67202-81-7

Usage

InChI:InChI=1/C12H15NO4/c1-3-16-12(15)8-17-11-6-4-10(5-7-11)13-9(2)14/h4-7H,3,8H2,1-2H3,(H,13,14)

Upstream product

• 103-90-2 4-acetaminophenol 
• 105-36-2 ethyl bromoacetate 
• 105-39-5 chloroacetic acid ethyl ester 

Downstream Products

• 2298-36-4 4-aminophenoxyacetic acid 
• 1616074-87-3 2-(4-acetamidophenoxy)-N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)acetamide 
• 39149-13-8 p-N-acetylaminophenoxyacetic acid 
• 1370361-38-8 N-(4-((5-(4-ethoxyphenyl)-1,3,4-oxadiazol-2-yl)methoxy)phenyl)acetamide 
• 204651-73-0 N-(4-((5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methoxy)phenyl)acetamide 
• 1370361-35-5 N-(4-((5-(2-fluorophenyl)-1,3,4-oxadiazol-2-yl)methoxy)phenyl)acetamide 
• 1370361-33-3 N-(4-((5-(4-chloro-3-nitrophenyl)-1,3,4-oxadiazol-2-yl)methoxy)phenyl)acetamide 
• 1370361-31-1 N-(4-((5-(2-chloro-5-nitrophenyl)-1,3,4-oxadiazol-2-yl)methoxy)phenyl)acetamide 
• 1370361-29-7 N-(4-((5-(2-aminophenyl)-1,3,4-oxadiazol-2-yl)methoxy)phenyl)acetamide 
• 1370361-27-5 N-(4-((5-(3-aminophenyl)-1,3,4-oxadiazol-2-yl)methoxy)phenyl)acetamide 
• 1370361-45-7 N-(4-((5-(pyridin-3-yl)-1,3,4-oxadiazol-2-yl)methoxy)phenyl)acetamide 
• 204651-70-7 N-(4-((5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)methoxy)phenyl)acetamide 

Relevant academic research and scientific papers

3,4,5-trisubstituted-1,2,4-triazole derivatives as antiproliferative agents: Synthesis, in vitro evaluation and molecular modelling

Background: Cancer is the name given to various diseases that are mainly uncontrolled, related to cell growth and can affect various organs. Among them, lung cancer is the one, which, in its earliest stages, is difficult to diagnose, and it is asymptomati

PRMT5 INHIBITORS AND USES THEREOF

Described herein are compounds of Formula (I), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5-mediated disorders are also described.

Synthesis and antiproliferative evaluation of novel 2-(4H-1,2,4-triazole-3-ylthio)acetamide derivatives as inducers of apoptosis in cancer cells

In this study, a series of thiosemicarbazide derivatives 12–14, 1,2,4-triazol-3-thione derivatives 15–17 and compounds bearing 2-(4H-1,2,4-triazole-3-ylthio)acetamide structure 18–32 have been synthesized starting from phenolic compounds such as 2-naphthol, paracetamol and thymol. Structures and purity of the target compounds were confirmed by the use of their chromatographic and spectral data besides microanalysis. All of the synthesized new compounds 12–32 were evaluated for their anti-HIV activity. Among these compounds, three representatives 18, 19 and 25 were selected and evaluated by the National Cancer Institute (NCI) against the full panel of 60 human cancer cell lines derived from nine different cancer types. Antiproliferative effects of the selected compounds were demonstrated in human tumor cell lines K-562, A549 and PC-3. These compounds inhibited cell growth assessed by MTT assay. Compound 18, 19 and 25 exhibited anti-cancer activity with IC50values of 5.96?μM (PC-3?cells), 7.90?μM (A549/ATCC cells) and 7.71?μM (K-562?cells), respectively. After the cell viability assay, caspase activation and Bcl-2 activity of the selected compounds were measured and the loss of mitochondrial membrane potential (MMP) was detected. Compounds 18, 19 and 25 showed a significant increase in caspase-3 activity in a dose-dependent manner. This was not observed for caspase-8 activity with compound 18 and 25, while compound 19 was significantly elevated only at the dose of 50?μM. In addition, all three compounds significantly decreased the mitochondrial membrane potential and expression of Bcl-2.

Convergent Versus Divergent Three-Step Synthesis of the First (4-Aminophenoxy)alkanoic Acid-Based Tripodal Melamines

Starting from N-(4-hydroxyphenyl)acetamide (Paracetamol, convergent approach) or from cyanuric chloride in reaction with 4-aminophenol (divergent approach), two synthetic routes toward novel tripodal N-substituted melamines as s-triazine derivatives of (4-aminophenoxy)acetic acid or of 4-(4-aminophenoxy)butyric acid are comparatively defined. The key steps consist of Williamson etherification of N-masked forms of 4-aminophenol and acidic hydrolysis of the N- and/or O-protected (4-aminophenoxy)alkanoic segments.

PRMT5 INHIBITORS CONTAINING A DIHYDRO- OR TETRAHYDROISOQUINOLINE AND USES THEREOF

Described herein are compounds of Formula (A), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5- mediated disorders are also described.

Synthesis and evaluation of anti-inflammatory and analgesic activity of 3-[(5-substituted-1,3,4-oxadiazol-2-yl-thio)acetyl]-2H-chromen-2-ones

A novel series of 3-[(5-substituted-1,3,4-oxadiazol- 2-yl-thio)acetyl]-2H- chromen-2-one (7a-i) were synthesized by the condensation between the appropriately substituted 5-substituted-1,3,4-oxadiazolyl-2-thione (4a-i) derived from various existing NSAIDs and 3-(2-bromoacetyl)- 2H-chromen-2-one (6) under reflux in the presence of sodium ethoxide. Structure of the synthesized compounds was established on the basis of physicochemical, elemental analysis, and spectral data. The title compounds were screened for in vivo acute anti-inflammatory and analgesic activities at a dose of 200 mg/kg bw. Among the series, four compounds 7c, 7e, 7f, and 7h were found to possess a significant anti-inflammatory and analgesic activity profile. In addition, these compounds were also found to possess a less degree of ulcerogenic potential as compared to standard NSAIDs. Springer Science+Business Media, LLC 2010.

Synthesis and antimicrobial screening of some novel 2, 5-disubstituted 1, 3, 4-oxadiazole derivatives

The syntheses of series of 2, 5-disubstituted 1, 3, 4-oxadiazole derivatives are described. A total of twelve new compounds were synthesized and characterized by IR, 1H-NMR and Mass spectral data. All newly synthesized compounds were screened f

FUNCTIONALIZED PHENOLIC COMPOUNDS AND POLYMERS THEREFROM

The present invention relates to compounds of formula I, which are functionalized phenolic compounds, and polymers formed from the same. Ar—[O—(X)p—R′]q??I Polymers formed from the functionalized phenolics are expected to have controllable degradation profiles, enabling them to release an active component over a desired time range. The polymers are also expected to be useful in a variety of medical applications.

Synthesis of some novel thiourea derivatives obtained from 5-[(4-aminophenoxy)methyl]-4-alkyl/aryl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and evaluation as antiviral/anti-HIV and anti-tuberculosis agents

As a continuation of our previous efforts on N-alkyl/aryl-N′-[4-(4-alkyl/aryl-2,4-dihydro-3H-1,2,4-triazole-3-thione-5-yl)phenyl]thioureas 1-19 and N-alkyl/aryl-N′-[4-(3-aralkylthio-4-alkyl/aryl-4H-1,2,4-triazole-5-yl)phenyl]thioureas 20-22, a series of novel 5-[(4-aminophenoxy)methyl]-4-alkyl/aryl-2,4-dihydro-3H-1,2,4-triazole-3-thiones 23-26 and several related thioureas, N-alkyl/aryl-N′-{4-[(4-alkyl/aryl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methoxy]phenyl}thioureas 27-42 were synthesized for evaluation of their antiviral potency. Structures of the synthesized compounds were confirmed by the use of 1H NMR, 13C NMR and HR-MS data. All compounds 1-42 were evaluated in vitro against HIV-1 (IIIB) and HIV-2 (ROD) strains in MT-4 cells, as well as other selected viruses such as HSV-1, HSV-2, Coxsackie virus B4, Sindbis virus and Varicella-zoster virus using HeLa, Vero, HEL and E6SM cell cultures, and anti-tuberculosis activity against Mycobacterium tuberculosis H37Rv. Compounds 4 and 5 showed weak activity against HSV-1, HSV-2 and TK- HSV, whereas eight compounds showed marginal activity against Coxsackie virus B4. The most active derivative in this series was compound 38 which showed moderate protection against Coxsackie virus B4 with an MIC value of 16 μg/ml and a selectivity index of 5. This compound was also active against thymidine kinase positive Varicella-zoster virus (TK+ VZV, OKA strain) with an EC50 value of 9.9 μg/ml. Compound 38 was the most active compound with 79% inhibition against M. tuberculosis H37Rv.

Functionalized drugs and polymers derived therefrom

Compounds selected from: where DRUG-OH, DRUG-COOH and DRUG-NH2 are biologically active compounds; each X is independently selected from —CH2COO— (glycolic acid moiety), —CH(CH3)COO— (lactic acid moiety), —CH2CH2OCH2COO— (dioxanone moiety), —CH2CH2CH2CH2CH2COO— (caprolactone moiety), —(CH2)yCOO—, where y is 2-4 or 6-24 and —(CH2CH2O)zCH2COO—, where z is 2-24; each Y is independently selected from —COCH2O— (glycolic ester moiety), —COCH(CH3)O— (lactic ester moiety), —COCH2OCH2CH2O— (dioxanone ester moiety), —COCH2CH2CH2CH2CH2O— (caprolactone ester moiety), —CO(CH2)mO—, where m is 2-4 or 6-24 and —COCH2O(CH2CH2O)n— where n is between 2-24; R′ is hydrogen, benzyl or an alkyl group, the alkyl group being either straight-chained or branched; and p is 1-6. Multi-functional compounds and drug dimers, oligomers and polymers are also disclosed.