52446-51-2

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 25, p. 57, 1982 DOI: 10.1021/jm00343a011

Upstream product

• 4973-29-9 4-phenoxystyrene 
• 591-50-4 iodobenzene 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 4664-61-3 methyl [p-(phenoxy)phenyl]acetate 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 67-36-7 4-phenoxy benzaldehyde 
• 75-21-8 oxirane 
• 14062-26-1 ethyl 2-(4-phenoxyphenyl)acetate 
• 101-55-3 4-Bromodiphenyl ether 

Downstream Products

• 79807-86-6 1-(2-bromoethyl)-4-phenoxybenzene 
• 36207-23-5 1-ethyl-4-phenoxybenzene 
• 1433543-94-2 N-hydroxy-2-(2-(4-phenoxyphenyl)ethylsulfonamido)acetamide 
• 1433545-97-1 C₁₇H₁₉NO₅S 
• 344596-80-1 Na⁽¹⁺⁾*C₁₄H₁₃O₄S^(1-) 
• 64723-44-0 Toluene-4-sulfonic acid 2-(4-phenoxy-phenyl)-ethyl ester 
• 107291-94-1 7-Phenoxy-isothiochroman-1-carboxylic acid ethyl ester 
• 107291-86-1 Chloro-[2-(4-phenoxy-phenyl)-ethylsulfanyl]-acetic acid ethyl ester 
• 107291-79-2 [2-(4-Phenoxy-phenyl)-ethylsulfanyl]-acetic acid ethyl ester 
• 107292-00-2 7-phenoxyisothiochroman-1-carboxylic acid 
• 79807-87-7 2-({3-[2-(4-Phenoxy-phenyl)-ethoxy]-phenylamino}-methylene)-malonic acid diethyl ester 

Relevant academic research and scientific papers

Ligand- and Counterion-Assisted Phenol O-Arylation with TMP-Iodonium(III) Acetates

High reactivity of trimethoxyphenyl (TMP)-iodonium(III) acetate for phenol O-arylation was achieved. It was first determined that the TMP ligand and acetate anion cooperatively enhance the electrophilic reactivity toward phenol oxygen atoms. The proposed method provides access to various diaryl ethers in significantly higher yields than the previously reported techniques. Various functional groups, including aliphatic alcohol, boronic ester, and sterically hindered groups, were tolerated during O-arylation, verifying the applicability of this ligand- and counterion-assisted strategy.

1-(1-Arylethylpiperidin-4-yl)thymine analogs as antimycobacterial TMPK inhibitors

A series of Mycobacterium tuberculosis TMPK (MtbTMPK) inhibitors based on a reported compound 3 were synthesized and evaluated for their capacity to inhibit MtbTMPK catalytic activity and the growth of a virulent M. tuberculosis strain (H37Rv). Modifications of the scaffold of 3 failed to afford substantial improvements in MtbTMPK inhibitory activity and antimycobacterial activity. Optimization of the substitution pattern of the D ring of 3 resulted in compound 21j with improved MtbTMPK inhibitory potency (three-fold) and H37Rv growth inhibitory activity (two-fold). Moving the 3-chloro substituent of 21j to the para-position afforded isomer 21h, which, despite a 10-fold increase in IC50-value, displayed promising whole cell activity (minimum inhibitory concentration (MIC) = 12.5 μM).

Synthesis and structure activity relationships of cyanopyridone based anti-tuberculosis agents

Mycobacterium tuberculosis, the causative agent of tuberculosis, relies on thymidylate kinase (MtbTMPK) for the synthesis of thymidine triphosphates and thus also DNA synthesis. Therefore, this enzyme constitutes a potential Achilles heel of the pathogen. Based on a previously reported MtbTMPK 6-aryl-substituted pyridone inhibitor and guided by two co-crystal structures of MtbTMPK with pyridone- and thymine-based inhibitors, we report the synthesis of a series of aryl-shifted cyanopyridone analogues. These compounds generally lacked significant MtbTMPK inhibitory potency, but some analogues did exhibit promising antitubercular activity. Analogue 11i demonstrated a 10-fold increased antitubercular activity (MIC H37Rv, 1.2 μM) compared to literature compound 5. Many analogues with whole-cell antimycobacterial activity were devoid of significant cytotoxicity.

GLYCOLATE OXIDASE INHIBITORS AND USE THEREOF

The present invention provides pyrazoles, isoxazoles, isothiazoles, thiadiazoles, and pyridazines according to Formula I as described herein, and pharmaceutically acceptable salts thereof. Pharmaceutical compositions and methods for treating primary hyperoxaluria, type I (PH) and kidney stones are also described.

Inhibitors of squalene synthetase and protein farnesyltransferase

The present invention provides a compound of the formula STR1 which inhibit squalene synthetase and cholesterol biosynthesis and are useful in the treatment of e.g., hyperlipidaemia, atherosclerosis, or fungal infections, processes for the preparation of the compounds of the invention, intermediates useful in these processes, and pharmaceutical compositions containing the compounds.

Inhibitors of protein farnesyltransferase and squalene synthase

The present invention provides a compound of the formula STR1 or a pharmaceutically acceptable salt thereof, which are useful in inhibiting protein farnesyltransferase and the farnesylation of the oncogene protein Ras or inhibiting de novo squalene production resulting in the inhibition of cholesterol biosynthesis, processes for the preparation of the compounds of the invention in addition to intermediates useful in these processes, a pharmaceutical composition, and to methods of using such compounds.

Lewis-acid Promoted Aromatic Cyclization of &α-Chlorosulfides: Synthesis of Ethyl Isothiochroman-1-carboxylate and Related Compounds

A variety of ethyl isothiochroman-1-carboxylates and related compounds were synthesized by treatment of 2-chloro-2-acetates with stannic chloride in methylene chloride.The same procedure was applied to the synthesis of ethyl 4-chloro-4-methyltetrahydrothiopyran-2-carboxylate.Some isothiochroman-1-carboxylic acids were prepared and evaluated for antiinflammatory activity.Among the compounds tested, 7-phenoxyisothiochroman-1-carboxylic acid showed weak activity.