Tertiary phosphines in reactions with substituted cinnamic acids

Romanov, S. R.; Aksunova, A. F.; Bakhtiyarova, Yu. V.; Shulaeva, Marina P.; Поздеев, О. К.; Егорова, С. Н.; Галкина, И. В.; Галкин, В. И.

doi:10.1016/j.jorganchem.2020.121130

Cited by 14 publications

(2 citation statements)

References 11 publications

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“…Chemically, it is an aromatic fatty acid composed of a phenyl ring substituted with an acrylic acid group, commonly in the trans-geometry, and has low toxicity in human exposure. Cinnamic acid derivatives have been evaluated as pharmacologically active compounds [ 23 ]. They show a remarkable variety of biological activities and are often used as promising starting compounds for the development of new, highly effective drugs [ 24 , 25 , 26 ].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Anticancer Evaluation of Substituted Cinnamic Acid Bearing 2-Quinolone Hybrid Derivatives

et al. 2021

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A new series of hybrid molecules containing cinnamic acid and 2-quinolinone derivatives were designed and synthesized. Their structures were confirmed by 1H-NMR, 13C-NMR and mass analyses. All the synthesized hybrid molecules were assessed for their in vitro antiproliferative activity against more than one cancer cell lines. Compound 3-(3,5-dibromo-7,8-dihydroxy-4-methyl-2-oxoquinolin-1(2H)-ylamino)-3-phenylacrylic acid (5a) with IC50 = 1.89 μM against HCT-116 was proved to the most potent compound in this study, as compared to standard drug staurosporin. DNA flow cytometry assay of compound 5a revealed G2/M phase arrest and pre-G1 apoptosis. Annexin V-FITC showed that the percentage of early and late apoptosis was increased. The results of topoisomerase enzyme inhibition activity showed that the hybrid molecule 5a displays potent inhibitory activity compared with control.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Anticancer Evaluation of Substituted Cinnamic Acid Bearing 2-Quinolone Hybrid Derivatives

et al. 2021

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“…Salts for n = 2 were obtained from tri(4-methoxyphenyl)phosphine, tri (2,4,6-trimethoxyphenyl)phosphine, and bromopropionic acid [137,138]. The second approach is the addition of triphenylphosphine to unsaturated carboxylic acids (Scheme 4b) followed by treatment with gaseous or concentrated HCl or HBr [139,140]. It should be mentioned the reactions of lactones with triphenylphosphine in the presence of hydro-the bioavailability and cellular uptake of obtained functionalized phosphonium salts, the nanotechnology-based approach was developed.…”

Section: Introductionmentioning

confidence: 99%

Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties

et al. 2021

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It has been shown for a wide range of epoxy compounds that their interaction with triphenylphosphonium triflate occurs with a high chemoselectivity and leads to the formation of (2-hydroxypropyl)triphenylphosphonium triflates 3 substituted in the 3-position with an alkoxy, alkylcarboxyl group, or halogen, which were isolated in a high yield. Using the methodology for the disclosure of epichlorohydrin with alcohols in the presence of boron trifluoride etherate, followed by the substitution of iodine for chlorine and treatment with triphenylphosphine, 2-hydroxypropyltriphenylphosphonium iodides 4 were also obtained. The molecular and supramolecular structure of the obtained phosphonium salts was established, and their high antitumor activity was revealed in relation to duodenal adenocarcinoma. The formation of liposomal systems based on phosphonium salt 3 and L-α-phosphatidylcholine (PC) was employed for improving the bioavailability and reducing the toxicity. They were produced by the thin film rehydration method and exhibited cytotoxic properties. This rational design of phosphonium salts 3 and 4 has promising potential of new vectors for targeted delivery into mitochondria of tumor cells.

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New α‐Imido‐β‐diarylphosphorylpropanoates and their Complexes with Gadolinium(III)

et al. 2022

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A practical route is described for the preparation of α‐imido‐β‐diarylphosphorylpropanoates based on the phosphine‐catalyzed α‐umpolung/β‐Michael addition reaction. One of the products has been tested for coordination the Gd3+ cation using NMR relaxation method in solution and by IR spectroscopy to solids. The exact structures of two isomers of the obtained complex have been determined by single crystal analysis. The structures of all isomers were investigated by quantum‐chemical calculations in solution. Quantum‐chemical calculations results show the presence of stereoselective effect in solution: the trans‐isomer with two ligands having different chirality is energetically more favorable. The cis‐isomer with ligands of different chirality is the least advantageous in terms of energy and therefore presents in solution in small amounts. The cis‐ and trans‐isomers with two ligands of the same chirality are very close in energy but are somewhat inferior to the most stable isomer.

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Tertiary phosphines in reactions with substituted cinnamic acids

Cited by 14 publications

References 11 publications

Design, Synthesis and Anticancer Evaluation of Substituted Cinnamic Acid Bearing 2-Quinolone Hybrid Derivatives

Design, Synthesis and Anticancer Evaluation of Substituted Cinnamic Acid Bearing 2-Quinolone Hybrid Derivatives

Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties

New α‐Imido‐β‐diarylphosphorylpropanoates and their Complexes with Gadolinium(III)

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