USING PLASMODIUM FALCIPARUM", J ETHNOPHARMACOL (1986) 15 (2) P. 201-209., DEPT PHARMACOG, FAC PHARM, UNIV KHARTOUM, KHARTOUM SUDAN, XP001039769
KAIJ A KAMB M ET AL: "Search for New Antiviral Agents of Plant Origin.", PHARM.ACTA HELV. (67, NO. 5-6, 130-47, 1992) 2 TAB. 86 REF. CODEN: PAHEAA ISSN: 0031-6865, XP001039765
WLEKLIK, M. ET AL: "Structural basis for antiviral activity of flavonoids - naturally occurring compounds", ACTA VIROL. (ENGL. ED.) (1988), 32(6), 522-5, XP001039754
TSUCHIYA, YOSHINORI ET AL: "Antiviral activity of natural occurring flavonoids in vitro", CHEM. PHARM. BULL. (1985), 33(9), 3881-6, XP002101665
KUSUMOTO I T ET AL: "A COMPARATIVE STUDY ON THE INHIBITORY EFFECTS OF FLAVONOIDS AND ALKALOIDS ON REVERSE TRANSCRIPTASES OF DIFFERENT RETROVIRUSES", SHOYAKUGAKU ZASSHI (1993) 47 (3) P. 291-294., RES INST ORIENTAL MED, TOYAMA MED & PHARM UNIV, TOYAMA 930-01 JAPAN, XP001039764
KUSUMOTO, INES TOMOCO ET AL: "Effects of flavonoids and alkaloids on reverse transcriptase", SHOYAKUGAKU ZASSHI (1991), 45(3), 240-54, XP000579880
WACKER A ET AL: "Antiviral activity of plant components. Part 1. Flavonoids.", ARZNEIM.-FORSCH, (1978).VOL. 28, NO. 3, PP. 347-50. CODEN: ARZNAD., Zentr. Biol. Chem., Univ. Frankfurt, Frankfurt/Main, Ger., XP002101663
LIN, YUH-MEEI ET AL: "In Vitro Anti-HIV Activity of Biflavanoids Isolated from Rhus succedanea and Garcinia multiflora", J. NAT. PROD. (1997), 60(9), 884-888, XP001039752
GRAEL C F F ET AL: "Trypanocidal activity of crude extracts and compounds from Lychnophora granmongolense (Duarte) semir and leitao filho (vernonieae, asteraceae).", BOLL.CHIM.FARM. (138, NO. 2, LVII, FEB. 1999) 5 REF. CODEN: BCFAAI ISSN: 0006-6648, Univ.Sao-Paulo, XP001039822
SCHINOR E C ET AL: "Biological activity of the crude extracts and some isolated substances from Moquinia kiingi (DC) H. Robinson.", BOLL.CHIM.FARM. (138, NO. 2, LXXIII, FEB. 1999) CODEN: BCFAAI ISSN: 0006-6648, Univ.Sao-Paulo, XP001039842
LOPES N P ET AL: "Flavonoids and lignans from Virola surinasmensis twigs and their in vitro activity against Trypanosoma cruzi.", PLANTA MED. (64, NO. 7, 667-69, 1998) 1 FIG. 1 TAB. 16 REF. CODEN: PLMEAA ISSN: 0032-0943, Univ.Sao-Paulo;Univ.Paulista-State, XP001039767
MAHMOOD N ET AL: "Inhibition of HIV Infection by Flavanoids.", ANTIVIRAL RES. (22, NO. 2-3, 189-99, 1993) 1 FIG. 6 TAB. 23 REF. CODEN: ARSRDR ISSN: 0166-3542, Univ.Naples, XP001039821
KAUL T N ET AL: "INTERACTION OF FLAVONOIDS AND VIRUSES IN-VITRO POTENTIAL ROLE IN ANTI VIRAL THERAPY.", 38TH ANNUAL MEETING OF THE AMERICAN ACADEMY OF ALLERGY, MONTREAL, QUEBEC, CANADA, MARCH 6-10, 1982. J ALLERGY CLIN IMMUNOL. (1982) 69 (1 PART 2), 104., XP001039866
BURNHAM, WELDON S. ET AL: "Synthesis and antiviral activity of 4'-hydroxy-5,6,7,8- tetramethoxyflavone", J. MED. CHEM. (1972), 15(10), 1075-6, XP001031173
RAZ B ET AL: "Phytochemical investigation of the African medicinal plant Ehretia amoena for the identification of trypanocidal molecules.", TROP.MED.INT.HEALTH (1, NO. 6, A30-A31, 1996) CODEN: TMIHFL ISSN: 1360-2276, Swiss-Trop.Inst.;Univ.Lausanne, XP001039869
ZANI C.L. ET AL: "Trypanocidal components of Pluchea quitoc L..", PHYTOTHERAPY RESEARCH, (1994) 8/6 (375-377)., XP001039757
GONZALEZ J ET AL: "IN VITRO ACTIVITY OF NATURAL PRODUCTS AGAINST THE TRYPOMASTIGOTE FORMOF TRYPANOSOMA CRUZI", PHYTOTHER RES (1990) 4 (1) P. 1-4., DEPT PRECLIN SCI, UNIV ANTOFAGASTA, ANTOFAGASTA CHILE, XP001039755
DATABASE DRUGU [online] CASTRILLO J L ET AL: "3-Methylquercetin Is a Potent and Selective Inhibitor of Poliovirus RNA Synthesis.", XP002183222, retrieved from STN Database accession no. 1986-48913
HORIE, TOKUNARU ET AL: "Syntheses of 3',4'-dihydroxy-5,6,7- and 5,7,8-trioxygenated 3',4'-dihydroxy flavones having alkoxy groups and their inhibitory activities against arachidonate 5-lipoxygenase", J. MED. CHEM. (1986), 29(11), 2256-62, XP001031172
LIEN, ERIC J. ET AL: "Epstein-Barr virus DNA polymerase inhibitors from Chinese herbs: use of preliminary screening, physicochemical properties and taxonomy for new lead compounds generation", CHIN. PHARM. J. (TAIPEI) (1998), 50(4), 233-247, XP001039794
RIBEIRO A ET AL: "Trypanocidal flavonoids from Trixis vauthieri.", JOURNAL OF NATURAL PRODUCTS, (1997 AUG) 60 (8) 836-41., XP001039751
KAUL T N ET AL: "ANTIVIRAL EFFECT OF FLAVONOIDS ON HUMAN VIRUSES", JOURNAL OF MEDICAL VIROLOGY, NEW YORK, NY, US, vol. 15, no. 1, January 1985 (1985-01-01), pages 71 - 80, XP000990920
FORMICA J V ET AL: "REVIEW OF THE BIOLOGY OF QUERCETIN AND RELATED BIOFLAVONOIDS", FOOD AND CHEMICAL TOXICOLOGY, XX, XX, vol. 33, no. 12, 1995, pages 1061 - 1080, XP000886722, ISSN: 0278-6915
FESEN M R ET AL: "INHIBITION OF HIV-1 INTEGRASE BY FLAVONES, CAFFEIC ACID PHENETHYL ESTER (CAPE) AND RELATED COMPOUNDS", BIOCHEMICAL PHARMACOLOGY, PERGAMON, OXFORD, GB, vol. 48, no. 3, 1994, pages 595 - 608, XP000911085, ISSN: 0006-2952
ALVES, C. N. ET AL: "A quantum chemical and statistical study of flavonoid compounds with anti-HIV activity", THEOCHEM (1999), 491, 123-131, XP001039687
VLIETINCK A J ET AL: "PLANT-DERIVED LEADING COMPOUNDS FOR CHEMOTHERAPY OF HUMAN IMMUNODEFICIENCY VIRUS (HIV) INFECTION", PLANTA MEDICA, THIEME, STUTTGART, DE, vol. 64, no. 2, March 1998 (1998-03-01), pages 97 - 109, XP001028147, ISSN: 0032-0943
DATABASE CAPLUS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002183223
EGAN D ET AL: "The Pharmacology, Metabolism, Analysis and Applications of Coumarin and Coumarin-Related Compounds.", DRUG METAB.REV. (22, NO. 5, 503-29, 1990) 4 FIG. 2 TAB. 89 REF. CODEN: DMTRAR ISSN: 0360-2532, XP001039763
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