Abstract
Thirteen, 1,3,5-triazine core containing tetrazole dendrimeric chalcones have been synthesized in three steps. In the first step (1-(4-(1H-tetrazole-1-yl)phenyl)ethanone) is synthesized from sodium azide and triethyl orthoformate. In the second step, the first-generation of dendrimer, 2,4,6-(tris(tetrazole-1-yl-(4-acetylphenyl))-1,3,5-triazine(G1) is generated from cyanuric chloride and 4-tetrazoylacetophenone by Friedel–Crafts reaction. In the third step, 2,4,6-tris(tetrazol-1-yl-(4-phenyl(3-arylpropene-1-on-1-yl))-1,3,5-triazine(G2) dendrimers are prepared from G1 by Claisen–Schmidt reaction with appropriate aldehydes in ethanol at room temperature. The synthesized compounds (G2, 7a–m) are characterized by Fourier transform infrared (FT-IR), Mass, Matrix-assisted laser ionization Time-of-flight (MALDI-TOF), 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, and elemental analysis. Antifungal activities of triazine-based dendrimeric chalcones (7a–m) are investigated by minimum inhibition concentration method at different concentrations. Some compounds exhibit moderate activities against tested organisms. Compounds 7b, 7c, and 7f showed good activities and 7l and 7m are emerged as lead molecules showing excellent antifungal activities against a panel of fungi.
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References
Astruc D, Boisselier E, Ornelas C (2010) Dendrimers designed for functions: from physical, photo physical, and supramolecular properties to applications in sensing, catalysis, molecular electronics, photonics, and nanomedicine. Chem Rev 110(4):1857–1959
Dichtel WR et al. (2004) Singlet oxygen generation via two-photon excited FRET. J Am Chem Soc 126(17):5380–5381
D’Emanuele A, Attwood D (2005) Dendrimer-drug interactions. Adv Drug Deliv Rev 57(15):2147–2162
Esfand R and Tomalia DA (2001) Poly(amidoamine) (PAMAM) dendrimers: from biomimicry to drug delivery and biomedical applications. Drug Discov Today 6(8):427–436
Frechet JM (1994) Functional polymers and dendrimers: reactivity, molecular architecture and interfacial energy. Science 263(5154):1710–1715
Huh AJ and Kwon YJ (2011) “Nanoantibiotics”: a new paradigm for treating infectious diseases using nanomaterials in the antibiotics resistant era. J Control Release 156(2):128–145
Janiszewska J, Sowińska M, Rajnisz A, Solecka J, Łącka I, Milewski S, Urbańczyk-Lipkowska Z. (2012) Novel dendrimeric lipopeptides with antifungal activity, Bioorg Med Chem Lett. 22(3) 1388–1393
Joshi N, Grinstaff M (2008) Applications of dendrimers in tissue engineering. Curr Top Med Chem 8(14):1225–1236
Klajnert B, Bryszewska M (2001) Dendrimers: properties and applications. Acta Biochi Pol 48(1):199–208
Lee CC, MacKay JA, Frechet JM, Szoka FC (2005) Designing dendrimers for biological applications. Nat Biotechnol 23(12):1517–1526
Majoros IJ, Williams CR, Baker Jr. JR (2008) Current dendrimer applications in cancer diagnosis and therapy. Curr Top Med Chem 8(14):1165–1179
Martic S, Labib M, Shipman PO, Kraatz HB (2011) Ferrocene-peptido conjugates: from synthesis to sensory applications. Dalton Trans 40(28):7264–7290
Medina SH, El-Sayed ME (2009) Dendrimers as carriers for delivery of chemotherapeutic agents. Chem Rev 109(7):3141–3157.
Mur VI (1964) 2,4,6-trichloro-1,3,5-triazine and its future applications Russian. Chem Rev 33(2):92–103
Naylor AM, Porter DW, Lincoln DW (1990) Central administration of corticotrophin-releasing factor in the sheep: effects on secretion of gonadotrophins, prolactin and cortisol. J Endocrinol 124(1):117–125.
Polcyn P, Jurczak M, Rajnisz A, Solecka J, Urbanczyk-Lipkowska Z (2009) Design of antimicrobially active small amphiphilic peptide dendrimers. Molecules 14(10):3881–3905
Roglin L, Lempens EH, Meijer EW (2011) A synthetic “tour de force”: well-defined multivalent and multimodal dendritic structures for biomedical applications. Angew Chem Int Ed Engl 50(1):102–112
Steffensen MB, Hollink E, Kuschel F, Bauer M, Simanek EE (2006) Dendrimers Based on [1,3,5]-Triazines. J Polym Sci A Polym Chem 44(11):3411–3433
Svenson S, Tomalia DA (2005) Dendrimers in biomedical applications--reflections on the field. Adv Drug Deliv Rev 57(15):2106–2129
Tomalia DA, Baker H, Dewald J, Hall M, Kallos G, Martin S, Roeck J, Ryder J, Smith P (1985) A new class of polymers: Starburst-Dendritic macromolecules. Polym J 17:117–132.
Tomalia A, Uppuluri S, Swanson DR, Li J (2000) Dendrimers as reactive modules for the synthesis of new structure-controlled, higher-complexity megamers. Pure and Applied Chemistry 72(12):2343–2358
Zeng F, Zimmerman SC (1997) Dendrimers in supramolecular chemistry: from molecular recognition to self-assembly. Chem Rev 97(5):1681–1712
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One of the authors S.Vembu is thankful to UGC, New Delhi for providing Financial Assistance.
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Vembu, S., Pazhamalai, S. & Gopalakrishnan, M. Synthesis, spectral characterization, and effective antifungal evaluation of 1H-tetrazole containing 1,3,5-triazine dendrimers. Med Chem Res 25, 1916–1924 (2016). https://doi.org/10.1007/s00044-016-1627-6
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DOI: https://doi.org/10.1007/s00044-016-1627-6