Homoisoflavonoids are in the subclass of the larger family of flavonoids having one more alkyl carbon than flavonoids. Among them, 8-C-Methylated homoisoflavones have not been extensively studied for synthesis and biological evaluation. Author’s current objective is to synthesize 8-C-Methylated homoisoflavones by the reaction of 3-C-methylated dihydrochalcones with N,N’-dimethyl (chloromethylene) ammonium chloride generated in situ from DMF and PCl5 for one carbon extension at about room temperature. The 3-C-methylated dihydrochalcones were synthesized by the reduction of 3-C-methylated chalcones, which were prepared from 3-C-methylated acetophenones and aromatic aldehydes in the presence of base. All the synthesized novel homoisoflavones’s structures were characterized by NMR and Tandem Mass Spectrometry.
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Lin, L.G., Liu, Q.Y. and Ye, Y. (2014) Naturally Occurring Homoisoflavonoids and Their Pharmacological Activities. Planta Med., 80, 1053-1066. https://doi.org/10.1055/s-0034-1383026
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Abegaz, B.M., Mutanyatta-Comar, J. and Nindi, M. (2007) Naturally Occurring Homoisoflavonoids: Phytochemistry, Biological Activities and Synthesis. Natural Product communications, 2, 475-498. https://doi.org/10.1177/1934578X0700200418
[17]
Asano, T., Murayama, T., Hirai, Y. and Shoji, J. (1993) Comparative Studies on the Constituents of Ophiopogonis Tuber and Its Congeners. VII. Studies on the Homoisoflavonoids of the Subterranean Part of Ophiopogon Japonicas Ker-Gawler cv. Nanus. Chemical and Pharmaceutical Bulletin, 41, 566-570. https://doi.org/10.1248/cpb.41.391
[18]
Tada, A., Kasai, R., Saitoh, T. and Shoji, J. (1980) Studies on the Constituents of Ophiopogonis Tuber. VI. Structures of Homoisoflavonoids. Chemical and Pharmaceutical Bulletin, 28, 2039-2044. https://doi.org/10.1248/cpb.28.2039
[19]
Watanabe, Y., Sanada, S., Ida, Y. and Shoji, J. (1985) Comparative Studies on the Constituents of Ophiopogonis Tuber and Its Congeners. IV. Studies on the Homoisoflavonoids of the Subterranean Part of Ophiopogon Ohwii Okuyama and Ophiopogon Jaburan (Kunth) Lodd. Chemical and Pharmaceutical Bulletin, 33, 5358-5363. https://doi.org/10.1248/cpb.33.5358
Chang, J.M., Shen, C.C., Huang, Y.L., Chien, M.Y., Ou, J.C., Shieh, B.J. and Chen, C.C. (2002) Five New Homoisoflavonoids from the Tuber of Ophiopogon japonicus. Journal of Natural Products, 65, 1731-1733. https://doi.org/10.1021/np020204o
[22]
Kumar, R., Ilyas, M., Parveen, M. and Shafiullah (2006) A New Chromone from Cassia nodosa. Journal of Asian Natural Products Research, 8, 595-598. https://doi.org/10.1080/10286020500179470
[23]
Kirkiacharian, S., Tongo, H.G., Bastide, J., Bastide P. and Grenie, M.M. (1989) Synthe`se et Activite′s Angioprotectrice, Anti-Allergique et Antihistaminique de Benzyl-3 Chromones (Homo-Isoflavones) Synthesis and Angioprotective, Antiallergic and Antihistaminic Activities of 3-Benzyl-Chromones (Homoisoflavones). European Journal of Medicinal Chemistry, 24, 541-546. https://doi.org/10.1016/0223-5234(89)90060-3
[24]
Siddaiah, V., Rao, C.V., Venkateswarlu, S. and Subbaraju, G.V. (2006) A Concise Synthesis of Polyhydroxydihydrochalcones and Homoisoflavonoids. Tetrahedron, 62, 841-846. https://doi.org/10.1016/j.tet.2005.10.059
[25]
Aghoramurthy, K., Narascimhachari, N. and Seshadri, T.R. (1951) Synthetic Experiments in the Benzopyrone Series. Part XVI. Isoformononetin and Its Derivatives. Proceedings of the Indian Academy of Sciences-Section A, 33, Article No. 257. https://doi.org/10.1007/BF03173259
[26]
Ahluwalia, V.K., Bhagat, P., Agarwal, R. and Chandra, R. (2005) Intermadiates for Organic Synthesis. I K International Publishing House, Delhi.
[27]
Brophy, J.J., Fookes, C.J.R. and Houset, A.P.N. (1992) 2,4,6-Trimethoxytoluene from the Genus ‘Stockwellia’. Phytochemistry, 31, 324-325. https://doi.org/10.1016/0031-9422(91)83064-R
[28]
Babu, A.V., Rambabu, A., Giriprasad, P.V., Chandra Rao, R.S. and Babu, B.H. (2013) Synthesis of (±)-Pisonivanone and Other Analogs as Potent Antituberculosis Agents. Journal of Chemistry, 2013, Article ID: 961201. https://doi.org/10.1155/2013/961201
