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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 8, pp 812–818 | Cite as

Synthesis and Antiproliferative Activity of Novel Pyranocarbazoles

  • Pannala Padmaja
  • Jaya Shree Anireddy
  • Pedavenkatagari Narayana Reddy
Article

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.

Keywords

carbazoles (E)-N-methyl-1-(methylthio)-2-nitroethenamine pyranocarbazoles antiproliferative activity 

Notes

Supplementary material

10593_2018_2354_MOESM1_ESM.pdf (3.4 mb)
ESM 1 (PDF 3518 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Pannala Padmaja
    • 1
  • Jaya Shree Anireddy
    • 1
  • Pedavenkatagari Narayana Reddy
    • 2
  1. 1.Centre for Chemical Sciences and Technology, ISTJawaharlal Nehru Technological UniversityHyderabadIndia
  2. 2.Department of Chemistry, School of TechnologyGitam UniversityHyderabadIndia

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