An excellent candidate in the fight against damage caused by nuclear radiation is 2-[4-(1,3-dioxo-1H,3Hbenzoisoquinolin-2-yl)butylsulfamoyl]benzoic acid (DBIBB), a lipid agonist of lysophospholipid acid receptor 2. In this study, a novel method that synthesizes DBIBB was developed. In this method, saccharin was replaced singly by 1,4-dibromobutane, reacted with 1,8-naphthalimide, hydrolyzed by sodium hydroxide, and finally acidified by hydrochloric acid to obtain DBIBB. The new synthesis route was shorter, milder, and simpler than previously reported approaches. The method also produced higher total yield than that of existing ones. Thus, it is applicable to the large-scale synthesis of DBIBB.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
G. N. Kiss, S. C. Lee, J. I. Fells, J. Liu, W. J. Valentine, Y. Fujiwara, K. E. Thompson, C. R. Yates, B. Sumegi, and G. Tigyi, Biochim. Biophys. Acta, 1831, 117 (2013).
W. Deng, E. Shuyu, R. Tsukahara, W. J. Valentine, G. Durgam, V. Gududuru, L. Balazs, V. Manickam, M. Arsura, L. VanMiddlesworth, L. R. Johnson, A. L. Parrill, D. D. Miller, and G. Tigyi, Gastroenterology, 132, 1834 (2007).
S. A. Knowlden, S. E. Hillman, T. J. Chapman, R. Patil, D. Miller, and G. Tigyi, Am. J. Respir. Cell Mol. Biol., 54, 402 (2016).
A. Balogh, Y. Shimizu, S. C. Lee, D. Norman, R. Gangwar, M. Bavaria, C. Moon, P. Shukla, R. Rao, R. Ray, A. P. Naren, S. Banerje, D. Miller, L. Balazs, L. Pelus, and G. Tigyi, Cell. Signal., 27, 1751 (2015).
G. N. Kiss, J. I. Fells, R. Gupte, S. C. Lee, J. Liu, N. Nusser, K. G. Lim, R. M. Ray, F. T. Lin, A. L. Parrill, B. Sumegi, D. D. Miller, and G. Tigyi, Mol. Pharmacol., 82, 1162 (2012).
Y. Fujiwara, V. Sardar, A. Tokumura, D. Baker, K. Murakami-Murofushi, A. Parrill, and G. Tigyi, J. Biol. Chem., 280, 35038 (2005).
V. M. Sardar, D. L. Bautista, D. J. Fischer, K. Yokoyama, N. Nusser, T. Virag, D. A. Wang, D. L. Baker, G. Tigyi, and A. L. Parrill, Biochim. Biophys. Acta, 1582, 309 (2002).
R. Patil, E. Szabo, J. Fells, A. Balogh, K. G. Lim, Y. Fujiwara, D. Norman, S. C. Lee, L. Balazs, F. Thomas, S. Patil, E-T. Karin, A. Boler, J. Strobos, S. McCool, C. Yates, J. Stabenow, G. Byrne, D. Miller, and G. Tigyi, Biol. Chem., 22, 206 (2015).
Y. T. Lee, C. J. Cui, E. Chow, N. Pue, T. Lonhienne, J. G. Wang, J. A. Fraser, and L. W. Guddat, J. Med. Chem., 56, 210 (2013).
A. Kamal, R. Ramu, V. Tekumalla, G. B. Khanna, M. S. Barkume, A. S. Juvekar, and S. M. Zingde, Bioorg. Med. Chem., 16, 7218 (2008).
R. Patil, J. Fells, E. Szabo, K. G. Lim, D. Norman, A. Balogh, S. Patil, J. Strobos, D. Miller, and G. Tigyi, J. Med. Chem., 57, 7136 (2014).
Acknowledgment
This research was supported by the Chinese Natural Science Foundation (Nos. 81273431, 81072531, and 21102176).
Author information
Authors and Affiliations
Corresponding authors
Additional information
Published in Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2018, pp. 423–425.
Rights and permissions
About this article
Cite this article
Yang, HP., Zhang, SG., Wang, G. et al. Improved Synthesis of Dbibb as a New Anti-Radiation Agent. Chem Nat Compd 54, 499–501 (2018). https://doi.org/10.1007/s10600-018-2388-x
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-018-2388-x