Oxidative Reactivities of 2-Furylquinolines: Ubiquitous Scaffolds in Common High-Throughput Screening Libraries

Journal of Medicinal Chemistry

Volumn 58, Issue 18, 2015, Pages 7419-7430

  Olson, Margaret E ^a   Abate Pella, Daniel ^a   Perkins, Angela L ^a   Li, Ming ^a   Carpenter, Michael A ^a   Rathore, Anurag ^a   Harris, Reuben S ^a,b   Harki, Daniel A ^a,b  

^a UNIVERSITY OF MINNESOTA   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 FURYLQUINOLINE DERIVATIVE; ALDEHYDE; APOLIPOPROTEIN B MESSENGER RNA EDITING ENZYME CATALYTIC POLYPEPTIDE 3G; CARBOXYLIC ACID; ENDOPEROXIDE; FURAN; LACTAM; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; APOBEC3G PROTEIN, HUMAN; CYTIDINE DEAMINASE; DIMETHYL SULFOXIDE; FURAN DERIVATIVE; MOLECULAR LIBRARY; SOLUTION AND SOLUBILITY; THIADIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; CONFORMATIONAL TRANSITION; CYCLOADDITION; DRUG DECOMPOSITION; DRUG SCREENING; DRUG STRUCTURE; HIGH THROUGHPUT SCREENING; OXIDATION; ANTAGONISTS AND INHIBITORS; CHEMISTRY; DOSE RESPONSE; DRUG STABILITY; HEK293 CELL LINE; HELA CELL LINE; HUMAN; MOLECULAR LIBRARY; OXIDATION REDUCTION REACTION; SOLUTION AND SOLUBILITY; STRUCTURE ACTIVITY RELATION;

CYTIDINE DEAMINASE; DIMETHYL SULFOXIDE; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG STABILITY; FURANS; HEK293 CELLS; HELA CELLS; HIGH-THROUGHPUT SCREENING ASSAYS; HUMANS; OXIDATION-REDUCTION; QUINOLINES; SMALL MOLECULE LIBRARIES; SOLUTIONS; STRUCTURE-ACTIVITY RELATIONSHIP; THIADIAZOLES;

EID: 84942280010     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b00930     Document Type: Article

References (50)

1. Bibette, J. Gaining confidence in high-throughput screening Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 649-650 10.1073/pnas.1119350109
2. Inglese, J.; Shamu, C. E.; Guy, R. K. Reporting data from high-throughput screening of small-molecule libraries Nat. Chem. Biol. 2007, 3, 438-441 10.1038/nchembio0807-438
3. Baell, J. B. Observations on screening-based research and some concerning trends in the literature Future Med. Chem. 2010, 2, 1529-1546 10.4155/fmc.10.237
4. Baell, J. B.; Holloway, G. A. New substructure filters for removal of pan assay interference compounds (PAINS) from screening libraries and for their exclusion in bioassays J. Med. Chem. 2010, 53, 2719-2740 10.1021/jm901137j
5. Dahlin, J. L.; Nissink, J. W.; Strasser, J. M.; Francis, S.; Higgins, L.; Zhou, H.; Zhang, Z.; Walters, M. A. PAINS in the assay: chemical mechanisms of assay interference and promiscuous enzymatic inhibition observed during a sulfhydryl-scavenging HTS J. Med. Chem. 2015, 58, 2091-2113 10.1021/jm5019093
6. Hussain, J.; Harper, G.; Blaxill, Z.; Areri, I.; Saremi-Yarahmadi, F.; Pickett, S.; Sidebottom, P. Use of data mining to help identify compounds that are unstable in DMSO. In International Conference on Chemical Structures, Noordwijkerhout, The Netherlands, 2008; pp 58-59.
7. Baell, J.; Walters, M. A. Chemistry: Chemical con artists foil drug discovery Nature 2014, 513, 481-483 10.1038/513481a
8. Feng, B. Y.; Simeonov, A.; Jadhav, A.; Babaoglu, K.; Inglese, J.; Shoichet, B. K.; Austin, C. P. A high-throughput screen for aggregation-based inhibition in a large compound library J. Med. Chem. 2007, 50, 2385-2390 10.1021/jm061317y
9. Zitha-Bovens, E.; Maas, P.; Wife, D.; Tijhuis, J.; Hu, Q. N.; Kleinoder, T.; Gasteiger, J. COMDECOM: predicting the lifetime of screening compounds in DMSO solution J. Biomol. Screening 2009, 14, 557-565 10.1177/1087057109336953
10. Chen, A.; Zhao, X.; Mercer, L.; Su, C.; Zalameda, L.; Liu, Y.; Lembke, A.; Eastwood, H.; Dang, S.; Oung, T.; Xia, X.; Young, S. W.; Xiao, S.; McCarter, J. D. Assessment of the integrity of compounds stored in assay-ready plates using a kinase sentinel assay Comb. Chem. High Throughput Screening 2013, 16, 644-651 10.2174/13862073113169990145
11. Hermann, J. C.; Chen, Y.; Wartchow, C.; Menke, J.; Gao, L.; Gleason, S. K.; Haynes, N.-E.; Scott, N.; Petersen, A.; Gabriel, S.; Vu, B.; George, K. M.; Narayanan, A.; Li, S. H.; Qian, H.; Beatini, N.; Niu, L.; Gan, Q.-F. Metal impurities cause false positives in high-throughput screening campaigns ACS Med. Chem. Lett. 2013, 4, 197-200 10.1021/ml3003296
12. Johnston, P. A. Redox cycling compounds generate H2O2 in HTS buffers containing strong reducing reagents-real hits or promiscuous artifacts? Curr. Opin. Chem. Biol. 2011, 15, 174-182 10.1016/j.cbpa.2010.10.022
13. Soares, K. M.; Blackmon, N.; Shun, T. Y.; Shinde, S. N.; Takyi, H. K.; Wipf, P.; Lazo, J. S.; Johnston, P. A. Profiling the NIH Small Molecule Repository for compounds that generate H2O2 by redox cycling in reducing environments Assay Drug Dev. Technol. 2010, 8, 152-174 10.1089/adt.2009.0247
14. Rishton, G. M. Reactive compounds and in vitro false positive in HTS Drug Discovery Today 1997, 2, 382-384 10.1016/S1359-6446(97)01083-0
15. Kozikowski, B. A.; Burt, T. M.; Tirey, D. A.; Williams, L. E.; Kuzmak, B. R.; Stanton, D. T.; Morand, K. L.; Nelson, S. L. The effect of freeze/thaw cycles on the stability of compounds in DMSO J. Biomol. Screening 2003, 8, 210-215 10.1177/1087057103252618
16. Kozikowski, B. A.; Burt, T. M.; Tirey, D. A.; Williams, L. E.; Kuzmak, B. R.; Stanton, D. T.; Morand, K. L.; Nelson, S. L. The effect of room-temperature storage on the stability of compounds in DMSO J. Biomol. Screening 2003, 8, 205-209 10.1177/1087057103252617
17. Blaxill, Z.; Holland-Crimmin, S.; Lifely, R. Stability through the ages: the GSK experience J. Biomol. Screening 2009, 14, 547-556 10.1177/1087057109335327
18. Li, M.; Shandilya, S. M.; Carpenter, M. A.; Rathore, A.; Brown, W. L.; Perkins, A. L.; Harki, D. A.; Solberg, J.; Hook, D. J.; Pandey, K. K.; Parniak, M. A.; Johnson, J. R.; Krogan, N. J.; Somasundaran, M.; Ali, A.; Schiffer, C. A.; Harris, R. S. First-in-class small molecule inhibitors of the single-strand DNA cytosine deaminase APOBEC3G ACS Chem. Biol. 2012, 7, 506-517 10.1021/cb200440y
19. Stenglein, M. D.; Burns, M. B.; Li, M.; Lengyel, J.; Harris, R. S. APOBEC3 proteins mediate the clearance of foreign DNA from human cells Nat. Struct. Mol. Biol. 2010, 17, 222-229 10.1038/nsmb.1744
20. Albin, J. S.; Harris, R. S. Interactions of host APOBEC3 restriction factors with HIV-1 in vivo: implications for therapeutics Expert Rev. Mol. Med. 2010, 12, e4 10.1017/S1462399409001343
21. Refsland, E. W.; Stenglein, M. D.; Shindo, K.; Albin, J. S.; Brown, W. L.; Harris, R. S. Quantitative profiling of the full APOBEC3 mRNA repertoire in lymphocytes and tissues: implications for HIV-1 restriction Nucleic Acids Res. 2010, 38, 4274-4284 10.1093/nar/gkq174
22. Harris, R. S. Enhancing immunity to HIV through APOBEC Nat. Biotechnol. 2008, 26, 1089-1090 10.1038/nbt1008-1089
23. Burns, M. B.; Lackey, L.; Carpenter, M. A.; Rathore, A.; Land, A. M.; Leonard, B.; Refsland, E. W.; Kotandeniya, D.; Tretyakova, N.; Nikas, J. B.; Yee, D.; Temiz, N. A.; Donohue, D. E.; McDougle, R. M.; Brown, W. L.; Law, E. K.; Harris, R. S. APOBEC3B is an enzymatic source of mutation in breast cancer Nature 2013, 494, 366-370 10.1038/nature11881
24. Sieuwerts, A. M.; Willis, S.; Burns, M. B.; Look, M. P.; Meijer-Van Gelder, M. E.; Schlicker, A.; Heideman, M. R.; Jacobs, H.; Wessels, L.; Leyland-Jones, B.; Gray, K. P.; Foekens, J. A.; Harris, R. S.; Martens, J. W. Elevated APOBEC3B correlates with poor outcomes for estrogen-receptor-positive breast cancers Horm. Cancer 2014, 5, 405-413 10.1007/s12672-014-0196-8
25. Burns, M. B.; Temiz, N. A.; Harris, R. S. Evidence for APOBEC3B mutagenesis in multiple human cancers Nat. Genet. 2013, 45, 977-983 10.1038/ng.2701
26. Roberts, S. A.; Lawrence, M. S.; Klimczak, L. J.; Grimm, S. A.; Fargo, D.; Stojanov, P.; Kiezun, A.; Kryukov, G. V.; Carter, S. L.; Saksena, G.; Harris, S.; Shah, R. R.; Resnick, M. A.; Getz, G.; Gordenin, D. A. An APOBEC cytidine deaminase mutagenesis pattern is widespread in human cancers Nat. Genet. 2013, 45, 970-976 10.1038/ng.2702
27. Giardina, G. A. M.; Sarau, H. M.; Farina, C.; Medhurst, A. D.; Grugni, M.; Raveglia, L. F.; Schmidt, D. B.; Rigolio, R.; Luttmann, M.; Vecchietti, V.; Hay, D. W. P. Discovery of a novel class of selective non-peptide antagonists for the human neurokinin-3 receptor. 1. Identification of the 4-quinolinecarboxamide framework J. Med. Chem. 1997, 40, 1794-1807 10.1021/jm960818o
28. Strigacova, J.; Hudecova, D.; Varecka, L.; Lasikova, A.; Vegh, D. Some biological properties of new quinoline-4-carboxylic acid and quinoline-4-carboxamide derivatives Folia Microbiol. 2000, 45, 305-309 10.1007/BF02817551
29. Cai, X.; Zhang, J.; Chen, M.; Wu, Y.; Wang, X.; Chen, J.; Shen, X.; Qu, D.; Jiang, H. The effect of the potential PhoQ histidine kinase inhibitors on Shigella flexneri virulence PLoS One 2011, 6, e23100 10.1371/journal.pone.0023100
30. Shankerrao, S.; Bodke, Y. D.; Mety, S. S. Synthesis, antioxidant, and antibacterial studies of phenolic esters and amides of 2-(1-benzofuran-2-yl) quinoline-4-carboxylic acid Med. Chem. Res. 2013, 22, 1163-1171 10.1007/s00044-012-0117-8
31. Spinks, D.; Shanks, E. J.; Cleghorn, L. A.; McElroy, S.; Jones, D.; James, D.; Fairlamb, A. H.; Frearson, J. A.; Wyatt, P. G.; Gilbert, I. H. Investigation of trypanothione reductase as a drug target in Trypanosoma brucei ChemMedChem 2009, 4, 2060-2069 10.1002/cmdc.200900262
32. Matsuno, K.; Masuda, Y.; Uehara, Y.; Sato, H.; Muroya, A.; Takahashi, O.; Yokotagawa, T.; Furuya, T.; Okawara, T.; Otsuka, M.; Ogo, N.; Ashizawa, T.; Oshita, C.; Tai, S.; Ishii, H.; Akiyama, Y.; Asai, A. Identification of a new series of STAT3 inhibitors by virtual screening ACS Med. Chem. Lett. 2010, 1, 371-375 10.1021/ml1000273
33. Lack, N. A.; Axerio-Cilies, P.; Tavassoli, P.; Han, F. Q.; Chan, K. H.; Feau, C.; LeBlanc, E.; Guns, E. T.; Guy, R. K.; Rennie, P. S.; Cherkasov, A. Targeting the binding function 3 (BF3) site of the human androgen receptor through virtual screening J. Med. Chem. 2011, 54, 8563-8573 10.1021/jm201098n
34. Ghodsi, R.; Zarghi, A.; Daraei, B.; Hedayati, M. Design, synthesis and biological evaluation of new 2,3-diarylquinoline derivatives as selective cyclooxygenase-2 inhibitors Bioorg. Med. Chem. 2010, 18, 1029-1033 10.1016/j.bmc.2009.12.060
35. Yu, P.; Hu, J.; Zhou, T.-Y.; Wang, P.; Xu, Y.-H. Synthesis, insecticidal evaluation of novel 1,3,4-thiadiazole chrysanthemamide derivatives formed by an EDCI/HOBt condensation J. Chem. Res. 2011, 35, 703-706 10.3184/174751911X13230201951890
36. Olson, M. E.; Li, M.; Harris, R. S.; Harki, D. A. Small-molecule APOBEC3G DNA cytosine deaminase inhibitors based on a 4-amino-1,2,4-triazole-3-thiol scaffold ChemMedChem 2013, 8, 112-117 10.1002/cmdc.201200411
37. Mirek, J.; Sygula, A. Semiempirical MNDO and UV Absorption Studies on Tautomerism of 2-Quinolones Z. Naturforsch., A: Phys. Sci. 1982, 37A, 1276-1283 10.1515/zna-1982-1111
38. Galstyan, G.; Knapp, E. W. Computations of 36 tautomer/isomer equilibria of different lactams J. Phys. Chem. A 2012, 116, 6885-6893 10.1021/jp302569g
39. Gerega, A.; Lapinski, L.; Nowak, M. J.; Furmanchuk, A.; Leszczynski, J. Systematic effect of benzo-annelation on oxo-hydroxy tautomerism of heterocyclic compounds. Experimental matrix-isolation and theoretical study J. Phys. Chem. A 2007, 111, 4934-4943 10.1021/jp070408j
40. Kaila, N.; Janz, K.; DeBernardo, S.; Bedard, P. W.; Camphausen, R. T.; Tam, S.; Tsao, D. H.; Keith, J. C., Jr.; Nickerson-Nutter, C.; Shilling, A.; Young-Sciame, R.; Wang, Q. Synthesis and biological evaluation of quinoline salicylic acids as P-selectin antagonists J. Med. Chem. 2007, 50, 21-39 10.1021/jm0602256
41. Foote, C. S.; Wexler, S.; Ando, W.; Higgins, R. Chemistry of singlet oxygen. IV. Oxygenations with hypochlorite-hydrogen peroxide J. Am. Chem. Soc. 1968, 90, 975-981 10.1021/ja01006a023
42. Schenck, G. O. Colloquium am 26. Juni 1944 Angew. Chem. 1944, 57, 101-102 10.1002/ange.19440571305
43. Criegee, R. Mechanism of ozonolysis Angew. Chem., Int. Ed. Engl. 1975, 14, 745-752 10.1002/anie.197507451
44. Wasserman, H. H.; Liberles, A. Formation of epoxides in the pyrrole and furan series by photooxidation J. Am. Chem. Soc. 1960, 82, 2086-2086 10.1021/ja01493a070
45. Bailey, P. S. Ozonation in Organic Chemistry; Academic Press: New York, 1978; Vol. 1.
46. Matsuura, T.; Saito, I. Photochemistry of Heterocyclic Compounds; Wiley: New York, 1976.
47. Adam, W.; Rodriguez, A. On the question of carbonyl oxide intermediates in the oxygen transfer by furan endoperoxides and bicyclic ozonides: intramolecular trapping experiments Tetrahedron Lett. 1981, 22, 3509-3512 10.1016/S0040-4039(01)81944-4
48. Graziano, M. L.; Lesce, M. R.; Scarpati, R. Photosensitized oxidation of furans. Part 1. Synthesis and properties of furan endo-peroxides J. Chem. Soc., Perkin Trans. 1 1980, 1955-1959 10.1039/p19800001955
49. Dufraisse, C.; Ecary, S. Photooxidation on the cyclopentane ring: photooxydi-phenylisobenzofuran C. R. Acad. Sci. Paris 1946, 233, 735-737
50. Palacios, F.; Alonso, C.; Amezua, P.; Rubiales, G. Synthesis of Aza Polycyclic Compounds Derived from Pyrrolidine, Indolizidine, and Indole via Intramolecular Diels-Alder Cycloadditions of Neutral 2-Azadienes J. Org. Chem. 2002, 67, 1941-1946 10.1021/jo016325v