Pyrazole containing natural products: Synthetic preview and biological significance

European Journal of Medicinal Chemistry

Volumn 69, Issue , 2013, Pages 735-753

  Kumar, Vinod ^a   Kaur, Kamalneet ^a   Gupta, Girish Kumar ^a   Sharma, Anil Kumar ^a  

^a MAHARISHI MARKANDESHWAR DEEMED TO BE UNIVERSITY   (India)

Author keywords

Isolation; Natural products; Pharmacological activities; Pyrazoles

Indexed keywords

3 N NONYLPYRAZOLE; 4 HYDROXYWITHASOMNINE; 4 METHOXYWITHASOMNINE; 4 METHYL PYRAZOLE 3(5) CARBOXYLIC ACID; FLUVIOL A; FLUVIOL B; FLUVIOL C; FLUVIOL D; FLUVIOL E; FORMYCIN; LEVO ALPHA AMINO BETA(PYRAZOLY N)PROPANOIC ACID; NATURAL PRODUCT; NOSTOCINE A; OXOFORMYCIN; PIRAZOFURIN; PIRAZOFURIN B; PYRAZOLE 3(5) CARBOXYLIC ACID; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG; WITHASOMNINE;

ALKYLATION; ANTIDIABETIC ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; AYURVEDA; BROMINATION; CHLORINATION; CLEMMENSEN REDUCTION; CURTIUS REARRANGEMENT; CYCLIZATION; CYCLOADDITION; DEAMINATION; DEBENZYLATION; DIAZOTIZATION; DRUG CYTOTOXICITY; ENANTIOMER; HUMAN; HYDROBORATION; HYDROGENATION; MELTING POINT; METHANOLYSIS; MICHAEL ADDITION; MICROWAVE IRRADIATION; NONHUMAN; OXIDATION REDUCTION REACTION; PHOTOLYSIS; RACEMIC MIXTURE; REVIEW; RING OPENING; ROOM TEMPERATURE; STRECKER SYNTHESIS; WITTIG REACTION;

ISOLATION; NATURAL PRODUCTS; PHARMACOLOGICAL ACTIVITIES; PYRAZOLES;

ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; BIOLOGICAL PRODUCTS; HYPOGLYCEMIC AGENTS; MOLECULAR STRUCTURE; PYRAZOLES;

EID: 84884931642     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.08.053     Document Type: Review

References (80)

1. J. Watchueng, P. Kamnaing, J.M. Gao, T. Kiyota, F. Yeboah, and Y. Konishi Efficient purification of paclitaxel from yews using high-performance displacement chromatography technique J. Chromatogr. A. 1218 2011 2929 2935
2. V. Dhingra, K.V. Rao, and M.L. Narasu Current status of artemisinin and its derivatives as antimalarial drugs Life Sci. 66 1999 279 300
3. J. Ziegler, P.J. Facchini, R. Geibler, J. Schmidt, C. Ammer, R. Kramell, S. Voigtlander, A. Gesell, S. Pienknya, and W. Brandt Evolution of morphine biosynthesis in opium poppy Phytochemistry 70 2009 1696 1707
4. H.W. Kreglewska Antimalarial medications from native remedy Cent. Eur. J. Immunol. 36 2011 100 103
5. A. Gomes, B. Giri, A. Saha, R. Mishra, S.C. Dasgupta, A. Debnath, and A. Gomes Bioactive molecules from amphibian skin: their biological activities with reference to therapeutic potentials for possible drug development Indian J. Exp. Biol. 45 2007 579 593
6. Z. Jin Muscarine, imidazole, oxazole and thiazole alkaloids J. Nat. Prod. 20 2003 584 605 (Pubitemid 38024763)
7. J.R. Wisner Jr., and I.G. Renner Asperlicin, a nonpeptidal cholecystokinin receptor antagonist, attenuates sodium taurocholate-induced acute pancreatitis in rats Pancreas 3 1988 174 179
8. M.E. Osman, O.H. Khattab, G.M. Zaghlol, and R.M. Abd El-Hameed Screening for the production of cholesterol lowering drugs (lovastatin) by some Fungi Aust. J. Basic Appl. Sci. 5 2011 698 703
9. A.D. Rodriguez, and I.C. Pina The structures of aplysinamisines I, II, III: new bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina cauliformis J. Nat. Prod. 56 1993 907 914 (Pubitemid 23195619)
10. A.M. Vijesh, A.M. Isloor, P. Shetty, S. Sundershan, and H.K. Fun New pyrazole derivatives containing 1,2,4-triazoles and benzoxazoles as potent antimicrobial and analgesic agents Eur. J. Med. Chem. 62 2013 410 415
11. V. Kumar, R. Aggarwal, and P. Tyagi Synthesis and antibacterial activity of some new 1-heteroaryl-5-mino-4-phenyl-3-trifluoromethylpyrazoles Eur. J. Med. Chem. 40 2005 922 927 (Pubitemid 41376307)
12. R. Aggarwal, V. Kumar, P. Tyagi, and S.P. Singh Synthesis and antibacterial activity of some new 1-heteroaryl-5-amino-3H/methyl-4- phenylpyrazoles Bioorg. Med. Chem. 14 2006 1785 1791 (Pubitemid 43199511)
13. V. Kumar, K. Kaur, G.K. Gupta, and S. Kumar Developments in synthesis of the anti-inflammatory drug, celecoxib: a review Recent Pat Inflamm. Allergy Drug Discov. 7 2013 124 134
14. R. Aggarwal, V. Kumar, and S.P. Singh Synthesis of some new 1-(6-fluorobenzothiazol-2-yl)-3-(4-fluoro-phenyl)-5-arylpyrazolines and their iodine(III) mediated oxidation to corresponding pyrazoles Indian J. Chem. Sect. B 46 2007 1332 1336
15. S.P. Singh, R. Aggarwal, and V. Kumar Synthesis and NMR spectral studies of new 1-heteroaryl-5-amino-4-cyano-3-alkyl/arylpyrazoles Indian J. Chem. Sect. B 45 2006 1426 1430 (Pubitemid 44090345)
16. R. Aggarwal, V. Kumar, R. Kumar, and S.P. Singh Approaches towards the synthesis of 5-aminopyrazoles Beilstein J. Org. Chem. 7 2011 179 197
17. P. Singh, K. Paul, and W. Holzer Synthesis of pyrazole - based hybrid molecules: search for potent multidrug resistance modulators Bioorg. Med. Chem. 14 2006 5061 5071 (Pubitemid 43767121)
18. U. Tiwari, C. Ameta, M.K. Ranwal, R. Ameta, and P.B. Punjabi MW assisted synthesis of some pyrazoles containing benzotriazole moiety: an environmentally benign approach Indian J. Chem. Sect. B Org. Chem. Incl. Med. Chem. 52 2013 432 439
19. M. Suri, T. Jousseaume, J.J. Neumann, and F. Glorius An efficient copper-catalyzed formation of highly substituted pyrazoles using molecular oxygen as the oxidant Green Chem. 14 2012 2193 2196
20. E.G. Brown, and F.M. Diffin Biosynthesis and metabolism of pyrazole by Cucumis sativas: enzymic cyclization and dehydrogenation of 1,3-diaminopropane Phytochemistry 29 1990 469 478
21. E.G. Brown, K.A.M. Flayeh, and J.R. Gallon The biosynthetic origin of the pyrazole moiety of β-pyrazol-1-yl-l-alanine Phytochemistry 21 1982 863 867
22. N.C. Seeman, E.L. McGandy, and R.D. Rosenstein Crystal and molecular structure of beta-(3-pyrazolyl)-l-alanine J. Am. Chem. Soc. 94 1972 1717 1720
23. F.F. Noe, and L. Fowden α-Amino-β-(pyrzolyl-N)propanoic acid: a new amino acid from Citrullus vulgaris (water melon) Nature 184 1959 B.A.69 B.A.70
24. N. Sugimoto, H. Watanbe, and A. Ide The synthesis of l-α-amino- β-(pyrazolyl-N)-propanoic acid in Citrullus vulgaris Tetrahedron 11 1960 231 233
25. I. Chibata, T. Ishikawa, and S. Yamada Studies of amino acids. VIII Bull. Agric. Chem. Soc. Jpn. 21 1957 304 307
26. C.N. Farthing, J.E. Baldwin, A.T. Russell, J. Schofield, and A.C. Spivey Synthesis of (S)-β-pyrazolylalanine and (S)-quisqualic acid from a serine-derived aziridine Tetrahedron Lett. 37 1995 5225 5226 (Pubitemid 26288764)
27. V. Rolland-Fulcrand, N. Haroune, M.L. Roumestant, and J. Martinez Efficient chemoenzymatic synthesis of enatiomerically pure β-heterocyclic amino acid derivatives Tetrahedron Asymmetry 11 2000 4719 4724 (Pubitemid 32332828)
28. L.D. Arnold, R.G. May, and J.C. Vederas Synthesis of optically pure α-amino acids via salts of α-amino-β-propiolactone J. Am. Chem. Soc. 110 1988 2237 2241
29. P.M.T. Ferreira, H.L.S. Maia, and L.S. Monteiro High yielding synthesis of heterocyclic-β-substituted alanine derivatives Tetrahedron Lett. 40 1999 4099 4102 (Pubitemid 29225820)
30. A. Schmidt, and A. Dregar Recent advances in the chemistry of pyrazoles, properties, biological activities, and syntheses Curr. Org. Chem. 15 2011 1423 1463
31. H.B. Schroter, and D. Neumann Withasomnine a pyrazole alkaloid from withania somifera dun Tetrahedron 22 1966 2895 2897
32. 4 and COX-1 and -2 inhibitory activities Phytochemistry 69 2008 982 987
33. 3SnH-mediated radical cyclization onto azoles Tetrahedron 64 2008 7745 7758
34. A.J. Aladesanmi, R. Nia, and A. Nahrstedt New pyrazole alkaloids from the root bark of Newbouldia laevis Planta Med. 64 1998 90 91 (Pubitemid 28060012)
35. M. Pangerl, C.C. Hughes, and D. Trauner Total synthesis of newbouldine via reductive N-N bond formation Tetrahedron 66 2010 6626 6631
36. V. Ravikanth, P. Ramesh, P.V. Diwan, and Y. Venkateswarlu Pyrazole alkaloids from Elytraria acaulis Biochem. Syst. Ecol. 29 2001 753
37. O. Kulinkovich, N. Masalov, and V. Tyvorskii New synthetic route to the alkaloid withasomnine by ring transformation of a functionalized cyclopropanol via the parent pyrrolo[1, 2-b] pyrazole Tetrahedron 37 1996 1095 1096 (Pubitemid 26053415)
38. S. Majumder, K.R. Gipson, R.J. Staples, and A.L. Odom Pyrazole synthesis using a titanium-catalyzed multicomponent coupling reaction and synthesis of withasomnine Adv. Synth. Catal. 351 2009 2013 2023
39. R. Kumar, and I.N.N. Namboothiri Regioselective synthesis of sulfonylpyrazoles via base mediated reaction of diazosulfones with nitroalkene an a facile entry into withasomnine Org. Lett. 13 2011 4016 4019
40. R.S. Foster, J. Huang, J.F. Vivat, D.L. Browne, and J.P.A. Harrity A divergent strategy to the withasomnines Org. Biomol. Chem. 7 2009 4052 4056
41. H. Ichikawa, R. Watanbe, Y. Fujino, and Y. Usami Divergent synthesis of withasomnines via synthesis of 4-hydroxy-1H-pyrazoles and Claisen rearrangement of their 4-O-allylethers Tetrahedron Lett. 52 2011 4448 4451
42. S.M. Allin, W.R.S. Barton, W.R. Bowman, and T. McInally Radical cyclisation onto pyrazoles: synthesis of withasomnine Tetrahedron Lett. 43 2002 4191 4193 (Pubitemid 34603182)
43. A. Morimoto, K. Noda, T. Watanbe, and H. Takasugi Radical cyclisation onto pyrazoles: synthesis of withasomnine Tetrahedron Lett. 9 1968 5707 5710
44. D. Verma, R. Kumar, and I.N.N. Namboothiri Synthesis of withasomnines and their non-natural analogues from aldehydes and 4-nitro-1-butanol in three steps J. Org. Chem. 78 2013 3482 3486
45. S.A. Adesanya, R. Nia, C. Fontaine, and M. Pais Pyrazole alkaloids from Newbouldia laevis Phytochemistry 35 1994 1053 1055 (Pubitemid 2054703)
46. P.F. Crain, J.A. McCloskey, A.F. Lewis, K.H. Schram, and L.B. Townsend Mass spectra of C-nucleosides II. An unusual fragmentation reaction of the heterocyclic J. Heterocyclic Chem. 10 1973 843 847
47. G.E. Gutowski, M.O. Chaney, R.L. Jones, R.L. Hamil, F.A. Davis, and R.D. Miller Pyrazomycin B: isolation and characterization of an α-C-nucleoside antibiotic related to pyrazomycin Biochem. Biophys. Res. Commun. 51 1973 312 317
48. K. Mizuno, M. Takada, M. Hayashi, K. Atsumi, K. Asano, and T. Matsuda Studies on bredinin. I. Isolation, characterization and biological properties J. Antibiot. 27 1974 775 782
49. J.T. Witkowski, R.K. Robins, R.W. Sidwell, and L.N. Simon Design, synthesis, and broad spectrum antiviral activity of 1-beta-d-ribofuranosyl-1,2, 4-triazole-3-carboxamide and related nucleosides J. Med. Chem. 15 1972 1150 1154
50. C.R. Petrie, G.R. Revankar, N.K. Dalley, R.D. George, P.A. McKernan, R.L. Hamill, and R.K. Robins Synthesis and biological activity of certain nucleoside and nucleotide derivatives of pyrazofurin J. Med. Chem. 29 1986 268 278 (Pubitemid 16181612)
51. W.M. Shannon Selective inhibition of RNA tumor virus replication in vitro and evaluation of candidate antiviral agents in vivo Ann. N. Y. Acad. Sci. 284 1977 472 507 (Pubitemid 8067783)
52. M.J. Sweeney, F.A. Davis, G.E. Gutowski, R.L. Hamill, D.H. Hoffman, and G.A. Poore Experimental antitumor activity of pyrazomycin Cancer Res. 33 1973 2619 2623
53. J. Farkas, Z. Flegelova, and F. Sorm Synthesis of pyrazomycin Tetrahedron Lett. 13 1972 2279 2280
54. J.G. Buchanan, A. Stobie, and R.H. Wightman A new synthesis of pyrazofurin J. Chem. Soc. Chem. Commun. 1980 916 917
55. N. Karagiri, K. Takashima, T. Haneda, and T. Kato Synthesis of pyrazofurin and its analogues J. Chem. Soc. Perkin Trans. 1 0 1984 553 560
56. S.D. Bernardo, and M. Weigele A synthesis of the pyrazomycin J. Org. Chem. 41 1976 287 290
57. J.G. Buchanan, M.R. Hamblin, G.R. Sood, and R.H. Wightman The biosynthesis of pyrazofurin and formycin J. Chem. Soc. Chem. Commun. 1980 917 918
58. G. Koyama, K. Maeda, and H. Umezawa The structural studies of formycin and formycin b Tetrahedron Lett. 7 1966 597 602
59. K. Ochi, S. Iwamoto, E. Hayase, S. Yashima, and Y. Okami Biosynthesis of formycin role of amino acids in formycin biosynthesis J. Antibiot. 27 1974 909 916
60. N. Otake, S. Aizawa, T. Hidhaka, H. Seto, and H. Yonehara Biological and chemical transformations of formycin to laurusin Agric. Biol. Chem. 29 1965 377 378
61. J.G. Buchanan, A.R. Edgar, R.J. Hutchison, A. Stobie, and R.H. Wightman A new synthesis of formycin via nitropyrazole derivatives J. Chem. Soc. Chem. Commun. 1980 237 238
62. W.E.G. Muller, H.J. Rohde, R. Steffen, A. Maidhof, M. Lachmann, R.K. Zahn, and H. Umezawa Influence of formycin B on polyadenosine diphosphoribose synthesis in vitro and in vivo Cancer Res. 35 1975 3673 3681
63. T. Sawa, Y. Fukagawa, I. Homma, T. Wakashiro, T. Takeuchi, and M. Hori Metabolic conversion of formycin B to formycin A and to oxoformycin B in Nocardia interforma J. Antibiot. 21 1968 334 339
64. R.P. Ozha, M. Roychoudhury, and N.K. Sanyal Interaction energy studies on pyrazolopyrimidine nucleoside antibiotics-A theoretical study: oxoformycin B J. Biosci. 12 1987 311 320
65. J. Wierzchowski, J. Kusmierek, J. Giziewicz, D. Salvi, and D. Shugar Analogues of formycins A and B: synthesis and some properties of methyl derivatives of 7-amino and 7-keto pyrazolo[4,3-d] pyrimidines Acta Biochim. Pol. 27 1980 35 56
66. M.R. Sheen, H.F. Martin, and R.E. Parks Jr. The interaction of the nucleoside analogues, formycin A and B with xanthine oxidase and hepatic aldehyde oxidase Mol. Pharmacol. 6 1970 255 265
67. I. Tsukada, T. Kunimoto, M. Hori, and T. Komai Isolation and properties of the enzyme which catalyzes the oxidation of formycin B J. Antibiot. 22 1969 36 38
68. J.G. Buchanan, A.O. Jurnash, G. Kerr, and R.R. Talekar C-Nucleoside studies. Part 22. Cine substitution in 1,4-dinitropyrazoles: further model studies, an improved synthesis of formycin and pyrazofurin and the synthesis of some 3(5)-alkylsulphonyl-4-amino-5(3)-β-d-ribofuranosylpyrazoles J. Chem. Soc. Perkin Trans. 1991 1077 1083
69. R.A. Long, A.F. Lewis, R.K. Robins, and L.B. Townsend Pyrazolopyrimidine nucleosides. Part-II. 7-substituted 3-β-d-ribofuranosylpyrazolo[4,3-d] pyrimidines related to and derived from the nucleoside antibiotic formycin and formycin B J. Chem. Soc. C 1971 2443 2446
70. L. Kalvoda The synthesis of pyrazoles a simple preparative synthesis of C-nucleoside antibiotic formycin and formycin B Collect. Czech. Chem. Commun. 43 1978 1431 1437 (Pubitemid 8365374)
71. E.D. Acton, K.J. Ryan, D.W. Henry, and L. Goodman Synthesis of the nucleoside antibiotic formycin B Chem. Commun. 1971 986 988
72. J. Farkas, and F. Sorm Nucleic acid components and their analogues. Synthesis of 3-(β-d-ribofuranosyl)-5,7-dihydroxy-1H-pyrazolo[4,3-d] pyrimidine (oxoformycin) Collect. Czech. Chem. Commun. 37 1972 2798 2803
73. K. Hirata, S. Yoshitoml, S. Dwi, O. Iwabe, A. Mahakhant, J. Polchai, and K. Miyamoto Bioactivities of nostocine A produced by a freshwater cyanobacterium Nostoc spongiaeforme TISTR 8169 J. Biosci. Bioeng. 95 2003 512 517 (Pubitemid 36688176)
74. K. Hirata, S. Yoshitoml, S. Dwi, O. Iwabe, A. Mahakhant, J. Polchai, and K. Miyamoto Generation of reactive oxygen species undergoing redox cycle of nostocine A: a cytotoxic violet pigment produced by fresh water cyanobacterium Nostoc spongiaeforme J. Biotechnol. 110 2004 29 35 (Pubitemid 38510251)
75. V.V. Smirnov, E.A. Kiprianova, A.D. Garagulya, S.E. Esipov, and S.A. Dovjenko Fluviols, bicyclic nitrogen rich antibiotics produced by pseudomonas fluorescens FEMS Microbiol. Lett. 153 1997 357 361 (Pubitemid 27359732)
76. T.S. Kelly, E.L. Elliott, R. Lebedav, and J. Pagalday Synthesis of the pyrazolo [4,3-e] triazine family of natural products: nostocine A, fluviol A, and pseudoiodinine J. Am. Chem. Soc. 128 2006 5646 5647 (Pubitemid 43724362)
77. M.J. Robins, and B. Uznanski Nucleic acid related compounds. 33. Conversions of adenosine and guanosine to 2,6-dichloro, 2-amino-6-chloro, and derived purine nucleosides Can. J. Chem. 59 1981 2601 2607 (Pubitemid 12209078)
78. P.S. Parameswaran, C.G. Naik, and V.R. Hegde Secondary metabolites from the sponge Tedania anhelans: isolation and characterization of two novel pyrazole acids and other metabolites J. Nat. Prod. 60 1997 802 803 (Pubitemid 27372006)
79. P.D. Mishra, S. Wahidullah, and S.Y. Karnat A heteroaromatic acid from marine sponge Suberites vestigium Indian J. Chem. Sect. B 37 1998 199 200 (Pubitemid 128485848)
80. T. Kosuage, and H. Okeda Nonylpyrazole, a new antimicrobial substance J. Biochem. 41 1954 183 186