Synthesis of tertiary propargylic phosphonates by addition of trialkynylaluminum reagents to acyl phosphonates and investigation of their antimicrobial activities
A series of propargylic alcohols containing phosphonates was synthesized by addition reactions of tris-(propynyl) and tris-(phenylethynyl)aluminum reagents to acyl phosphonates in good yields. Aromatic moieties of the acyl phosphonates with electron-withdrawing groups generally resulted in better isolated chemical yield. Selected propargylic phosphonates were tested for antimicrobial activities. Compounds 3a and 3h showed noticeable antifungal activity, especially against molds.
Synthesis of tertiary propargylic phosphonates by addition of trialkynylaluminum reagents to acyl phosphonates and investigation of their antimicrobial activities
A series of propargylic alcohols containing phosphonates was synthesized by addition reactions of tris-(propynyl) and tris-(phenylethynyl)aluminum reagents to acyl phosphonates in good yields. Aromatic moieties of the acyl phosphonates with electron-withdrawing groups generally resulted in better isolated chemical yield. Selected propargylic phosphonates were tested for antimicrobial activities. Compounds 3a and 3h showed noticeable antifungal activity, especially against molds.
___
- Auge, J.; Lubin-Germain N.; Seghrouchni, L. Tetrahedron Lett. 2003, 44, 819–821.
- Cozzi, P. G.; Rudolph, J.; Bolm, C.; Norrby, P.; Tomasini, C. J. Org. Chem. 2005, 70, 5733–5736.
- Niwa, S.; Soai, K. J. Chem. Soc. Perkin Trans. 1990, 1, 937–943.
- Boobalan, R.; Chen, C.; Lee G. H. Org. Biomol. Chem. 2012, 10, 1625–1638 and the references related with the addition of alkyne to carbonyl compounds therein.
- Brinkmeyer, R. S.; Kapoor, V. M. J. Am. Chem. Soc. 1977, 99, 8339–9341.
- Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738–8739.
- Wieland, L. C.; Deng, H.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 15453–15456.
- Ohshima, T.; Kawabata, T.; Takeuchi, Y.; Kakinuma, T.; Iwasaki, T.; Yonezawa, T.; Murakami, H.; Nishiyama, H.; Mashima, K. Angew. Chem. Int. Ed. 2011, 50, 6296–6300.
- Infante, R.; Gago, A.; Nieto, J.; Andres, C. Adv. Synth. Catal. 2012, 354, 2797–2804.
- Jiang, B.; Chen, Z.; Tang, X. Org. Lett. 2002, 4, 3451–3453.
- Aikawa, K.; Hioki, Y.; Mikami, K. Org. Lett. 2010, 12, 5716–5719.
- Funabashi, K.; Jachmann, M.; Kanai, M.; Shibasaki, M. Angew. Chem. 2003, 115, 5647–5650.
- Bauer, T.; Gajewiak, J. Tetrahedron-Asymmetr. 2005, 16, 851–855.
- Biswas, K.; Prieto, O.; Goldsmith, P. J.; Woodward, S. Angew. Chem. Int. Ed. 2005, 44, 2232–2234.
- Chan, A. S. C.; Zhang, F. Y.; Yip, C. W. J. Am. Chem. Soc. 1997, 119, 4080–4081.
- Mata, Y.; Dieguez, M.; Pamies, O.; Woodward, S. J. Org. Chem. 2006, 71, 8159–8165.
- Pagenkopf, B. L.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 9593–9596.
- Haraguchi, K.; Kubota, Y.; Tanak, H. J. Org. Chem. 2004, 69, 1831–1836.
- Pompliano, D. L.; Rands, E.; Schaber, M. D.; Mosser, S. D.; Anthony, N. J.; Gibbs, J. B. Biochemistry 1992, 31, 3800–3807.
- Dellaria, J. F., Jr.; Maki, R. G.; Stein, H. H.; Cohen, J.; Whittern, D.; Marsh, K.; Hoffman, D. J.; Plattner, J. J.; Perun, T. J. J. Med. Chem. 1990, 33, 534–542.
- Tao, M.; Bihovsky, R.; Wells, G. J.; Mallamo, J. P. J. Med. Chem. 1998, 41, 3912–3916.
- Asano, M.; Yukita, A.; Matsumoto, T.; Kondo, S.; Suzuki, H. Cancer Res. 1995, 55, 5296–5301.
- Yokomatsu, T.; Hayakawa, Y.; Suemune, K.; Kihara, T.; Soed, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. Lett. 1999, 9, 2833–2836.
- Yokomatsu, T.; Abe, H.; Sato, M.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. 1998, 6, 2495–2505.
- Ganzhorn, A. J.; Hoflack, J.; Pelton, P. D.; Strasser, F.; Chanal, M. C.; Piettre, S. R. Bioorg. Med. Chem. 1998, 6, 1865–1874.
- Stowasser, B.; Budt, K. H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625–6628.
- Seven, O.; Polat-Cakir, S.; Hossain, M. S.; Emrullahoglu, M.; Demir, A. S. Tetrahedron 2011, 67, 3464–3469.
- Berlin, K. D.; Taylor, H. A. J. Am. Chem. Soc. 1964, 86, 3862–3866.
- Hammerschmidt, F.; Schneyder, E.; Zbiral, E. Chem. Ber. 1980, 113, 3891–3897.
- Mohammadhosseini, N.; Alipanahi, Z.; Alipour, E.; Emami, S.; Faramarzi, M. A.; Samadi, N.; Khoshnevis, N.; Shafiee, A.; Foroumadi, A. DARU J. Pharm. Sciences 2012, 20, 1–6.
- Azerang, P.; Rezayan, A. H.; Sardari, S.; Kobarfard, F.; Bayat, M.; Tabib, K. DARU J. Pharm. Sciences 2012, 20, 1–
- Bauer, A. W.; Kirby, W. M. M.; Sheris, J. C.; Truck, M. Am. J. Clin. Pathol. 1996, 36, 493–496.
- Unsal, T. O.; Ozadali, K.; Yogeeswari, P.; Sriram, D.; Balkan, A. Med. Chem. Res. 2012, 21, 2388–2394.