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ZnO nanoparticles in the synthesis of AB ring core of camptothecin

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Abstract

For the first time, synthesis of AB ring core of camptothecin synthons such as (2-chloroquinolin-3-yl)methanols (Va-Vg) using zinc oxide nanoparticles is reported. The desired attractive products were obtained in high yields, short reaction time, using a simple work-up procedure with the purification of products by non-chromatographic methods.

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References

  • Alonso, F., Riente, P., & Yus, M. (2008). Hydrogen-transfer reduction of carbonyl compounds catalysed by nickel nanoparticles. Tetrahedron Letters, 49, 1939–1942. DOI: 10.1016/j.tetlet.2008.01.097.

    Article  CAS  Google Scholar 

  • Chaicharoenwimolkul, L., Munmai, A., Chairam, S., Tewasekson, U., Sapudom, S., Lakliang, Y., & Somsook, E. (2008). Effect of stabilizing ligands bearing ferrocene moieties on the gold nanoparticle-catalyzed reactions of arylboronic acids. Tetrahedron Letters, 49, 7299–7302. DOI: 10.1016/j.tetlet.2008.10.040.

    Article  CAS  Google Scholar 

  • Comins, D. L., Hong, H., & Jianhua, G. (1994). Asymmetric synthesis of camptothecin alkaloids: A nine-step synthesis of (S)-camptothecin. Tetrahedron Letters, 35, 5331–5334. DOI: 10.1016/S0040-4039(00)73492-7.

    Article  CAS  Google Scholar 

  • Khan, F. N., Roopan, S. M., Hathwar, V. R., & Ng, S. W. (2010). 2-Chloro-3-hydroxymethyl-7,8-dimethylquinoline. Acta Crystallographica Section E, E66, o200. DOI: 10.1107/S160053680905404X.

    Article  CAS  Google Scholar 

  • Khan, F. N., Roopan, S. M., Hathwar, V. R., & Ng, S. W. (2010b). 2-Chloro-3-hydroxymethyl-6-methoxyquinoline. Acta Crystallographica Section E, E66, o201. DOI: 10.1107/S1600536809054051.

    Article  CAS  Google Scholar 

  • Kidwai, M., Mishra, N. K., Bansal, V., Kumar, A., & Mozumdar, S. (2009). Novel one-pot Cu-nanoparticles-catalyzed Mannich reaction. Tetrahedron Letters, 50, 1355–1358. DOI: 10.1016/j.tetlet.2009.01.031.

    Article  CAS  Google Scholar 

  • Kim, Y. J., & Varma, R. S. (2004). Microwave-assisted preparation of cyclic ureas from diamines in the presence of ZnO. Tetrahedron Letters, 45, 7205–7208. DOI: 10.1016/j.tetlet.2004.08.042.

    Article  CAS  Google Scholar 

  • Maghsoodlou, M. T, Hassankhani, A., Shaterian, H. R., Habibi-Khorasani, S. M., & Mosaddegh, E. (2007). Zinc oxide as an economical and efficient catalyst for the one-pot preparation of β-acetamido ketones via a four-component condensation reaction. Tetrahedron Letters, 48, 1729–1734. DOI: 10.1016/j.tetlet.2007.01.060.

    Article  CAS  Google Scholar 

  • Niizuma, S., Tsukazaki, M., Suda, H., Murata, T., Ohwada, J., Ozawa, S., Fukuda, H., Murasaki, C., Kohchi, M., Morikami, K., Yoshinari, K., Endo, M., Ura, M., Tanimura, H., Miyazaki, Y., Takasuka, T., Kawashima, A., Nanba, E., Nakano, K., Ogawa, K., Kobayashi, K., Okabe, H., Umeda, I., & Shimma, N. (2009). Synthesis of new camptothecin analogs with improved antitumour activities. Bioorganic & Medicinal Chemistry Letters, 19, 2018–2021. DOI: 10.1016/j.bmcl.2009.02.031.

    Article  CAS  Google Scholar 

  • Rath, G., Schneider, C., Langlois, B., Sartelet, H., Morjani, H., Btaouri, H. E. L., Dedieu, S., & Martiny, L. (2009). De novo ceramide synthesis is responsible for the anti-tumor properties of camptothecin and doxorubicin in follicular thyroid carcinoma. The International Journal of Biochemistry & Cell Biology, 41, 1165–1172. DOI: 10.1016/j.biocel.2008.10.021.

    Article  CAS  Google Scholar 

  • Roopan, S. M., & Khan, F. R. N. (2010). ZnO nanorods catalyzed N-alkylation of piperidin-4-one, 4(3H)-pyrimidone, and ethyl 6-chloro-1,2-dihydro-2-oxo-4-phenylquinoline-3-carboxylate. Chemical Papers, 64, 678–682. DOI: 10.2478/s11696-010-0045-3.

    Article  CAS  Google Scholar 

  • Roopan, S. M., & Khan, F. R. N. (2009). Synthesis, antioxidant, hemolytic and cytotoxicity activity of AB ring core of mappicine. ARKIVOC, xiii, 161–169.

    Google Scholar 

  • Roopan, S. M., & Khan, F. N. (2008). Free radical scavenging activity of nitrogen heterocyclics-quinazolinones and tetrahydrocarbazolones. Indian Journal of Heterocyclic Chemistry, 18, 183–184.

    CAS  Google Scholar 

  • Roopan, S. M., Khan, F. R. N., & Mandal, B. K. (2010). Fe nano particles mediated C-N bond-forming reaction: Regioselective synthesis of 3-[(2-chloroquinolin-3-yl)methyl]pyrimidin-4(3H)ones. Tetrahedron Letters, 51, 2309–2311. DOI: 10. 1016/j.tetlet.2010.02.128.

    Article  CAS  Google Scholar 

  • Roopan, S. M., Khan, F. N., Subashini, R., Hathwar, V. R., & Ng, S. W. (2009). 2-Chlorobenzo[h]quinoline-3-carbaldehyde. Acta Crystallographica Section E, E65, o2711. DOI: 10.1107/S1600536809040720.

    Article  CAS  Google Scholar 

  • Roopan, S. M., Maiyalagan, T., & Khan, F. N. (2008). Solvent-free syntheses of some quinazolin-4(3H)-ones derivatives. Canadian Journal of Chemistry, 86, 1019–1025. DOI: 10.1139/V08-149.

    Article  CAS  Google Scholar 

  • Sapkal, S. B., Shelke, K. F., Shingate, B. B., & Shingare, M. S. (2009). Nickel nanoparticle-catalyzed facile and efficient onepot synthesis of polyhydroquinoline derivatives via Hantzsch condensation under solvent-free conditions. Tetrahedron Letters, 50, 1754–1756. DOI: 10.1016/j.tetlet.2009.01.140.

    Article  CAS  Google Scholar 

  • Srivastava, A., & Singh, R. M. (2005). Vilsmeier-Haack reagent: A facile synthesis of 2-chloro-3-formylquinolines from Narylacetamides and transformation into different functionalities. Indian Journal of Chemistry Section B, 44B, 1868–1875.

    CAS  Google Scholar 

  • Wall, M. E., Wani, M. C., Cook, C. E., Palmer, K. H., McPhail, A. T., & Sim, G. A. (1966). Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata. Journal of the American Chemical Society, 88, 3888–3890. DOI: 10.1021/ja00968a057.

    Article  CAS  Google Scholar 

  • Wu, C., Qiao, X., Chen, J., Wang, H., Tan, F., & Li, S. (2006). A novel chemical route to prepare ZnO nanoparticles. Materials Letters, 60, 1828–1832. DOI: 10.1016/j.matlet.2005.12.046.

    Article  CAS  Google Scholar 

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Correspondence to Fazlur Rahman Nawaz Khan.

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Roopan, S.M., Nawaz Khan, F.R. ZnO nanoparticles in the synthesis of AB ring core of camptothecin. Chem. Pap. 64, 812–817 (2010). https://doi.org/10.2478/s11696-010-0058-y

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  • DOI: https://doi.org/10.2478/s11696-010-0058-y

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