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Usage

Uses

Used in Pharmaceutical Industry:
Phosphonic acid, [2-oxo-2-(phenylamino)ethyl]-, diethyl ester is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure containing a phenylamino group allows it to be incorporated into the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, Phosphonic acid, [2-oxo-2-(phenylamino)ethyl]-, diethyl ester serves as a building block for the synthesis of agrochemicals. Its reactivity and functional groups make it suitable for the development of new compounds with pesticidal or herbicidal properties, contributing to more effective crop protection solutions.
Used in Organic Synthesis:
Phosphonic acid, [2-oxo-2-(phenylamino)ethyl]-, diethyl ester is utilized as a versatile reagent in organic synthesis. Its ability to form stable phosphonate esters with various functional groups makes it a valuable component in the preparation of complex organic molecules, including natural products, pharmaceuticals, and specialty chemicals.

Upstream product

• 34170-81-5 diethyl (2-chloro-2-oxoethyl)phosphonate 
• 62-53-3 aniline 
• 683-08-9 Diethyl methylphosphonate 
• 103-71-9 phenyl isocyanate 
• 3095-95-2 diethylphosphonoacetic acid 
• 5326-87-4 N-(phenyl)bromoacetamide 
• 122-52-1 triethyl phosphite 
• 27784-76-5 tert-butyl diethylphosphonoacetate 
• 587-65-5 N-chloroacetyl-aniline 

Downstream Products

• 113348-19-9 4-Phenyl-hexa-2,3-dienoic acid phenylamide 
• 113348-16-6 4,4-Diphenyl-buta-2,3-dienoic acid phenylamide 

Relevant academic research and scientific papers

Lead Optimization of Benzoxepin-Type Selective Estrogen Receptor (ER) Modulators and Downregulators with Subtype-Specific ERα and ERβ Activity

Estrogen receptor α (ERα) is an important target for the design of drugs such as tamoxifen (2a) and fulvestrant (5). Three series of ER-ligands based on the benzoxepin scaffold structure were synthesized: series I containing an acrylic acid, series II with an acrylamide, and series III with a saturated carboxylic acid substituent. These compounds were shown to be high affinity ligands for the ER with nanomolar IC50 binding values. Series I acrylic acid ligands were generally ERα selective. In particular, compound 13e featuring a phenylpenta-2,4-dienoic acid substituent was shown to be antiproliferative and downregulated ERα and ERβ expression in MCF-7 breast cancer cells. Interestingly, from series III, the phenoxybutyric acid derivative compound 22 was not antiproliferative and selectively downregulated ERβ. A docking study of the benzoxepin ligands was undertaken. Compound 13e is a promising lead for development as a clinically relevant SERD, while compound 22 will be a useful experimental probe for helping to elucidate the role of ERβ in cancer cells.

Synthesis and evaluation of 3-ylideneoxindole acetamides as potent anticancer agents

Indirubin, an active component in the traditional Chinese medicine formula Danggui Longhui Wan, shows promising anticancer effects. Meisoindigo is an analog derived from indirubin, which is less toxic and appears to be even more potent against cancer. In considering meisoindigo as a structural template for the development of new drugs, we designed and synthesized a series of 3-ylideneoxindole acetamides as novel anticancer agents. The acetamides were then evaluated for in vitro and in vivo anticancer activities. The 3-ylideneoxindole acetamides were found to have better anticancer activity than was indirubin-3'-oxime in several cancer cell lines and also displayed a spectrum of activity similar to that of the drug candidate roscovitine, a CDK inhibitor. Among the 3-ylideneoxindole acetamides, compound 10 showed particularly good efficacy. Cell cycle analysis further revealed that compound 10 arrested cells in the G1 phase and caused an increase in the sub-G1 population, indicating that the apoptosis pathway had been induced. In addition, exposure of cells to compound 10 led to the upregulation of the cell-cycle regulator cyclin D1, which was sustained at a high level. In contrast, the same compound induced a short-term elevation in the level of cyclin E, which was followed by a rapid decrease and the attenuation of Rb phosphorylation. Furthermore, a docking model suggests that compound 10 binds to the active site of CDK4. In testing the therapeutic potency of compound 10 on CT26-xenografted BALB/c mice, a significant reduction in tumor size comparable to that of cisplatin was found when administrated via the i.p. route. The mice presented no loss of body weight, indicating that this compound possesses low toxicity. In the future, we are planning in vivo investigations of these new active anticancer agents to better elucidate active mechanisms at the cellular level and thus benefit the development of anticancer therapies.

Microwave-enhanced synthesis of phosphonoacetamides

An efficient microwave protocol is described for the Michaelis-Arbuzov synthesis of secondary and tertiary N-aryl (and alkyl) (diethylphosphono) acetamides 1, by reaction of chloro- and bromoacetamides with triethyl phosphite in the presence of catalytic

Efficient method to prepare diethylphosphonacetamides

An efficient and versatile synthetic method is described to synthesize diethylphosphonacetamides in a single step.

PHOSPHONATES α-LITHIES, AGENTS DE TRANSFERT FONCTIONNEL. PREPARATION DE PHOSPHONATES α-AMIDES ET D'AMIDES α,β-INSATURES, α-SUBSTITUES

Lithiated anions (9) or (10) of secondary or tertiary α-amidophosphonates are prepared either by reaction between an α-phosphonyl carbanion and an isocyanate or a carbamate (first strategy), or by condensation of an amide enolate with diethylchlorophosphate (second strategy).Acidic hydrolysis of (9) or (10) gives α-amidophosphonate (1) alkylated or not in the α-position. (9) and (10) react with aromatic or aliphatic aldehydes to produce α,β-unsatured secondary or tertiary amides (2).