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Synthetic Studies on Fused Benzodiazepines: A Class of Medicinally Privileged Heterocycles

Anup K Sasmal

Abstract


1,4-Benzodiazepine is an important nitrogen heterocyclic scaffold because of its presence in various natural products, drugs and biologically active molecules. Henceforth, it is also known as privileged heterocycle in the field of medicinal to synthetic organic chemistry. Reactions towards the synthesis of five- and six- membered heterocycles are very easy and facile. On the other hand, synthesis of medium ring heterocycles is more difficult because of the thermodynamic limitations. Thus synthesis of benzodiazepines (medium ring) fused with other heterocycles is highly challenging and demanding. This review focuses on the synthetic studies on difficulty obtainable tricyclic to pentacyclic triazole and or pyrazole fused benzodiazepines. It is anticipated that this study will assist scientists for the further synthetic and biological investigation on fused privileged benzodiazepines to enrich synthetic organic chemistry as well as medicinal chemistry. Keywords: Benzodiazepines, privileged heterocycle, fused heterocycle, triazole, pyrazole

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Smalley, R. K. In Comprehensive Heterocyclic Chemistry: Katritzky, A. R.; Rees, C. W.; Eds: Pergamon: Oxford; 1984, vol. 7, p 491.

Evans, P. A.; Holmes, A. B. Tetrahedron 1991, 47, 9131-9166.

(a) Moore, J. A.; Anet, F. A. L. ibid 1984, vol. 7, Ch. 5, 653. (b) Mitchinson, A.; Nadin, A. J. Chem. Soc., Perkin Trans. 1, 2000, 2862-2892. (c) Maier, M. E. Angew. Chem. Int. Ed. 2000, 39, 2073-2077. (d) Dolman, S. J.; Sattely, E. S.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 2002, 124, 6991-6997.

Yet, L. Chem. Rev. 2000, 100, 2963-3008.

(a) Eliel, E. L.; Wilen, S. H. in Stereochemistry of Organic Compounds, Wiley, New York, NY, 1994. (b) Spring, D. R.; Krishna, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354-1363. (c) Appukkuttan, P.; Dehaen, W.; Van Der Eycken, E. Org. Lett. 2005, 7, 2723-2726.

(a) Evans, B. E.; Rittle, K. E.; Bock, M. G.; DiPardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.; Anderson, P. S. J. Med. Chem. 1988, 31, 2235-2246. (b) Patchett, A. A.; Nargund, R. P. Annu. Rep. Med. Chem. 2000, 35, 289-298.

(a) Greenblatt, D. J. ; Shader, R. I. in Benzodiazepines in Clinical Practice, Raven Press, New York, 1974; (b) Sternbach, L. H. in The Benzodiazepine Story, ed. F. Hoffmann-La Roche, Roche Scientific Services, Basel, 2nd edn, 1983, P. 5; (c) Landquist, J. K. in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C.W. Rees, Pergamon, Oxford, 1984, Vol. 1, p. 170.

(a) Mohiuddin, G.; Reddy, P. S.; Ahmed, K.; Ratnam, C. V. Heterocycles 1986, 24, 3489-3530. (b) Thurston, D. E.; Bose, D. S. Chem. Rev. 1994, 94, 433-465.

Witt, A.; Bergman, J. J. Org. Chem. 2001, 66, 2784-2788.

(a) Goetz, M. A.; Lopez, M.; Monaghan, R. L.; Chang, R. S. L.; Lotti, V. J.; Chen, T. B. J. Antibiot. 1985, 38, 1633-1637. (b) Sun, H. H.; Byard, S. J.; Copper, R. J. Antibiot. 1994, 47, 599-601.

(a) Sun, H. H.; Barrow, C. J.; Sedlock, D. M.; Gillum, A. M.; Copper, R. J. Antibiot. 1994, 47, 515-522. (b) Sugimori, T.; Okawa, T.; Eguchi, S.; Kakehi, A.; Yashima, E.; Okamoto, Y. Tetrahedron 1998, 54, 7997-8008.

Joshi, B. K.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. J. Nat. Prod. 1999, 62, 650-652.

(a) Kshirsagar, U. A.; Argade, N. P. Org. Lett. 2010, 12, 3716-3719. (b) Dai, J.-R.; Carte, B. K.; Sidebottom, P. J.; Yew, A. L. S.; Ng, S.-B.; Huang, Y.; Butler, M. S. J. Nat. Prod. 2001, 64, 125-1266. (c) Ookura, R.; Kito, K.; Ooi, T.; Namikishi, M.; Kusumi, T. J. Org. Chem. 2008, 73, 4245-4247.

(a) Antonow, D.; Thurston, D. E. Chem. Rev. 2011, 111, 2815–2864. (b) Tsunakawa, M.; Kamei, H.; Konishi, M.; Miyaki, T.; Oki, T.;Kawaguchi, H. J. Antibiot. 1988, 41, 1366-1373. (c) Michels, T. D.; Kier, M. J.; Kearney, A. M.; Vanderwal, C. D. Org. Lett. 2010, 12, 3093-3095. (d) Thurston, D. E. In Molecular Aspects of Anticancer Drug-DNA Interactions; Neidle, S., Waring, M. J., Eds.; The Macmillan Press Ltd.: London, 1993; Vol. 1, pp 54.

(a) Post, G. L.; Patrick, R. O.; Crowder, J. E.; Houston, J.; Ferguson, J. M.; Bielski, R. J.; Bailey, L.; Pearlman, H. G.; Shu, V. S.; Pierce, M. W. J. Clin. Psychopharmacol. 1991, 11, 249-253. (b) Greenblatt, D. J.; Harmatz, J. S.; Shapiro, L.; Engelhardt, N.; Gouthro, T. A.; Shader, T. A N. Engl. J. Med. 1991, 324, 1691-1698. (c) Levine, J.; Cole, D. P.; Roy Chengappa, K. N.; Gerson, S.; Depress. Anxiety 2001, 14, 94-104. (d) Snyder, P. J.; Werth, J.; Giordani, B.; Caveney, A. F.; Feltner, D.; Maruff, P. Hum. Psychopharmacol. Clin. Exp. 2005, 20, 263-273.

(a) Kaneko, T.; Wong, H.; Doyle, T. W.; Rose, W. C.; Bradner, W. T J. Med. Chem. 1985, 28, 388-392. (b) Keenam, R. M.; Callaham, J. F.; Samanen, J. M.; Bondinell, W. E.; Calvo, R. R.; Chen, I.; DeBrosse, C.; Eggleston, D. S.;. Haltiwanger, R. C. ; Hwang, S. M.; Jakes, D. R.; Ku, T. W.; Miller, W. H.; Newlander, K. A.; Nichols, A.; Parker, M. F.; Southhall, L. S.; Uzinskas, I.; Vasko-Moser, J. A.; Venslavsky, J. W. ; Wong, A. S.; Huffmann, W. F. J. Med. Chem. 1999, 42, 545-559. (c) Novelli, F.; Sparatore, A.; Tass, B.; Sparatore, F. Bioorg. Med. Chem. Lett. 1999, 9, 3031-3034. (d) Zhang, W.; William, J. P.; Lu, Y.; Nagashima, T.; Chu, Q. Tetrahedron Lett. 2007, 48, 563-565. (e) Fier, P. S.; Whittaker, A. M. Org. Lett. 2017, 19, 1454-1457.

(a) Frostl, W.; Maitre, L. Pharmacopsychiatry 1989, 22, 54-100. (b) Katsifis, A. G.; McPhee, M. E.; Mattner, F.; Ridley, D. D. Aust. J. Chem. 1999, 52, 1061-1069. (c) Thomas, A. W. Bioorg. Med. Chem. Lett. 2002, 12, 1881-1884. (d) Donohue, S. R.; Dannals, R. F. Tetrahedron Lett. 2009, 50, 7271-7273. (e) Mohapatra, D. K.; Maity, P. K.; Shabab, M., Khan, M. I. Bioorg. Med. Chem. Lett. 2009, 19, 5241-5245.

(a) Buckle, D. R.; Rockell, C. J. M.; Smith, H.; Spicer, B. A. J. Med. Chem. 1986, 29, 2262-2267. (b) Alvarez, R.; Velazquez, S.; San-Felix, A.; Aquaro, S.; Clercq, E. De.; Perno, C.-F. N.; Karlsson, A.; Balzarini, J.; Camarasa, M. J. J. Med. Chem. 1994, 37, 4185-4194. (b) Soltis, M. J.; Yeh, H. J.; Cole, K. A.; Whittaker, N.; Wersto, R. P.; Kohn, E. C. Drug Metab. Dispos. 1996, 24, 799-806. (c) Genin, M. J.; Allwine, D. A.; Anderson, D. J.; Barbachyn, M. R.; Emmert, D. E.;Garmon, S. E.; Graber, D. R.; Grega, K. C.; Hester, J. B.; Hutchinson, D. K.; Morris, J.; Reischer, R. J.; Ford, C. W.; Zurenko, G. E.; Hamel, J. C.; Schaadt, R. D.; Stapert, D.; Yagi, B. H. J. Med. Chem. 2000, 43, 953-970. (d) Li J, Zheng M, Tang W, He PL, Zhu W, Li T, Zuo JP, Liu H, Jiang H. Bioorg. Med. Chem. Lett. 2006, 16, 5009-5013. (e) Puig-Basagoiti, F.; Qing, M.; Dong, H.; Zhang, B.; Zou, G.; Yuan, Z.; Shi, P.-Y. Anti. Viral. Res. 2009, 83, 71-79. (f) Maurya, S. K.; Gollapalli, D. R.; Kirubakaran, S.; Zhang, M.; Johnson, C. R.; Benjamin, N. N.; Hedstrom, L.; Cuny, G. D. J. Med. Chem. 2009, 52, 4623-4630. (g) Dheer, D.; Singh, V., Shankar, R. Biorg. Chem. 2017, 71, 30-54.

(a) Elguero, J.; Goya, P.; Jagerovic, N.; Silva, A. M. S. in Targets in Heterocyclic Systems (Eds.: O. A. Attanasi, D. Spinelli), Italian Society of Chemistry: Roma, 2002; Vol. 6, pp 52. (b) Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P.W.; Docter, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins,W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. J. Med. Chem. 1997, 40, 1347-1365. (c) Rinaldi-Carmona, M.; Barth, F.; Heaulme, M.; Shire, D.; Calandra, B.; Congy, C.; Martinez, S.; Maruani, J.; Neliat, G.; Caput, D.; Ferrara, P.; Soubrie, P.; Breliere, J. C.; Le Fur, G. FEBS Lett. 1994, 350, 240-244. (d) Seltzman, H. H. Drug Dev. Res. 2009, 70, 601-615. (e) Khan, M. F.; Alam, M. M.; Verma, G.; Akhtar, W.; Akhter, M.; Shaquiquzzaman, M. Eur J Med Chem. 2016, 120, 170-201.

Broggini, G.; Molteni, G.; Zecchi, G. Synthesis, 1995, 647-648.

Broggini, G.; Molteni, G.; Terraneo, A.; Zecchi, G. Tetrahedron 1999, 55, 14803-14806.

Akritopoulou-Zanze, I.; Gracias, V.; Djuric, S. W. Tetrahedron Lett. 2004, 45, 8439-8441.

Mohapatra, D. K.; Maity, P. K.; Shabab, M., Khan, M. I. Bioorg. Med. Chem. Lett. 2009, 19, 5241-5245.

Gracias,V.; Darczak, D.; Gasiecki, A. F.; Djuric, S. W. Tetrahedron Lett. 2005, 46, 9053-9056.

Thomas, A. W. Bioorg. Med. Chem. Lett. 2002, 12, 1881-1884.

Alajarin, M.; Cabrera, J.; Pastor, A.; Villalgordo, J. M. Tetrahedron Lett. 2007, 48, 3495-3499.

Chowdhury, C.; Sasmal, A. K.; Achari, B. Org. Biomol. Chem. 2010, 8, 4971-4977.

Donald, J. R.; Martin, S. F. Org. Lett. 2011, 13, 852-855.

Granger, B. A.; Kaneda, K.; Martin, S. F. Org. Lett. 2011, 13, 4542-4545.

Guggenheim, K. G.; Toru, H.; Kurth, M. J. Org. Lett. 2012, 14, 3732-3735.

Nguyen, H. H.; Palazzo, T. A.; Kurth, M. J. Org. Lett. 2013, 15, 4492-4495.

Hussain, M. K.; Ansari, M. I.; Kant, R.; Hajela, K. Org. Lett. 2014, 16, 2, 560-563.

Donald, J. R.; Wood, R. R.; Martin, S. F. ACS Comb. Sci. 2012, 14, 135-143.

Vroemans, R.; Bamba, F.; Winters, J.; Thomas, J.; Jacobs, J.; Meervelt, L. V.; John, J.; Dehaen, W. Beilstein J. Org. Chem. 2018, 14, 626–633.

Bruche, L. ; Zecchi, G. Tetrahedron 1989, 45, 7427-7432.

(a) Broggini, G.; Garanti, L.; Molteni, G.; Pilati, T. Synth. Commun. 2001, 31, 2649-2656; (b) R. R. Phillips, Org. React. 1959, 10, 143-1778.

Broggini, G.; Marchi, I. D.; Martinelli, M.; Paladino, G.; Pilati, T.; Terraneo, A. Synthesis 2005, 2246-2252.

Basolo, L.; Beccalli, E. M.; Borsini, E.; Broggini, G.; Khansaa, M.; Rigamonti, M. Eur. J. Org. Chem. 2010, 1694-1703.

Brahma, K.; Sasmal, A. K.; Chowdhury, C. Org. Biomol. Chem. 2011, 9, 8422-8429.

Nayaka, M.; Batraa, S. Adv. Synth. Catal. 2010, 352, 3431-3437.

Kolinsky, K.; Tovar, C.; Zhang, Y.-E; Railkar, A.; Yang, H.; Carvajal, D.; Nevins, T.; Geng, W.; Linn, M.; Packman, K.; Liu, J.-J.; Zhang, Z.; Wovkulich, P.; Ju, G.; Higgins, B. Cancer Chemother. Pharmacol. 2011, 68, 1585–1594.

Katte, T. A.; Reekie, T. A.; Jorgensen, W. T.; Kassiou, M. J. Org. Chem. 2016, 81, 4883-4889.


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