New Convenient Synthesis of 8-C-Methylated Homoisoflavones and Analysis of Their Structure by NMR and Tandem Mass Spectrometry — Oak Academic Publishing
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New Convenient Synthesis of 8-C-Methylated Homoisoflavones and Analysis of Their Structure by NMR and Tandem Mass Spectrometry
Department of Organic Chemistry & FDW, Andhra University, Visakhapatnam, India
,
DMPK, Sai Life Sciences Ltd., Pune, Maharashtra, India
1 Department of Organic Chemistry & FDW, Andhra University, Visakhapatnam, India
2 DMPK, Sai Life Sciences Ltd., Pune, Maharashtra, India
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 PCl 5 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.
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
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
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
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
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
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
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
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
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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
Ahluwalia, V.K., Bhagat, P., Agarwal, R. and Chandra, R. (2005) Intermadiates for Organic Synthesis. I K International Publishing House, Delhi.
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
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
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
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
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
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
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
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
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
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
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
Ahluwalia, V.K., Bhagat, P., Agarwal, R. and Chandra, R. (2005) Intermadiates for Organic Synthesis. I K International Publishing House, Delhi.
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
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