Bis(9-aminoacridinium) bis(pyridine-2,6-dicarboxylato)zincate(II) trihydrate

Mirzaei, Masoud; Eshtiagh‐Hosseini, Hossein; Eydizadeh, Ehsan; Yousefi, Zakieh; Molčanov, Krešimir

doi:10.1107/s1600536812005764

Cited by 2 publications

(2 citation statements)

References 14 publications

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“…Logically, protonated 9-aminoacridine molecules are arranged in an antiparallel stacking mode [40]. The geometry, bond distances and angles of 3 are comparable with similar compounds reported in the literature [41][42][43].…”

Section: Crystal Structures Of 3 Andsupporting

confidence: 64%

Syntheses and X-ray crystal structure studies of four new coordination complexes and salts based on proton-transferred pyridine-2,6-dicarboxylic acid N-oxide

2015

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Four new supramolecular coordination complexes and salts based on proton-transferred pyridine-2,6-dicarboxylic acid N-oxide formulated as (Htata) (Hpydco)ÁH 2 O (1), (Htata) 2 (pydco)Á2H 2 O (2), (H9a-acr) 2 [Zn(pydco) 2 (H 2 O) 2 ]Á4H 2 O (3), and (H9a-acr) 2 [Co(pydco) 2 (H 2 O) 2 ]Á4H 2 O (4) (where H 2 pydco = pyridine-2,6-dicarboxylic acid N-oxide, tata = 2,4,6-triamino-1,3,5-triazine (melamine) and 9a-acr = 9-aminoacridine) have been synthesized by proton transfer from H 2 pydco as ligand and to tata and 9a-acr. The structures of 1-4 were characterized by elemental analysis, infrared spectroscopy, and single crystal X-ray diffraction methods. Compounds 1 and 2 are salts of proton-transferred H 2 pydco and melamine with two separate formulas. There is a difference between the anionic fragment in 1 and 2, the anionic part of 1 retains one acid proton (Hpydco -) which is involved in a strong, intramolecular hydrogen bonding with the oxygen attached to nitrogen, while the acid units in 2 are fully deprotonated (pydco 2-). The linear chains of melaminium cations with an anionic motif and water molecules lead to 2-D zipper layers in 1 and 2-D zigzag layers in 2. These layers are held together via an extensive network of hydrogen bonds, p ? -p 1 stacking, N ? -H_p ? , and lp_p ? interactions to extend the structures into the 3-D supramolecular framework. Single-crystal studies revealed that 3 and 4 are isostructural with distorted octahedral geometry about the metal consisting of two pydco 2-ligands acting in bidentate fashion and two transdisposed water molecules. They also adopt alternating cationic and anionic layers with 9-aminoacridinium cations and transition metal complex anions which are linked to each other by a variety of noncovalent interactions such as ion pairing, hydrogen bonding and p-p stacking.

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Section: Crystal Structures Of 3 Andsupporting

confidence: 64%

Syntheses and X-ray crystal structure studies of four new coordination complexes and salts based on proton-transferred pyridine-2,6-dicarboxylic acid N-oxide

2015

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“…The independent part of the unit cell of 2 contains an H-bonded contact ionic pair: the chloride anion and the protonated substituted acridine as a cation. According to a Cam-bridge Structural Database [43] search, the structure of 2 is one of many known examples of protonated acridine salts [44][45][46][47][48]. Note that in all these structures, the acridinium cation is nearly flat, while this is not the case for 2, where the angle between mean-squared planes composed of the carbon atoms of two lateral hydrocarbon rings is 21.6 (2) • .…”

Section: Single-crystal X-ray Diffraction Studies Of N 9 -Azidoacridinementioning

confidence: 99%

New Boron Containing Acridines: Synthesis and Preliminary Biological Study

Druzina,

Dudarova,

Ananyev

et al. 2023

Molecules

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The synthesis of the first conjugates of acridine with cobalt bis(dicarbollide) are reported. A novel 9-azido derivative of acridine was prepared through the reaction of 9-methoxyacridine with N3CH2CH2NH2, and its solid-state molecular structure was determined via single-crystal X-ray diffraction. The azidoacridine was used in a copper (I)-catalyzed azide-alkyne cycloaddition reaction with cobalt bis(dicarbollide)-based terminal alkynes to give the target 1,2,3-triazoles. DNA interaction studies via absorbance spectroscopy showed the weak binding of the obtained conjugates with DNA. The antiproliferative activity (IC50) of the boronated conjugates against a series of human cell lines was evaluated through an MTT assay. The results suggested that acridine derivatives of cobalt bis(dicarbollide) might serve as a novel scaffold for the future development of new agents for boron neutron capture therapy (BNCT).

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Bis(9-aminoacridinium) bis(pyridine-2,6-dicarboxylato)zincate(II) trihydrate

Cited by 2 publications

References 14 publications

Syntheses and X-ray crystal structure studies of four new coordination complexes and salts based on proton-transferred pyridine-2,6-dicarboxylic acid N-oxide

Syntheses and X-ray crystal structure studies of four new coordination complexes and salts based on proton-transferred pyridine-2,6-dicarboxylic acid N-oxide

New Boron Containing Acridines: Synthesis and Preliminary Biological Study

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