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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 22
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Synthetic Communications Reviews

1,2-Benzisoxazole-3-acetamide derivatives as dual agents for DPP-IV inhibition and anticancer activity

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Pages 2877-2887 | Received 14 Jun 2018, Published online: 30 Oct 2018

References

  • Drucker, D. J.; Nauck, M. A. The Incretin System: Glucagon-Like Peptide-1 Receptor Agonists and Dipeptidyl Peptidase-4 Inhibitors in Type 2 Diabetes. Lancet 2006, 368, 1696–1705. DOI:10.1016/S0140-6736(06)69705-5
  • Kshirsagar, A. K.; Aggarwal, A. S.; Harle, U. N.; Deshpande, A. V. DPP IV Inhibitors: Successes, Failures and Future Prospects. Diabetes Metab. Syndr. 2011, 5, 105–112. DOI:10.1016/j.dsx.2012.02.017
  • Abbott, C. A.; McCaughan, G. W.; Baker, E.; Sutherland, G. R. Genomic Organization, Exact Localization, and Tissue Expression of the Human CD26 (Dipeptidyl Peptidase IV) Gene. Immunogenetics 1994, 40, 331–338. DOI:10.1007/BF01246674
  • Cheng, H. C.; Abdel-Ghany, M.; Elble, R. C.; Pauli, B. U. Lung Endothelial Dipeptidyl Peptidase IV Promotes Adhesion and Metastasis of Rat Breast Cancer Cells via Tumor Cell Surface-Associated Fibronectin. J. Biol. Chem. 1998, 273, 24207–24215. DOI:10.1074/jbc.273.37.24207
  • Wesley, U. V.; Albino, A. P.; Tiwari, S.; Houghton, A. N. A Role for Dipeptidyl Peptidase IV in Suppressing the Malignant Phenotype of Melanocytic Cells. J. Exp. Med. 1999, 190, 311–322. DOI:10.1084/jem.190.3.311
  • Pethiyagoda, C. L.; Welch, D. R.; Fleming, T. P. Dipeptidyl Peptidase IV (DPPIV) Inhibits Cellular Invasion of Melanoma Cells. Clin. Exp. Metastasis. 2000, 18, 391–400. DOI:10.1023/A:1010930918055
  • Aytac, U.; Clart, F. X.; Ho, L.; Sato, K.; Ohnuma, K.; Mills, G. B.; Cabanillas, F.; Morimoto, C.; Dang, N. H. Expression of CD26 and Its Associated Dipeptidyl Peptidase IV Enzyme Activity Enhances Sensi-Tivity to Doxorubicin-Induced Cell Cycle Arrest at the G(2)/M Checkpoint. Cancer Res. 2001, 61, 7204–7210.
  • (a) Villhauer, E. B.; Brinkman, J. A.; Naderi, G. B.; Burkey, B. F.; Dunning, B. E.; Prasad, K.; Mangold, B. L.; Russell, M. E.; Hughes, T. E. 1-[[(3-Hydroxy-1-Adamantyl)Amino]Acetyl]-2-Cyano-(S)-Pyrrolidine: A Potent, Selective, and Orally Bioavailable Dipeptidyl Peptidase IV Inhibitor with Antihyperglycemic Properties. J. Med. Chem. 2003, 46, 2774–2789. (b) Kim, D.; Wang, L.; Beconi, M.; Eiermann, G. J.; Fisher, M. H.; He, H.; Hickey, G. J.; Kowalchick, J. E.; Leiting, B.; Lyons, K.; et al. (2R)-4-Oxo-4-[3-(Trifluoromethyl)-5,6-Dihydro[1,2,4]Triazolo[4,3-a]Pyrazin-7(8H)-Yl]-1-(2,4,5-Trifluorophenyl)Butan-2-Amine: A Potent, Orally Active Dipeptidyl Peptidase IV Inhibitor for the Treatment of Type 2 Diabetes. J. Med. Chem. 2005, 48, 141–151.
  • Biftu, T.; Sinha-Roy, R.; Chen, P.; Qian, X.; Feng, D.; Kuethe, J. T.; Scapin, G.; Gao, Y. D.; Yan, Y.; Krueger, A.; et al. Omarigliptin (MK-3102): A Novel Long-Acting DPP-4 Inhibitor for Once-Weekly Treatment of Type 2 Diabetes. J. Med. Chem. 2014, 57, 3205–3212.
  • Hansen, J.; Deacon, C. F.; Orskov, C.; Holst, J. J. Glucagon-like Peptide-1-(7–36)Amide is Transformed to Glucagon-like Peptide-1-(9–36)Amide by Dipeptidyl Peptidase IV in the Capillaries Supplying the L Cells of the Porcine Intestine. Endocrinology 1999, 140, 5356–5363.
  • (a) Dang, N. H.; Morimoto, C. CD26: An Expanding Role in Immune Regulation and Cancer. Histol. Histopathol. 2002, 1. 1213–1226. (b) Iwata, S.; Morimoto, C. CD26/Dipeptidyl Peptidase IV in Context. The Different Roles of a Multifunctional Ectoenzyme in Malignant Transformation. J. Exp. Med 1999, 190, 301–306.
  • Liotta, L. A.; Kohn, E. C. The Microenvironment of the Tumour-Host Interface. Nature 2001, 411, 375–379.
  • Bušek, P.; Malik, R.; Šedo, A. Dipeptidyl Peptidase IV Activity and/or Structure Homologues (DASH) and Their Substrates in Cancer. Int. J. Biochem. Cell Biol. 2004, 36, 408–421.
  • Deng, B. L.; Zhao, Y.; Hartman, T. L.; Watson, K.; Buckheit, R. W.Jr; , Pannecouque, C.; Clercq, E. D.; Cushman, M. Synthesis of Alkenyldiarylmethanes (ADAMs) Containing Benzo[d]Isoxazole and Oxazolidin-2-One Rings, a New Series of Potent Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors. Eur. J. Med. Chem. 2009, 44, 1210–1214.
  • Lamani, R. S.; Shetty, N. S.; Kamble, R. R.; Khazi, I. A. M. Synthesis and Antimicrobial Studies of Novel Methylene Bridged Benzisoxazolyl Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives. Eur. J. Med. Chem. 2009, 44, 2828–2833.
  • (a) Aiello, S.; Wells, G.; Stone, E. L.; Kadri, H.; Bazzi, R.; Bell, D. R.; Stevens, M. F. G.; Matthews, C. S.; Bradshaw, T. D.; Westwel, A. D. Synthesis and Biological Properties of Benzothiazole, Benzoxazole, and Chromen-4-One Analogues of the Potent Antitumor Agent 2-(3,4-Dimethoxyphenyl)-5-Fluorobenzothiazole (PMX 610, NSC 721648). J. Med. Chem. 2008, 51, 5135–5139. (b) Arakawa, K.; Inamasu, M.; Matsumoto, M.; Okumura, K.; Yasuda, K. Novel Benzoxazole-2,4-Thiazolidinediones as Potent Hypoglycemic Agents. Synthesis and Structure-Activity Relationships. Chem. Pharm. Bull. 1997, 45, 1984–1993.
  • Sharath Chandra, S. P.; Vishwaprakash Mahadimane, P. Effect of Novel Benzisoxazole Derivatives against Ehrlich Ascites Carcinoma Cells in Swiss Albino Mice: Cytotoxic and Haematological Studies. Int. J. Pharma Sci. Res. 2015, 6, 3606–3611.
  • Rajashekar, R. C. B.; Reddy, R.; Revathy, S. T.; Krish, S.; Sabiah, S. Res. J. Pharm. Biol. Chem. Sci. 2014, 5, 873–880.
  • Shi, G. Q.; Dropinski, J. F.; McKeever, B. M.; Xu, S.; Becker, J. W.; Berger, J. P.; MacNaul, K. L.; Elbrecht, A.; Zhou, G.; Doebber, T. W.; et al. Design and Synthesis of α-Aryloxyphenylacetic Acid Derivatives: A Novel Class of PPARα/γ Dual Agonists with Potent Antihyperglycemic and Lipid Modulating Activity. J. Med. Chem. 2005, 48, 4457–4468.
  • Benaka Prasad, S. B.; Vinaya, K.; Ananda Kumar, C. S.; Swarup, S.; Rangappa, K. S. Synthesis of Novel 6-Fluoro-3-(4-Piperidinyl)-1,2-Benzisoxazole Derivatives as Antiproliferative Agents: A Structure–Activity Relationship Study. Invest. New Drugs 2009, 27, 534–542.
  • Ashwini, N.; Garg, M.; Mohan, C. D.; Fuchs, J. F.; Rangappa, S.; Anusha, S.; Swaroop, T. R.; Rakesh, K. S.; Kanojia, D.; Madan, V.; et al. Synthesis of 1,2-Benzisoxazole Tethered 1,2,3-Triazoles That Exhibit Anticancer Activity in Acute Myeloid Leukemia Cell Lines by Inhibiting Histone Deacetylases, and Inducing p21 and Tubulin Acetylation. Bioorg. Med. Chem. 2015, 23, 6157–6165.
  • (a) Soni, R.; Durgapal, S.; Soman, S. S.; Georrge, J. J. Design, Synthesis and anti-Diabetic Activity of Chromen-2-One Derivatives. Arabian J. Chem. 2016, DOI:10.1016/j.arabjc.2016.11.01. (b) Sharma, R.; Soman, S. S. Design and Synthesis of Sulfonamide Derivatives of Pyrrolidine and Piperidine as anti-Diabetic Agents. Eur. J. Med. Chem. 2015, 90, 342–350.
  • Patel, J. M.; Soman, S. S. Studies on the Synthesis of Furobenzisoxazole Derivatives. Chem. Heterocycl. Comp. 2009, 45, 1081–1088.
  • Soman, S. S.; Soni, J.; Patel, T. Synthesis of New Naphthoisoxazole Amide Derivatives and Study of Their Biological Evaluations. Med. Chem. Res. 2014, 23, 3803–3809.
  • Boyd, J.; Robertson, A. The Chemistry of the “Insoluble Red” Woods. Part II. A New Synthesis of 4-Hydroxycoumarins. J. Chem. Soc. 1948, 0, 174–176.
  • Posner, I.; Hess, R. Unsaturated Compounds. X. Action of Free Hydroxylamine on Coumarins. Ber. Dtsch. Chem. Ges. 1913, 46, 3816–3833.
  • (a) Almansa, R.; Guijarro, D.; Meyers, A. Enantioselective Addition of Dialkylzinc Reagents to N-(Diphenylphosphinoyl)Imines Catalyzed by β-Aminoalcohols with the Prolinol Skeleton. Tetrahedron Asymmetry 2007, 18, 2828–2840. (b) Tang, F. Y.; Qu, L. Q.; Xu, Y.; Ma, R. J.; Chen, S. H.; Li, G. Practical Synthesis of Structurally Important Spirodiamine Templates. Synt. Commun. 2007, 37, 3793–3799.

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