Selected organophosphorus compounds with biological activity. Applications in medicine

Demkowicz, Sebastian; Rachoń, Janusz; Daśko, Mateusz; Kozak, Witold

doi:10.1039/c5ra25446a

Cited by 206 publications

(106 citation statements)

References 111 publications

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“…Other directional interactions such as those involving aromatic rings (π-effects) also play an important role in crystal engineering. [4,5] An important class of chemical compounds which are largely used in medicine, [6,7] industry [8,9] and agriculture [10,11] are phosphoramide compounds with the base-segment NÀ P═O. Development of new applications of these compounds is certainly needed to more focus on the analysis of intermolecular interactions in the crystal structures and their molecular assemblies.…”

Section: Introductionmentioning

confidence: 99%

Association of Non‐covalent Interactions C−H…X(X=O, F, Cl, π) and Cl…π with Hydrogen Bond Interactions N−H…O in Molecular Assembly of New Phosphoramides: A Combined X‐Ray Crystallography and Topology (AIM and Hirshfeld) Analysis

2020

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Crystal structures of six new phosphoramides with the main parts [C(O)NH]P(O)[N]2 and [NH]2P(O)[N] were determined by single crystal X‐ray diffraction and characterized by spectroscopic methods (FT‐IR and 1H, 13C, 31P NMR). X‐ray crystallography data manifest that the hydrogen bond interactions N−H…O (in all structures) accompanied by some contacts such as C−H…X (X=π, O, F and Cl) and π…π dominate the molecular architectures. Some non‐classical interactions such as Cl…π are also found in feature packing of some studied structures. A detailed investigation of these intermolecular interactions in order to illustrate the importance of non‐classical interactions in construction of molecular assemblies is presented by Hirshfeld surface (HS) analysis reflected the most important van der Waals (vdW) contributions and “Quantum Theory Atom In Molecule” (QTAIM) method especially in term of energetic feature. Hirshfeld surface analysis reveals that the prevalent interactions are of the type O…H for all structures coupled with some other short contacts such as C…C and H…F recognized by red spots on Hirshfeld surfaces and enrichment ratios (E) larger than unity (E > 1). These results are confirmed by AIM method classifying the hydrogen bond interactions N−H…O as moderate non‐covalent closed‐shell interactions and the remaining interactions above‐mentioned as vdW closed‐shell interactions in the studies phosphoric triamides. Such study to categorize the popular hydrogen bond interactions N−H…O in phosphoric triamides and the weak interactions in their molecular packing are used for the first time.

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Section: Introductionmentioning

confidence: 99%

Association of Non‐covalent Interactions C−H…X(X=O, F, Cl, π) and Cl…π with Hydrogen Bond Interactions N−H…O in Molecular Assembly of New Phosphoramides: A Combined X‐Ray Crystallography and Topology (AIM and Hirshfeld) Analysis

2020

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“…The phosphorous analogs of amino acids are synthetically important compounds because of their diverse biological and biochemical properties . They can be used as antibacterial agents, enzyme inhibitors, haptens for catalytic antibodies, and anti‐HIV agents .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Evaluation of Cytotoxic Activities of Novel Aziridinyl Phosphonic Acid Derivatives

Khan

Ulusan

Banerjee

et al. 2019

Chemistry & Biodiversity

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New aziridine 2‐phosphonic acids were prepared by monohydrolysis of the aziridine 2‐phosphonates that were obtained by the modified Gabriel−Cromwell reaction of vinyl phosphonate or α‐tosylvinyl phosphonate with a primary amine or a chiral amine. The cellular cytotoxicity of these compounds was tested against the HCT‐116 colorectal cancer cell lines and the CCD‐18Co normal colon fibroblast lines using the MTT assay. Three of the synthesized phosphonic acid derivatives 2e (ethyl hydrogen {(2S)‐1‐[(1S)‐1‐(naphthalen‐2‐yl)ethyl]aziridin‐2‐yl}phosphonate), 2h (ethyl hydrogen (1‐benzylaziridin‐2‐yl)phosphonate), and 2i (ethyl hydrogen (1‐cyclohexylaziridin‐2‐yl)phosphonate) showed higher cytotoxicity than the reference cancer treatment agent etoposide. Cell death was through a robust induction of apoptosis even more effectively than etoposide, a well‐known apoptosis inducing agent.

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“…On the other hand, organophosphorus compounds have received much attention whether linear or cyclic. They were demonstrated to be pesticides , herbicides , antifungal , anti‐inflammatory , anti‐HIV , anticancer , and good cytotoxic on K562 and colo205 cancerous cells . These aforementioned reasons with our interest in organophosphorus chemistry encouraged us to synthesize new organophosphorus compounds incorporating 1,2,4‐triazinone moiety through reaction of 4‐amino‐6‐methyl‐3‐sulfanyl‐1,2,4‐triazin‐5(4 H )‐one ( 1 ) with different phosphorus reagents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some Novel Thiadiazaphosphole, Oxazaphospholothiadiazaphosphole, Thiadiazaphosphinine, and Phosphonates Containing a 1,2,4‐Triazine Moiety

Abdel‐Kariem

2019

Journal of Heterocyclic Chem

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Synthesis of some novel organophosphorus compounds bearing 1,2,4‐triazinone moiety was achieved. The methodology depended on simple reactions between 4‐amino‐6‐methyl‐3‐sulfanyl‐1,2,4‐triazin‐5(4H)‐one (1) and variable phosphorus reagents such as phosphorus halides and phosphorus sulfides as well as phosphorous acid and its esters. These reactions were performed in proper solvents under mild conditions giving good yields of phosphorylated 1,2,4‐triazinones.

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Selected organophosphorus compounds with biological activity. Applications in medicine

Abstract: The purpose of this article is to provide an overview of the latest applications of organophosphorus compounds (OPs) that exhibit biological activity.

Cited by 206 publications

References 111 publications

Association of Non‐covalent Interactions C−H…X(X=O, F, Cl, π) and Cl…π with Hydrogen Bond Interactions N−H…O in Molecular Assembly of New Phosphoramides: A Combined X‐Ray Crystallography and Topology (AIM and Hirshfeld) Analysis

Association of Non‐covalent Interactions C−H…X(X=O, F, Cl, π) and Cl…π with Hydrogen Bond Interactions N−H…O in Molecular Assembly of New Phosphoramides: A Combined X‐Ray Crystallography and Topology (AIM and Hirshfeld) Analysis

Synthesis, Characterization and Evaluation of Cytotoxic Activities of Novel Aziridinyl Phosphonic Acid Derivatives

Synthesis of Some Novel Thiadiazaphosphole, Oxazaphospholothiadiazaphosphole, Thiadiazaphosphinine, and Phosphonates Containing a 1,2,4‐Triazine Moiety

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