208
Views
4
CrossRef citations to date
0
Altmetric
Review

Therapeutic potential of oxazole scaffold: a patent review (2006–2017)

, , , &
Pages 783-812 | Received 12 Jun 2018, Accepted 17 Sep 2018, Published online: 26 Sep 2018

References

  • Haider S. Heterocycles, back bone of drug design. J Phytochemistry Biochem. 2017;1:1.
  • Eftekhari-Sis B, Zirak M, Akbari A. Arylglyoxals in synthesis of heterocyclic compounds. Chem Rev. 2013;113:2958–3043.
  • Ansari A, Ali A, Asif A, et al. Review: biologically active pyrazole derivatives. New J Chem. 2017;41:16–41.
  • Al-Mulla A. A review: biological importance of heterocyclic compounds. Der Pharma Chem.. 2017;9:141–147.
  • Bansal RK. Heterocyclic chemistry. New Delhi: New Age International Publishers; 2017.
  • Gilchrist TL. Heterocyclic chemistry. England: Pearson; 1997.
  • Turchi IJ, Dewar MJS. Chemistry of oxazoles. Chem Rev. 1975;75:389–437.
  • Karimoto RS, Axelrod B, Wolinsky J, et al. The structure and synthesis of annuloline, an oxazole alkaloid occurring in annual rye grass. Phytochemistry. 1964;3:349–355.
  • Cornforth JW, Cornforth RH. A new synthesis of oxazoles and iminazoles including its application to the preparation of oxazole. J Chem Soc. 1947;0:96–102.
  • Bredereck H, Gompper, R, Hayer D. Imidazole synthesis with formamide. Chem Ber. 1953;86:88–96.
  • Bredereck H, Bangert R. Synthesis of oxazole. Angew Chem Int Ed Engl. 1962;12:662–663.
  • Wasserman HH, Vinick FJ. Mechanism of the Robinson-Gabriel synthesis of oxazoles. J Org Chem. 1973;38:2407–2408.
  • Schill G, Sosnovsky G, Ziegler H.J. Reactiones Organicae. Synthesis. 1972;3:148.
  • Van Leusen AM, Hoogenboom BE, Siderius H. A novel and efficient synthesis of oxazoles from tosylmethylisocyanide and carbonyl compounds. Tetrahedron Lett. 1972;23:2369–2372.
  • Joshi S, Bisht AS, Juyal D. Systematic scientific study of 1, 3-oxazole derivatives as a useful lead for pharmaceuticals: a review. Pharma Innov. 2017;6:109–117.
  • Peng XM, Cai GX, Zhou CH. Recent developments in azole compounds as antibacterial and antifungal agents. Curr Top Med Chem. 2013;13:1963–2010.
  • Zhang H-Z, Zhao Z-L, Zhou C-H. Recent advance in oxazole-based medicinal chemistry. Eur J Med Chem. 2018;144:444–492.
  • Knowles RR, Carpenter J, Blakey SB, et al. Total synthesis of diazonamide A. Chem Sci. 2011;2:308–311.
  • Glockner S, Tran DS, Ingham RJ, et al. The rapid synthesis of oxazolines and their heterogeneous oxidation to oxazoles under flow conditions. Org Biomol Chem. 2015;13:207–214.
  • Chandrasekhar S, Sudhakar A. Total synthesis of bengazole A. Org Lett. 2010;12:236–238.
  • Yokokawa F, Asano T, Shioiri T. Total synthesis of the antiviral marine natural product (−)-hennoxazole A. Org Lett. 2000;2:4169–4172.
  • Balasubramanian M. Oxazoles and benzoxazoles. In: Li JJ, Gribble GW, editors. Palladium in heterocyclic chemistry: a guide for the synthetic chemist. New York: Elsevier; 2007. p. 380–383.
  • Qiu G, Li Y, Wu J. Recent developments for the photoinduced Ar-X bond dissociation reaction. Org Chem Front. 2016;3:1011–1027.
  • Nishida A, Fuwa M, Fujikawa Y, et al. First total synthesis of martefragin A, a potent inhibitor of lipid peroxidation isolated from sea alga. Tetrahedron Lett. 1998;39:5983–5986.
  • Webb MR, Addie MS, Crawforth CM, et al. The syntheses of rac-inthomycin A, (+)-inthomycin B and (+)-inthomycin C using a unified synthetic approach. Tetrahedron. 2008;64:4778–4791.
  • Lin -C-C, Tantisantisom W, McAlpine SR. Total synthesis and biological activity of natural product urukthapelstatin A. Org Lett. 2013;15:3574–3577.
  • Matsuo Y, Kanoh K, Yamori T, et al. Urukthapelstatin A, a novel cytotoxic substance from marine-derived mechercharimyces asporophorigenens YM11-542. I. Fermentation, isolation and biological activities. J Antibiot (Tokyo). 2007;60:251–255.
  • Lazo JS, Reese CE, Vogt A, et al. Identifying a resistance determinant for the antimitotic natural products disorazole C1 and A1. J Pharmacol Exp Ther. 2010;332:906–911.
  • Fallona MC, McMorris TC, De Mayo P, et al. Griseoviridin. J Am Chem Soc. 1962;84:4162–4163.
  • Ahmed F, Donaldson W. Chemistry and biology of streptogramin A antibiotics. Mini Rev Org Chem. 2007;4:159–181.
  • Shin Y, Kim GD, Jeon J, et al. Antimetastatic effect of halichondramide, a trisoxazole macrolide from the marine sponge chondrosia corticata, on human prostate cancer cells via modulation of epithelial-to-mesenchymal transition. Mar Drugs. 2013;11:2472–2485.
  • https://www.drugbank.ca/drugs/DB00991[Last accessed 2018 Mar 05
  • Qian J, Chen H, Birnbaum Y, et al. Aleglitazar, a balanced dual pparalpha and -gamma agonist, protects the heart against ischemia-reperfusion injury. cardiovasc drugs ther. 2016;30:129–141.
  • Zhang Y, Rodney GG, Schneider MF. Effects of azumolene on Ca2+ sparks in skeletal muscle fibers. J Pharmacol Exp Ther. 2005;314:94–102.
  • Jain J, Almquist SJ, Shlyakhtar D, et al. VX-497: a novel, selective IMPDH inhibitor and immunosuppressive agent. J Pharm Sci. 2001;90:625–637.
  • Self CR, Barber WE, Machin PJ, et al. Romazarit: a potential disease-modifying antirheumatic drug. J Med Chem. 1991;34:772–777.
  • Zhang HZ, Gan LL, Wang H, et al. New progress in azole compounds as antimicrobial agents. Min Rev Med Chem. 2017;17:122–166.
  • Zhang L, Peng XM, Damu GL, et al. Comprehensive review in current developments of imidazole-based medicinal chemistry. Med Res Rev. 2014;34:340–437.
  • Zhou CH, Wang Y. Recent researches in triazole compounds as medicinal drugs. Curr Med Chem. 2012;19:239–280.
  • Li YS, Hu DK, Zhao DS, et al. Design, synthesis and biological evaluation of 2,4-disubstituted oxazole derivatives as potential PDE4 inhibitors. Bioorg Med Chem. 2017;25:1852–1859.
  • Sadek B, Fahelelbom KM. Synthesis, characterization, and antimicrobial evaluation of oxadiazole congeners. Molecules. 2011;16:4339–4347.
  • Demmer CS, Bunch L. Benzoxazoles and oxazolopyridines in medicinal chemistry studies. Eur J Med Chem. 2015;97:778–785.
  • Sysak A, Obmińska-Mrukowicz B. Isoxazole ring as a useful scaffold in a search for new therapeutic agents. Eur J Med Chem. 2017;137:292–309.
  • Blumberg LC, Munchhof MJ Novel triazole and oxazole compounds as transforming growth factor (TGF) inhibitors. OA012927A (2006)
  • Sutton JC, Wiesmann M, Wang W, et al. 6-O-Substituted benzoxazole and benzothiazole compounds and methods of inhibiting CSF-1R signaling. WO2007121484A2 (2007)
  • Johann L, Harald S, Kristina W, et al. Novel heterocyclic NF-κB inhibitors. NZ565470A (2010)
  • Rebek J Jr, Moisan L, Oxazole-pyridazine-oxazole apha-helix mimetic. US20100113466A1 (2010)
  • Brown M, Johnson M Oxazole compounds compositions and methods of use. US20110060011A1 (2011)
  • Feng Y, Lograsso P, Schroeter T, et al. Benzo[d]oxazoles and benzo[d]thiazoles as kinase inhibitors. WO2010024903A1 (2010)
  • Adjabeng G, Bifuclo N, Davis-Ward RG, et al. Thiazole and oxazole kinase inhibitors. US20110098296A1 (2011)
  • Adjabeng G, Baum E, Bifulco N, et al. Thaizole sulfonamide and oxazole sulfonamide kinase inhibitors. US20110319392A1 (2011)
  • Adamas JL, Faitg T, Kasparec J, et al. Benzene sulphonamide thiazole and oxazole compounds. WO2011059610A1 (2011)
  • Turkson J, Sebti S, Jove R, et al. STAT3 inhibitor having anticancer activity and methods. US20110124602A1 (2011)
  • Ahmed K, Shetti RV, Reddy KS, et al. Pyrrolo[2,L-C][L,4] benzodiazepine-benzothiazole or benzoxazole conjugates linked through piperazine moiety and process for the preparation thereof. US20120316335A1 (2012)
  • Diamond MI, Jones JO, Renslo AR Small-molecule inhibitors of the androgen receptor. US20130096095A1 (2013)
  • Ren P, Liu Y, Li L, et al. Heterocyclic compounds and uses thereof. US20130261102A1 (2013)
  • Pfahl M, Piedrafita FJ, Venkat LRC, et al. Novel substituted biarylheterocycle derivatives as protein kinase inhibitors for the treatment of cancer and other diseases. WO2013016720A2 (2013)
  • Desai LS, Chittaboina S Aminooxazole inhibitors of cyclin dependent kinases. US20140051694A1 (2014)
  • Reader JC, Ellard JM, Boffey H, et al. Oxazole tyrosine kinase inhibitors. US20150057282A1 (2015)
  • Stefanski T, Rozanski J, Mikstacka R, et al. The new derivatives of (Z)-1,2-diphenylethene. US20150065727A1 (2015)
  • Song JY, Ahn JY, Jung IS, et al. Anticancer supplement agent including benzo[d]oxazol derivative as effective ingredient. US20150197498A1 (2015)
  • Dasgupta R, Rajulu GG, Dickson JK Novel oxazole compounds as β-catenin modulators and uses thereof. WO2016081451A1 (2016)
  • Dasgupta R, Gonsalves F Oxazole and thiazole compounds as beta-catenin modulators and uses thereof. US20170049751A1 (2017)
  • Puelles S, Sancho S Derivatives of 2-phenyl-7,7a-dihydro-3Ah-pyrano[3,4-d]oxazole-6(4H)-one. WO2016091789A1 (2016)
  • Wolff, Bregman, Goller. Oxazole and thiazole derivatives and pharmaceutical compositions containing the same. IL147939B (2008)
  • Luzzatto. Substituted oxazole and thiazole derivatives pharmaceutical compositions comprising the same and their use for the manufacture of medicaments for the treatment of hPPAR alpha disease or condition. IL149582B (2008)
  • Birch AM, Davies R, Whalley DP Oxazole derivatives and their use in the treatment of diabetes and obesity. US20100160397A1 (2010)
  • Luzzatto. Oxazolo/Thiazolo-pyridine derivatives and benzo-oxazole/thiazole derivatives, process for their preparation and pharmaceutical compositions comprising the same. IL189664B (2011)
  • Grauert M, Bakker R, Breitfelder S, et al. Pyridazinones as GPR119 agonists. US20130172323A1 (2013)
  • Rongze K, David B, Neng-Yang S, et al. Substituted 2-quinolyl-oxazoles useful as PDE4 inhibitors. NZ551017 (2010)
  • Chobanian H, Lin LS, Liu P, et al. Oxazole derivatives useful as inhibitors of FAAH. US20110021531A1 (2011)
  • Choo HYP, Kim YK, Choi JH, et al. Benzoxazole derivatives having inhibitory activity against Interleukin-6, preparation method thereof, and pharmaceutical composition containing the same. US20130090480A1 (2013)
  • Martos JL, Carling WR, Woodward DF, et al. Compounds act at multiple prostaglandin receptors giving a general anti-inflammatory response. US20160068520A1 (2016)
  • Frank-Foltyn R, Habermann C, Bahrenberg G, et al. Substituted oxazole- and thiazole-based carboxamide and urea derivatives as vanilloid receptor ligands II. WO2016082930A9 (2016)
  • Corminboeuf O, Cren S, Pozzi D Difluoroethyl-oxazole substituted bridged spiro[2,4]Heptane derivatives as ALX receptor agonists. US20160289221A1 (2016)
  • gChen L, Dillon MP, Feng L, et al. Thiazole and oxazole-substituted arylamides as P2X3 and P2X2/3 antagonists. US20170182057A1 (2017)
  • Le Poul E, Palombi G, Rocher JP Oxazole derivatives as positive allosteric modulators of metabotropic glutamate receptors. US20100081690A1 (2010)
  • Conn PJ, Lindsley CW, Stauffer SR, et al. Bicyclic oxazole lactams as allosteric modulators of MGLUR5 receptors. US20130252943A1 (2013)
  • Conn PJ, Lindsley CW, Stauffer SR, et al. Bicyclic oxazole and thiazole compounds and their use as allosteric modulators of MGLUR5 receptors. US20130261107A1 (2013)
  • Boger DL Substituted oxazole ketone modulators of fatty acid amide hydrolase. US20100075931A1 (2010)
  • Boger DL. C-4 substituted alpha-keto oxazoles. US20120302607A1 (2012)
  • Boger DL Tricyclic inhibitors of Fatty acid amide hydrolase. US20100216750A1; (2010)
  • Gijsen HJM, Bischoff FP, Zhuang W, et al. Novel substituted benzoxazole, benzimidazole, oxazolopyridine and imidazopyridine derivatives as Gamma Secretase modulators. WO2010094647A1 (2010)
  • Chabrier De Lassauniere PE, Harnett J, Bigg D et al. Derivatives of heterocycles with 5 members, their preparation and their use as medicaments. US 20110172434A1 (2011)
  • Krause KH, Preynat-Seauve O Methods and compositions related to dopaminergic neuronal cells. US20130149717A1 (2013)
  • Munakata R, Inoue M, Tominaga H, et al. Chromane compounds. US20150225386A1 (2015)
  • Liverton N, Bishore DC, Kuduk SD, et al. Oxazole orexin receptor antagonists. US 2016176858A1 (2016)
  • Kuduk SD, Liverton N, Luo Y Oxazole orexin receptor antagonists. WO2016069515A1 (2016)
  • Kuduk SD, Liverton N, Luo Y Methyl oxazole orexin receptor antagonists. WO 2016089721A1 (2016)
  • Kuduk SD, Liverton N, Reger TS, et al. 5,5-Bicyclic oxazole orexin receptor antagonists. WO2016100162A2 (2016)
  • Pevarello P, Lohmer S, Liberati C, et al. Substituted thiazole or oxazole P2X7 receptor antagonists. US20170008883A1 (2017)
  • Ivachtchenko AV, Mitkin OD, Kadieva MG Substituted methyl amines, serotonin 5-ht6 receptor antagonists, methods for the production and use thereof. EP3072882A1 (2016)
  • Wolff, Bregman, Goller. Fused imidazole and oxazole derivatives and pharmaceutical compositions containing the same as anti-bacterial agents. IL156031B (2011)
  • Nan F, Zuo J, Wang W, et al. 2-Thiophen-2-yl-oxazole, 2-thiophen-2-yl-thiazole and 2-thiophen-2-yl-1H-imidazole derivatives as antiviral agents and the use thereof. SG172716A1 (2011)
  • Fatheree PR, Hudson R, McKinnell RM Dual-acting oxazole antihypertensive agents. US20140194426A1 (2014)
  • Wulff H, Coleman N, Brown BM, et al. Selective activators of the intermediate conductance CA2+ activated K+ channel KCA3.1 and their methods of use. US20170056376A1 (2017)
  • Tinsley JM Pharmaceutical composition for the treatment of Duchenne muscular dystrophy. US20150238467A1 (2015)
  • Moussy A, Benjahad A, Pez D, et al. Novel oxazole derivatives that inhibit SYK. WO2017046302A1 (2017)

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.