How to cite this paper
Deepu, C., Raghavendra, G., Rekha, N., Mantelingu, K., Rangappa, K & Bhadregowda, D. (2015). Synthesis and biological evaluation of novel 1,5-benzothiazepin-4(5H)-ones as potent antiangiogenic and antioxidant agents.Current Chemistry Letters, 4(4), 133-144.
Refrences
1. Wu H.; Chen H.; Sun Y.; Wan Y.; Wang F.; Ji B.; Su X. (2013) Imaging integrin ?(v)B(3) positive glioma with a novel RGD dimer probe and the impact of antiangiogenic agent (Endostar) on its tumor uptake. Cancer Lett., 335, 75–80.
2. Jeon K. S.; Na H-J.; Kim Y-M.; Kwon H. J. (2005) Antiangiogenic activity of 4-O-methylgallic acid from Canavalia gladiata, a dietary legume. Biochem. Biophys. Res. Commun., 330, 1268-1274.
3. Gangjee A., Kurup S., Ihnat M. A., Thorpe J. E., Shenoy S. S. (2010) Synthesis and biological activity of N4-phenylsubstituted-6-(2,4-dichloro phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamines as vascular endothelial growth factor receptor-2 inhibitors and antiangiogenic and antitumor agents. Bioorg. Med. Chem., 18, 3575-3587.
4. Shenvi S., Kumar K., Hatti K. S., Rijesh K.; Diwakar L., Reddy G. C. (2013) Synthesis, anticancer and antioxidant activities of 2,4,5-trimethoxy chalcones and analogues from asaronaldehyde: Structureeactivity relationship. Eur. J. Med. Chem., 62, 435-442.
5. Cunha C. R. M. D., Neto S. A. M., Silva C. C. D., Cortez A. P., Gomes M. D. N., Martins F. I., Alonso A., Rezende K. R., Menegatti R., M. T. Q. D. Magalh?es M. T. Q. D., Valadares M. C. (2013) 4-Nerolidylcatechol and its synthetic analogues: Antioxidant activity and toxicity evaluation. Eur. J. Med. Chem., 62, 371-378.
6. Andreani A., Leoni A., Locatelli A., Morigi R., Rambaldi M., Rinaldo, Cervellati, Greco, E., Kondratyuk, T. P., Park, E-J., Huang, K., Breemend. R. B. V., Pezzuto, J. M. (2013) Chemopreventive and antioxidant activity of 6-substituted imidazo[2,1-b]thiazoles. Eur. J. Med. Chem., 68, 412-421.
7. Atwal K. S., Ahmed S. Z., Floyd D. M., Moreland S., Hedberg A. (1993) (cis)-3-methyl-1,5-benzothiazepine-4-ones: potent analogs of the calcium channel blocker diltiazen. Bioorg. Med. Chem. Lett., 12, 2797-2800.
8. Itoh K., Kori M., Inada Y., Nishikawa K., Kawamatsu Y., Sugihara H. (1986) Synthesis and angiotensin converting enzyme inhibitory activity of 1,5-benzothiazepine and 1,5-benzoxazepine derivatives. Chem Pharm Bull., 34(5), 2078-2089.
9. Sarro G. D., Chimirri A., Sarro A. D., Gitto R., Grasso S., Zappala M. (1995) 5H- [1,2,4]Oxadiazolo[5,4-d][1,5]benzothiazepines as anticonvulsant agents in DBA/2 mice. Eur. J. Med. Chem., 30, 925-929.
10. Grandolini G., Perioli L., Ambrogi V. (1999) Synthesis of some new 1,4-benzothiazine and 1,5-benzothiazepine tricyclic derivatives with structural analogy with TIBO and their screening for anti-HIV activity. Eur. J. Med. Chem., 34, 701-709.
11. Ham W-H., Yang J-G., Lim T. G., Jung Y-H. (1994) Synthesis of antihypertensive agents via coupling reaction of Benzothiazepinone and 1,4-dihydropyridine derivatives. Archives of Pharmacal Research., 17, 119-123.
12. Dumont L., Libersan D., Chartrand C., Levy E., Garceau D. (1990) Inhibition of platelet aggregation by a new 1.5-benzothiazepine calcium antagonist, TA-3090. Eur. J. Pharmacol., 183, 638.
13. Kapil A., Anshu D. (2008) The expedient synthesis of 1,5-benzothiazepines as a family of cytotoxic drugs. Bioorg. Med. Chem. Lett., 18, 114-119.
14. Wang L., Zhang P., Zhang X., Zhang Y., Li Y., Wang Y. (2009) Synthesis and biological evaluation of a novel series of 1,5-benzothiazepine derivatives as potential antimicrobial agents. Eur. J. Med. Chem., 44, 2815-2821.
15. Mor S., Pahal, P., Narasimhan B. (2012) Synthesis, characterization, biological evaluation and QSAR studies of 11-p-substituted phenyl-12-phenyl-11a,12-dihydro-11H-indeno[2,1-c][1,5]benzothiazepines as potential antimicrobial agents. Eur. J. Med. Chem., 57, 196-210.
16. Amblard M., Daffix I., Bedos P., Berge G., Pruneau D., Paquet J-L., Luccarini J-M., Lichard P. B., Dodey P., Martinez J. (1999) Design and synthesis of potent bradykinin agonists containing a benzothiazepine moiety. J. Med. Chem., 42, 4185-4192.
17. Phippen C. B. W., McErlean C. S. P. (2011) A 1,5-benzothiazepine synthesis. Tetrahedron Letters., 52, 1490.
18. Micheli F., Degiorgis F., Feriani A., Paio A., Pozzan A., Zarantonello P., Seneci P. (2001) A Combinatorial Approach to [1,5]Benzothiazepine Derivatives as Potential Antibacterial Agents. J. Comb. Chem., 3, 224-228.
19. Akbarzadeh R., Amanpour T., Khavasi H. R., Bazgir. A. (2014) Atom-economical isocyanide-based multicomponent synthesis of 2,5-dioxopyrrolidines, spirobenzothiazinechromans and 1,5-benzothiazepines. Tetrahedron., 70, 169-173.
20. (a) David M. F., Robert V. M., Karnail S. A., Syed Z. A., Steven H. S., Jack Z. G., Mary F. M. (1990) Synthesis of Benzazepinone and 3-Methylbenzothiazepinone Analogues of Diltiazem. J. Org. Chem., 55, 5572-5579. (b) Balasubramaniyan V., Balasubramaniyan P., Shaikh A. S. (1986) Reactions of o-aminothiophenol with ?,B-unsaturated dicarbonyl systems, facile synthesis of benzothiazines and benzothiazepines. Tetrahedron., 42, 2731-2738.
21. Slade J., Stanton J. L., Ben-David D., Mazzenga G. C. (1985) Angiotensin converting enzyme inhibitors: 1,5-benzothiazepine derivatives. J. Med. Chem., 28, 1517-1521.
22. Revanna C. N., Raghavendra G. M., Jenifer Vijay T. A., Rangappa K. S., Bhadregowda D. G., Mantelingu K. (2014) Propylphosphonic anhydride-catalyzed tandem approach for biginelli reaction starting from alcohols. Chemistry Letters, 43, 178-180.
23. Revanna C. N., Basappa., Srinivasan V., Feng Li., Kodappully S. S., Xiaoyun D., Shivananju N. S., Bhadregowda D. G., Gautam S., Mantelingu K., Andreas B., Rangappa K. S. (2014) Synthesis and biological evaluation of tetrahydropyridinepyrazoles (‘PFPs’) as inhibitors of STAT3 phosphorylation. Journal of the European Federation for Medicinal Chemistry., 5, 32-40.
24. Yamaguchi T., Takamura H., Matoba T., Terao J. (1998) HPLC method for evaluation of free radical-scavenging activity of foods by using 1,1-diphenyl-1-2-picrylhydrazyl. Biosci. Biotechnol. Biochem., 62, 1201–1204.
25. Hochestein P., Atallah A.S. (1988) The nature of oxidant and antioxidant systems in the inhibition of mutation and cancer. Mutat. Res., 202, 363–375.
26. Moncada A, Palmer R. M. J., Higgs E. (1991) Nitric oxide: physiology, pathophysiology and pharmacology. Pharmacol Rev., 43, 109-142.
27. Rojas-Walker T. D., Tamir S., Ji, H., Wishnok J. S., Tannenbaum S. R. (1995) Chem. Res. Toxicol., 8, 473-477.
28. Gutteridge J. M.; Halliwell B. (1990) Reoxygenation injury and antioxidant protection: a tale of two paradoxes. Arch Biochem Biophys., 283, 223-226.
29. Gordon M. H. (1990) The mechanism of antioxidant action in vitro. in Hudson BJF, ed. Food antioxidants. Elsevier Applied Science, London. pp. 1-18.
30. Los M., Roodhart J. M., Voest E. E. (2007) Target practice: lessons from phase III trials with bevacizumab and vatalanib in the treatment of advanced colorectal cancer. Oncologist., 12, 443-450.
31. Reardon D. A., Fink K. L., Mikkelsen T., Cloughesy T. F., O’Neill A., Plotkin S., Glantz M., Ravin P., Raizer J. J., Rich K. M., Schiff D., Shapiro W. R., Burdette-Radoux S., Dropcho E. J., Wittemer S. M., Nippgen J., Picard M., Nabors L. B. (2008) Randomized phase II study of cilengitide, an integrin-targeting arginine-glycine-aspartic acid peptide, in recurrent glioblastoma multiforme. J. Clin. Oncol., 26, 5610-5617.
32. Scherer R., Godoy H. T. (2009) Antioxidant activity index (AAI) by the 2,2-diphenyl-1-picrylhydrazyl method. .Food Chem.,112, 654-658.
33. Halliwell B., Gutteridge J. M. C., Aruoma O. I. (1987) The deoxyribose method: a simple test tube assay for determination of rate constants for hydroxyl radicals. Anal Biochem., 165, 215-219.
34. Marcocci L., Maguire J. J., M. T. Droy-Lefaix M. T. (1994) The nitric oxide-scavenging properties of Ginkgo biloba extract EGb 761. Biochem. Biophys. Res. Commun., 15, 748-755.
35. Suter M.; Richter C. (2000) Anti- and pro-oxidative properties of PADMA 28, a Tibetan herbal formulation’. Redox Report. 5, 17-22.
36. Auerbach R., Kubai L., Knighton D., Folkman J. (1974) A Simple Procedure for the Long-Term Cultivation of Chicken Embryos. Dev. Biol., 41, 391-394.
2. Jeon K. S.; Na H-J.; Kim Y-M.; Kwon H. J. (2005) Antiangiogenic activity of 4-O-methylgallic acid from Canavalia gladiata, a dietary legume. Biochem. Biophys. Res. Commun., 330, 1268-1274.
3. Gangjee A., Kurup S., Ihnat M. A., Thorpe J. E., Shenoy S. S. (2010) Synthesis and biological activity of N4-phenylsubstituted-6-(2,4-dichloro phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamines as vascular endothelial growth factor receptor-2 inhibitors and antiangiogenic and antitumor agents. Bioorg. Med. Chem., 18, 3575-3587.
4. Shenvi S., Kumar K., Hatti K. S., Rijesh K.; Diwakar L., Reddy G. C. (2013) Synthesis, anticancer and antioxidant activities of 2,4,5-trimethoxy chalcones and analogues from asaronaldehyde: Structureeactivity relationship. Eur. J. Med. Chem., 62, 435-442.
5. Cunha C. R. M. D., Neto S. A. M., Silva C. C. D., Cortez A. P., Gomes M. D. N., Martins F. I., Alonso A., Rezende K. R., Menegatti R., M. T. Q. D. Magalh?es M. T. Q. D., Valadares M. C. (2013) 4-Nerolidylcatechol and its synthetic analogues: Antioxidant activity and toxicity evaluation. Eur. J. Med. Chem., 62, 371-378.
6. Andreani A., Leoni A., Locatelli A., Morigi R., Rambaldi M., Rinaldo, Cervellati, Greco, E., Kondratyuk, T. P., Park, E-J., Huang, K., Breemend. R. B. V., Pezzuto, J. M. (2013) Chemopreventive and antioxidant activity of 6-substituted imidazo[2,1-b]thiazoles. Eur. J. Med. Chem., 68, 412-421.
7. Atwal K. S., Ahmed S. Z., Floyd D. M., Moreland S., Hedberg A. (1993) (cis)-3-methyl-1,5-benzothiazepine-4-ones: potent analogs of the calcium channel blocker diltiazen. Bioorg. Med. Chem. Lett., 12, 2797-2800.
8. Itoh K., Kori M., Inada Y., Nishikawa K., Kawamatsu Y., Sugihara H. (1986) Synthesis and angiotensin converting enzyme inhibitory activity of 1,5-benzothiazepine and 1,5-benzoxazepine derivatives. Chem Pharm Bull., 34(5), 2078-2089.
9. Sarro G. D., Chimirri A., Sarro A. D., Gitto R., Grasso S., Zappala M. (1995) 5H- [1,2,4]Oxadiazolo[5,4-d][1,5]benzothiazepines as anticonvulsant agents in DBA/2 mice. Eur. J. Med. Chem., 30, 925-929.
10. Grandolini G., Perioli L., Ambrogi V. (1999) Synthesis of some new 1,4-benzothiazine and 1,5-benzothiazepine tricyclic derivatives with structural analogy with TIBO and their screening for anti-HIV activity. Eur. J. Med. Chem., 34, 701-709.
11. Ham W-H., Yang J-G., Lim T. G., Jung Y-H. (1994) Synthesis of antihypertensive agents via coupling reaction of Benzothiazepinone and 1,4-dihydropyridine derivatives. Archives of Pharmacal Research., 17, 119-123.
12. Dumont L., Libersan D., Chartrand C., Levy E., Garceau D. (1990) Inhibition of platelet aggregation by a new 1.5-benzothiazepine calcium antagonist, TA-3090. Eur. J. Pharmacol., 183, 638.
13. Kapil A., Anshu D. (2008) The expedient synthesis of 1,5-benzothiazepines as a family of cytotoxic drugs. Bioorg. Med. Chem. Lett., 18, 114-119.
14. Wang L., Zhang P., Zhang X., Zhang Y., Li Y., Wang Y. (2009) Synthesis and biological evaluation of a novel series of 1,5-benzothiazepine derivatives as potential antimicrobial agents. Eur. J. Med. Chem., 44, 2815-2821.
15. Mor S., Pahal, P., Narasimhan B. (2012) Synthesis, characterization, biological evaluation and QSAR studies of 11-p-substituted phenyl-12-phenyl-11a,12-dihydro-11H-indeno[2,1-c][1,5]benzothiazepines as potential antimicrobial agents. Eur. J. Med. Chem., 57, 196-210.
16. Amblard M., Daffix I., Bedos P., Berge G., Pruneau D., Paquet J-L., Luccarini J-M., Lichard P. B., Dodey P., Martinez J. (1999) Design and synthesis of potent bradykinin agonists containing a benzothiazepine moiety. J. Med. Chem., 42, 4185-4192.
17. Phippen C. B. W., McErlean C. S. P. (2011) A 1,5-benzothiazepine synthesis. Tetrahedron Letters., 52, 1490.
18. Micheli F., Degiorgis F., Feriani A., Paio A., Pozzan A., Zarantonello P., Seneci P. (2001) A Combinatorial Approach to [1,5]Benzothiazepine Derivatives as Potential Antibacterial Agents. J. Comb. Chem., 3, 224-228.
19. Akbarzadeh R., Amanpour T., Khavasi H. R., Bazgir. A. (2014) Atom-economical isocyanide-based multicomponent synthesis of 2,5-dioxopyrrolidines, spirobenzothiazinechromans and 1,5-benzothiazepines. Tetrahedron., 70, 169-173.
20. (a) David M. F., Robert V. M., Karnail S. A., Syed Z. A., Steven H. S., Jack Z. G., Mary F. M. (1990) Synthesis of Benzazepinone and 3-Methylbenzothiazepinone Analogues of Diltiazem. J. Org. Chem., 55, 5572-5579. (b) Balasubramaniyan V., Balasubramaniyan P., Shaikh A. S. (1986) Reactions of o-aminothiophenol with ?,B-unsaturated dicarbonyl systems, facile synthesis of benzothiazines and benzothiazepines. Tetrahedron., 42, 2731-2738.
21. Slade J., Stanton J. L., Ben-David D., Mazzenga G. C. (1985) Angiotensin converting enzyme inhibitors: 1,5-benzothiazepine derivatives. J. Med. Chem., 28, 1517-1521.
22. Revanna C. N., Raghavendra G. M., Jenifer Vijay T. A., Rangappa K. S., Bhadregowda D. G., Mantelingu K. (2014) Propylphosphonic anhydride-catalyzed tandem approach for biginelli reaction starting from alcohols. Chemistry Letters, 43, 178-180.
23. Revanna C. N., Basappa., Srinivasan V., Feng Li., Kodappully S. S., Xiaoyun D., Shivananju N. S., Bhadregowda D. G., Gautam S., Mantelingu K., Andreas B., Rangappa K. S. (2014) Synthesis and biological evaluation of tetrahydropyridinepyrazoles (‘PFPs’) as inhibitors of STAT3 phosphorylation. Journal of the European Federation for Medicinal Chemistry., 5, 32-40.
24. Yamaguchi T., Takamura H., Matoba T., Terao J. (1998) HPLC method for evaluation of free radical-scavenging activity of foods by using 1,1-diphenyl-1-2-picrylhydrazyl. Biosci. Biotechnol. Biochem., 62, 1201–1204.
25. Hochestein P., Atallah A.S. (1988) The nature of oxidant and antioxidant systems in the inhibition of mutation and cancer. Mutat. Res., 202, 363–375.
26. Moncada A, Palmer R. M. J., Higgs E. (1991) Nitric oxide: physiology, pathophysiology and pharmacology. Pharmacol Rev., 43, 109-142.
27. Rojas-Walker T. D., Tamir S., Ji, H., Wishnok J. S., Tannenbaum S. R. (1995) Chem. Res. Toxicol., 8, 473-477.
28. Gutteridge J. M.; Halliwell B. (1990) Reoxygenation injury and antioxidant protection: a tale of two paradoxes. Arch Biochem Biophys., 283, 223-226.
29. Gordon M. H. (1990) The mechanism of antioxidant action in vitro. in Hudson BJF, ed. Food antioxidants. Elsevier Applied Science, London. pp. 1-18.
30. Los M., Roodhart J. M., Voest E. E. (2007) Target practice: lessons from phase III trials with bevacizumab and vatalanib in the treatment of advanced colorectal cancer. Oncologist., 12, 443-450.
31. Reardon D. A., Fink K. L., Mikkelsen T., Cloughesy T. F., O’Neill A., Plotkin S., Glantz M., Ravin P., Raizer J. J., Rich K. M., Schiff D., Shapiro W. R., Burdette-Radoux S., Dropcho E. J., Wittemer S. M., Nippgen J., Picard M., Nabors L. B. (2008) Randomized phase II study of cilengitide, an integrin-targeting arginine-glycine-aspartic acid peptide, in recurrent glioblastoma multiforme. J. Clin. Oncol., 26, 5610-5617.
32. Scherer R., Godoy H. T. (2009) Antioxidant activity index (AAI) by the 2,2-diphenyl-1-picrylhydrazyl method. .Food Chem.,112, 654-658.
33. Halliwell B., Gutteridge J. M. C., Aruoma O. I. (1987) The deoxyribose method: a simple test tube assay for determination of rate constants for hydroxyl radicals. Anal Biochem., 165, 215-219.
34. Marcocci L., Maguire J. J., M. T. Droy-Lefaix M. T. (1994) The nitric oxide-scavenging properties of Ginkgo biloba extract EGb 761. Biochem. Biophys. Res. Commun., 15, 748-755.
35. Suter M.; Richter C. (2000) Anti- and pro-oxidative properties of PADMA 28, a Tibetan herbal formulation’. Redox Report. 5, 17-22.
36. Auerbach R., Kubai L., Knighton D., Folkman J. (1974) A Simple Procedure for the Long-Term Cultivation of Chicken Embryos. Dev. Biol., 41, 391-394.