Synthesis of admantane substituted spiro 1,2,4-trioxanes using simple and cheap starting material

L. Kumar, N. Kaushik, A. Malik, P. Kumar

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Spiro 1,2,4-trioxane are synthetic derivative of artemisinin (1,2,4-trioxane is supposed to be a pharmacophore of artemisinin) which is a well known antimalarial drug from leaves of Artemisia annua found in China. Spiro 1,2,4-trioxane substituted with admantane and its 4 different derivatives were synthesized using well standardized method. These compounds were purified by simple column chromatography and successfully analyzed using 'H NMR, IR and FAB-MS techniques.
Original languageEnglish
Pages (from-to)3540-3546
Number of pages7
JournalAsian Journal of Chemistry
Volume21
Issue number5
Publication statusPublished - 2009
Externally publishedYes

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Derivatives
Column chromatography
Antimalarials
Nuclear magnetic resonance
1,2,4-trioxane
artemisinine

Cite this

Kumar, L. ; Kaushik, N. ; Malik, A. ; Kumar, P. / Synthesis of admantane substituted spiro 1,2,4-trioxanes using simple and cheap starting material. In: Asian Journal of Chemistry. 2009 ; Vol. 21, No. 5. pp. 3540-3546.
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title = "Synthesis of admantane substituted spiro 1,2,4-trioxanes using simple and cheap starting material",
abstract = "Spiro 1,2,4-trioxane are synthetic derivative of artemisinin (1,2,4-trioxane is supposed to be a pharmacophore of artemisinin) which is a well known antimalarial drug from leaves of Artemisia annua found in China. Spiro 1,2,4-trioxane substituted with admantane and its 4 different derivatives were synthesized using well standardized method. These compounds were purified by simple column chromatography and successfully analyzed using 'H NMR, IR and FAB-MS techniques.",
author = "L. Kumar and N. Kaushik and A. Malik and P. Kumar",
note = "Cited By :1 Export Date: 10 November 2017 CODEN: AJCHE Correspondence Address: Kumar, L.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal Academy of Higher Education, Manipal-576 119, India References: W.H.O. Drug Information Bulletin, 13, p. 9 (1999); Phytochemistry Section, Institute of Materia Medica, Chinese Academy of Medical Sciences, Summary of the Research of Chinese Traditional and Herbal Medicines (1979) Acta Pharm. Sinica, 14, p. 746; Xu, X.X., Zhu, J., Huang, D.Z., Zhou, W.S., (1991) Tetrahedron Lett, 32, p. 5785; Jaquet, C., Stohler, H.R., Chollet, J., Peters, W., (1994) Trop. Med. Parasitol, 45, p. 266; Hofheinz, W., Burgin, H., Gocke, E., Jaquet, C., Masciadri, R., Schmid, G., Stohler, H., (1994) Trop. Med. Parasitol, 45, p. 261; Jefford, C.W., Jaggi, D., Boukouvalas, J., Kohmoto, S., (1983) J. Am. Chem. Soc, 105, p. 6498; Kepler, J.A., Philip, A., Lee, Y.W., Morey, M.C., Caroll, F.I., (1988) J. Med. Chem, 31, p. 713; Fujisakum, T., Miura, M., Nojima, M., Kasabayashi, S., (1989) J. Chem. Soc. Perkin Trans. I, 1031; Avery, M.A., Jennings-White, C., Chong, W.K.M., (1989) J. Org. Chem, 54, p. 1792; Bloodworth, A.J., Shah, A., (1991) J. Chem. Soc. Chem. Commun, 947; Posner, G.H., Oh, C.H., Milhous, W.K., (1991) Tetrahedron Lett, 32, p. 4235; Bunnelle, W.H., Isbell, T.A., Barnes, C.L., Quails, S., (1991) J. Am. Chem. Soc, 113, p. 8168; Bloodworth, A.J., Johnson, K.A., (1994) Tetrahedron Lett, 35, p. 8057; O'Neill, P.M., Pugh, M., Davies, J., Ward, S.A., Park, B.K., (2001) Tetrahedron Lett, 42, p. 4569; O'Neill, P.M., Mukhtar, A., Ward, S.A., Bickley, J.F., Davies, J., Bachi, M.D., Stocks, P.A., (2004) Org. Lett, 6, p. 3035; Singh, C., (1990) Tetrahedron Lett, 31, p. 6901; Singh, C., Misra, D., Saxena, G., Chandra, S., (1992) Bioorg. Med. Chem. Lett, 2, p. 497; Singh, C., Misra, D., Saxena, G., Chandra, S., (1995) Bioorg. Med. Chem. Lett, 5, p. 1913; Singh, C., Gupta, N., Puri, S.K., (2002) Bioorg. Med. Chem. Lett, 12, p. 1913; Singh, C., Malik, H., Puri, S.K., (2004) Bioorg. Med. Chem. Lett, 12, p. 1177; Singh, C., Srivastav, N.C., Puri, S.K., (2004) Bioorg. Med. Chem, 12, p. 5745; Singh, C., Malik, H., Puri, S.K., (2004) Bioorg. Med. Chem, 14, p. 459; Singh, C., Gupta, N., Puri, S.K., (2004) Bioorg. Med. Chem, 12, p. 5553; Singh, C., Gupta, N., Puri, S.K., (2005) Tetrahedron Lett, 46, p. 205; Singh, C., Malik, H., Puri, S.K., (2006) J. Med. Chem, 49, p. 2794; Singh, C., Kanchan, R., Srivastava, D., Puri, S.K., (2006) Bioorg. Med. Chem. Lett, 16, p. 584; Singh, C., Kanchan, R., Sharma, U., Puri, S.K., (2007) J. Med. Chem, 50, p. 521; Adam, W., Duran, N., (1972) J. Chem. Soc. Chem. Commun, 798; Dussault, P.H., Trullinger, T.K., Noor-e-Ain, F., (2002) Org. Lett, 4, p. 4591; Oh, C.H., Kang, J.H., (1998) Tetrahedron Lett, 39, p. 2771; Dussault, P.H., Davies, D.R., (1996) Tetrahedron Lett, 37, p. 463; Ushigoe, Y., Kano, Y., Nojima, M., (1997) J. Chem. Soc. Perkin Trans. 1, 5; Ushigoe, Y., Torao, Y., Masuyama, A., Nojima, M., (1997) J. Org. Chem, 62, p. 4949; Ushigoe, Y., Masuyama, A., Nojima, M., McCullough, K.J., (1997) Tetrahedron Lett, 38, p. 8753. , e; Ahmed, A., Dussault, P.H., (2004) Org. Lett, 6, p. 3609; Amewu, R., Stachulski, A.V., Berry, N.G., Ward, S.A., Davies, J., Labat, G., Rossignol, J.F., O'Neill, P.M., (2006) Bioorg. Med. Chem. Lett, 16, p. 6124; Singh, C., Pandey, S., Saxena, G., Srivastava, N., Sharma, M., (2006) J. Org. Chem, 71, p. 9057",
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Kumar, L, Kaushik, N, Malik, A & Kumar, P 2009, 'Synthesis of admantane substituted spiro 1,2,4-trioxanes using simple and cheap starting material', Asian Journal of Chemistry, vol. 21, no. 5, pp. 3540-3546.

Synthesis of admantane substituted spiro 1,2,4-trioxanes using simple and cheap starting material. / Kumar, L.; Kaushik, N.; Malik, A.; Kumar, P.

In: Asian Journal of Chemistry, Vol. 21, No. 5, 2009, p. 3540-3546.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of admantane substituted spiro 1,2,4-trioxanes using simple and cheap starting material

AU - Kumar, L.

AU - Kaushik, N.

AU - Malik, A.

AU - Kumar, P.

N1 - Cited By :1 Export Date: 10 November 2017 CODEN: AJCHE Correspondence Address: Kumar, L.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal Academy of Higher Education, Manipal-576 119, India References: W.H.O. Drug Information Bulletin, 13, p. 9 (1999); Phytochemistry Section, Institute of Materia Medica, Chinese Academy of Medical Sciences, Summary of the Research of Chinese Traditional and Herbal Medicines (1979) Acta Pharm. Sinica, 14, p. 746; Xu, X.X., Zhu, J., Huang, D.Z., Zhou, W.S., (1991) Tetrahedron Lett, 32, p. 5785; Jaquet, C., Stohler, H.R., Chollet, J., Peters, W., (1994) Trop. Med. Parasitol, 45, p. 266; Hofheinz, W., Burgin, H., Gocke, E., Jaquet, C., Masciadri, R., Schmid, G., Stohler, H., (1994) Trop. Med. Parasitol, 45, p. 261; Jefford, C.W., Jaggi, D., Boukouvalas, J., Kohmoto, S., (1983) J. Am. Chem. Soc, 105, p. 6498; Kepler, J.A., Philip, A., Lee, Y.W., Morey, M.C., Caroll, F.I., (1988) J. Med. Chem, 31, p. 713; Fujisakum, T., Miura, M., Nojima, M., Kasabayashi, S., (1989) J. Chem. Soc. Perkin Trans. I, 1031; Avery, M.A., Jennings-White, C., Chong, W.K.M., (1989) J. Org. Chem, 54, p. 1792; Bloodworth, A.J., Shah, A., (1991) J. Chem. Soc. Chem. Commun, 947; Posner, G.H., Oh, C.H., Milhous, W.K., (1991) Tetrahedron Lett, 32, p. 4235; Bunnelle, W.H., Isbell, T.A., Barnes, C.L., Quails, S., (1991) J. Am. Chem. Soc, 113, p. 8168; Bloodworth, A.J., Johnson, K.A., (1994) Tetrahedron Lett, 35, p. 8057; O'Neill, P.M., Pugh, M., Davies, J., Ward, S.A., Park, B.K., (2001) Tetrahedron Lett, 42, p. 4569; O'Neill, P.M., Mukhtar, A., Ward, S.A., Bickley, J.F., Davies, J., Bachi, M.D., Stocks, P.A., (2004) Org. Lett, 6, p. 3035; Singh, C., (1990) Tetrahedron Lett, 31, p. 6901; Singh, C., Misra, D., Saxena, G., Chandra, S., (1992) Bioorg. Med. Chem. Lett, 2, p. 497; Singh, C., Misra, D., Saxena, G., Chandra, S., (1995) Bioorg. Med. Chem. Lett, 5, p. 1913; Singh, C., Gupta, N., Puri, S.K., (2002) Bioorg. Med. Chem. Lett, 12, p. 1913; Singh, C., Malik, H., Puri, S.K., (2004) Bioorg. Med. Chem. Lett, 12, p. 1177; Singh, C., Srivastav, N.C., Puri, S.K., (2004) Bioorg. Med. Chem, 12, p. 5745; Singh, C., Malik, H., Puri, S.K., (2004) Bioorg. Med. Chem, 14, p. 459; Singh, C., Gupta, N., Puri, S.K., (2004) Bioorg. Med. Chem, 12, p. 5553; Singh, C., Gupta, N., Puri, S.K., (2005) Tetrahedron Lett, 46, p. 205; Singh, C., Malik, H., Puri, S.K., (2006) J. Med. Chem, 49, p. 2794; Singh, C., Kanchan, R., Srivastava, D., Puri, S.K., (2006) Bioorg. Med. Chem. Lett, 16, p. 584; Singh, C., Kanchan, R., Sharma, U., Puri, S.K., (2007) J. Med. Chem, 50, p. 521; Adam, W., Duran, N., (1972) J. Chem. Soc. Chem. Commun, 798; Dussault, P.H., Trullinger, T.K., Noor-e-Ain, F., (2002) Org. Lett, 4, p. 4591; Oh, C.H., Kang, J.H., (1998) Tetrahedron Lett, 39, p. 2771; Dussault, P.H., Davies, D.R., (1996) Tetrahedron Lett, 37, p. 463; Ushigoe, Y., Kano, Y., Nojima, M., (1997) J. Chem. Soc. Perkin Trans. 1, 5; Ushigoe, Y., Torao, Y., Masuyama, A., Nojima, M., (1997) J. Org. Chem, 62, p. 4949; Ushigoe, Y., Masuyama, A., Nojima, M., McCullough, K.J., (1997) Tetrahedron Lett, 38, p. 8753. , e; Ahmed, A., Dussault, P.H., (2004) Org. Lett, 6, p. 3609; Amewu, R., Stachulski, A.V., Berry, N.G., Ward, S.A., Davies, J., Labat, G., Rossignol, J.F., O'Neill, P.M., (2006) Bioorg. Med. Chem. Lett, 16, p. 6124; Singh, C., Pandey, S., Saxena, G., Srivastava, N., Sharma, M., (2006) J. Org. Chem, 71, p. 9057

PY - 2009

Y1 - 2009

N2 - Spiro 1,2,4-trioxane are synthetic derivative of artemisinin (1,2,4-trioxane is supposed to be a pharmacophore of artemisinin) which is a well known antimalarial drug from leaves of Artemisia annua found in China. Spiro 1,2,4-trioxane substituted with admantane and its 4 different derivatives were synthesized using well standardized method. These compounds were purified by simple column chromatography and successfully analyzed using 'H NMR, IR and FAB-MS techniques.

AB - Spiro 1,2,4-trioxane are synthetic derivative of artemisinin (1,2,4-trioxane is supposed to be a pharmacophore of artemisinin) which is a well known antimalarial drug from leaves of Artemisia annua found in China. Spiro 1,2,4-trioxane substituted with admantane and its 4 different derivatives were synthesized using well standardized method. These compounds were purified by simple column chromatography and successfully analyzed using 'H NMR, IR and FAB-MS techniques.

M3 - Article

VL - 21

SP - 3540

EP - 3546

JO - Asian Journal of Chemistry

JF - Asian Journal of Chemistry

SN - 0970-7077

IS - 5

ER -