Microwave-Assisted Synthesis and Antitumor Activity of Salicyl Acyloxy Phosphonate Derivatives

Yang, Jing‐Fang; Ma, Jun; Che, Wan-li; Li, Minggang; Li, Gang; Song, Baoan

doi:10.6023/cjoc201406026

Cited by 9 publications

(6 citation statements)

References 4 publications

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“…Carboxylic acids may also be efficient acylating agents of α-hydroxyphosphonates 1 in the presence of N , N ′-dicyclohexylcarbodiimide (DCC) as the coupling reagent, and 4-dimethyl-aminopyridine (DMAP) as the base [ 27 , 90 , 91 ]. This is exemplified by the reaction of 2-(4,6-dimethoxypyrimidin-2-yloxy)benzoic acid ( 23 ) at 25 °C to give α-acyloxyphosphonates 24 possessing herbicidal activity ( Scheme 11 ) [ 27 ].…”

Section: Reactions Of α-Hydroxyphosphonatesmentioning

confidence: 99%

Synthesis and Reactions of α-Hydroxyphosphonates

Rádai

Keglevich

2018

Molecules

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This review summarizes the main synthetic routes towards α-hydroxyphosphonates that are known as enzyme inhibitors, herbicides and antioxidants, moreover, a number of representatives express antibacterial or antifungal effect. Special attention is devoted to green chemical aspects. α-Hydroxyphosphonates are also versatile intermediates for other valuable derivatives. O-Alkylation and O-acylation are typical reactions to afford α-alkoxy-, or α-acyloxyphosphonates, respectively. The oxidation of hydroxyphosphonates leads to ketophosphonates. The hydroxy function at the α carbon atom of hydroxyphosphonates may be replaced by a halogen atom. α-Aminophosphonates formed in the nucleophilic substitution reaction of α-hydroxyphosphonates with primary or secondary amines are also potentially bioactive compounds. Another typical reaction is the base-catalyzed rearrangement of α-hydroxy-phosphonates to phosphates. Hydrolysis of the ester function of hydroxyphosphonates leads to the corresponding phosphonic acids.

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Section: Reactions Of α-Hydroxyphosphonatesmentioning

confidence: 99%

Synthesis and Reactions of α-Hydroxyphosphonates

Rádai

Keglevich

2018

Molecules

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“…Beyond their potential bioactivity, the α-hydroxyphosphonates may be important intermediates in a series of syntheses [ 1 ]. The most important reactions are alkylations [ 1 ], acylations [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ], phosphorylations [ 28 ], substitutions [ 1 ], rearrangements [ 1 ], and dealkylations [ 1 ]. As regards acylations, a series of α-(aryloxyacetoxy)-alkylphosphonate derivatives [ 12 , 13 , 14 , 15 ] was prepared mainly by acylation of different α-hydroxyphosphonates with carboxylic acid chlorides, including aryloxy-butyryloxy or -valeroxy [ 16 ] and heterocyclic derivatives [ 17 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

“…Among the more complex examples, modification of α-hydroxyphosphonates with acetyl chloride was also described, but in a complicated manner (see below) [ 19 ]. Carboxylic acid anhydrides [ 20 , 21 , 22 , 23 ] and the acids themselves [ 24 , 25 , 26 ] were also used in the acylation of hydroxyphosphonates. Among the carboxylic acids, benzoic acid and propionic acid were also applied [ 25 , 26 ].…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of Acylated, Dialkyl α-Hydroxy-Benzylphosphonates and Their Anticancer Activity

et al. 2022

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An efficient method applying acyl chlorides as reagents was developed for the acylation of the hindered hydroxy group of dialkyl α-hydroxy-benzylphosphonates. The procedure did not require any catalyst. A few acylations were also performed with the SC-enantiomer of dimethyl α-hydroxy-benzylphosphonate, and the optical purity was retained. A part of the acyloxyphosphonates was tested against eight tumor cell lines of different tissue origin at c = 50 μM concentration. The compounds elicited moderate cytostatic effect against breast, skin, prostate, colon, and lung carcinomas; a melanoma cell line; and against Kaposi’s sarcoma cell lines. Then, dose-dependent cytotoxicity was assayed, and benzoylation of the α-hydroxy group was identified as a moiety that increases anticancer cytotoxicity across all cell lines. Surprisingly, a few analogues were more toxic to multidrug resistant cancer cell lines, thus evading P-glycoprotein mediated drug extrusion.

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“…The acylation of -hydroxyphosphonates is of special importance due to the potential biological activity of the products so obtained. Acid chlorides [26][27][28][29][30] including aryloxyacetyl chlorides 31 and 2,6-pyridinedicarboxylic acid chloride, 32 acetic anhydrides [33][34][35] and carboxylic acids 36,37 were used as the acylating agents. A part of the acylated and phosphorylated hydroxy-benzylphosphonates and the -aminophosphonates prepared by us displayed a significant cytotoxic activity.…”

mentioning

confidence: 99%

The Addition of α-Hydroxy-benzylphosphonates to Dialkyl Acetylenedicarboxylates; Catalytic Hydrogenation of the Adducts

Milen,

Keglevich,

Bese

et al. 2024

Synthesis

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alfa-Hydroxy-benzylphosphonates obtained by the Pudovik reaction of substituted benzaldehydes and dialkyl phosphites were added on the triple bond of dialkyl acetylenedicarboxylates. Optimum conditions involved a 24 h’ stirring in the presence of 10% of diazabicycloundecene in dichloromethane to afford the adducts as a mixture of predominant “E” and a minor “Z” izomers in 75–90% yields after flash chromatography. Structure of the geometrical isomers was confirmed by NOE- and ROE measurements. Catalytic hydrogenation of the olefinic moiety of the adducts led to the diastereomers of corresponding saturated derivatives.

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Microwave-Assisted Synthesis and Antitumor Activity of Salicyl Acyloxy Phosphonate Derivatives

Cited by 9 publications

References 4 publications

Synthesis and Reactions of α-Hydroxyphosphonates

Synthesis and Reactions of α-Hydroxyphosphonates

Efficient Synthesis of Acylated, Dialkyl α-Hydroxy-Benzylphosphonates and Their Anticancer Activity

The Addition of α-Hydroxy-benzylphosphonates to Dialkyl Acetylenedicarboxylates; Catalytic Hydrogenation of the Adducts

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Microwave-Assisted Synthesis and Antitumor Activity of Salicyl Acyloxy Phosphonate Derivatives

Cited by 9 publications

References 4 publications

Synthesis and Reactions of α-Hydroxyphosphonates

Synthesis and Reactions of α-Hydroxyphosphonates

Efficient Synthesis of Acylated, Dialkyl α-Hydroxy-Benzylphosphonates and Their Anticancer Activity

The Addition of α-Hydroxy-benzylphosphonates to Dialkyl Acetyl­enedicarboxylates; Catalytic Hydrogenation of the Adducts

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The Addition of α-Hydroxy-benzylphosphonates to Dialkyl Acetylenedicarboxylates; Catalytic Hydrogenation of the Adducts