772-79-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Chlorophenyl phosphorodichloridate is used as a reactant for the preparation of antimicrobial agents, contributing to the development of new drugs to combat resistant bacterial strains. Its ability to form stable bonds with biologically active molecules enhances the effectiveness of these agents.
Used in Antioxidant Applications:
In the field of antioxidants, 4-Chlorophenyl phosphorodichloridate is utilized as a reactant for the synthesis of antioxidant agents. These antioxidants are essential in various industries, including food, cosmetics, and pharmaceuticals, to prevent oxidation and extend the shelf life of products.
Used in Antitumor Applications:
4-Chlorophenyl phosphorodichloridate is employed as a reactant in the preparation of antitumor agents, playing a crucial role in the development of novel cancer therapies. Its unique chemical properties allow for the creation of compounds that can target and inhibit the growth of cancer cells.
Used in Nucleotide Anti-Viral Prodrug Development:
In the area of anti-viral drug development, 4-Chlorophenyl phosphorodichloridate is used as a reactant for the synthesis of nucleotide anti-viral prodrugs. These prodrugs are designed to be activated within the body, providing a targeted approach to treating viral infections and minimizing side effects.
Overall, 4-Chlorophenyl phosphorodichloridate is a valuable chemical intermediate with diverse applications across various industries, particularly in the development of pharmaceuticals and other specialty chemicals. Its unique properties and reactivity make it an essential component in the synthesis of a wide range of compounds with potential therapeutic and commercial applications.

InChI:InChI=1/C6H4Cl3O2P/c7-5-1-3-6(4-2-5)11-12(8,9)10/h1-4H

Upstream product

• 871896-25-2 4-dichlorophosphoryloxy-benzenesulfonyl chloride 
• 106-48-9 4-chloro-phenol 
• 98-67-9 p-hydoroxybenzenesulfonic acid 
• 10026-13-8 phosphorus pentachloride 
• 13388-88-0 4-chlorophenyl phosphate 

Downstream Products

• 38319-20-9 N,N'-diphenyl-diamidophosphoric acid-(4-chloro-phenyl ester) 
• 13388-88-0 4-chlorophenyl phosphate 
• 54113-49-4 Dimethyl-phosphoramidic acid 4-chloro-phenyl ester methyl ester 
• 19670-19-0 Methyl-phosphoramidic acid 4-chloro-phenyl ester methyl ester 
• 54113-47-2 Phosphoramidic acid 4-chloro-phenyl ester methyl ester 
• 35652-38-1 5,5-Bis-bromomethyl-2-(4-chloro-phenoxy)-[1,3,2]dioxaphosphinane 2-oxide 
• 38578-33-5 5,5-Bis-chloromethyl-2-(4-chloro-phenoxy)-[1,3,2]dioxaphosphinane 2-oxide 
• 18351-15-0 ethyl 4-chlorophenyl chlorophosphate 
• 54638-63-0 Phosphoric acid 4-chloro-phenyl ester bis-(2,2,2-trichloro-1-methoxy-ethyl) ester 
• 113813-41-5 (2-Oxo-oxazol-3-yl)-phosphonic acid 4-chloro-phenyl ester 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 81265-94-3 5'-dimethoxytrityl 2'-tert-butyldimethyl silyl uridine 3'-p-chlorophenyl β-cyanoethyl phosphotriester 
• 82444-82-4 4-(1,2,4-triazol-1-yl)-1-<5'-O-(dimethoxytrityl)-3'-O-((p-chlorophenoxy)(2-cyanoethoxy)phosphoryl)-2'-O-(tert-butyldimetylsilyl)-β-D-ribofuranosyl>pyrimidin-2-(1H)-one 
• 62420-37-5 (p-chlorophenyl) di(1,2,4-triazolido)phosphate 
• 81279-40-5 4-tetrazolo-1-(β-D-5'-dimethoxytrityl-2'-tert-butyldimethyl silyl ribofuranosyl)-2(1H)-pyrimidinone 3'-p-chlorophenyl β-cyanoethyl phosphotriester 

Relevant academic research and scientific papers

Prodrug compound and application ofprodrug compound in treatment of cancer

The present invention provides a compound indicated by a formula (I), pharmaceutically acceptable salts or esters thereof, a pharmaceutical composition of the compound, and application of the compoundand the pharmaceutical composition in the inhibition or regulation of the activity of tyrosine kinase and treating disease symptoms or symptoms including cancer mediated by tyrosine kinase.

PRODRUGS OF THE TYROSINE KINASE INHIBITOR FOR TREATING CANCER

There are provided compounds of Formula (I), and pharmaceutically acceptable salts and esters thereof, and pharmaceutical compositions thereof, useful for inhibition or modulation of the activity of tyrosine kinases and treatment of disease states or conditions mediated by tyrosine kinases, including cancers. (I)

A convenient solid phase approach to obtain lipophilic 5′-phosphoramidate derivatives of DNA and RNA oligonucleotides

This paper explores the potential of a modified phosphotriester approach to the synthesis of 5′-phosphoramidate derivatives of DNA and RNA oligonucleotides. The modification of 5′-deprotected support-bound oligonucleotides is done in two steps: i) conversion of the 5′-OH group of an oligonucleotide into an activated phosphodiester, and ii) treatment of the activated phosphodiester with an aminocompound. The approach is efficient and compatible with conventional solid phase oligonucleotide synthesis. It can be used for the conjugation of therapeutically relevant oligonucleotides with functional moieties or carrier constructions, which are to be removed after endocytosis.

Emtricitabine phosphonate compound

The invention belongs to the field of synthesis of organic compounds and medicine and relates to an emtricitabine phosphonate compound, a preparation method thereof, a medicinal compound containing the compound and application of the compound in antiviral drugs for treatment. A provided phosphonate compound of a nucleoside analog has equivalent or superior stability in human plasma, artificial gastric juice and artificial intestinal juice under comparison with emtricitabine and can remarkably reduce the quantity of hepatitis B viruses in animal bodies; compared with emtricitabine, the compoundhas obviously higher anti-HBV activity, excellent liver targeting and smaller toxic and side effects and is a therapeutic agent with a clinical application prospect for HIV and HBV.

SUBSTITUTED NUCLEOSIDES, NUCLEOTIDES AND ANALOGS THEREOF

Disclosed herein are nucleosides, nucleotide analogs, methods of synthesizing nucleotide analogs and methods of treating diseases and/or conditions such as a Filoviridae virus infection with one or more nucleosides and/or nucleotide analogs.

Synthesis and biological evaluation of LNA phosphoramidates

The synthesis of LNA phosphoramidates is presented. The LNA phosphoramidates were evaluated for their ability to inhibit cell proliferation of the human prostate cancer cell line 15PC3. A number of the LNA phosphoramidates showed cell proliferation inhibition determined by the MTS assay. Copyright Taylor & Francis Group, LLC.

Activation of p16 gene silenced by DNA methylation in cancer cells by phosphoramidate derivatives of 2′-deoxyzebularine

We report herein the application of the phosphoramidate ProTide technology to improve the metabolism of the DNA methytransferase inhibitor, zebularine (Z). Zebularine is a riboside that must undergo a complex metabolic transformation before reaching the critical 2′-deoxyzebularine 5′-triphosphate (dZTP). Because 2′-deoxyzebularine (dZ) is not phosphorylated and therefore inactive, the ProTide strategy was employed to bypass the lack of phosphorylation of dZ and the inefficient reduction of zebularine 5′-diphosphate by ribonucleotide-diphosphate reductase required for zebularine. Several compounds were identified as more potent inhibitors of DNA methylation and stronger inducers of p16 tumor suppressor gene than zebularine. However, their activity was dependent on the administration of thymidine to overcome the potent inhibition of thymidylate synthase (TS) and deoxycytidine monophosphate (dCMP) deaminase by dZMP, which deprives cells of essential levels of thymidine. Intriguingly, the activity of the ProTides was cell line-dependent, and activation of p16 was manifest only in Cf-Pac-1 pancreatic ductal adenocarcinoma cells.

Antiviral phosphoramidates

The invention provides novel nucleoside compounds of formula I wherein R1, R2a, R2b, R3, R4, R5, R6, R8a, R9 and R10 are as defined herein which are useful for the treatment of Hepatitis C Virus (HCV) mediated diseases. The invention further provides methods for treatment or prophylaxis of HCV mediated diseases with compounds of formula I and pharmaceutical compositions comprising these compounds,

Application of phosphoramidate ProTide technology significantly improves antiviral potency of carbocyclic adenosine derivatives

We report the application of phosphoramidate pronucleotide (ProTide) technology to the antiviral agent carbocyclic L-d4A (L-Cd4A). The phenyl methyl alaninyl parent ProTide of L-Cd4A was prepared by Grignard-mediated phosphorochloridate reaction and resulted in a compound with significantly improved anti-HIV (2600-fold) and HBV activity. We describe modifications of the aryl, ester, and amino acid regions of the ProTide and how these changes affect antiviral activity and metabolic stability. Separate and distinct SARs were noted for HIV and HBV. Additionally, ProTides were prepared from the D-nucleoside D-Cd4A and the dideoxy analogues L-CddA and D-CddA. These compounds showed more modest potency improvements over the parent drug. In conclusion, the ProTide approach is highly successful when applied to L-Cd4A with potency improvements in vitro as high as 9000-fold against HIV. With a view to preclinical candidate selection we carried out metabolic stability studies using cynomolgus monkey liver and intestinal S9 fractions.

Anti-cancer ProTides: Tuning the activity of BVDU phosphoramidates related to thymectacin

Based on our wide ranging knowledge of phosphoramidate ProTides as anti-viral agents we have tuned the lead anti-cancer agent thymectacin in the ester and amino acid regions and revealed a substantial enhancement in in vitro potency versus colon and prostate cancer cell lines. Twelve analogues have been reported, with yields of 29-78%. The compounds are fully characterised and data clearly reveal the presence of two phosphate diastereoisomers, as expected, in roughly equi-molar proportions. The compounds were evaluated in tissue culture versus three different tumour cell lines, using thymectacin as the control. It is notable that minor structural modification of the parent phenyl methoxyalaninyl structure of thymectacin leads to significant enhancements in potency. In particular, replacement of the methyl ester moiety in the lead by a benzyl ester gave a 175-fold boost in potency versus colon cancer HT115. This derivative emerges as a low micromolar inhibitor of HT115 cells and a new lead for further optimisation.