DDQ mediated stereoselective intermolecular benzylic C[sbnd]N bond formation: Synthesis of (−)-cytoxazone, (−)-4-epi-cytoxazone and their analogues and immunological evaluation of their cytokine modulating activity

Macha Lingamurthy; Gopalal Rao Nalliboina; Maddimsetti Venkateswara Rao; Batchu Venkateswara Rao; Bonam Srinivasa Reddy; Halmuthur Mahabalarao Sampath Kumar

doi:10.1016/j.tet.2017.01.059

DDQ mediated stereoselective intermolecular benzylic C[sbnd]N bond formation: Synthesis of (−)-cytoxazone, (−)-4-epi-cytoxazone and their analogues and immunological evaluation of their cytokine modulating activity

Macha Lingamurthy
, Gopalal Rao Nalliboina
, Maddimsetti Venkateswara Rao
, Batchu Venkateswara Rao
, Bonam Srinivasa Reddy
, Halmuthur Mahabalarao Sampath Kumar

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

A short and efficient strategy for the synthesis of (−)-cytoxazone, (−)-4-epi-cyoxazone and their analogues by using DDQ mediated diastereoselective intermolecular benzylic amination has been described. Immunological evaluation of their cytokine modulating activity revealed that the change of hydroxy methyl to methyl group increased the cellular immunity in in-vitro cultures. Changes in the stereochemistry of oxazolidine haven't influenced the biological activity.

Original language	English (US)
Pages (from-to)	1473-1481
Number of pages	9
Journal	Tetrahedron
Volume	73
Issue number	11
DOIs	https://doi.org/10.1016/j.tet.2017.01.059
State	Published - 2017
Externally published	Yes

Keywords

Benzylic amination
Cellular immunity
Cytoxazone
Oxazolidine

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2017.01.059

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Lingamurthy, M., Nalliboina, G. R., Rao, M. V., Rao, B. V., Reddy, B. S., & Sampath Kumar, H. M. (2017). DDQ mediated stereoselective intermolecular benzylic C[sbnd]N bond formation: Synthesis of (−)-cytoxazone, (−)-4-epi-cytoxazone and their analogues and immunological evaluation of their cytokine modulating activity. Tetrahedron, 73(11), 1473-1481. https://doi.org/10.1016/j.tet.2017.01.059

DDQ mediated stereoselective intermolecular benzylic C[sbnd]N bond formation: Synthesis of (−)-cytoxazone, (−)-4-epi-cytoxazone and their analogues and immunological evaluation of their cytokine modulating activity. / Lingamurthy, Macha; Nalliboina, Gopalal Rao; Rao, Maddimsetti Venkateswara et al.
In: Tetrahedron, Vol. 73, No. 11, 2017, p. 1473-1481.

Research output: Contribution to journal › Article › peer-review

Lingamurthy, M, Nalliboina, GR, Rao, MV, Rao, BV, Reddy, BS & Sampath Kumar, HM 2017, 'DDQ mediated stereoselective intermolecular benzylic C[sbnd]N bond formation: Synthesis of (−)-cytoxazone, (−)-4-epi-cytoxazone and their analogues and immunological evaluation of their cytokine modulating activity', Tetrahedron, vol. 73, no. 11, pp. 1473-1481. https://doi.org/10.1016/j.tet.2017.01.059

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abstract = "A short and efficient strategy for the synthesis of (−)-cytoxazone, (−)-4-epi-cyoxazone and their analogues by using DDQ mediated diastereoselective intermolecular benzylic amination has been described. Immunological evaluation of their cytokine modulating activity revealed that the change of hydroxy methyl to methyl group increased the cellular immunity in in-vitro cultures. Changes in the stereochemistry of oxazolidine haven't influenced the biological activity.",

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AU - Lingamurthy, Macha

AU - Nalliboina, Gopalal Rao

AU - Rao, Maddimsetti Venkateswara

AU - Rao, Batchu Venkateswara

AU - Reddy, Bonam Srinivasa

AU - Sampath Kumar, Halmuthur Mahabalarao

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KW - Benzylic amination

KW - Cellular immunity

KW - Cytoxazone

KW - Oxazolidine

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DDQ mediated stereoselective intermolecular benzylic C[sbnd]N bond formation: Synthesis of (−)-cytoxazone, (−)-4-epi-cytoxazone and their analogues and immunological evaluation of their cytokine modulating activity

Abstract

Keywords

ASJC Scopus subject areas

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