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Synthesis and Antiproliferative Activity of Novel Pyranocarbazoles

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Chemistry of Heterocyclic Compounds Aims and scope

A new series of pyrano[3,2-c]carbazole and pyrano[2,3-a]carbazole derivatives have been synthesized by one-pot three-component coupling of 4-hydroxycarbazole or 2-hydroxycarbazole, aromatic substituted aldehydes, and (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine under microwave irradiation. This rapid one-pot reaction does not require a catalyst, is solvent-free, avoids chromatographic purification, and provides good yields. The synthesized pyranocarbazole derivatives were evaluated for their antiproliferative activity against four cancer cell lines: DU 145 (prostate cancer), MDA-MB-231 (breast cancer), SKOV3 (ovarian cancer), and B16-F10 (skin cancer). N-Methyl-3-nitro-4-(3,4,5-trimethoxyphenyl)-4,7-dihydropyrano[3,2-c]carbazol-2-amine exhibited the most potent antiproliferative activity against the tested cell lines, while other test compounds showed weak or moderate antiproliferative activity, among them N-methyl-3-nitro-4-phenyl-4,7-dihydropyrano[3,2-c]carbazol-2-amine, 4-(4-fluorophenyl)-N-methyl-3-nitro-4,7-dihydropyrano[3,2-c]carbazol-2-amine, and N-methyl-2-nitro-1-phenyl-1,11-dihydropyrano[3,2-a]carbazol-3-amine displayed IC50 values in the low micromolar range.

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Authors and Affiliations

  1. Centre for Chemical Sciences and Technology, IST, Jawaharlal Nehru Technological University, Kukatpally, Hyderabad, Telangana, 500085, India

    Pannala Padmaja & Jaya Shree Anireddy

  2. Department of Chemistry, School of Technology, Gitam University, Rudraram, Hyderabad, Telangana, 502329, India

    Pedavenkatagari Narayana Reddy

Authors
  1. Pannala Padmaja
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  2. Jaya Shree Anireddy
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  3. Pedavenkatagari Narayana Reddy
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Correspondence to Pedavenkatagari Narayana Reddy.

Additional information

Supplementary information file containing 1H and 13C NMR data of compounds 9a,b,e–g,i,j and 1H NMR data of compounds 11a,f is available at the journal website at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(8), 812–818

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Padmaja, P., Anireddy, J.S. & Reddy, P.N. Synthesis and Antiproliferative Activity of Novel Pyranocarbazoles. Chem Heterocycl Comp 54, 812–818 (2018). https://doi.org/10.1007/s10593-018-2354-3

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