<i>In Vitro</i> Antimicrobial Activity of Some Novel 3-(Substituted Phenyl) Isocoumarins, 1(2<i>H</i>)-Isoquinolones and Isocoumarin-1-Thiones
- 1 Department of Chemistry, Allama Iqbal Open University, Islamabad, Pakistan
- 2 Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan
Abstract
The work reports antibacterial and antifungal activity of some 3-(substituted phenyl) isocouma rins (1 H -2-benzopyran-1-ones), isocarbostyrils 1( 2 H )-isoquinolones, the nitrogen analogues of isocoumarins and isocoumarin-1-thiones, the thio derivatives of isocoumarins. The antimicrobial activity was determined against ten different Gram positive and Gram negative bacterial strains and three fungal strains. The bacterial strains were Klebsiella pneumonae (ATCC 6633), Staphylo coccus aureus (ATCC 29213), Micrococcus luteus (ATCC 9341), Pseudomonas aeruginosa (ATCC 33347), Escherichia coli (ATCC 25922), Salmonella typhi (ATCC 19430), Lactobacillus bulgaricus, (ATCC 25929), Pasteurella multocida A (ATCC 9150), Staphylococcus epidermidis (ATCC 29232) and Proteus vulgaris (ATCC 49565) and fungal strains were Aspergillus flavus, Aspergillus nigar and Aspergillus pterus . Agar well diffusion method was followed for antibacterial activity and poi son plate method was adopted for antifungal assay. Chloramphenicol and fluconazole used as standard drugs for antibacterial and antifungal activity respectively. In general, these compounds exhibited high antibacterial potential than antifungal. Comparative study reveals that the 1-thio derivatives are more active than parent isocoumarins but 1( 2H )-isoquinolones, are less active. Most of these compounds showed poor activity but some of these compounds exhibited moderate to good activity against Staphylococcus epidermidis , Klebsiella pneumonae , Escherichia coli and Proteus vulgaris , compared with the standard drug.
- Napolitano, E. (1997) The Synthesis of Isocoumarins over the Last Decade. Organic Preparations and Procedures International, 29, 631-634. http://dx.doi.org/10.1080/00304949709355245
- Sankawa, U. (1999) Comprehensive Natural Products Chemistry. Elsevier Science Publishers Ltd., Amsterdam.
- Hisashi, M., Hiroshi, S. and Masayuki, Y. (1999) Structure-Requirement of Isocoumarins, Phthalides and Stilbenes from Hydrangeae Dulcis Folium for Inhibitory Activity on Histamine Release from Rat Peritoneal Mast Cells. Bioorganic & Medicinal Chemistry, 7, 1445-1450. http://dx.doi.org/10.1016/S0968-0896(99)00058-9
- Masayuki, Y., Emiko, H., Yoshikazu, N., Kimiyo, I., Hisashi, M., Hiroshi, S., Johji, Y. and Nobutoshi, M. (1994) Development of Bioactive Functions in Hydrangeae Dulcis Folium. III. On the Antiallergic and Antimicrobial Principles of Hydrangeae Dulcis Folium (1). Thunberginol A, B, and F. Chemical and Pharmaceutical Bulletin, 42, 2225-2230. http://dx.doi.org/10.1248/cpb.42.2225
- (a) Hisashi, M., Hiroshi, S., Johji, Y. and Masayuki, Y. (1998) Immunomodulatory Activity of Thunberginol A and Related Compounds Isolated from Hydrangeae Dulcis Folium on Splenocyte Proliferation Activated by Mitogens. Bioorganic & Medicinal Chemistry Letters, 8, 215-220. http://dx.doi.org/10.1016/S0960-894X(97)10221-9
- Authrine, C.W., James, B.G., James, A.S. and David, M. (1996) Cercophorins A-C: Novel Anti Fungal and Cytotoxic Metabolites from the Coprophilous Fungus Cercophora Areolata. Journal of Natural Products, 59, 765-769. http://dx.doi.org/10.1021/np9603232
- Koohei, N., Mikikio, Y., Yoshiko, T., Kenichi, K. and Shoichi, N. (1981) Antifungal Activity of Oosponol, Oospolactone, Phyl-loducin, Hydrangenol, and Some Other Related Compounds. Chemical and Pharmaceutical Bulletin, 29, 2689-2691. http://dx.doi.org/10.1248/cpb.29.2689
- Takuya, F., Yoshiyasu, F. and Yoshinori, A. (1986) Polygonolide, an Isocumarin from Polygonum Hydropiper Possessing Anti-Inflammatory Activity. Phytochemistry, 25, 517-520. http://dx.doi.org/10.1016/S0031-9422(00)85513-2
- Jeong, H.L., Yun, J.P., Hang, S.K., Young, S.H., Kyu-Won, K. and Jung, J.L. (2001) Anti-Angiogenic Activities of Novel Isocoumarins, AGI-7 and Sescandelin. The Journal of Antibiotics, 54, 463-466. http://dx.doi.org/10.7164/antibiotics.54.463
- Ozoe, Y., Kuriyama, T., Tachibana, Y., Harimaya, K., Takahashi, N., Yaguchi, T., Suzuki, E., Imamura, K. and Oyama, K. (2004) Isocumarin Derivatives as a Novel GABA Receptor Ligand from Neosartorya Quadricincta. Journal of Pest Science, 29, 328-331. http://dx.doi.org/10.1584/jpestics.29.328