Synthesis of 3-(1-phenyl-vinyl)-1, 2, 5-trioxa-spiro undecane and its derivatives

L. Kumar, P. Kumar, N. Kaushik

Research output: Contribution to journalArticle

Abstract

3-(1-Phenyl-vinyl)-1, 2, 5-trioxa-spiro undecane is synthetic derivative of Artemisinin. Artemisinin is a well known antimalarial drug from leaves of Artemisia annua find in china. Five different derivatives of 3-(1-Phenyl-vinyl)-1, 2, 5-trioxa-spiro undecane were synthesized using well standardized method. These compounds were purified by simple column chromatography and successfully analysed using H1NMR, IR and FAB-MS techniques.
Original languageEnglish
Pages (from-to)595-600
Number of pages6
JournalOriental Journal of Chemistry
Volume24
Issue number2
Publication statusPublished - 2008

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chromatography
drug
Artemisia annua
Derivatives
Column chromatography
Antimalarials
Chromatography
China
undecane
artemisinine
method

Cite this

@article{4bf6d93e0d984530b561ea900eb7cc10,
title = "Synthesis of 3-(1-phenyl-vinyl)-1, 2, 5-trioxa-spiro undecane and its derivatives",
abstract = "3-(1-Phenyl-vinyl)-1, 2, 5-trioxa-spiro undecane is synthetic derivative of Artemisinin. Artemisinin is a well known antimalarial drug from leaves of Artemisia annua find in china. Five different derivatives of 3-(1-Phenyl-vinyl)-1, 2, 5-trioxa-spiro undecane were synthesized using well standardized method. These compounds were purified by simple column chromatography and successfully analysed using H1NMR, IR and FAB-MS techniques.",
author = "L. Kumar and P. Kumar and N. Kaushik",
note = "Export Date: 10 November 2017 Correspondence Address: Kumar, L.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal Academy of Higher Education, Manipal, Karnataka, India References: W.H.O. Drug Information Bulletin 13: 9 (1999); Department of Phytochemistry, Institute of Materia Medica, Chinese Academy of Medical Sciences.Summary of the research of Chinese traditional and herbal medicines. Acta Pharm Sinica 14: 746-768 (1979); Xu, X.X., Zhu, J., Huang, D.Z., Zhou, W.S., (1991) Tetrahedron Left, 32, pp. 5785-5788; Jaquet, C., Stohler, H.R., Chollet, J., Peters, W., (1994) Trop Med Parasitol, 45, pp. 266-271; Hofheinz, W., Burgin, H., Gocke, E., Jaquet, C., Masciadri, R., Schmid, G., Stohler, H., (1994) Trop Med Parasitol, 45, pp. 261-265; 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, 1, p. 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, p. 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., Qualls, 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, pp. 459-462; 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.J., (1972) Chem. Soc. Chem. Comm, p. 798; Dussault, P.H., Trullinger, T.K., Noor-e- Ain (2002) F. 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. J. Chem. Soc. Perkin Trans. 1 1997, 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; 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. , For in vitro activity of 1,2,4-trioxepanes, see; Singh, C., Pandey, S., Saxena, G., Srivastava, N., Sharma, M., (2006) J. Org. Chem, 71, p. 9057",
year = "2008",
language = "English",
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pages = "595--600",
journal = "Oriental Journal of Chemistry",
issn = "0970-020X",
publisher = "Bhopal, S.A. Iqbal",
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}

Synthesis of 3-(1-phenyl-vinyl)-1, 2, 5-trioxa-spiro undecane and its derivatives. / Kumar, L.; Kumar, P.; Kaushik, N.

In: Oriental Journal of Chemistry, Vol. 24, No. 2, 2008, p. 595-600.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of 3-(1-phenyl-vinyl)-1, 2, 5-trioxa-spiro undecane and its derivatives

AU - Kumar, L.

AU - Kumar, P.

AU - Kaushik, N.

N1 - Export Date: 10 November 2017 Correspondence Address: Kumar, L.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal Academy of Higher Education, Manipal, Karnataka, India References: W.H.O. Drug Information Bulletin 13: 9 (1999); Department of Phytochemistry, Institute of Materia Medica, Chinese Academy of Medical Sciences.Summary of the research of Chinese traditional and herbal medicines. Acta Pharm Sinica 14: 746-768 (1979); Xu, X.X., Zhu, J., Huang, D.Z., Zhou, W.S., (1991) Tetrahedron Left, 32, pp. 5785-5788; Jaquet, C., Stohler, H.R., Chollet, J., Peters, W., (1994) Trop Med Parasitol, 45, pp. 266-271; Hofheinz, W., Burgin, H., Gocke, E., Jaquet, C., Masciadri, R., Schmid, G., Stohler, H., (1994) Trop Med Parasitol, 45, pp. 261-265; 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, 1, p. 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, p. 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., Qualls, 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, pp. 459-462; 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.J., (1972) Chem. Soc. Chem. Comm, p. 798; Dussault, P.H., Trullinger, T.K., Noor-e- Ain (2002) F. 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. J. Chem. Soc. Perkin Trans. 1 1997, 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; 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. , For in vitro activity of 1,2,4-trioxepanes, see; Singh, C., Pandey, S., Saxena, G., Srivastava, N., Sharma, M., (2006) J. Org. Chem, 71, p. 9057

PY - 2008

Y1 - 2008

N2 - 3-(1-Phenyl-vinyl)-1, 2, 5-trioxa-spiro undecane is synthetic derivative of Artemisinin. Artemisinin is a well known antimalarial drug from leaves of Artemisia annua find in china. Five different derivatives of 3-(1-Phenyl-vinyl)-1, 2, 5-trioxa-spiro undecane were synthesized using well standardized method. These compounds were purified by simple column chromatography and successfully analysed using H1NMR, IR and FAB-MS techniques.

AB - 3-(1-Phenyl-vinyl)-1, 2, 5-trioxa-spiro undecane is synthetic derivative of Artemisinin. Artemisinin is a well known antimalarial drug from leaves of Artemisia annua find in china. Five different derivatives of 3-(1-Phenyl-vinyl)-1, 2, 5-trioxa-spiro undecane were synthesized using well standardized method. These compounds were purified by simple column chromatography and successfully analysed using H1NMR, IR and FAB-MS techniques.

M3 - Article

VL - 24

SP - 595

EP - 600

JO - Oriental Journal of Chemistry

JF - Oriental Journal of Chemistry

SN - 0970-020X

IS - 2

ER -