In Vitro Antimicrobial Activity of Some Novel 3-(Substituted Phenyl) Isocoumarins, 1(2H)-Isoquinolones and Isocoumarin-1-Thiones

Zaman  Ashraf; Aamer  Saeed

doi:10.4236/ijoc.2014.41010

Zaman Ashraf^*, Aamer Saeed

Abstract: The work reports antibacterial and antifungal activity of some 3-(substituted phenyl) isocoumarins (1H-2-benzopyran-1-ones), isocarbostyrils 1(2H)-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), Staphylococcus 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 poison 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.

Keywords: Antimicrobial Activity; Isocoumarins; Isocarbostyrils; 1-Thioisocoumarins

Cite this paper: Ashraf, Z. and Saeed, A. (2014) In Vitro Antimicrobial Activity of Some Novel 3-(Substituted Phenyl) Isocoumarins, 1(2H)-Isoquinolones and Isocoumarin-1-Thiones. International Journal of Organic Chemistry, 4, 82-89. doi: 10.4236/ijoc.2014.41010.

References

[1] 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

[2] Sankawa, U. (1999) Comprehensive Natural Products Chemistry. Elsevier Science Publishers Ltd., Amsterdam.

[3] 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

[4] 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

[5] (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

[6] 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

[7] 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

[8] 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

[9] 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

[10] 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

[11] Hudson, J.B., Graham, E.A., Harris, L. and Ashwood-Smith, M.J. (1993) The Unusual UVA-Dependent Antiviral Properties of the Furoisocoumarin, Coriandrin. Phytochemistry and Photobiology, 57, 491-496.

[12] Corinne, L.R., Naoki, A., Jennifer, G.T., Michael, B., William, M.D., George, D.K., Susan, L.R., Michael, M., Robert, F., Raghu, K., Donald, K. and Surender, K. (2002) Antineoplastic Effects of Chemotherapeutic Agents Are Potentiated by NM-3, an Inhibitor of Angiogenesis. Cancer Research, 62, 789-795.

[13] Chen, C.Y., Chang, F.R. and Teng, C.M. (1999) Cheritamina, a New N-Fatty Acyl Tryptamine and Other Constituents from the Stem of Annona Cherimola. Journal of the Chinese Chemical Society, 46, 77-86.

[14] Pettit, G.R., Meng, Y.H., Herald, D.L., Graham, K.A.N., Pettit, R.K. and Doubek, D.L. (2003) Isolation and Structure of Ruprechstyril from Ruprechtia tangarana. Journal of Natural Products, 66, 1065-1069.
http://dx.doi.org/10.1021/np0300986

[15] David, G., Theodore, M. and Tomas, H. (1999) A Short Chemoenzymatic Synthesis of (+)-Narciclasine. Tetrahedron Letters, 40, 3077-3283.

[16] Richard, C.T. and James, K. (1990) An Annulative, Carbohydrate-Based Approach to Pancratistatin and Structurally-Related Phenanthridone Alkaloids. Synthesis of (+)-Tetrabenzyllycoricidine. The Journal of Organic Chemistry, 55, 6076-6078.
http://dx.doi.org/10.1021/jo00312a007

[17] Ekpendu, T.O., Akshomeju, A.A. and Okogun, J.I. (1994) Anti-inflamatory, Antimicrobial Activity. Letters in Applied Microbiology, 30, 379-384.

[18] Cohen, M.L. (1992) Epidemiology of Drug Resistance, Implications for a Post-Antimicrobial Era. Science, 257, 1050-1057.
http://dx.doi.org/10.1126/science.257.5073.1050

[19] Aamer, S. and Zaman, A. (2008) Synthesis of Some 3-Aryl-1H-Isochromene-1-Thiones. Journal of Heterocyclic Chemistry, 45, 679-682.
http://dx.doi.org/10.1002/jhet.5570450307

[20] Aamer, S. and Zaman, A. (2008) An Efficient Synthesis of Some 3-Aryl-Isoquinolin-1(2H)-Ones; Chemistry of Heterocyclic Compounds, 8, 1203-1208.

[21] Zaman, A., Aun, M., Muhammad, I. and Ahmed, H. (2011) In Vitro Antibacterial and Antifungal Activity of Methanol, Chloroform and Aqueous Extracts of Origanum vulgare and Their Comparative Analysis. International Journal of Organic Chemistry, 1, 257-261.
http://dx.doi.org/10.4236/ijoc.2011.14037

[22] Shastri, R.V. and Varudkar, J.S. (2009) Synthesis and Antimicrobial Activity of 3-Propen-1,2-Benzisoxazole Derivatives. Indian Journal of Chemistry, 48B, 1156-1160.