Article
Synthesis and Characterization of Thiazepine/Benzothiazepine Derivatives Through Intramolecular C-2 Ring Expansion Pathway
Simer Preet,
Damanjt Singh Cannoo,
Simer Preet
Department of Chemistry, Sant Longowal Institute of Engineering and Technology, Longowal 148106, India
Search for more papers by this authorCorresponding Author
Damanjt Singh Cannoo
Department of Chemistry, Sant Longowal Institute of Engineering and Technology, Longowal 148106, India
Corresponding author. Email: [email protected]Search for more papers by this authorSimer Preet,
Damanjt Singh Cannoo,
Simer Preet
Department of Chemistry, Sant Longowal Institute of Engineering and Technology, Longowal 148106, India
Search for more papers by this authorCorresponding Author
Damanjt Singh Cannoo
Department of Chemistry, Sant Longowal Institute of Engineering and Technology, Longowal 148106, India
Corresponding author. Email: [email protected]Search for more papers by this authorAbstract
A facile and highly efficient one-pot synthesis of novel thiazepine and benzothiazepine derivatives was established by ring expansion. With a greener methodology (ultrasonication), a polysubstituted ring system with the thiazepine core moiety can be easily synthesized from simple and easily available reactants in good yields. Moreover, the synthesized compounds show fluorescence and also antioxidant activity.
Supporting Information
| Filename | Description |
|---|---|
| jccs201600778-sup-0001-supInfo.docxWord 2007 document , 2.5 MB | Supporting Information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1 M. J. Urbanski, R. H. Chen, K. T. Demarest, J. Gunnet, R. Look, E. Ericson, W. V. Murray, P. J. Rybczynski, X. Zhang, Bioorg. Med. Chem. Lett. 2003, 13, 4031.
- 2 S. R. Cherkupally, P. R. Gurrala, N. Adki, S. Avula, Org. Commun. 2008, 1, 84.
- 3(a) F. L. Ansari, F. Iftikhar, I. U. Haq, B. Mirza, M. Baseer, U. Rashid, Bioorg. Med. Chem. 2008, 16, 7691; (b) L. Smith, W. C. Wong, A. S. Kiselyov, S. B. Wizemann, Y. Mao, Y. Xu, M. A. J. Duncton, K. Kim, E. L. Piatnitski, J. F. Doody, Y. Wang, R. L. Rosler, D. Milligan, J. Columbus, C. Balagtas, S. P. Lee, A. Konovalova, Y. R. Hadari, Bioorg. Med. Chem. Lett. 2006, 16, 5102.
- 4 F. J. M. Sanz, R. L. Cuesta, L. G. Lafuente, A. J. M. Ortega, E. Punzon, M. F. C. Abad, C. de Ríos, Eur. J. Med. Chem. 2016, 109, 114.
- 5 R. N. Guo, K. Gao, Z. S. Ye, L. Shi, Y. Li, Y. G. Zhou, Pure Appl. Chem. 2013, 85, 843.
- 6 A. K. Sharma, G. Singh, A. K. Yadav, L. Prakash, Molecules 1997, 2, 129.
- 7 M. S. Youssef, M. E. Azab, M. M. Youssef, Molecules 2012, 17, 6930.
- 8 F. Aiello, A. Brizzi, A. Garofalo, A. F. Grande, G. Ragno, R. Dayamc, N. Neamati, Bioorg. Med. Chem. 2004, 12, 4459.
- 9(a) V. R. Vutla, R. P. Yejellab, R. Nadendla, N. V. Ramaraoa, Pharm. Lett. 2013, 5, 93; (b) J. H. Tailor, P. C. Patel, G. M. Malik, Indian J. Chem. Sect. B 2014, 53 B, 1263.
- 10(a) P. Matyus, I. Varga, E. Zara, A. Mezei, A. Behr, A. Simay, N. Haider, S. Boros, A. Bakonyi, E. Horvath, K. Horvath, Bioinorg. Med. Chem. Lett. 1997, 7, 2857; (b) S. Kaur, H. Kumar, A. Chaudhary, A. Kumar, Arab. J. Chem. 2012, 5, 271.
- 11 C. D. Ellis, K. A. Oppong, M. C. Laufersweiler, S. V. O'Neil, D. L. Soper, Y. Wang, J. A. Wos, A. N. Fancher, W. Lu, M. K. Suchanek, R. L. Wang, B. De, T. P. Demuth Jr.. , Bioorg. Med. Chem. Lett. 2006, 16, 4728.
- 12 J. Drewe, S. Kasibhatla, B. Tseng, E. Shelton, D. Sperandio, R. M. Yee, J. Litvak, M. Sendzik, J. R. Spencerb, S. X. Cai, Bioorg. Med. Chem. Lett. 2007, 17, 4987.
- 13 A. Zask, J. Kaplan, X. Du, G. MacEwan, V. Sandanayaka, N. Eudy, J. Levin, G. Jin, J. Xu, T. Cummons, D. Barone, S. A. Kaloustiana, J. Skotnicki, Bioorg. Med. Chem. Lett. 2005, 15, 1641.
- 14 H. Ding, Y. Zhang, M. Bian, W. Yao, C. Ma, J. Org. Chem. 2008, 73, 578.
- 15 G. D. Mahale, A. Kumar, D. Singh, A. V. Ramaswamy, S. B. Waghmode, J. Serb. Chem. Soc. 2008, 4, 385.
- 16 G. D. Mahale, Y. M. Kolekar, A. Kumar, D. Singh, K. M. Kodam, S. B. Waghmode, Indian J. Chem. Sect. B 2011, 50B, 1196.
- 17 L. Fodor, P. Csomós, T. Holczbauer, A. Kálmán, A. Csámpai, P. Sohár, Tetrahedron Lett. 2011, 52, 224.
- 18 G. Roman, Acta Chim. Slov. 2013, 60, 70.
- 19 J. Szabo, L. Fodor, A. Katbcs, G. Berncith, P. Sohar, Chem. Ber. 1986, 119, 2904.
- 20
B. V. Kendre, M. G. Landge, S. R. Bhusare, Arab. J. Chem. 2015, xxx, xxx-xxx. doi:10.1016/j.arabjc.2015.01.007.
10.1016/j.arabjc.2015.01.007 Google Scholar
- 21 L. Fodor, P. Csomós, F. A. Csámpai, P. Sohár, J. Mol. Struct. 2010, 983, 54.
- 22 T. A. Farghaly, H. M. E. Hassaneen, Arab. J. Chem. 2014, xxx, xxx-xxx. doi:10.1016/j.arabjc.2013.12.024.
- 23 M. Bakavoli, H. Beyzaei, M. Rahimizadeh, J. Tajabadi, Synth. Commun. 2009, 1, 1324.
- 24 V. M. Berestovitskaya, R. I. Baichurin, N. I. Aboskalova, V. V. Gurzhiy, Mendeleev Commun. 2014, 24, 380.
- 25 T. S. Safonova, M. P. Nemeryuk, N. A. Grineva, A. F. Keremov, O. S. Anisimova, N. P. Solov'eva, Chem. Hetero. Comp. 2004, 40, 1609.
- 26 H. Ishibashi, M. Uegaki, M. Sakai, Y. Takeda, Tetrahedron 2001, 57, 2115.
- 27 K. K. Kononowicz, J. K. Wojciechowska, B. Michalak, E. B. Pvkala, B. Schumacher, C. E. Müller, Eur. J. Med. Chem. 2004, 39, 205.
- 28 V. K. Tandon, H. K. Maurya, N. N. Mishra, P. K. Shukla, Eur. J. Med. Chem. 2009, 44, 3130.
- 29 G. D. Sarro, A. Chimirri, A. D. Sarro, R. Gitto, S. Grasso, M. Zappala, Eur. J. Med. Chem. 1995, 30, 925.
- 30 V. Ambrogil, G. Grandolinl, L. Periolil, L. Giustiz, A. Lucacchinia, C. Martini, Eur. J. Med. Chem. 1995, 30, 429.
- 31 S. Preet, D. S. Cannoo, RSC Adv. 2015, 5, 79232.
- 32 N. Khandelwal, Abhilasha, N. Gautam, D. C. Gautam, J. Chem. Sci. 2013, 125, 85.
- 33 E. Yalcin, K. Cavusoglu, Turk. J. Biochem. 2010, 35, 243.
