Synthesis, Raman, FT-IR, NMR spectroscopic characterization, antimicrobial activity, cytotoxicity and DNA binding of new mixed aza-oxo-thia macrocyclic compounds

Agh-Atabay, Naz M.; Baş, Ali; Kircali, Aslihan; Şen, G.; Yazıcıoğlu, M.; Gücin, Fahrettin; Dülger, Başaran

doi:10.1016/j.ejmech.2009.07.003

Cited by 13 publications

(6 citation statements)

References 46 publications

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“…It forms complexes with different metal ions, such as lanthanides (Zhang et al, 2002), cobalt (Grairrane, Pastor, Alvrez, Mealli et al, 2005), magnesium , zinc (Grairrane et al, 2006;Wyrzykowski et al, 2013), copper (Alarcon-Payer et al, 2005;Baggio et al, 1999), vanadium (Alvarez et al, 2010), lead (Gabriel et al, 2013;Wu et al, 2013), tin (Sandhu & Sharma, 1996), calcium and strontium (Grairrane et al, 2007), uranium(VI) (Kirishima & Sato, 2014;Di Bernardo et al, 2006), ruthenium (Zangl et al, 2009) and manganese (Grairrane et al, 2003(Grairrane et al, , 2011. Multidentate macrocyclic ligands have been synthesized using Tda and triazine (Aghatabay et al, 2009;Steenland et al, 1999). An extensive literature survey revealed that chargetransfer complexes of thiodiacetic acid have not yet been reported.…”

Section: Introductionmentioning

confidence: 99%

Hydrogen-bonded assemblies in the molecular crystals of 2,2′-thiodiacetic acid with ethylenediamine ando-phenylenediamine

Gomathi

Theivarasu

2017

Acta Crystallogr C Struct Chem

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Carboxylate molecular crystals have been of interest due to the presence of hydrogen bonding, which plays a significant role in chemical and crystal engineering, as well as in supramolecular chemistry. Acid-base adducts possess hydrogen bonds which increase the thermal and mechanical stability of the crystal. 2,2'-Thiodiacetic acid (Tda) is a versatile ligand that has been widely explored, employing its multidendate and chelating coordination abilities with many metals; however, charge-transfer complexes of thiodiacetic acid have not been reported. Two salts, namely ethylenediaminium 2,2'-thiodiacetate, CHN·CHOS, denoted Tdaen, and 2-aminoanilinium 2-(carboxymethylsulfanyl)acetate, CHN·CHOS, denoted Tdaophen, were synthesized and characterized by IR, H andC NMR spectroscopies, and single-crystal X-ray diffraction. In these salts, Tda reacts with the aliphatic (ethylenediamine) and aromatic (o-phenylenediamine) diamines, and deprotonates them to form anions with different valencies and different supramolecular networks. In Tdaen, the divalent Tda anions form one-dimensional linear supramolecular chains and these are extended into a three-dimensional sandwich-type supramolecular network by interaction with the ethylenediaminium cations. However, in Tdaophen, the monovalent Tda anions form one-dimensional zigzag supramolecular chains, which are extended into a three-dimensional supramolecular network by interaction with the 2-aminoanilinium cations. Thus, both three-dimensional structures display different ring motifs. The structures of these diamines, which are influenced by hydrogen-bonded assemblies in the molecular crystals, are discussed in detail.

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Section: Introductionmentioning

confidence: 99%

Hydrogen-bonded assemblies in the molecular crystals of 2,2′-thiodiacetic acid with ethylenediamine ando-phenylenediamine

Gomathi

Theivarasu

2017

Acta Crystallogr C Struct Chem

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“…These results suggested 37 to 44 % covalent nature in bonding. Racah inter-electronic repulsion parameter (B l ) was calculated by Equation 3.…”

Section: Ligand Field Parameters Of Cesmentioning

confidence: 99%

“…Macrocycle (MC) and its derivatives act as donor centre capable of performing various specific molecular activities with perfect use to design and develop magnetic resonance imaging (MRI) contrasting agents, radiopharmaceuticals and chemotherapeutics [3,4]. Further, computational calculations offer a deep appreciation in theoretical interest and evaluation of practical findings to determine their great availability and flexibility as ligand.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural elucidation and antimicrobial effectiveness of coordination entities of cobalt (II) and nickel (II) derived from 9,17-diaza-2,6,11,15-tetrathia-1,7,10,16-(1,2)-tetrabenzenacyclooctadecaphan-8,17-diene

2012

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“…Because of the potent pharmacological activities of these compounds, there has been an overwhelming interest in exploring their isolation from natural sources (within all kingdoms) and at the same time improving the synthetic methodology for these compounds . The syntheses of these cyclopeptides by cyclocondensation reactions are well documented . Because of their structural versatility and suitability for synthetic modifications, amide cyclophanes incorporated with sulfur atoms will offer interesting properties.…”

Section: Introductionmentioning

confidence: 99%

“…We have recently reported the synthesis of mixed aza‐oxo‐thia macrocyclic tetra‐amides and their respective antimicrobial studies . In this paper, we focus on the synthesis, spectroscopic characterization, and pharmacologic investigation of the four new [1 + 1] condensed 12‐membered macrocycles, with similar cavity size and bearing nitrogen and sulfur donor centers.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structural Aspects, Antimicrobial Activity, and Ion Transport Investigations of Four New [1 + 1] Condensed 12‐Membered Cyclophane Amides

Gürbüz

Agh-Atabay

Karabulut

2016

Journal of Heterocyclic Chem

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Two new diamines (a, b) and their four [1 + 1] condensed macrocyclic peptides (c–f) were synthesized via dilution method affording the expected dilactams in reasonably high‐yield yields. The compounds were characterized by elemental analyses, mass, FT‐IR, 1H, and 13C NMR spectral data. Mass spectra reveal their [1 + 1] cyclic condensation. The macrocycles having two peptide units in the ring would constitute three configurational isomers: cisoid–cisoid, transoid–transoid, and cisoid–transoid. Their 1H and 13C NMR show one signal for each chemically equivalent SCH2 and CONH and could be assigned symmetrical structures lacking any configurational isomerism. The ion transport activity of the compounds (c) and (d) on Na+ and K+ ions were evaluated by CH2Cl2 liquid–liquid membrane method using a U tube system. Slightly higher affinity for potassium than sodium was also observed, which is undoubtedly related to the matching size of the cavity between K+ and cyclic peptides. The antimicrobial and antifungal activities of four macrocyclic amides (c, d, e, and f) were illuminated using disk diffusion method in dimethyl sulfoxide as well as the minimal inhibitory concentration dilution method, against several bacteria and yeast cultures. Comparing all methods, in most cases, the (e) and (f) compound seems to show slightly higher biological activity than the (c) and (d) macrocycles. This may be because of the presence of extra chlorine atoms on the exterior part of the molecules.

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Synthesis, Raman, FT-IR, NMR spectroscopic characterization, antimicrobial activity, cytotoxicity and DNA binding of new mixed aza-oxo-thia macrocyclic compounds

Cited by 13 publications

References 46 publications

Hydrogen-bonded assemblies in the molecular crystals of 2,2′-thiodiacetic acid with ethylenediamine ando-phenylenediamine

Hydrogen-bonded assemblies in the molecular crystals of 2,2′-thiodiacetic acid with ethylenediamine ando-phenylenediamine

Synthesis, structural elucidation and antimicrobial effectiveness of coordination entities of cobalt (II) and nickel (II) derived from 9,17-diaza-2,6,11,15-tetrathia-1,7,10,16-(1,2)-tetrabenzenacyclooctadecaphan-8,17-diene

Synthesis, Structural Aspects, Antimicrobial Activity, and Ion Transport Investigations of Four New [1 + 1] Condensed 12‐Membered Cyclophane Amides

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