Reliable structural information for rational design of benzoxazole type potential cholesteryl ester transfer protein (CETP) inhibitors through multiple validated modeling techniques

References

• Adhikari, N., Halder, A. K., Mondal, C., & Jha, T. (2014). Structural findings of quinolone carboxylic acids in cytotoxic, antiviral, and anti-HIV-1 integrase activity through validated comparative molecular modeling studies. Medicinal Chemistry Research, 23(6), 3096–3127.
   Web of Science ®Google Scholar
• Adhikari, N., Amin, S. A., Saha, A., & Jha, T. (2017). Understanding chemico-biological interactions of glutamate MMP-2 inhibitors through rigorous alignment-dependent 3D-QSAR analyses. ChemistrySelect, 2(26), 7888–7898.
   Web of Science ®Google Scholar
• Amin, S. A., Adhikari, N., & Jha, T. (2018). Diverse classes of HDAC8 inhibitors: In search of molecular fingerprints that regulate activity. Future Medicinal Chemistry, 10(13), 1589–1602.
   PubMed Web of Science ®Google Scholar
• Amin, S. A., Adhikari, N., Gayen, S., & Jha, T. (2017). An integrated ligand-based modelling approach to explore the structure–property relationships of influenza endonuclease inhibitors. Structural Chemistry, 28(6), 1663–1678.
   Web of Science ®Google Scholar
• Amin, S. A., Adhikari, N., Gayen, S., & Jha, T. (2017). First report on the structural exploration and prediction of new BPTES analogs as glutaminase inhibitors. Journal of Molecular Structure, 1143, 49–64. doi:10.1016/j.molstruc.2017.04.020
   Web of Science ®Google Scholar
• Amin, S. A., Bhargava, S., Adhikari, N., Gayen, S., & Jha, T. (2018). Exploring pyrazolo[3,4-d]pyrimidine phosphodiesterase 1 (PDE1) inhibitors: A predictive approach combining comparative validated multiple molecular modelling techniques. Journal of Biomolecular Structure and Dynamics, 36(3), 590–608.
   PubMed Web of Science ®Google Scholar
• Arakawa, K., Inamasu, M., Matsumoto, M., Okumura, K., Yasuda, K., Akatsuka, H., … Iijima, I. (1997). Novel benzoxazole 2,4-thiazolidinediones as potent hypoglycemic agents. Synthesis and structure–activity relationships. Chemical & Pharmaceutical Bulletin, 45(12), 1984–1993. doi:10.1248/cpb.45.1984
   PubMed Web of Science ®Google Scholar
• Barkowski, R. S., & Frishman, W. H. (2008). HDL metabolism and CETP inhibition. Cardiology in Review, 16(3), 154–162.
   PubMed Web of Science ®Google Scholar
• Barter, P. J., & Kastelein, J. J. (2006). Targeting cholesteryl ester transfer protein for the prevention and management of cardiovascular disease. Journal of the American College of Cardiology, 47(3), 492–499.
   PubMed Web of Science ®Google Scholar
• Braun, S., Botzki, A., Salmen, S., Textor, C., Bernhardt, G., Dove, S., & Buschauer, A. (2011). Design of benzimidazole- and benzoxazole-2-thione derivatives as inhibitors of bacterial hyaluronan lyase. European Journal of Medicinal Chemistry, 46(9), 4419–4429.
   PubMed Web of Science ®Google Scholar
• Cramer, R. D. (2003). Topomer CoMFA: A design methodology for rapid lead optimization. Journal of Medicinal Chemistry, 16, 374–388.
   Web of Science ®Google Scholar
• Cramer, R. D., Patterson, D. E., & Bunce, J. D. (1988). Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. Journal of the American Chemical Society, 110(18), 5959–5967.
   PubMed Web of Science ®Google Scholar
• David, R., & Mathew, H. (2010). Extended-connectivity fingerprints. Journal of Chemical Information and Modeling, 50, 742–754.
   PubMed Web of Science ®Google Scholar
• Debnath, A. K. (2002). Pharmacophore mapping of a series of 2, 4-diamino-5-deazapteridine inhibitors of Mycobacterium avium complex dihydrofolate reductase. Journal of Medicinal Chemistry, 45(1), 41–53.
   PubMed Web of Science ®Google Scholar
• Discovery Studio 3.0 (DS 3.0). (2011). San Diego, CA: Accelrys Inc. Software available at: http://www.accelrys.com
   Google Scholar
• Elhady, H. A., El-Sayed, R., & Al-Nathali, H. S. (2018). Design, synthesis and evaluation of anticancer activity of novel 2-thioxoimidazolidin-4-one derivatives bearing pyrazole, triazole and benzoxazole moieties. Chemistry Central Journal, 12, 51.
   PubMed Web of Science ®Google Scholar
• Elnima, E. I., Zubair, M. U., & Al-Badr, A. A. (1981). Antibacterial and antifungal activities of benzimidazole and benzoxazole derivatives. Antimicrobial Agents and Chemotherapy, 19(1), 29–32.
   PubMed Web of Science ®Google Scholar
• Eren, E., Yilmaz, N., & Aydin, O. (2012). High density lipoprotein and it's dysfunction. The Open Biochemistry Journal, 6(1), 78–93.
   PubMedGoogle Scholar
• Ertan-Bolelli, T., Yildiz, I., & Ozgen-Ozgacar, S. (2016). Synthesis, molecular docking and antimicrobial evaluation of novel benzoxazole derivatives. Medicinal Chemistry Research, 25(4), 553–567.
   Web of Science ®Google Scholar
• Halder, A. K., Amin, S. A., Jha, T., & Gayen, S. (2017). Insight into the structural requirements of pyrimidinebased phosphodiesterase 10A (PDE10A) inhibitors by multiple validated 3D QSAR approaches. SAR and QSAR in Environmental Research, 28(3), 253–273.
   PubMed Web of Science ®Google Scholar
• Haugwitz, R. D., Angel, R. G., Jacobs, G. A., Maurer, B. V., Narayanan, V. L., Cruthers, L. R., & Szanto, J. (1982). Antiparasitic agents. 5. Synthesis and anthelmintic activities of novel 2-heteroaromatic-substituted isothiocyanatobenzoxazoles and benzothiazoles. Journal of Medicinal Chemistry, 25(8), 969–974. doi:10.1021/jm00350a017
   PubMed Web of Science ®Google Scholar
• Hunt, J. A., Gonzalez, S., Kallashi, F., Hammond, M. L., Pivnichny, J. V., Tong, X., … Sinclair, P. J. (2010). 2-Arylbenzoxazoles as CETP inhibitors: Substitution and modification of the a-alkoxyamide moiety. Bioorganic & Medicinal Chemistry Letters, 20, 1019–1022. doi:10.1016/j.bmcl.2009.12.046
   PubMed Web of Science ®Google Scholar
• Jana, D., Halder, A. K., Adhikari, N., Maiti, M. K., Mondal, C., & Jha, T. (2011). Chemometric modeling and pharmacophore mapping in coronary heart disease: 2-arylbenzoxazoles as cholesteryl ester transfer protein inhibitors. MedChemComm, 2(9), 840–852.
   Web of Science ®Google Scholar
• Jones, G., Willett, P., Glen, R. C., Leach, A. R., & Taylor, R. (1997). Development and validation of a genetic algorithm for flexible docking. Journal of Molecular Biology, 267(3), 727–748.
   PubMed Web of Science ®Google Scholar
• Jonckers, T. H., Rouan, M. C., Haché, G., Schepens, W., Hallenberger, S., Baumeister, J., & Sasaki, J. C. (2012). Benzoxazole and benzothiazole amides as novel pharmacokinetic enhancers of HIV protease inhibitors. Bioorganic and Medicinal Chemistry Letters, 22(15), 4998–5002. doi:10.1016/j.bmcl.2012.06.022
   PubMed Web of Science ®Google Scholar
• Kallashi, F., Kim, D., Kowalchick, J., Park, Y. J., Hunt, J. A., Ali, A., … Sinclair, P. J. (2011). 2-Arylbenzoxazoles as CETP inhibitors: Raising HDL-C in cynoCETP transgenic mice. Bioorganic & Medicinal Chemistry Letters, 21, 558–561. doi:10.1016/j.bmcl.2010.10.062
   PubMed Web of Science ®Google Scholar
• Katsiki, N., Athyros, V. G., Karagiannis, A., & Mikhailidis, D. P. (2014). High-density lipoprotein, vascular risk, cancer and infection: A case of quantity and quality? Current Medicinal Chemistry, 21(25), 2917–2926.
   PubMed Web of Science ®Google Scholar
• Kaur, A., Pathak, D. P., Sharma, V., & Wakode, S. (2018). Synthesis, biological evaluation and docking study of a new series of di-substituted benzoxazole derivatives as selective COX-2 inhibitors and anti-inflammatory agents. Bioorganic and Medicinal Chemistry, 26(4), 891–902.
   PubMed Web of Science ®Google Scholar
• Kaur, A., Pathak, D. P., Sharma, V., Narasimhan, B., Sharma, P., Mathur, R., & Wakode, S. (2018). Synthesis, biological evaluation and docking study of N-(2-(3,4,5-trimethoxybenzyl)benzoxazole-5-yl) benzamide derivatives as selective COX-2 inhibitor and anti-inflammatory agents. Bioorganic Chemistry, 81, 191–202.
   PubMed Web of Science ®Google Scholar
• Khajondetchairit, P., Phuangsawai, O., Suphakun, P., Rattanabunyong, S., Choowongkomon, K., & Gleeson, M. P. (2017). Design, synthesis, and evaluation of the anticancer activity of 2-amino-aryl-7-aryl-benzoxazole compounds. Chemical Biology & Drug Design, 90(5), 987–994. doi:10.1111/cbdd.13025
   PubMed Web of Science ®Google Scholar
• Klebe, G., Abraham, U., & Mietzner, T. (1994). Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. Journal of Medicinal Chemistry, 37(24), 4130–4146.
   PubMed Web of Science ®Google Scholar
• Klimesová, V., Kocí, J., Waisser, K., Kaustová, J., & Möllmann, U. (2009). Preparation and in vitro evaluation of benzylsulfanyl benzoxazole derivatives as potential antituberculosis agents. European Journal of Medicinal Chemistry, 44, 2286–2293.
   PubMed Web of Science ®Google Scholar
• Kuroyanagi, J. I., Kanai, K., Horiuchi, T., Takeshita, H., Kobayashi, S., Achiwa, I., … Kawakami, K. (2011). Structure–activity relationships of 1,3-benzoxazole-4-carbonitriles as novel antifungal agents with potent in vivo efficacy. Chemical & Pharmaceutical Bulletin, 59(3), 341–352. doi:10.1248/cpb.59.341
   PubMed Web of Science ®Google Scholar
• Liu, S., Mistry, A., Reynolds, J. M., Lloyd, D. B., Griffor, M. C., Perry, D., … Qiu, X. (2012). Crystal structures of cholesteryl ester transfer protein in complex with inhibitors. Journal of Biological Chemistry, 287(44), 37321–37329. doi:10.1074/jbc.M112.380063
   PubMed Web of Science ®Google Scholar
• Luo, B., Li, D., Zhang, A. L., & Gao, J. M. (2018). Synthesis, antifungal activities and molecular docking studies of benzoxazole and benzothiazole derivatives. Molecules, 23(10), 2457.
   PubMed Web of Science ®Google Scholar
• Mabuchi, H., Nohara, A., & Inazu, A. (2014). Cholesteryl ester transfer protein (CETP) deficiency and CETP inhibitors. Molecules and Cells, 37(11), 777–784.
   PubMed Web of Science ®Google Scholar
• Misra, R. S., Barthwal, J. P., Parmar, S. S., & Brumleve, S. J. (1974). Substituted benzoxazole-benzthiazole-2-thiones: Interrelationship between anticonvulsant activity and inhibition of nicotinamide adenine dinucleotide-dependent oxidations and monoamine oxidase. Journal of Pharmaceutical Sciences, 63(3), 401–404.
   PubMed Web of Science ®Google Scholar
• Mohammadpour, A. H., & Akhlaghi, F. (2013). Future of cholesteryl ester transfer protein (CETP) inhibitors: A pharmacological perspective. Clinical Pharmacokinetics, 52(8), 615–626.
   PubMed Web of Science ®Google Scholar
• Mondal, C., Halder, A. K., Adhikari, N., & Jha, T. (2013). Cholesteryl ester transfer protein inhibitors in coronary heart disease: Validated comparative QSAR modeling of N, N-disubstituted trifluoro-3-amino-2-propanols. Computers in Biology and Medicine, 43(10), 1545–1555.
   PubMed Web of Science ®Google Scholar
• Oksuzoglu, E., Tekiner-Gulbas, B., Alper, S., Temiz-Arpaci, O., Ertan, T., Yildiz, I., … Yalcin, I. (2008). Some benzoxazoles and benzimidazoles as DNA topoisomerase I and II inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry, 23(1), 37–42. doi:10.1080/14756360701342516
   PubMed Web of Science ®Google Scholar
• Pavadai, E., E., Mazouni, F., Wittlin, S., de Kock, C., Phillips, M. A., & Chibale, K. (2016). Identification of new human malaria parasite Plasmodium falciparum dihydroorotate dehydrogenase inhibitors by pharmacophore and structure based virtual screening. Journal of Chemical Information and Modelling, 56(3), 548–562.
   PubMed Web of Science ®Google Scholar
• Pourbasheer, E., Aalizadeh, R., Shokouhi Tabar, S., Ganjali, M. R., Norouzi, P., & Shadmanesh, J. (2014). 2D and 3D quantitative structure–activity relationship study of hepatitis C virus NS5B polymerase inhibitors by comparative molecular field analysis and comparative molecular similarity indices analysis methods. Journal of Chemical Information and Modeling, 54(10), 2902–2914. doi:10.1021/ci500216c
   PubMed Web of Science ®Google Scholar
• Rida, S. M., Ashour, F. A., El-Hawash, S. A., ElSemary, M. M., Badr, M. H., & Shalaby, M. A. (2005). Synthesis of some novel benzoxazole derivatives as anticancer, anti-HIV-1 and antimicrobial agents. European Journal of Medicinal Chemistry, 40(9), 949–959.
   PubMed Web of Science ®Google Scholar
• Rogers, D., Brown, R. D., & Hahn, M. (2005). Using extended-connectivity fingerprints with Laplacian-modified Bayesian analysis in high-throughput screening follow-up. Journal of Biomolecular Screening, 10(7), 682–686.
   PubMedGoogle Scholar
• Sainy, J., & Sharma, R. (2015). QSAR analysis of thiolactone derivatives using HQSAR, CoMFA and CoMSIA. SAR and QSAR in Environmental Research, 26(10), 873–892.
   PubMed Web of Science ®Google Scholar
• Satyendra, R. V., Vishnumurthy, K. A., Vagdevi, H. M., Rajesh, K. P., Manjunatha, H., & Shruthi, A. (2011). Synthesis, in vitro antioxidant, anthelmintic and molecular docking studies of novel dichloro substituted benzoxazole-triazolo-thione derivatives. European Journal of Medicinal Chemistry, 46(7), 3078–3084.
   PubMed Web of Science ®Google Scholar
• Smith, C. J., Ali, A., Chen, L., Hammond, M. L., Anderson, M. S., Chen, Y., … Sinclair, P. J. (2010). 2-Arylbenzoxazoles as CETP inhibitors: Substitution of the benzoxazole moiety. Bioorganic & Medicinal Chemistry Letters, 20, 346–349. doi:10.1016/j.bmcl.2009.10.099
   PubMed Web of Science ®Google Scholar
• Song, M. X., Wang, Z. Y., He, S. H., Yu, S. W., Chen, S. L., Guo, D. F., … Deng, X. Q. (2018). Synthesis and evaluation of the anticonvulsant activities of 4-(2-(alkylthio)benzo[d]oxazol-5-yl)-2,4-dihydro-3H-1,2,4-triazol-3-ones. Molecules, 23(4), 756.
   Web of Science ®Google Scholar
• Sweis, R. F., Hunt, J. A., Kallashi, F., Hammonda, M. L., Chen, Y., Eveland, S. S., … Sinclair, P. J. (2011). 2-(4-Carbonylphenyl)benzoxazole inhibitors of CETP: Scaffold design and advancement in HDLc-raising efficacy. Bioorganic & Medicinal Chemistry Letters, 21, 1890–1895. doi:10.1016/j.bmcl.2010.11.090
   PubMed Web of Science ®Google Scholar
• SYBYL-X 2.0. (2015). St. Louis, MO: Tripos Inc. Software available at http://www.certara.com
   Google Scholar
• Tall, A. R., Yvan-Charvet, L., Terasaka, N., Pagler, T., & Wang, N. (2008). HDL, ABC transporters, and cholesterol efflux: Implications for the treatment of atherosclerosis. Cell Metabolism, 7(5), 365–375.
   PubMed Web of Science ®Google Scholar
• Tall, R. (2018). Plasma high density lipoproteins: Therapeutic targeting and links to atherogenic inflammation. Atherosclerosis, 276, 39–43.
   PubMed Web of Science ®Google Scholar
• Trott, O., & Olson, A. J. (2010). AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading. Journal of Computational Chemistry, 31, 455–461.
   PubMed Web of Science ®Google Scholar
• Wang, G., Peng, Z., Wang, J., Li, J., & Li, X. (2016). Synthesis, biological evaluation and molecular docking study of N-arylbenzo[d]oxazol-2-amines as potential α-glucosidase inhibitors. Bioorganic and Medicinal Chemistry, 24(21), 5374–5379.
   PubMed Web of Science ®Google Scholar
• Wang, X., Li, W., Hao, L., Xie, H., Hao, C., Liu, C., … Zhao, D. (2018). The therapeutic potential of CETP inhibitors: A patent review. Expert Opinion on Therapeutic Patents, 28(4), 331–340.
   PubMed Web of Science ®Google Scholar
• Xia, X. Y., Maliski, E. G., Gallant, P., & Rogers, D. (2004). Classification of kinase inhibitors using a Bayesian model. Journal of Medicinal Chemistry, 47(18), 4463–4470.
   PubMed Web of Science ®Google Scholar
• Yalçin, İ., Ören, İ., Şener, E., Akin, A., & Uçartürk, N. (1992). The synthesis and the structure-activity relationships of some substituted benzoxazoles, oxazolo(4,5-b)pyridines, benzothiazoles and benzimidazoles as antimicrobial agents. European Journal of Medicinal Chemistry, 27(4), 401–406.
   Web of Science ®Google Scholar
• Yatam, S., Jadav, S. S., Gundla, R., Gundla, K. P., Reddy, G. M., Ahsan, M. J., & Chimakurthy, J. (2018). Design, synthesis and biological evaluation of 2 (((5‐aryl‐1,2,4‐oxadiazol‐3‐yl)methyl)thio)benzo[d]oxazoles: New antiinflammatory and antioxidant agents. ChemistrySelect, 3(37), 10305–10310. doi:10.1002/slct.201801558
   Web of Science ®Google Scholar
• Yu, S., Yuan, J., Shi, J., Ruan, X., Zhang, T., Wang, Y., & Du, Y. (2015). HQSAR and topomer CoMFA for predicting melanocortin-4 receptor binding affinities of trans-4-(4-chlorophenyl) pyrrolidine-3-carboxamides. Chemometrics and Intelligent Laboratory Systems, 146, 34–41.
   Web of Science ®Google Scholar