Synthesis and anti-picornavirus activity of homo-isoflavonoids

Antiviral Chemistry and Chemotherapy

Volumn 8, Issue 6, 1997, Pages 545-555

  Desideri, N ^a   Olivieri, S ^a   Stein, M L ^a   Sgro, R ^a   Orsi, N ^a   Conti, C ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Anti poliovirus activity; Anti rhinovirus activity; Homo isoflavonoids

Indexed keywords

ANTIVIRUS AGENT; ISOFLAVONOID;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG SYNTHESIS; ENTEROVIRUS; HELA CELL; HUMAN; HUMAN CELL; HUMAN RHINOVIRUS; PICORNAVIRUS; PICORNAVIRUS INFECTION; POLIOMYELITIS VIRUS; PRIORITY JOURNAL; RHINOVIRUS; SEROTYPE; VIRUS INHIBITION;

EID: 0030734938     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: 10.1177/095632029700800609     Document Type: Article

References (44)

1. Al Nakib T, Bezjak V, Meegan MJ & Chandy R (1990) Synthesis and antifungal activity of some 3-benzylidenechroman-4-ones, 3-benzylidenethiochroman-4-ones and 2-benzylidene-1-tetralones. European Journal of Medicinal Chemistry 25: 455-462.
2. Amschler G, Frahm AW, Hatzelmann A, Kilian U, Müller-Doblies D & Müller-Doblies U (1996) Constituents of Veltheimia viridifolia; I. Homoisoflavanones of the bulbs. Planta Medica 62: 534-539.
3. Andrieux J, Barton DHR & Patin H (1977) Rhodium-catalyzed isomerization of some unsaturated organic substrates. Journal of the Chemical Society Perkin Transactions I: 359-363.
4. Batchelor JF, Bauer DJ, Hodson HF, Selway JWT & Young DAB (1979) Flavans and pharmaceutical compositions containing them. European Patent Application No. 4579. Chemical Abstracts (1980) 92: 128727j.
5. Bauer DJ, Selway JWT, Batchelor JF, Tisdale M, Caldwell JC & Young DAB (1981) 4′,6-Dichloroflavan (BW683C), a new antirhinovirus compound. Nature 292: 369-370.
6. Blaskò G & Cordell G (1988) Biomimetic total synthesis of dracaenone derivatives. Heterocycles 27: 445-452.
7. Bohler P & Tamm C (1967) The homoisoflavanones, a new class of natural products. Isolation and structure of eucomin and eucomolo. Tetrahedron Letters 36: 3479-3483.
8. Burali C, Desideri N, Stein ML, Conti C & Orsi N (1987) Synthesis and anti-rhinovirus activity of halogen substituted isoflavenes and isoflavans. European Journal of Medicinal Chemistry 22: 119-123.
9. Canalini G, Degani I, Fochi R & Spunta G (1967) Cationi eteroaromatici. - Nota X. Idrolisi di alcuni derivati del perclorato di cromilio. Annali di Chimica 57: 1045-1072.
10. Chatterjea JN, Shaw SC & Singh JN (1974) Synthesis of anhydrobrazilic acid. Isomerization of arylidenechroman-4-ones to homoisoflavones. Journal of the Indian Chemical Society 51: 281-288.
11. Chatterjea JN, Shaw SC, Lal PK & Singh JN (1979) Homoisoflavones. Part IV. Further synthetical experiments. Journal of the Indian Chemical Society 56: 1006-1009.
12. Conti C, Orsi N & Stein ML (1988) Effect of isoflavans and isoflavenes on rhinovirus 1B and its replication in HeLa cells. Antiviral Research 10: 117-127.
13. Conti C, Desideri N, Orsi N, Sestili I & Stein ML (1990a) Synthesis and anti-rhinovirus activity of cyano and amidino substituted flavanoids. European Journal of Medicinal Chemistry 25: 725-730.
14. Conti C, Genovese D, Santoro R, Stein ML, Orsi N & Fiore L (199Ob) Activities and mechanisms of action of halogen-substituted flavanoids against poliovirus type 2 infection in vitro. Antimicrobial Agents and Chemotherapy 34: 460-466.
15. Conti C, Tomao P, Genovese D, Desideri N, Stein ML & Orsi N (1992) Mechanisms of action of antirhinovirus flavanoid 4′,6-dicyanoflavan. Antimicrobial Agents and Chemotherapy 36: 95-99.
16. Darmanaden R, Dhanutrirto H, Castel J, Loubatiere J & Flandre O (1984) Nouveaux dérivés de la benzopyrannone-4, a activités analgésique, anti-inflammatoire et antiagrégante plaquettaire. Il Farmaco 39: 876-887.
17. Della Loggia R, Del Negro P, Tubaro A, Barone G & Parrilli M (1989) Homoisoflavanones as anti-inflammatory principles of Muscari comosum. Planta Medica 55: 587-588.
18. De Meyer N, Haemers A, Mishra L, Pandey HK, Pieters LAC, Vanden Berghe DA & Vlietinck AJ (1991) 4′-hydroxy-3-methoxyflavones with potent antipicornavirus activity. Journal of Medicinal Chemistry 34: 736-746.
19. Desideri N, Sestili I, Stein ML, Conti C, Tomao P & Orsi N (1990) Synthesis and anti-rhinovirus IB activity of oxazolinylflavans. Antiviral Chemistry and Chemotherapy 1: 307-312.
20. Desideri N, Conti C, Sestili I, Tomao P, Stein ML & Orsi N (1992) Synthesis and evaluation of anti-rhinovirus 1B activity of oxazolinyl-isoflavans and -3(2H)-isoflavenes. Antiviral Chemistry and Chemotherapy 3: 195-202.
21. Desideri N, Conti C, Sestili I, Tomao P, Stein ML & Orsi N (1995) In vitro evaluation of the anti-picornavirus activities of new synthetic flavonoids. Antiviral Chemistry and Chemotherapy 6: 298-306.
22. Farkas L, Gottsegen A, Nogradi M & Strelisky J (1971) Synthesis of homoisoflavanones - II. Constituents of Eucomis autumnalis and Eucomis punctata. Tetrahedron 27: 5049-5054.
23. Fiala M & Kenny GE (1966) Enhancement of rhinovirus plaque formation in human heteroploid cell cultures by magnesium and calcium. Journal of Bacteriology 92: 1710-1715.
24. Fujui M, Suhara Y & Ishitsuka H (1980) Substituted acetophenones. European Patent Application No. 13960. Chemical Abstracts (1981) 94: 83777y.
25. Genovese D, Conti C, Tomao P, Desideri N, Stein ML, Catone S & Fiore L (1995) Effect of chloro, cyano, and amidino-substituted flavanoids on enterovirus infection in vitro. Antiviral Research 27: 123-136.
26. Ishitsuka H, Ohsawa C, Ohiwa T, Umeda I & Suhara Y (1982) Antipicornavirus flavone Ro 09-0179. Antimicrobial Agents and Chemotherapy 22: 611-616.
27. Kirkiacharian S & Aloulou M (1984) Homoisoflavonoids: new biomimetic type method for synthesis of 3-benzyl-4-chro-manones and 3-benzyl-3-(hydroxymethyl)-4-chromanones. Comptes Rendus de l'Academie des Sciences Serie II 299: 187-190.
28. Kirkiacharian S, Tongo HG, Bastide J, Bastide P & Grenie MM (1989) Synthèse et activites angioprotectrice, anti-allergique et antihistaminique de benzyl-3-chromones (homo-isoflavones) European Journal of Medicinal Chemistry 24: 541-546.
29. Levai A & Schag JB (1979) Synthesis of 3-benzylidenechroman-4-ones and -1-thiochroman-4-ones. Pharmazie 34: 749.
30. Levai A & Szabò Z (1992) Synthesis of exocyclic a,b-unsaturated ketones. Pharmazie 47: 56-57.
31. Levai A, Dinya Z, Schag JB & Szollosy A (1981) Synthesis of 3-benzyl-4-chromones and 3-benzyl-1-thio-4-chromones. Pharmazie 36: 465-466.
32. Lonberg-Holm K & Butterworth BE (1976) Investigation of the structure of polio-rhinovirions through the use of selective chemical reactivity. Virology 71: 207-216.
33. Loudon JD & Razdan RK (1954) Rearrangements of chromanones and dihydrocoumarins by aluminium chloride. Journal of the Chemical Society: 4299-4303.
34. Merchant JR & Upasani RB (1980) A simplified synthesis of chromanones. Current Science 49: 587-589.
35. Mulvagh D, Meegan MJ & Donnelly D (1979) Rearrangment of 3-benzylidenechroman-4-ones. Journal of Chemical Research (Synopses): 137.
36. Namikoshi M, Nakata H, Yamada H, Naga, M & Saitoh T (1987) Homoisoflavonoids and related compounds. II. Isolation and absolute configurations of 3,4-dihydroxylated homoisoflavans and brazilins from Caesalpinia sappan L. Chemical and Pharmaceutical Bulletin 35: 2761-2773.
37. Newman JFE, Rowlands DJ & Brown F (1973) A physico-chemical sub-grouping of the mammalian picornaviruses. Journal of General Virology 18: 171-180.
38. Pfeiffer P, Grimm K & Schmidt H (1949) Zur Kenntnis der Chromene und Chromane. Annalem der Chemie 564: 208-219.
39. Quagha MG, Desideri N, Bossù E, Melchiorre P & Conti C (1991) Enantiomeric separation by HPLC/DAD of substituted flavanoids. Journal of Pharmaceutical and Biomedical Analysis 9: 811-815.
40. Quaglia MG, Desideri N, Bossù E, Sestili I & Conti C (1992) 4′,6-Dichloroflavan (BW863C): enantiomeric separation by HPLC/DAD and antirhinovirus activity. Chirality 4: 65-67.
41. Quaglia MG, Desideri N, Bossu′ E, Sestili I, Tomao P, Conti C & Orsi N (1993) Chiral discrimination and antipicornavirus activity of 6-oxazolinyusoflavan. Chirality 5: 356-358.
42. Ravisé A & Kirkiacharian BS (1978) Influence de la structure de composes phénoliques sur l'inhibition du Phytophthora parasitica et d'enzymes participant aux processus parasitaires. III. Homoisoflavanones. Phythofathologtsche Zeitschrift 92: 36-50.
43. Superti F, Segant, L, Ors, N, Divizia M, Gabrieli R, Panà A & Stein ML (1989) Effect of isoflavans and isoflavenes on the infection of Frp/3 cells by hepatitis A virus. Antiviral Research 11: 247-254.
44. Wall ME, Wani MC, Manikumar HT, Taylor H & McGivney R (1989) Plant antimutagens, 6. Intricatin and intricatinol, new antimutagenic homoisoflavonoids from Hoffmanossegia Intricata. Journal of Natural Products 52: 774-778