Pyridoxonium salts of chiral and cyclic dithiophosphoric and bisdithiophosphonic acids and their antimicrobial activities

Nizamov, I. S.; Belov, Timur; Nikitin, Yevgeniy N.; Akhmedova, Gulnaz R.; Shilnikova, Olga V.; Timushev, Ildus D.; Salikhov, Ramazan Z.; Shulaeva, Marina P.; Поздеев, О. К.; Батыева, Э. С.; Черкасов, Р. А.

doi:10.1080/10426507.2020.1854255

Cited by 8 publications

(2 citation statements)

References 23 publications

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“…Organo-dithiophosphorus compounds can be in the form of dithiophosphates (DTP), dithiophosphonates (DTPOA) and dithiophosphinates (DTPA). All of the three classes have practical applications in agriculture (e.g., insecticides, pesticides) [8,9], industry (as antioxidants in lubricants) [10], solvent-based metal extracting reagents [11], the mineral flotation agents [12,13] and pharmacology (such as possible antibiotics, antimicrobials and anticancer agents) [14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Studies on new dithiophosphonic acid derivatives: Synthesis, characterization, DFT and molecular docking calculations and in vitro cytotoxicity assessment

Bulat,

Sağlam,

Akkoç

et al. 2024

Preprint

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2,4-bis(3,4-dimethoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide (SAV-A1) was treated with five different alcohols to obtain dithiophosphonic acids (HLn, HS2P((2,4-CH3O)2-C6H3)(ORn); n=1-5, R1=n-pentyl-; R2=2-pentyl-; R3=4-tert-but-benzyl-; R4=2-propyl-; R5=2-butyl-). HLn series were converted to their ammonium salts, ([NH4Ln]). [NH4Ln] were reacted with NiCl2.6H2O to obtain the corresponding Ni(II) coordination compounds ([Ni(Ln)2]) in ethanol medium. The structures of all the compounds were elucidated by spectroscopic techniques. Single-crystal X-ray diffraction analysis of [Ni(L1)2], [Ni(L2)2], [Ni(L4)2] and [Ni(L5)2] were also carried out. The ligands and their nickel complexes were tested on human liver and colon cancer cell lines using (MTT) assay method. The salts [NH4L2] and [NH4L5] demonstrated more antiproliferative effects than others in colon cancer cell line with IC50 values 82.73 and 74.87 µM, respectively. Density Functional Theory (DFT) calculations of [Ni(L1)2], [Ni(L2)2], [Ni(L4)2] and [Ni(L5)2] were done. The molecular docking studies of [Ni(L1)2], [Ni(L2)2], [Ni(L4)2] and [Ni(L5)2] with colon cancer antigen proteins, ID 2HQ6 and liver cancer protein, PDB ID: 3WZE were done to foresee the interactions of the complexes.

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Section: Introductionmentioning

confidence: 99%

Studies on new dithiophosphonic acid derivatives: Synthesis, characterization, DFT and molecular docking calculations and in vitro cytotoxicity assessment

Bulat,

Sağlam,

Akkoç

et al. 2024

Preprint

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“…Organodithiophosphorus compounds find practical uses in, for example, agriculture (as insecticides and pesticides) [21,22] ; industry (as antioxidant-additives for lubricants) [23] ; solvent-extraction reagents for metals [24] ; flotation agents for mineral ores [25,26] ; and medicine (as potential antibiotics, antimicrobial agents, and possible anticancer agents). [27][28][29][30][31][32] Their use in metal mining is based on the fact that they provide two soft-base type sulfur ligands [33] so as to form a four-ring chelate. Depending on the metal cation, they usually form either four-or six-coordinate complexes.…”

Section: Introductionmentioning

confidence: 99%

Ni(II) complexes with 1,3,2,4‐dithiadiphosphetane 2,4‐disulfide‐based ligands: Structural insights, theoretical studies, and anticancer activities

Bulat

Sağlam

Zeyrek

et al. 2022

Applied Organom Chemis

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The first synthesis of 2,4‐bis(3,4‐dimethoxyphenyl)‐1,3‐dithia‐2,4‐diphosphetane 2,4‐disulfide (SAV‐A1 reagent) was achieved. Seven oxo‐alkyl esters (HLn) were synthesized thereof. Ni(II) complexes ([Ni(Ln)2]) of these ligands were prepared in ethanol. The structures were identified by spectral studies. Ni(II) complexes were unambiguously determined by X‐ray crystallography. In addition, the ligands and their Ni(II) complexes were tested on two different human cancer cell lines, including liver and colon. Moreover, density functional theory (DFT) calculations of the Ni(II) complexes were performed, and the molecular docking studies of these compounds with liver cancer protein, PDB ID: 3WZE and colon cancer antigen proteins, ID 2HQ6 were presented to investigate and predict potential interactions.

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Quinquevalent phosphorus acids

Bałczewski,

Owsianik

2024

Organophosphorus Chemistry

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This chapter shows, as in previous years, the most important achievements of the 2021 year in the area of organo-phosphorus compounds containing: three P–O bonds (Section 2: phosphoric acids and their derivatives), two P–O and one P–C bonds (Section 3: phosphonic acids and their derivatives) as well as one P–O and two P–C bonds (Section 4: phosphinic acids and their derivatives), in addition to the phosphoryl group P═O, present in all three groups of compounds. Each of the main sections covers “synthesis and reactions” including pure synthesis without applications, “synthesis and biological applications” and “synthesis and miscellaneous applications” including synthesis directed towards non-biological applications. At the end of each subsection, the corresponding achievements are shown for hetero-analogues in which phosphorus–oxygen bonds have been replaced by phosphorus–heteroatom P–X and/or P═Y bonds (X, Y = N, S or Se). The subsection on quinquevalent phosphorus acids and their derivatives as catalysts has been placed, as usual, at the end of the entire chapter, after a review of all three main groups of compounds. As in previous years, the area devoted to phosphoric and phosphonic acids and their derivatives dominated over a smaller section of phosphinic acids and their derivatives, and literature references for these sections remained at a ratio of 4 : 12 : 1. A dynamic, five-fold increase in the number of works, in the subject of chiral phosphoric acids as catalysts, has been recorded in this year.

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Pyridoxonium salts of chiral and cyclic dithiophosphoric and bisdithiophosphonic acids and their antimicrobial activities

Cited by 8 publications

References 23 publications

Studies on new dithiophosphonic acid derivatives: Synthesis, characterization, DFT and molecular docking calculations and in vitro cytotoxicity assessment

Studies on new dithiophosphonic acid derivatives: Synthesis, characterization, DFT and molecular docking calculations and in vitro cytotoxicity assessment

Ni(II) complexes with 1,3,2,4‐dithiadiphosphetane 2,4‐disulfide‐based ligands: Structural insights, theoretical studies, and anticancer activities

Quinquevalent phosphorus acids

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