1,3,4-oxadiazole: A privileged structure in antiviral agents

Mini-Reviews in Medicinal Chemistry

Volumn 11, Issue 13, 2011, Pages 1130-1142

  Li, Z ^a   Zhan, P ^a   Liu, X ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

1; 3; 4 oxadiazole; Antiviral activity; Molecule modeling; Privileged structure; Solid phase synthesis; Structural modification

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; ANTIVIRUS AGENT; DICHLOROMETHANE; HUMAN IMMUNODEFICIENCY VIRUS PROTEINASE INHIBITOR; LAMIVUDINE; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; TRIFLUOROACETIC ACID;

DENGUE VIRUS 2; DRUG STRUCTURE; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; JUNIN VIRUS; PROCESS OPTIMIZATION; REVIEW; SYSTEMATIC REVIEW; T LYMPHOCYTE;

ANIMALS; ANTIVIRAL AGENTS; DRUG DISCOVERY; HUMANS; MODELS, MOLECULAR; OXADIAZOLES; SOLID-PHASE SYNTHESIS TECHNIQUES; VIRUS DISEASES; VIRUSES;

EID: 80054055210     PISSN: 13895575     EISSN: 18755607     Source Type: Journal    
DOI: 10.2174/138955711797655407     Document Type: Review

References (67)

1. Duarte, C.D.; Barreiro, E.J.; Fraga, C.A. Privileged structures: a useful concept for the rational design of new lead drug candidates. Mini-Rev. Med. Chem., 2007, 7, 1108-19.
2. De Clercq, E.; Field, H.J. Antiviral prodrugs - the development of successful prodrug strategies for antiviral chemotherapy. Br. J. Pharmacol., 2006, 147, 1-11.
3. De Clercq, E. New developments in anti-HIV chemotherapy. Curr. Med. Chem., 2001, 8, 1543-72.
4. De Clercq, E. New developments in anti-HIV chemotherapy. Biochim. Biophys. Acta, 2002, 1587, 258-75.
5. Sawhney, S.N.; Sharma, P.K.; Gupta, A. Synthesis and antiinflammatory activity of some 3-heterocyclyl-1,2- benzisothiazoles. Indian J. Chem. Sect. B, 1993, 32B, 1190-5.
6. Vashi, B.S.; Mehta, D.S.; Shah, V.H. Synthesis of 2,5- disubstituted-1,3,4-oxadiazole, 1,5-disubstituted-2-mercapto-1,3,4- triazole and 2,5-disubstituted-1,3,4-thiadiazole derivatives as potential antimicrobial agents. Indian J. Chem. Sect. B, 1996, 35B, 111-5.
7. Hiremath, S.P.; Biradir, J. S.; Kudari, S.M. Synthesis of substituted oxadiazoles, thiadiazoles and triazoles and evaluation of their biological-activity. J. Indian Chem. Soc., 1984, 61, 74-6.
8. Amir, M.; Kumar, S. Synthesis of some new 2,5-disubstituted 1,3,4-oxadiazole derivatives and their anti inflammatory activity. Indian J. Heterocycl. Chem., 2004, 14, 51-4.
9. Amir, M.; Khan, M. S. Y.; Zaman, M. S. Synthesis, characterization and biological activities of substituted oxadiazole, triazole, thiadiazole and 4-thiazolidinone derivatives. Indian J. Chem. Sect. B, 2004, 43B, 2189-94.
10. Omar, F.A.; Mahfouz, N.M.; Rahman, M.A. Design, synthesis and antiinflammatory activity of some 1,3,4-oxadiazole derivatives. Eur. J. Med. Chem., 1996, 31, 819-25.
11. Rauf, A.; Sharma, S.; Gangal, S. One-pot synthesis, antibacterial and antifungal activities of novel 2,5-disubstituted-1,3,4- oxadiazoles. Chin. Chem. Lett., 2008, 19, 5-8.
12. Tandon, V.K.; Chhor, R.B. An efficient one pot synthesis of 1,3,4- oxadiazoles. Synth. Commun., 2001, 3, 1727-32.
13. Liras, S.; Allen, M.P.; Segelstein, B.E. A mild method for the preparation of 1,3,4-oxadiazoles: triflic anhydride promoted cyclization of diacylhydrazines. Synth. Commun., 2000, 30, 437-43.
14. Cesarini, S.; Colombo, N.; Pulici, M.; Felder, E.R. Brill, W.K.D. 1,3,4-Oxadiazole formation as traceless release in solid phase organic synthesis. Tetrahedron, 2006, 62, 10223-36.
15. Carlsen, H.J.; Jorgensen, K.B. Synthesis of unsymmetrically substituted 4H-1,2,4-Triazoles. J. Heterocycl. Chem., 1994, 31, 805-7.
16. Chambers, W.J.; Coffman, D.D. Synthesis of 2,5- Bis(polyfluoroalkyl)-1,3,4-oxadiazoles and -thiadiazoles. J. Org. Chem., 1961, 26, 4410-2
17. Kain, L.E.; Menestrel, I.L.; Morgentin, R. Trichloroacetic acid hydrazones I: New formation of 1,3,4-oxadiazoles from aldehydes. Tetrahedron Lett., 1998, 39, 6885-8.
18. Talib, M.A.; Tashtoush, H.; Odeh, N. A convenient synthesis of alkyl and aryl substituted bis-1,3,4-oxadiazoles. Synth. Commun., 1990, 20, 1811-7.
19. Kerr, V.N.; Ott, D.G.; Hayes, F.N. Quaternary Salt Formation of Substituted Oxazoles and Thiazoles. J. Am. Chem. Soc., 1960, 82, 186-9.
20. Cao, S.; Qian, X.; Song, G.; Huang, Q. Syntheses and insecticidal activity of new 2-(5-(trifluoromethyl)pyridyloxymethyl)-1,3,4- oxadiazoles. J. Fluorine Chem., 2002, 117, 63-6.
21. Theocharis, A.B.; Alexandrou, N.E. Synthesis and spectral data of 4,5-bis[5-aryl-1,3,4-oxadiazoles -2-yl-1-benzyl-1,2,3-triazoles. J. Heterocycl. Chem., 1990, 27, 1685-8.
22. Klinsberg, E. Synthesis of Carboxylic Acid Hydrazides and s-Triazoles of the Anthraquinone Series. J. Am. Chem. Soc., 1958, 80, 5786-9.
23. Poindexter, G.S.; Bruce, M.A.; Breitenbucher, J.G.; Higgins, M.A.; Sit, S.Y.; Romine, J.I.; Marin, S.W.; Ward, S.A.; McGovern, R.T.; Clarke, W.; Russell, J.; Zimanyi, I.A. Dihydropyridine neuropeptide Y Y1 receptor antagonists 2: bioisosteric urea replacements. Bioorg. Med. Chem., 2004, 12, 507-21.
24. Hayes, F.N.; Rogers, B.S.; Ott, D.G. 2,5-Diaryloxazoles and 2,5- Diaryl-1,3,4-oxadiazoles. J. Am. Chem. Soc., 1955, 77, 1850-2.
25. Wang, C.; Pålsson, L.O.; Batsanov, A.S.; Bryce, M.R. Molecular Wires Comprising α-Extended Ethynyl- and Butadiynyl-2,5- Diphenyl-1,3,4-Oxadiazole Derivatives: Synthesis, Redox, Structural, and Optoelectronic Properties. J. Am. Chem. Soc., 2006, 128, 3789-99.
26. Shi, W.; Qian, X.; Song, G.; Zhang, R.; Li, R. Syntheses and insecticidal activities of novel 2-fluorophenyl-5-aryl/cyclopropyl- 1,3,4-oxadiazoles. J. Fluorine Chem., 2000, 106, 173-9.
27. Short, F.W.; Long, L.M. Synthesis of 5-aryl-2-oxazolepropionic acids and analogs antiinflammatory. J. Heterocycl. Chem., 1969, 6, 707-12.
28. Sharma, S.; Srivastava, V.K.; Kumar, A. Newer N-substituted anthranilic acid derivatives as potent anti-inflammatory agents. Eur. J. Med. Chem., 2002, 37, 689-97.
29. Tully, W.R.; Cardner, C.R.; Gillespie, R.J.; Westwood, R. 2- (oxadiazolyl)- and 2-(thiazolyl)imidazo[1,2-apyrimidines as agonists and inverse agonists at benzodiazepine receptors. J. Med. Chem., 1991, 34, 2060-7.
30. Kwak, C.K.; Leeb, C.H.; Lee, T.S. A new series of 2,5-bis(4- methylphenyl)-1,3,4-oxadiazole derivatives: their synthesis and fluorescence properties for anion sensors. Tetrahedron Lett., 2007, 48, 7788-92.
31. Tang, H.; Song, N.; Gao, Z.; Chen, X.; Fan, X.; Xiang, Q.; Zhou, Q. Synthesis and properties of 1,3,4-oxadiazole-containing highperformance bismaleimide resins. Polymer, 2007, 48, 129-38.
32. Sauer, J.; Huisgen, R.; Sturm, H.J. Zur acylierung von 5-aryltetrazolen; ein duplikationsverfahren zur darstellung von polyarylen. Tetrahedron, 1960, 11, 241-51.
33. Kangani, C.O.; Kelleya, D.E.; Day, B.W.; One pot direct synthesis of oxazolines, benzoxazoles, and oxadiazoles from carboxylic acids using the Deoxo-Fluor reagent. Tetrahedron Lett., 2006, 47, 6497-9.
34. Rajapakse, H.A.; Zhu, H.; Young, M.B.; Mott, B.T. A mild and efficient one pot synthesis of 1,3,4-oxadiazoles from carboxylic acids and acyl hydrazides. Tetrahedron Lett., 2006, 47, 4827-30.
35. Narayana, B.; Ashalatha, B.V.; Raj, K.K.V.; Fernandesb, J.; Sarojini, B.K. Synthesis of some new biologically active 1,3,4- oxadiazolyl nitroindoles and a modified Fischer indole synthesis of ethyl nitro indole-2-carboxylates. Bioorg. Med. Chem., 2005, 13, 4638-44.
36. Wang, Y.; Sauer, D.R.; Djuric, S.W. A simple and efficient one step synthesis of 1,3,4-oxadiazoles utilizing polymer-supported reagents and microwave heating. Tetrahedron Lett., 2006, 47, 105-8.
37. Coppo, F.T.; Evans, K.A.; Graybill, T.L.; Burton, G. Efficient onepot preparation of 5-substituted-2-amino-1,3,4-oxadiazoles using resin-bound reagents. Tetrahedron Lett., 2004, 45, 3257-60.
38. Chekler, E.L.P.; Elokdah, H.M.; Butera, J. Efficient one-pot synthesis of substituted 2-amino-1,3,4-oxadiazoles. Tetrahedron Lett., 2008, 49, 6709-11.
39. Liu, Z.; Zhao, J.; Huang, X. Solid-phase synthesis of 1,3,4- oxadiazoline-5-thione derivatives from resin-bound acylhydrazines. Bioorg. Med. Chem. Lett., 2006, 16, 1828-30.
40. Polshettiwar, V.; Varma, R.S. Greener and rapid access to bioactive heterocycles: one-pot solvent-free synthesis of 1,3,4- oxadiazoles and 1,3,4-thiadiazoles. Tetrahedron Lett., 2008, 49, 879-83.
41. Barreiro, G.; Kim, J.T.; Guimaraes, C.R.; Bailey, C.M.; Domaoal, R.A.; Wang, L.; Anderson, K.S.; Jorgensen, W.L. From docking false-positive to active anti-HIV agent. J. Med. Chem., 2007, 50, 5324-9.
42. Jorgensen, W.L. Efficient drug lead discovery and optimization. Acc. Chem. Res., 2009, 42, 724-33.
43. Zeevaart, J.G.; Wang, L.; Thakur, V.V.; Leung, C.S.; Tirado-Rives, J.; Bailey, C.M.; Domaoal, R.A.; Anderson, K.S.; Jorgensen, W.L. Optimization of azoles as anti-human immunodeficiency virus agents guided by free-energy calculations. J. Am. Chem. Soc., 2008, 130, 9492-9.
44. Lansdon, E.B.; Brendza, K.M.; Hung, M.; Wang, R.; Mukund, S.; Jin, D.; Birkus, G.; Kutty, N.; Liu, X. Crystal structures of HIV-1 reverse transcriptase with etravirine (TMC125) and rilpivirine (TMC278): implications for drug design. J. Med. Chem., 2010, 53, 4295-9.
45. Silvestri, M.A.; Nagarajan, M.; De Clercq, E.; Pannecouque, C.; Cushman, M. Design, synthesis, anti-HIV activities, and metabolic stabilities of alkenyldiarylmethane (ADAM) non-nucleoside reverse transcriptase inhibitors. J. Med. Chem., 2004, 47, 3149-62.
46. Deng, B.L.; Hartman, T.L.; Buckheit, R.W. Jr.; Pannecouque, C.; De Clercq, E.; Fanwick, P.E.; Cushman, M. Synthesis, anti-HIV activity, and metabolic stability of new alkenyldiarylmethane HIV- 1 non-nucleoside reverse transcriptase inhibitors. J. Med. Chem., 2005, 48, 6140-55.
47. Zhan, P.; Li, Z.; Liu, X. Cosalane and its analogues: a unique class of anti-HIV agents. Mini. Rev. Med. Chem., 2010, 10, 966-76.
48. Cullen, M.D.; Deng, B.L.; Hartman, T.L.; Watson, K.M.; Buckheit, R.W. Jr.; Pannecouque, C.; Clercq, E.D.; Cushman, M. Synthesis and biological evaluation of alkenyldiarylmethane HIV-1 nonnucleoside reverse transcriptase inhibitors that possess increased hydrolytic stability. J. Med. Chem., 2007, 50, 4854-67.
49. Cullen, M.D.; Ho, W.C.; Bauman, J.D.; Das, K.; Arnold, E.; Hartman, T.L.; Watson, K.M.; Buckheit, R.W.; Pannecouque, C.; De Clercq, E.; Cushman, M. Crystallographic study of a novel subnanomolar inhibitor provides insight on the binding interactions of alkenyldiarylmethanes with human immunodeficiency virus-1 reverse transcriptase. J. Med. Chem., 2009, 52, 6467-73.
50. Aquino, C.J.; Dickson, H.; Peat, A.J. Preparation of 1,3,4- oxadiazoles as a non-nucleoside reverse transcriptase inhibitor for treating human immunodeficiency virus infection. WO2008157330 A1, 2008.
51. Serrao, E.; Odde, S.; Ramkumar, K.; Neamati, N. Raltegravir, elvitegravir, and metoogravir: the birth of me-too HIV-1 integrase inhibitors. Retrovirology, 2009, 6, 25.
52. Hombrouck, A.; Voet, A.; Van Remoortel, B.; Desadeleer, C.; De Maeyer, M.; Debyser, Z.; Witvrouw, M. Mutations in human immunodeficiency virus type 1 integrase confer resistance to the naphthyridine L-870,810 and cross-resistance to the clinical trial drug GS-9137. Antimicrob. Agents Chemother., 2008, 52, 2069-78.
53. Sato, M.; Motomura, T.; Aramaki, H.; Matsuda, T.; Yamashita, M.; Ito, Y.; Kawakami, H.; Matsuzaki, Y.; Watanabe, W.; Yamataka, K.; Ikeda, S.; Kodama, E.; Matsuoka, M.; Shinkai, H. Novel HIV-1 integrase inhibitors derived from quinolone antibiotics. J. Med. Chem., 2006, 49, 1506-8.
54. Johns, B.A.; Weatherhead, J.G.; Allen, S.H.; Thompson, J.B.; Garvey, E.P.; Foster, S.A.; Jeffrey, J.L.; Miller, W.H. The use of oxadiazole and triazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 1: Establishing the pharmacophore. Bioorg. Med. Chem. Lett., 2009, 19, 1802-6.
55. Johns, B.A.; Weatherhead, J.G.; Allen, S.H.; Thompson, J.B.; Garvey, E.P.; Foster, S.A.; Jeffrey, J.L.; Miller, W.H. 1,3,4- Oxadiazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 2: SAR of the C5 position. Bioorg. Med. Chem. Lett., 2009, 19, 1807-10.
56. Kim, R.M.; Rouse, E.A.; Chapman, K.T.; Schleif, W.A.; Olsen, D.B.; Stahlhut, M.; Rutkowski, C.A.; Emini, E.A.; Tata, J.R. P1' oxadiazole protease inhibitors with excellent activity against native and protease inhibitor-resistant HIV-1. Bioorg. Med. Chem. Lett., 2004, 14, 4651-4.
57. Zhang, F.; Chapman, K.T.; Schleif, W.A.; Olsen, D.B.; Stahlhut, M.; Rutkowski, C.A.; Kuo, L.C.; Jin, L.; Lin, J.H.; Emini, E.A.; Tata, J.R. The design, synthesis and evaluation of novel HIV-1 protease inhibitors with high potency against PI-resistant viral strains. Bioorg. Med. Chem. Lett., 2003, 13, 2573-6.
58. Duffy, J.L.; Kirk, B.A.; Kevin, N.J.; Chapman, K.T.; Schleif, W.A.; Olsen, D.B.; Stahlhut, M; Rutkowski, C.A.; Kuo, L.C.; Jin, L.; Lin, J.H.; Emini, E.A.; Tata, J.R. HIV-1 protease inhibitors with picomolar potency against PI-resistant HIV-1 by modification of the P1' substituent. Bioorg. Med. Chem. Lett., 2003, 13, 3323-6.
59. Emam, A.A.E.; Deeb, O.A.A.; Omar, M.A.; Lehmann, J. Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamantyl)- 2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3- substituted aminomethyl-1,3,4-oxadiazoline-2-thiones. Bioorg. Med. Chem., 2004, 12, 5107-13.
60. Ahgren, C.; Backro, K.; Bell, F.W.; Cantrell, A.S.; Clemens, M.; Colacino, J.M.; Deeter, J.B.; Engelhardt, J.A.; Hogberg, M.; Jaskunas, S.R.; Johansson, N.G.; Jordan, C.L.; Kasher, J.S.; Kinnick, M.D.; Lind, P.; Lopez, C.; Morin, J.A.M., Jr.; Muesing, M.A.; Noreen, R.; Oberg, B.; Paget, C.J.; Palkowitz, J.A.; Parrish, C.A.; Pranc, P.; Rippy, M.K.; Rydergard, C.; Sahlberg, C.; Swanson, S.; Ternansky, R.J.; Unge, T.; Vasileff, R.T.; Vrang, L.; West, S.L.; Zhang, H.; Zhou, X. X. The PETT series, a new class of potent nonnucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. Antimicrob. Agents Chemother., 1995, 39, 1329-35.
61. Iqbal, R.; Zareef, M.; Ahmed, S.; Zaidi, J.H.; Arfan, M.; Shafique, M.; Masoudi, N.A.A. Synthesis, Antimicrobial and Anti-HIV Activity of Some Novel Benzenesulfonamides Bearing 2,5- Disubstituted-1,3,4-oxadiazole Moiety. J. Chin. Chem. Soc., 2006, 53, 689-96.
62. Liverton, N.J.; Holloway, M.K.; McCauley, J.A.; Rudd, M.T.; Butcher, J.W.; Carroll, S.S.; DiMuzio, J.; Fandozzi, C.; Gilbert, K.F.; Mao, S.S.; McIntyre, C.J.; Nguyen, K.T.; Romano, J.J.; Stahlhut, M.; Wan, B.L.; Olsen, D.B.; Vacca, J.P. Molecular modeling based approach to potent P2-P4 macrocyclic inhibitors of hepatitis C NS3/4A protease. J. Am. Chem. Soc., 2008, 130, 4607-9.
63. Di Francesco, M.E.; Dessole, G.; Nizi, E.; Pace, P.; Koch, U.; Fiore, F.; Pesci, S.; Di Muzio, J.; Monteagudo, E.; Rowley, M.; Summa, V. Novel macrocyclic inhibitors of hepatitis C NS3/4A protease featuring a 2-amino-1,3-thiazole as a P4 carbamate replacement. J. Med. Chem., 2009, 52, 7014-28.
64. Tan, T.M.; Chen, Y.; Kong, K.H.; Bai, J.; Li, Y.; Lim, S.G.; Ang, T.H.; Lam, Y. Synthesis and the biological evaluation of 2- benzenesulfonylalkyl-5-substituted-sulfanyl-[1,3,4-oxadiazoles as potential anti-hepatitis B virus agents. Antiviral Res., 2006, 71, 7-14.
65. Barradas, J.S.; Errea, M.I.; D'Accorso, N.B.; Sepúlveda, C.S.; Talarico, L.B.; Damonte, E.B. Synthesis and antiviral activity of azoles obtained from carbohydrates. Carbohydr. Res., 2008, 343, 2468-74.
66. Abdel-Aal, M.T.; El-Sayed, W.A.; El-Kosy, S.M.; El-Ashry el, S.H. Synthesis and antiviral evaluation of novel 5-(N-Arylaminomethyl- 1,3,4-oxadiazol-2-yl)hydrazines and their sugars, 1,2,4-triazoles, tetrazoles and pyrazolyl derivatives. Arch. Pharm. (Weinheim), 2008, 341, 307-13.
67. Zhan, P.; Li, D.; Chen, X.; Liu, X.; De Clercq, E. Functional roles of azoles motif in anti-HIV agents. Curr. Med. Chem., 2011, 18, 29-46.