Phosphoryl Analogs of Salicylic Acid: Synthesis and Analgesic and Anti-Inflammatory Activity

Баулин, В. Е.; Калашникова, И. П.; Vikharev, Yu. B.; Vikhareva, E. A.; Баулин, Д. В.; Tsivadze, A. Yu.

doi:10.1134/s1070363218090049

Cited by 8 publications

(9 citation statements)

References 17 publications

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“…The starting isopropyl salicylate 5a (R = COO-iPr, X = H) was purchase from Aldrich. Diethyl (2-hydroxy-5-ethylphenyl)phosphonate 5b (R = P(O)(OEt) 2 , X = Et, Figure 1) was synthesized, according to Reference [19].…”

Section: Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…This can significantly affect both the complexation and biological properties. It was found that (2-hydroxy-5-ethylphenyl)phosphonic acid is of interest as a potential non-steroidal anti-inflammatory drug [19]. In this work, two new ligands were synthesized and evaluated for their applicability as 68 Ga binding bone-seeking agents: 2-[(2-amino-2,2-diphosphono)ethyloxy]-benzoic acid (8) and 2-[(2-amino-2,2-diphosphono)ethyloxy]-5-ethyl-phenylphosphonic acid (9) (Figure 2).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Complexation Properties, and Evaluation of New Aminodiphosphonic Acids as Vector Molecules for 68Ga Radiopharmaceuticals

et al. 2021

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Two new aminodiphosphonic acids derived from salicylic acid and its phosphonic analogue were prepared through a simple and efficient synthesis. 2-[(2-Amino-2,2-diphosphono)ethyloxy]-benzoic acid 8 and 2-[(2-amino-2,2-diphosphono)ethyloxy]-5-ethyl-phenylphosphonic acid 9 were evaluated for their applicability as 68Ga binding bone-seeking agents. Protonation constants of 8 and 9 and stability constants of the Ga3+ complexes with 8 and 9 in water were determined. The stability constant of Ga3+ complex with fully phosphorylated acid 9 (logKGaL = 31.92 ± 0.32) significantly exceeds stability constant of Ga3+ complex with 8 (logKGaL = 26.63 ± 0.24). Ligands 8 and 9 are as effective for Ga3+ cation binding as ethylenediamine-N,N’-diacetic-N,N’-bis(methy1enephosphonic) acid and ethylenediamine-N,N,N’,N’-tetrakis(methylenephosphonic) acid, respectively. The labelling process and stability of [68Ga]Ga-8 and [68Ga]Ga-9 were studied. Both 8 and 9 readily form 68Ga-complexes stable to ten-fold dilution with saline. However, in fetal bovine serum, only [68Ga]Ga-9 was stable enough to be subject to biological evaluation. It was injected into rats with bone pathology and aseptic inflammation of soft tissues. For [68Ga]Ga-9 in animals with a bone pathology model in 60 and 120 min after injection, a slight accumulation in the pathology site, stable blood percentage level, and moderate accumulation in the liver were observed. For animals with an aseptic inflammation, the accumulation of [68Ga]Ga-9 in the pathology site was higher than that in animals with bone pathology. Moreover, the accumulation of [68Ga]Ga-9 in inflammation sites was more stable than that for [68Ga]Ga-citrate. The percentage of [68Ga]Ga-9 in the blood decreased from 3.1% ID/g (60 min) to 1.5% ID/g (120 min). Accumulation in the liver was comparable to that obtained for [68Ga]Ga-citrate.

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Section: Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Complexation Properties, and Evaluation of New Aminodiphosphonic Acids as Vector Molecules for 68Ga Radiopharmaceuticals

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“…Among them, 2-hydroxyphenylphosphonic acids occupy a special place, since they are phosphoryl analogues of salicylic acid and can be considered as physiologically active substances (Scheme 1). 2-Hyd-roxy-5-ethylphenylphosphonic acid (H 3 L 2 ) and its complex [Cu(H 2 L 2 ) 2 (Н 2 О) 2 ] exhibit analgesic activity [14,15]. With low toxicity, the analgesic effect of the complex significantly exceeds the effect of analgin.…”

Section: Doi: 101134/s1070363221110074mentioning

confidence: 99%

“…2-Hydroxyphenylphosphonic acids are rather inaccessible compounds [14,[29][30][31]. In the synthesis of H 3 L 1 acid (Scheme 2), we used the technique, which we developed earlier [14]. Its main advantage is the final reaction with in situ generated trimethylbromosilane.…”

Section: Doi: 101134/s1070363221110074mentioning

confidence: 99%

Synthesis and Complexation Properties of 2-Hydroxy-5-methoxyphenylphosphonic Acid (H3L1). Crystal Structure of the [Cu(H2L1)2(Н2О)2] Complex

et al. 2021

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2-Hydroxy-5-methoxyphenylphosphonic acid (H3L1) and the complex [Cu(H2L1)2(H2O)2] were synthesized and characterized by IR spectroscopy, thermogravimetry, and X-ray diffraction analysis. The polyhedron of the copper atom is an axially elongated square bipyramid with oxygen atoms of phenolic and of monodeprotonated phosphonic groups at the base and oxygen atoms of water molecules at the vertices. The protonation constants of the H3L1 acid and the stability constants of its Cu2+ complexes in water were determined by potentiometric titration. The protonation constants of the acid in water are significantly influenced by the intramolecular hydrogen bond and the methoxy group. The H3L1 acid forms complexes CuL‒ and CuL24‒ with Cu2+ in water.

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o‐Hydroxyarylphosphanes: Strategies for Syntheses of Configurationally Stable, Electronically and Sterically Tunable Ambiphiles with Multiple Applications

Heinicke

2023

Chemistry A European J

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o‐Hydroxyarylphosphanes are fascinating compounds by their multiple‐reactivity features, attributed to the ambident hard and soft Lewis‐ and also Brønstedt acid‐base properties, wide tuning opportunities via backbone substituents with ±mesomeric and inductive, at P and in o‐position to P and O also steric effects, and in addition, the configurational stability at three‐valent phosphorus. Air sensitivity may be overcome by reversible protection with BH3, but the easy oxidation to P(V)‐compounds may also be used. Since the first reports on the title compounds ca. 50 years ago the multiple reactivity has led to versatile applications. This includes various P‐E‐O and P=C‐O heterocycles, a multitude of O‐substituted derivatives including acyl derivatives for traceless Staudinger couplings of biomolecules with labels or functional substituents, phosphane‐phosphite ligands, which like the o‐phosphanylphenols itself form a range of transition metal complexes and catalysts. Also main group metal complexes and (bi)arylphosphonium‐organocatalysts are derived. Within this review the various strategies for the access of the starting materials are illuminated, including few hints to selected applications.

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Phosphoryl Analogs of Salicylic Acid: Synthesis and Analgesic and Anti-Inflammatory Activity

Cited by 8 publications

References 17 publications

Synthesis, Complexation Properties, and Evaluation of New Aminodiphosphonic Acids as Vector Molecules for 68Ga Radiopharmaceuticals

Synthesis, Complexation Properties, and Evaluation of New Aminodiphosphonic Acids as Vector Molecules for 68Ga Radiopharmaceuticals

Synthesis and Complexation Properties of 2-Hydroxy-5-methoxyphenylphosphonic Acid (H3L1). Crystal Structure of the [Cu(H2L1)2(Н2О)2] Complex

o‐Hydroxyarylphosphanes: Strategies for Syntheses of Configurationally Stable, Electronically and Sterically Tunable Ambiphiles with Multiple Applications

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