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An efficient synthesis of 8-substituted Odoratine derivatives by the Suzuki coupling reaction

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Abstract

An efficient method for the preparation of 8-substituted odoratine [(3-(3 ′, 4 ′-methylenedioxyphenyl)-5,6,7-trimethoxyisoflavone] derivatives, structurally similar to glaziovianin A, a known cytotoxic substance, has been described. The key steps in the synthesis are site selective bromination reaction followed by Suzuki coupling reaction in very good yield. The structural assignment of the bromo derivative was determined utilizing 2D-HMBC and NOEs NMR techniques.

An efficient method for the preparation of odoratine, a naturally occurring isoflavone, has been described. 8-substituted odoratine derivatives were prepared via the Suzuki coupling reaction. Site selective bromination reaction was explored to obtain the key intermediates required for the coupling reactions.

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Acknowledgements

Authors are grateful to GVK Biosciences management for the financial support. We thank Dr. Sudhir Kumar Singh for encouragement and motivation. Help from the analytical department for the analytical data is appreciated. PKH gratefully acknowledges UGC, New Delhi for providing UGC-FRPS research start-up grant.

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Authors and Affiliations

  1. Department of Medicinal Chemistry, GVK Biosciences Pvt. Ltd., Plot Nos 125(part) & 126, IDA, Mallapur, Hyderabad, 500 076, Telangana, India

    P RAVI KUMAR, C BALAKRISHNA, B MURALI, RAMAKRISHNA GUDIPATI, AVINASH B CHAUDHARY, SATYANARAYANA YENNAM & MANORANJAN BEHERA

  2. Centre for Chemical Sciences and Technology, Institute of Science and Technology, JNT University, Kukatpally, Hyderabad, 500 085, Telangana, India

    P RAVI KUMAR & A JAYA SHREE

  3. Department of Chemistry, School of Sciences, HNBG University, Srinagar (Garhwal), Uttarakhand, 246 174, India

    PRASANTA K HOTA

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  1. P RAVI KUMAR
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  2. C BALAKRISHNA
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  3. B MURALI
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  4. RAMAKRISHNA GUDIPATI
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  6. AVINASH B CHAUDHARY
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  7. A JAYA SHREE
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  8. SATYANARAYANA YENNAM
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  9. MANORANJAN BEHERA
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Correspondence to MANORANJAN BEHERA.

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Supplementary Information (SI)

The spectroscopic data (1H-NMR, 13C-NMR, IR and HRMS) of synthesized compounds are presented in the Supplementary Information, available at www.ias.ac.in/chemsci.

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KUMAR, P.R., BALAKRISHNA, C., MURALI, B. et al. An efficient synthesis of 8-substituted Odoratine derivatives by the Suzuki coupling reaction. J Chem Sci 128, 441–450 (2016). https://doi.org/10.1007/s12039-016-1042-z

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  • DOI: https://doi.org/10.1007/s12039-016-1042-z

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