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Microwave-assisted synthesis and characterization of novel symmetrical substituted 19-membered tetrathiadiaza metal-free and metallophthalocyanines and investigation of their biological activities

Authors
Journal
Journal of Organometallic Chemistry
0022-328X
Publisher
Elsevier
Publication Date
Volume
696
Issue
8
Identifiers
DOI: 10.1016/j.jorganchem.2011.01.035
Keywords
  • 1
  • 2-Bis(2-Iodomercaptoethyl)-4
  • 5-Dicyanobenzene
  • Metallophthalocyanine
  • Microwave-Assisted
  • Thermogravimetry
  • Metal-Free Phthalocyanine
  • Biological Activity
Disciplines
  • Biology

Abstract

Graphical abstract This work reports on a new symmetrically substituted metal-free phthalocyanine and its transition metal complexes which were prepared by a condensation of N,N′-[ propan-1,3-diilbis( tiyoetan-2,1-diil)] bis( 4-methylbenzenesulfonamid ( 1) and 1,2-bis ( 2-iodomercaptoethyl) -4,5-dicyanobenzene ( 2) with Ni(II), Zn(II), Co(II), Cu(II), and Pb(II) salts in DMAE, respectively. The novel phthalocyanines bearing thia and aza donor atoms at the peripheral position have been characterized by IR, UV–Vis, 1H NMR, 13C NMR, Mass spectra, and elemental analysis data. The thermal behavior of the metal-free phthalocyanine ( 4) and metallophthalocyanines ( 5–9) were investigated by TG/DTA. Novel phthalocyanines synthesized were also investigated for their possible biological activities by employing antimicrobial (antibacterial and antifungal), antineoplastic and antioxidative assays. Of all tested, four samples exhibited antimicrobial activity against test microorganisms, among which, B. catarrhalis was the most sensitive one with a MIC value around 0. 312 mg/mL followed by a yeast, C. albicans (MIC. 0.625 mg/mL). Due to their colored nature, the samples were found not to be applicable for antioxidative and antineoplastic assays. Highlights ► The synthesis of 4,14-bis[(4-methylphenyl)sulfonyl]-3,4,5,6,9,10,13,14,15,16-dekahydro-2H,8H,12H-1,17,7,11,4,14-benzotetrathiadiazacyclononadecin-19,20-dicarbonitrile ( 3) was obtained by base-catalyzed macrocyclization reaction of N,N′-( 2,2′-( propane-1,3-diylbis( sulfanediyl)) bis( ethane-2,1 diyl)) bis( 4-methylbenzene sulfonamide) ( 1) with the 1, 2-bis(2-iodomercaptoethyl)-4,5-dicyanobenzene ( 2). ► Of all tested, four samples exhibited antimicrobial activity against test microorganisms, among which, B. catarrhalis was the most sensitive one with a MIC value around 0.312 mg/mL followed by a yeast, C. albicans (MIC. 0.625 mg/mL). ► The thermal behaviors of the metal-free phthalocyanine ( 4) and metallophthalocyanines ( 5–9) were investigated by TG/DTA and it was seen that our novel compounds were not stable above 202 °C.

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