Generic placeholder image

Mini-Reviews in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

Review Article

Exploration of the Biological Potential of Benzoxazoles: An Overview

Author(s): Mayura Kale* and Vijayalaxmi Chavan

Volume 16, Issue 2, 2019

Page: [111 - 126] Pages: 16

DOI: 10.2174/1570193X15666180627125007

Price: $65

Abstract

The development of benzoxazole containing drugs and research compounds has been discussed in the present review along with its varied pharmacological activities such as antimicrobial, antiinflammatory, anticancer, antiviral, antiasthmatic, antitubercular, anticonvulsant, lipid modulating, anticoagulants, antidiabetic and anthelmintic activities. The present review is a compilation of the biological activities determined in the research work conducted on benzoxazole-based compounds fused and linked with various other heterocycles.

Keywords: Benzoxazole, anticancer, antiasthmatic, antitubercular, antiviral, antidiabetic.

Graphical Abstract
[1]
Vinsova, J. Biologically active Benzoxazoles. Ceska Slov. Farm., 2003, 52(6), 282-290.
[2]
Demmer, C.S. Benzoxazoles and oxazolopyridines in medicinal chemistry studies. Eur. J. Med. Chem., 2014, 97, 778-785.
[3]
Knights, K. Cassidy, m.; Drew, R. Benoxaprofen induced toxicity in isolated rat hepatocytes. Toxicology, 1986, 40, 327-339.
[4]
Sacchi, C.; Magni, F.; Toia, A.; Cazzaniga, F.; Galli, G.; Berti, F. Flunoxaprofen, a new non-steroidal anti-inflammatory drug, does not interfere with prostaglandin synthesis in rat gastric mucosa. Pharmacol. Res., 1989, 21, 177-182.
[5]
Breiner, R.; McComb, R.; Holtman, V. Chlorzoxazone mimics apobarbital in Toxilab drug screen. Clin. Chem., 1984, 30, 1719.
[6]
Kobayashi, J.; Madono, T.; Shigemori, H. Nakijinol, A novel sesquiterpenoid sontaining a benzoxazole ring from an okinawan sponge. Tetra. Lett., 1995, 36, 5589-5590.
[7]
Ueki, M.; Ueno, K.; Miyadoh, S.; Abe, K.; Shibata, K.; Taniguchi, M.; Oi, S. UK-1, a novel cytotoxic metabolite from Streptomyces sp. 517-02. I. Taxonomy, fermentation, isolation, physic-chemical and biological properties. J. Antibiot., 1993, 46, 1089.
[8]
Sato, S.; Kajiura, T.; Noguchi, M.; Takehana, K.; Kobayasho, T.; Tsuji, T. AJ-19591, a new cytotoxic benzoxazole derivative produced by Streptomyces sp. J. Antibiot., 2001, 54, 102.
[9]
Kumar, D.; Jacob, M.; Reynolds, M.; Kerwin, S. Synthesis and Evaluation of Anticancer Benzoxazoles and Benzimidazoles Related to UK-1. Bioorg. Med. Chem., 2002, 10, 3997-4004.
[10]
Rodriguez, A.; Ramirez, C.; Rodriguez, I.; Gonzalez, E. Novel antimycobacterial benzoxazole alkaloids, from the west Indian Sea whip Pseudopterogorgia elisabethae. Org. Lett., 1999, 1, 527-530.
[11]
Rodriguez, I.; Rodrigueza, A.; Wang, Y. Franzblau, S. Ileabethoxazole: a novel benzoxazole alkaloid with antimycobacterial activity. Tetra. Lett., 2006, 47, 3229-3232.
[12]
Don, M.; Shen, C.C.; Lin, Y.; Syu, W.; Ding, H.; Sun, C. Nitrogen-containing compounds from Salvia miltiorrhiza. J. Nat. Prod., 2005, 68, 1066-1070.
[13]
Zawahir, S.; Roberts, D.; Palangasinghe, C.; Mohamed, F.; Eddleston, M.; Dawson, A.; Buckley, N.; Ren, L.; Medley, G.; Gawarammana, I. Acute intentional self-poisoning with a herbicide product containing fenoxaprop-P-ethyl, ethoxysulfuron and isoxadifen ethyl. A prospective observational study. Clin. Toxicol. (Phila.), 2009, 47, 792-797.
[14]
Hohmann, C.; Schneider, K.; Bruntner, C.; Irran, E.; Nicholson, G.; Bull, A.; Jones, A.; Brown, R.; Stach, J.; Goodfellow, M.; Beil, W.; Kramer, M.; Imhoff, J.; Sussmuth, R.; Fiedler, H. Caboxamycin, a new antibiotic of the benzoxazole family produced by the deep-sea strain Streptomyces sp. NTK 937. J. Antibiot., 2009, 42, 1-6.
[15]
Pressman, B. Biological applications of ionophores. Annu. Rev. Biochem., 1976, 45, 501-530.
[16]
Q., Wu Liang, J.; Lin, S.; Zhou, X.; Bai, L.; Deng, Z.; Wang, Z. Characterization of the biosynthesis gene cluster for the pyrrole polyether antibiotic calcimycin (A23187) in Streptomyces chartreusis NRRL 3882. Antimicrob. Agents Chemother., 2011, 55, 974-982.
[17]
Bennett, T.; Bray, D.; Nevill, M. Suvorexant, a dual orexin receptor antagonist for the management of insomnia. Drug Forcast, 2014, 39, 266. 2014.
[18]
Satyendra, R.; Vishnumurthy, K.; Vagdevi, H.; Rajesh, K.; Manjunatha, H.; Shruthi, A. Synthesis, in vitro antioxidant, anthelmintic and molecular docking studies of novel dichloro substituted benzoxazole-triazolo-thione derivatives. Eur. J. Med. Chem., 2011, 46, 3078-3084.
[19]
Ongarora, D.; Gut, J.; Rosenthal, P.; Masimirembwa, C.; Kelly, C. Benzoheterocyclicamodiaquine analogues with potent antiplasmodial activity: Synthesis and pharmacological evaluation. Bioorg. Med. Chem. Lett., 2012, 22, 5046-5050.
[20]
Brown, R.; Cameron, R.; Chalmers, D.; Hamilton, S.; Luttick, A.; Krippner, G.; McConnell, D.; Nearn, R.; Stanislawski, P.; Tucker, S.; Watson, K. 2-Ethoxybenzoxazole as a bioisosteric replacement of an ethyl benzoate group in a human rhinovirus (HRV) capsid binder. Bioorg. Med. Chem. Lett., 2005, 15, 2051-2055.
[21]
Zhou, S.; Rynearson, K.; Ding, K.; Brunn, N.; Hermann, T. Screening for inhibitors of the hepatitis C virus internal ribosome entry site RNA. Bioorg. Med. Chem., 2013, 21, 6139-6144.
[22]
Jonckers, T.; Rouan, M.; Hache, G.; Schepens, W.; Hallenberger, S.; Baumeister, J.; Sasaki, J. Benzoxazole and benzothiazole amides as novel pharmacokinetic enhancers of HIV protease inhibitors. Bioorg. Med. Chem. Lett., 2012, 22, 4998-5002.
[23]
Sheng, C.; Xu, H.; Wang, W.; Cao, Y.; Dong, G.; Wang, S.; Che, X.; Ji, H.; Miao, Z.; Yao, J.; Zhang, W. Design, synthesis and antifungal activity of isosteric analogues of benzo heterocyclic N-myristoyltransferase inhibitors. Eur. J. Med. Chem., 2010, 4, 3531-3540.
[24]
Sheng, C.; Che, X.; Wang, W.; Wang, S.; Cao, Y.; Yao, J.; Miao, Z.; Zhang, W. Design and synthesis of antifungal benzoheterocyclic derivatives by scaffold hopping. Eur. J. Med. Chem., 2011, 46, 1706-1712.
[25]
Kuroyanagi, J.; Kanai, K.; Sugimoto, Y.; Horiuchi, T.; Achiwa, I.; Takeshita, H.; Kawakami, K. 1,3-Benzoxazole-4-carbonitrile as a novel antifungal scaffold of b-1,6-glucan synthesis inhibitors. Bioorg. Med. Chem., 2010, 18, 7593-7606.
[26]
Daboit, T. Stopiglia, C.; Carissimi,M.; Corbellini, V.; Stefani, V.; Scroferneker, V. In vitro antifungal activity of 2-(2′-hydroxy-5′-aminophenyl) benzoxazole in Candida spp. Strains. Mycoses, 2009, 52, 507-510.
[27]
Yang, Z.; Fairfax, D.; Maeng, J.; Masih, L.; Usyatinsky, A.; Hassler, C.; Isaacson, S.; Fitzpatrick, K.; Deorazio, R.; Chen, J.; Harding, J.; Isherwood, M.; Dobritsa, S.; Christensen, K.; Wierschke, J.; Bliss, B.; Peterson, L.; Beer, C.; Cioffi, C.; Lynch, M.; Rennells, W.; Richards, J.; Rust, T.; Khmelnitsky, Y.; Cohen, M.; Manning, D. Discovery of 2-substituted benzoxazole carboxamides as 5-HT3 receptor antagonists. Bioorg. Med. Chem. Lett., 2010, 20, 6538-6541.
[28]
Lopez-Tudanca, P.; Labeaga, L.; Innerarity, A.; Alonso-Cires, L.; Tapia, I.; Mosquera, R.; Orjales, A. Synthesis and Pharmacological Characteri,zation of a New Benzoxazole Derivative as a Potent 5-HT3 Receptor Agonist. Bioorg. Med. Chem., 2003, 11, 2709-2714.
[29]
Yoshida, S.; Watanabe, T.; Sato, Y. Regulatory molecules for the 5-HT3 receptor ion channel gating system. Bioorg. Med. Chem., 2007, 17, 3515-3523.
[30]
Liu, K.; Lo, J.; Comery, T.; Zhang, G.; Zhang, J.; Kowal, D.; Smith, D.; Di, L.; Kerns, E.; Schechter, L.; Robichaud, A. Identification of a series of benzoxazoles as potent 5-HT6 ligands. Bioorg. Med. Chem. Lett., 2009, 19, 1115-1117.
[31]
Geldern, T.; Lai, C.; Gum, R.; Daly, M.; Sun, C.; Fry, E.; Zapatero, C. Benzoxazole benzenesulfonamides are novel allosteric inhibitors of fructose-1,6bisphosphatase with a distinct binding mode. Bioorg. Med. Chem. Lett., 2006, 16, 1811-1815.
[32]
Gim, H.; Cheon, Y.; Ryu, J.; Jeon, R. Design and synthesis of benzoxazole containing indole analogs as peroxisome proliferator-activated receptor-c/d dual agonists. Bioorg. Med. Chem. Lett., 2011, 21, 3057-3061.
[33]
Chandrasekharappa, A.; Badiger, S.; Dubey, P.; Panigrahi, S.; Reddy, S.; Manukonda, V. Design and synthesis of 2-substituted benzoxazoles as novel PTP1B inhibitors. Bioorg. Med. Chem. Lett., 2013, 23, 2579-2584.
[34]
Omori, N.; Kouyama, N.; Yukimasa, A.; Watanabe, K.; Yokota, Y.; Tanioka, H.; Nambu, H.; Yukioka, H.; Sato, N.; Tanaka, Y.; Sekiguchi, K.; Okuno, T. Hit to lead SAR study on benzoxazole derivatives for an NPY Y5 antagonist. Bioorg. Med. Chem. Lett., 2012, 22, 2020-2023.
[35]
Kley, J.; Mack, J.; Hamilton, B.; Scheuerer, S.; Redemann, N. Discovery of BI 99179, a potent and selective inhibitor of type I fatty acid synthase with central exposure. Bioorg. Med. Chem. Lett., 2011, 21, 5924-5927.
[36]
Topcu, G.; Turkmen, Z.; Schilling, J. Cytotoxic Activity of Some Anatolian Salvia. Extracts and Isolated Abietane Diterpenoids. Pharm. Biol., 2008, 46, 180-184.
[37]
McKee, M.; Kerwin, S. Synthesis, metal ion binding, and biological evaluation of new anticancer 2-(20 hydroxyphenyl)benzoxazole analogs of UK-1. Bioorg. Med. Chem., 2008, 16, 1775-1783.
[38]
Kamal, A.; Reddy, K.; Khan, M.; Shett, I. R.; Ramaiah, J.; Pushpavalli, S.; Srinivas, C.; Pal-Bhadra, M.; Chourasia, M.; Sastry, G.; Juvekar,A.; Zingde, S.; Barkume, M. Synthesis, DNA-binding ability and anticancer activity of benzothiazole/benzoxazole–pyrrolo[2,1-c] [1,4]benzodiazepine conjugates. Bioorg. Med. Chem., 2010, 18, 4747-4761.
[39]
Huang, S.; Hsei, I.; Chen, C. Synthesis and anticancer evaluation of bis(benzimidazoles), bis(benzoxazoles), and benzothiazoles. Bioorg. Med. Chem., 2006, 14, 6106-6119.
[40]
Courtney, S.; Hay, P.; Buck, R.; Colville, C.; Phillips, D.; Scopes, D.; Pollard, D.; Page, M.; Bennett, J.; Hircock, M.; McKenzie, E.; Bhaman, M.; Felix, R.; Stubberfield, C.; Turner, P. Furanyl-1,3-thiazol-2-yl and benzoxazol-5-yl acetic acid derivatives: novel classes of heparanase inhibitor. Bioorg. Med. Chem. Lett., 2005, 15, 2295-2299.
[41]
Wang, B.; Maghami, N.; Goodlin, V.; Smith, P. Critical structural motif for the catalytic inhibition of human topoisomerase II by UK-1 and analogs. Bioorg. Med. Chem. Lett., 2004, 14, 3221-3226.
[42]
Salo, H.; Laitinen, T.; Poso, A.; Jarho, E.; Kakkonen, M. Identification of novel SIRT3 inhibitor scaffolds byvirtual screening. Bioorg. Med. Chem. Lett., 2013, 23, 2990-2995.
[43]
Peel, R.; Milstead, M.; Sternbach, D.; Besterman, J.; Leitner, P.; Morton, B. Novel A-ring modified camptothecins as topoisomerase I inhibitors. Bioorg. Med. Chem. Lett., 1995, 5, 2129-2132.
[44]
Gerspacher, M.; Furet, P.; Soldermann, C.; Gaul, C.; Holzer, P.; Vangrevelinghe, E.; Lang, M.; Erdmann, D.; Radimerski, T.; Regnier, C.; Chene, P.; Pover, A.; Hofmann, F.; Baffert, F.; Buhl, T.; Aichholz, R.; Blasco, F.; Endres, R.; Trappe, J.; Drueckes, P. 2-Amino-aryl-7-aryl-benzoxazoles as potent, selective and orally available JAK2 inhibitors. Bioorg. Med. Chem. Lett., 2010, 20, 1724-1727.
[45]
Schreiner, E.; Wolff, B.; Winiski, A.; Billich, A. 6-(2-Adamantan-2-ylidene-hydroxybenzoxazole)-O-sulfamate: A potent non-steroidal irreversible inhibitor of human steroid sulfatase. Bioorg. Med. Chem. Lett., 2003, 13, 4313-4316.
[46]
Abdelgawad, M.; Belal, A.; Omar, H.; Hegazy, L.; Rateb, M. Synthesis, anti-breast cancer activity and molecular modeling of some benzothiazole and benzoxazole derivatives. Arch. Pharm. Chem. Life Sci., 2013, 346, 534-541.
[47]
Russo, F.; Romeo, G.; Santagatil, N.; Caruso, A.; Cutuli, V.; Amore, D. Synthesis of new thienopyrimidobenzothiazoles and thienopyrimidobenzoxazoles with analgesic and antiinflammatory properties. Eur. J. Med. Chem., 1994, 29, 569-578.
[48]
Kablaoui, N.; Patel, S.; Shao, J.; Demian, D.; Hoffmaster, K.; Berlioz, F.; Vazquez, M.; Moore, W.; Nugent, R. Novel benzoxazole inhibitors of mPGES-1. Bioorg. Med. Chem. Lett., 2013, 23, 907-911.
[49]
Eren, G. G.; Unlü, S.; Nuñez, M.; Labeaga, L.; Ledo, F.; Entrena, A.; Banoglu, E.; Costantino, G.; Sahin, M. Synthesis, biological evaluation, and docking studies of novel heterocyclic diaryl compounds as selective COX-2 inhibitors. Bioorg. Med. Chem., 2010, 18, 6367-6376.
[50]
Walker, D.; Arhancet, G.; Lu, H.; Heasley, S.; Metz, S.; Kablaoui, N.; Franco, F.; Hanau, C.A.; Scholten, J.; Springer, J.; Fobian, Y.; Carter, J.; Xing, L.; Yang, S.; Shaffer, A.; Jerome, G.; Baratta, M.; Moore, W.; Vazquez, M. Synthesis and biological evaluation of substituted benzoxazoles as inhibitors of mPGES-1: Use of a conformation-based hypothesis to facilitate compound design. Bioorg. Med. Chem. Lett., 2013, 23, 1120-1126.
[51]
Wang, B.; Vernier, J.; Rao, S.; Chung, J.; Anderson, J.; Brodkin, J.; Jiang, X.; Gardner, M.; Yanga, X.; Munoz, B. Discovery of novel modulators of metabotropic glutamate receptor subtype-5. Bioorg. Med. Chem., 2004, 12, 17-21.
[52]
Unlu, S.; Baytasa, S.; Kupelib, E.; Yesilada, E. Studies on novel 7-acyl-5-chloro-2-oxo-3H-benzoxazole derivatives as potential analgesic and anti-Inflammatory agents. Arch. Pharm. Pharm. Med. Chem., 2003, 336, 310-321.
[53]
Praveen, C.; Nandakumar, A.; Dheenkumar, P.; Murlidharan, D.; Perumal, P. Microwave-assisted one-pot synthesis of benzothiazole and benzoxazole libraries as analgesic agents. J. Chem. Sci., 2012, 124, 609-624.
[54]
Abdou, W.; Barghash, R.; Sediek, A. Design of new arylamino-2-ethane-1,1-diyl- and benzoxazole-2 methylenebisphosphonates vs cytotoxicity and chronic inflammation diseases. Eur. J. Med. Chem., 2012, 57, 362-372.
[55]
Vinsova, J.; Horak, V.; Buchta, V.; Kaustova, J. Highly Lipophilic Benzoxazoles with Potential Antibacterial Activity. Molecules, 2005, 10, 783-793.
[56]
Vinsova, J.; Cermakova, K.; Tomeckova, A.; Ceckova, M.; Jampilek, J.; Cermak, P.; Kunes, J.; Dolezal, M.; Staud, F. Synthesis and antimicrobial evaluation of new 2-substituted 5,7-di-tert-butylbenzoxazoles. Bioorg. Med. Chem., 2006, 14, 5850-5865.
[57]
Pichota, A.; Duraiswamy, J.; Yin, Z.; Keller, T. Peptide deformylase inhibitors of Mycobacterium tuberculosis: Synthesis, structural investigations, and biological results. Bioorg. Med. Chem. Lett., 2008, 18, 6568-6572.
[58]
Rodríguez, I.I.; Rodríguez, A.D. Homopseudopteroxazole, a new antimycobacterial diterpene alkaloid from Pseudopterogorgia elisabethae. J. Nat. Prod., 2003, 66, 855-857.
[59]
Vodela, S.; Reddy Mekala, R.; Reddy Danda, R.; Kodhati, V. Design, synthesis and screening of some novel benzoxazole based 1,3,4-oxadiazoles as potential antimicrobial agents. Chin. Chem. Lett., 2013, 24, 625-628.
[60]
Arpac, O.; Yildiz, I.; Ozkan, S.; Kaynak, F.; Sxener, E.; Yalcinet, I. Synthesis and biological activity of some new benzoxazoles. Eur. J. Med. Chem., 2008, 43, 1423-1431.
[61]
Ertan, T.; Yildiz, I.; Gulbas, B.; Bolelli, K.; Arpaci, O.; Ozkan, S.; Kaynak, F.; Yalcin, F.; Aki, E. Synthesis, biological evaluation and 2D-QSAR analysis of benzoxazoles as antimicrobial agents. Eur. J. Med. Chem., 2009, 44, 501-510.
[62]
Padalkar, V.; Borse, B.; Gupta, V.; Phatangare, K.; Patil, V.; Umape, P.; Sekar, N. Synthesis and antimicrobial activity of novel 2-substituted benzimidazole, benzoxazole and benzothiazole derivatives. Asian J. Chem., 2012, 56, 324-326.
[63]
Sum, P.; How, D.; Torres, N.; Newman, H.; Petersen, P.; Mansour, T. Synthesis and Activity of Novel Benzoxazole Derivatives of Mannopeptimycin Glycopeptide Antibiotics. Bioorg. Med. Chem. Lett., 2003, 13, 2607-2610.
[64]
Aki-Seren;Yildiz-Oren.; Tekiner-Gulbas.; Yalcin, I.; Temiz-Arpaci.; Altanlar, N. Synthesis and Antimicrobial Activity of New 2-[p-Substituted-benzyl]-5-[substituted-carbonylamino]benzoxazoles. Arch. Pharm. (Weinheim), 2004, 337, 402-410.
[65]
Balaswamy, G.; Shrinivas, K.; Pradeep, P.; Sarangpani, M. Synthesis, characterization and antimicrobial activity of novel substituted benzoxazole derivatives. Int. J. Chem. Sci., 2012, 10, 619-626.
[66]
Song, H.; Oh, S.; Lee, H.; Han, G.; Kim, J.; Chang, H.; Doh, K.; Rhee, H.; Choo, H. Synthesis and evaluation of benzoxazole derivatives as 5-lipoxygenase inhibitors. Bioorg. Med. Chem., 2010, 18, 7580-7585.
[67]
Setoguchi, M.; Iimura, S.; Sugimoto, Y.; Yoneda, Y.; Chiba, J.; Watanabe, T.; Muro, F.; Iigo, Y.; Takayama, G.; Yokoyama, M.; Taira, T.; Aonuma, M. Takashi, t.; Nakayama, A.; Machinaga, N. A novel, potent, and orally active VLA-4 antagonist with good aqueous solubility: trans-4-[1-[[2-(5-Fluoro-2-methylphenylamino)-7-fluoro-6-benzoxazolyl]acetyl]-(5S)-[methoxy(methyl)amino]methyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid. Bioorg. Med. Chem., 2013, 21, 42-61.
[68]
Setoguchi, M.; Iimura, S.; Sugimoto, Y.; Yoneda, Y.; Chiba, J.; Watanabe, T.; Muro, F.; Iigo, Y.; Takayama, G.; Yokoyama, M.; Taira, T.; Aonuma, M. Takashi, t.; Nakayama, A.; Machinaga, N. Identification of trans-4-[1-[[7-fluoro-2-(1-methyl-3-indolyl)-6-benzoxazolyl] acetyl]-(4S)-fluoro-(2S) pyrrolidinylmethoxy]cyclohexanecarboxylic acidas a potent, orally active VLA-4 antagonist. Bioorg. Med. Chem., 2012, 20, 1201-1212.
[69]
Lin, L.; Lanza, T.; Castonguay, L.; Kamenecka, T.; McCauley, E.; Riper, G.; Egger, L.; Mumford, R.; Tong, X.; MacCoss, M.; Schmidt, J.; Hagmann, W. Bioisosteric replacement of anilide with benzoxazole: potent and orally bioavailable antagonists of VLA-4. Bioorg. Med. Chem. Lett., 2004, 14, 2331-2334.
[70]
Smith, C.; Ali, A.; Chen, L.; Hammond, M.; Anderson, M.; Chen, Y.; Eveland, S.; Guo, Q.; Hyland, S.; Milot, D.; Sparrow, C.; Wright, S.; Sinclair, P. 2-Arylbenzoxazoles as CETP inhibitors: Substitution of the benzoxazole moiety. Bioorg. Med. Chem. Lett., 2010, 20, 346-349.
[71]
Sweis, R.; Hunt, J.; Kallashi, F.; Hammonda, M.; Chen, Y.; Eveland, S.; Guo, Q.; Hyland, S.; Milot, D.; Cumiskey, A.; Latham, A.; Rosa, R.; Peterson, L.; Sparrow, C.; Wright, S.; Anderson, M.; Sinclair, P. 2-(4-Carbonylphenyl)benzoxazole inhibitors of CETP: Scaffold design and advancement in HDLc-raising efficacy. Bioorg. Med. Chem. Lett., 2011, 21, 1890-1895.
[72]
Sweis, R.; Hunt, J.; Sinclair, P.; Chen, Y.; Eveland, S.; Guo, Q.; Hyland, S.; Milot, D.; Cumiskey, A.; Latham, M.; Rosa, R.; Peterson, L.; Sparrow, C.; Anderson, M. 2-(4-Carbonylphenyl)benzoxazole inhibitors of CETP: Attenuation of hERG binding and improved HDLc-raising efficacy. Bioorg. Med. Chem. Lett., 2011, 21, 2597-2600.
[73]
Harikrishnan, L.; Kamau, M.; Herpin, T.; Morton, G.; Liu, Y.; Cooper, C.; Salvati, M.; Qiao, J.; Wang, T.; Adam, L.; Taylor, D.; Chen, A.; Yin, X.; Seethala, R.; Peterson, T.; Nirschl, D.; Miller, A.; Weigelt, C.; Appiah, K.; Connell, J.; Lawrence, R. 2-Arylbenzoxazoles as novel cholesteryl ester transferprotein inhibitors: Optimization via array synthesis. Bioorg. Med. Chem. Lett., 2008, 18, 2640-2644.
[74]
Kallashi, F.; Kim, D.; Kowalchick, J.; Park, Y.; Hunt, J.; Ali, A.; Smith, C.; Hammond, M.; Pivnichny, J.; Tong, X.; Xu, S.; Anderson, M.; Chen, Y.; Eveland, S.; Guo, Q.; Hyland, S.; Milot, D.; Cumiskey, A.; Latham, M.; Peterson, M.; Rosa, R.; Sparrow, C.; Wright, S.; Sinclair, P. 2-Arylbenzoxazoles as CETP inhibitors: Raising HDL-C in CETP transgenic mice. Bioorg. Med. Chem. Lett., 2011, 21, 558-561.
[75]
Misra, R.; Barthwal, J.; Parmar, S.; Brumleve, S. Substituted benzoxazole/benzthiazole-2-thiones: Interrelationship between anticonvulsant activity and inhibition of nicotinamide adenine dinucleotide-dependent oxidations and monoamine oxidase. J. Pharm. Sci., 1974, 6, 401-404.
[76]
Misra, R.; Barthwal, J.; Parmar, S.; Singh, S.; Stenberg, V. Synthesis of Substituted Thiobenzoxazoles/Benzothiazoles: Inhibition of Cellular Respiratory and Monoamine Oxidase Activities and Anticonvulsant Property. J. Pharm. Sci., 1976, 65, 405-409.
[77]
Deng, G.; Meng, Q.; Liu, Q.; Xu, X.; Xu, Q.; Ren, F.; Guo, T.; Lu, H.; Xiang, J.; Elliott, J.; Lin, X. Identification of benzoxazole analogs as novel, S1P3 sparing S1P1 agonists. Bioorg. Med. Chem. Lett., 2012, 22, 3973-3977.
[78]
Kim, M. Jeon, J777.; Song, J.; Suh, K.; Kim, Y.; Min, K.; Lee, K. Synthesis of proline analogues as potent and selective cathepsin S inhibitors. Bioorg. Med. Chem. Lett., 2013, 23, 3140-3144.
[79]
Sun, L.; Chen, J.; Bruce, M.; Deskus, J.; Epperson, J.; Takaki, K.; Johnson, G.; Iben, L.; Mahle, C.; Ryan, E.; Xu, C. Synthesis and structure–activity relationship of novel benzoxazole derivatives as melatonin receptor agonists. Bioorg. Med. Chem. Lett., 2004, 14, 3799-3802.
[80]
Sun, L.; Chen, J.; Takaki, K.; Johnson, G.; Iben, L.; Mahle, C.; Ryan, E.; Xu, C. Design and synthesis of benzoxazole derivatives as novel melatoninergic ligands. Bioorg. Med. Chem. Lett., 2004, 14, 1197-1200.
[81]
Sam, J.; Plampin, J. Benzoxazoles: Potent skeletal muscle relaxants. J. Pharm. Sci., 1964, 53, 538-544.
[82]
Jin, C.; Fix, S.; Kepler, J.; Cook, E. Synthesis and antihormonal properties of novel 11β-benzoxazole-substituted steroids. Bioorg. Med. Chem. Lett., 2012, 22, 1705-1708.
[83]
Xue, C.; Rafalski, M.; Roderick, J.; Eyermann, C.; Mousa, S.; Olson, R.; DeGrado, W. Design, synthesis and in vitro activity of series of benzimidazole/benzoxazole glycoprotein IIb/IIIa inhibitors. Bioorg. Med. Chem. Lett., 1996, 6, 339-344.
[84]
Proenca, C.; Serralheiro, M.; Araujo, M.; Pamplona, T.; Santos, S.; Santos, M.; Frazao, F. Novel sulfenamides as promising acetylcholinesterase inhibitors. J. Heterocycl. Chem., 2011, 48, 1287-1295.
[85]
Cho, S.; Han, S.; Ha, J.; Ryu, J.; Lee, C.; Jung, H.; Kang, N.; Kim, H.; Koh, J.; Lee, J. Discovery of aminopyridines substituted with benzoxazole as orally active c-Met kinase inhibitors. Bioorg. Med. Chem. Lett., 2010, 20, 4223-4227.
[86]
Sessions, E.; Yin, Y.; Bannister, T.; Weiser, A.; Griffin, E.; Pocas, J.; Cameron, M.; Ruiz, C.; Lin, L.; Schürer, S.; Schröter, T.; LoGrasso, P.; Feng, Y. Benzimidazole- and benzoxazole-based inhibitors of Rho kinase. Bioorg. Med. Chem. Lett., 2008, 18, 6390-6393.
[87]
Berta, D.; Villa, M.; Vulpetti, A.; Felder, E. Pyrazolyl–benzoxazole derivatives as protein kinase inhibitor: Design and validation of a combinatorial library. Tetrahedron, 2005, 61, 10801-10810.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy