Transition metal complexes of α-aminophosphonates Part I: synthesis, spectroscopic characterization, and in vitro anticancer activity of copper(II) complexes of α-aminophosphonates

El‐Boraey, Hanaa A.; El‐Gokha, Ahmed; El-Sayed, Ibrahim E.T.; Azzam, Mariam Ahmed

doi:10.1007/s00044-014-1282-8

Cited by 33 publications

(15 citation statements)

References 25 publications

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“…The combined organic extracts were dried over anhydrous Na 2 SO 4 and concentrated under reduced pressure to afford crude products 3a-n, which were further purified by crystallization from diethyl ether. Prepared following the general procedure from TADDOL Hphosphonate (0.80 g, 1.56 mmol) in CH 2 Cl 2 (15 mL), (S)-2-methyl-N-(2-methylpropylidene)propane-2-sulfinamid 2c (0.27 g, 1.56 mmol) in CH 2 Cl 2 (5 mL) and anhydrous K 2 CO 3 (0.21 g, Table 3 Removal of chiral auxiliaries: the synthesis of (R)-a-aminophosphonic acids 4a-d a 3,2]dioxaphosphepin-6-yl)(phenyl)methyl)-2-methylpropane-2-sulfinamide 3e Prepared following the general procedure from TADDOL H-phosphonate (0.80 g, 1.56 mmol) in CH 2 Cl 2 (15 mL), (S)-N-benzylidene-2-methylpropane-2-sulfinamide 2e (0.33 g, 1.56 mmol) in CH 2 Cl 2 (5 mL) and anhydrous K 2 CO 3 (0.21 g, 1.56 mmol). White solid, 0.97 g (85% yield, dr >95:5 Prepared following the general procedure from TADDOL H-phosphonate (0.80 g, 1.56 mmol) in CH 2 Cl 2 (15 mL), (S)-N-(4-methoxybenzylidene)-2-methylpropane-2-sulfinamide 2g (0.37 g, 1.56 mmol) in CH 2 Cl 2 (5 mL) and anhydrous K 2 CO 3 (0.…”

Section: Diastereoselective Hydrophosphonylation Of (S)-n-tertbutylsumentioning

confidence: 99%

Highly diastereoselective addition of chiral H-phosphonate to tert-butylsulfinyl aldimines: a convenient approach to (R)-α-aminophosphonic acids

Olszewski

Majewski

2015

Tetrahedron: Asymmetry

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Section: Diastereoselective Hydrophosphonylation Of (S)-n-tertbutylsumentioning

confidence: 99%

Highly diastereoselective addition of chiral H-phosphonate to tert-butylsulfinyl aldimines: a convenient approach to (R)-α-aminophosphonic acids

Olszewski

Majewski

2015

Tetrahedron: Asymmetry

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“…An important strategy in fighting antibiotic resistance is the discovery, development of novel antibiotics, and increasing the efficacy of the antibiotic that is already in a clinical study [ 7 ]. In this context, α-aminophosphonates gained great interest by medicinal chemists because of their diverse biological and industrial applications such as antibacterial [ 8 , 9 , 10 , 11 , 12 ], anticancer [ 13 , 14 , 15 ], enzyme inhibitors [ 16 , 17 ], and chelating material [ 18 , 19 , 20 , 21 ] which made them a promising drug candidate for further optimization. These compounds are phosphorus analogs of naturally occurring α-amino acids and therefore, are considered promising in the field of drug discovery and development [ 22 ].…”

Section: Introductionmentioning

confidence: 99%

Experimental and Molecular Docking Studies of Cyclic Diphenyl Phosphonates as DNA Gyrase Inhibitors for Fluoroquinolone-Resistant Pathogens

et al. 2022

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DNA gyrase and topoisomerase IV are proven to be validated targets in the design of novel antibacterial drugs. In this study, we report the antibacterial evaluation and molecular docking studies of previously synthesized two series of cyclic diphenylphosphonates (1a–e and 2a–e) as DNA gyrase inhibitors. The synthesized compounds were screened for their activity (antibacterial and DNA gyrase inhibition) against ciprofloxacin-resistant E.coli and Klebsiella pneumoniae clinical isolates having mutations (deletion and substitution) in QRDR region of DNA gyrase. The target compound (2a) that exhibited the most potent activity against ciprofloxacin Gram-negative clinical isolates was selected to screen its inhibitory activity against DNA gyrase displayed IC50 of 12.03 µM. In addition, a docking study was performed with inhibitor (2a), to illustrate its binding mode in the active site of DNA gyrase and the results were compatible with the observed inhibitory potency. Furthermore, the docking study revealed that the binding of inhibitor (2a) to DNA gyrase is mediated and modulated by divalent Mg2+ at good binding energy (–9.08 Kcal/mol). Moreover, structure-activity relationships (SARs) demonstrated that the combination of hydrazinyl moiety in conjunction with the cyclic diphenylphosphonate based scaffold resulted in an optimized molecule that inhibited the bacterial DNA gyrase by its detectable effect in vitro on gyrase-catalyzed DNA supercoiling activity.

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“…A number of reviews have been published on various aspects of the biological properties of α‐aminophosphonates . Certain α‐aminophosphonates and copper(II) complexes with α‐aminophosphonates as tridentate ligands exhibit significant anticancer activity.…”

Section: Introductionmentioning

confidence: 99%

Stereochemistry of the Kabachnik‐Fields Condensation of Terpenic Amino Oximes with Aldehydes and Dimethyl Phosphite

et al. 2020

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Three-component condensation of aldehydes and dimethyl phosphite with α-amino oximes derived from (À)-α-pinene and (+)-3-carene (Kabachnik-Fields reaction) resulted in amino phosphonates as pairs of diastereomers. Diastereomeric ratio depends on the catalyst used (SnCl 2 × 2H 2 O, SiO 2 , Al 2 O 3-H +) and the heating type (conventional or microwave). The best results were achieved by MW irradiation with simultaneous cooling. Stereochemical assignment of the key derivatives was made by X-ray diffractometry. According to quantum chemical calculations (DFT PBE0/def2-TZVPP) and spectroscopic data, the terpenic α-amino phosphonates should be conformationally inhomogeneous, exhibiting a tendency to form H-bonded dimers (DFT M06/def2-SVP, IR). One-bond spin-spin coupling 1 J P-C was found to be diagnostic for the configuration assignment since the value 1 J P-C depends on the dihedral angle between bond CÀ P and axis of the electron lone pair at the neighboring nitrogen (NMR, DFT PBE0/aug-cc-pVTZÀ J).

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Transition metal complexes of α-aminophosphonates Part I: synthesis, spectroscopic characterization, and in vitro anticancer activity of copper(II) complexes of α-aminophosphonates

Cited by 33 publications

References 25 publications

Highly diastereoselective addition of chiral H-phosphonate to tert-butylsulfinyl aldimines: a convenient approach to (R)-α-aminophosphonic acids

Highly diastereoselective addition of chiral H-phosphonate to tert-butylsulfinyl aldimines: a convenient approach to (R)-α-aminophosphonic acids

Experimental and Molecular Docking Studies of Cyclic Diphenyl Phosphonates as DNA Gyrase Inhibitors for Fluoroquinolone-Resistant Pathogens

Stereochemistry of the Kabachnik‐Fields Condensation of Terpenic Amino Oximes with Aldehydes and Dimethyl Phosphite

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