1758-46-9

Usage

Chemical Properties

Clear colorless to light yellow liquid

InChI:InChI=1/C8H11NO/c9-6-7-10-8-4-2-1-3-5-8/h1-5H,6-7,9H2/p+1

Upstream product

• 151-56-4 ethyleneimine 
• 108-95-2 phenol 
• 621-88-5 phenoxyacetamide 
• 100-97-0 hexamethylenetetramine 
• 589-10-6 phenoxyethyl bromide 
• 100-67-4 potassium phenolate 
• 689-98-5 chloroethylamine 
• 3598-14-9 phenoxyacetonitrile 
• 83725-61-5 2-(2-phenoxyethyl)-1H-isoindole-1,3(2H)-dione 
• 60-29-7 diethyl ether 
• 122-99-6 2-Phenoxyethanol 
• 122-59-8 2-phenoxyacetic acid 
• 591-50-4 iodobenzene 
• 141-43-5 ethanolamine 

Downstream Products

• 100122-24-5 (6-chloro-pyrimidin-4-yl)-(2-phenoxy-ethyl)-amine 
• 37075-71-1 N-(2-phenoxy-ethyl)-toluene-4-sulfonamide 
• 101266-09-5 [5-nitro-3-(2-phenoxy-ethyl)-tetrahydro-[1,3]oxazin-5-yl]-methanol 
• 99071-05-3 dichloro-acetic acid-(2-phenoxy-ethylamide) 
• 99421-77-9 trichloro-acetic acid-(2-phenoxy-ethylamide) 
• 68250-87-3 2-(4-chloro-phenyl)-3-(2-phenoxy-ethyl)-thiazolidin-4-one 
• 68251-52-5 2-(2-chloro-phenyl)-3-(2-phenoxy-ethyl)-thiazolidin-4-one 
• 68250-69-1 2-(4-methoxy-phenyl)-3-(2-phenoxy-ethyl)-thiazolidin-4-one 
• 4747-92-6 2-phenoxyethylisocyanate 
• 33312-20-8 N,N'-bis-(2-phenoxy-ethyl)-3,3'-disulfanediyl-bis-propionamide 
• 121594-01-2 [6-Methyl-2,3,4,9-tetrahydro-carbazol-(1E)-ylidene]-(2-phenoxy-ethyl)-amine 
• 135482-59-6 (2R,3R,4S,5R)-2-[6-Amino-2-(2-phenoxy-ethylamino)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol 
• 77176-24-0 N-(2-Allyloxy-phenyl)-N-[2-hydroxy-3-(2-phenoxy-ethylamino)-propyl]-methanesulfonamide; compound with toluene-4-sulfonic acid 
• 58048-18-3 1-(6-amino-purin-9-yl)-β-D-1-deoxy-ribofuranuronic acid 2-phenoxy-ethylamide 

Relevant academic research and scientific papers

Virtual screening for novel Atg5-Atg16 complex inhibitors for autophagy modulation

Two hit compounds (14 and 62) were identified using virtual high throughput screening (vHTS) inhibiting the autophagy process in A2780 ovarian cancer cells. The expression levels of the LC3-II and p62 autophagy marker proteins were monitored using Western blotting. Preliminary structure activity relationship (SAR) study of close structural analogues revealed another active compound 38. The three active compounds were tested in the MCF-7 human breast cancer cells and severe reduction of autophagosomes formation was observed confirming the activity of the inhibitors. The docking scaffold used for the vHTS was a lipophilic cleft on the Atg5 protein, which is occupied by a phenylalanine residue in the Atg16 polypeptide. To the best of our knowledge this is the first report on inhibitors that specifically modulate autophagy by directly inhibiting autophagy specific proteins, which is significant due the role autophagy plays in a number of morbid diseases such as cancer. This journal is

Efficient conversion of primary and secondary alcohols to primary amines

A convenient single-vessel conversion of primary and secondary alcohols to primary amines is reported. Use of this method results in substantially cleaner crude products than similar procedures reported in the literature. A simple work-up also makes this procedure ideal for parallel synthesis.

Synthesis and antitumor activity of 5-(5-halogenated-2-oxo-1H-pyrrolo[2,3-b]pyridin-(3Z)-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamides

We report herein the design and synthesis of a series of novel 5-halogenated-7-azaindolin-2-one derivatives containing a 2,4-dimethylpyrrole moiety. Nine target compounds with ≥70% inhibition against MCF-7 at 30 μM were further evaluated for their in vitro antitumor activity against seven human cancer cell lines by SRB assay. Results reveal that some compounds have potent antitumor activity, and the most active 13c7 (IC50s: 4.49-15.39 μM) was found to be more active than Sunitinib (IC50s: 4.70->30 μM) against all of the tested cancer cell lines.

Design, synthesis, crystal structure, and herbicidal activity of novel pyrrolidine-2,4-dione derivatives incorporating an alkyl ether pharmacophore with natural tetramic acids as lead compounds

In order to discover green herbicides with novel molecular scaffolds, natural tetramic acids were used as lead compounds to design and synthesize four pyrrolidine-2,4-dione derivatives incorporating a chainlike alkoxyalkyl moiety (4a-4d) and nineteen pyrrolidine-2,4-dione derivatives incorporating a substituted phenoxyethyl moiety (10a-10s)viasubstitution, acylation, cyclization, and acidification reactions. The synthesized target compounds were confirmed by FT-IR,1H NMR,13C NMR and HRMS spectral analyses. The single-crystal structure of compound10awas analyzed by X-ray diffraction, which revealed that the 1-hydroxyethylidene group links the third position of the pyrrolidine heterocycle through a double bond with theZ-configuration. The herbicidal activity was evaluated using barnyard grass (Echinochloa crus-galli) and rape (Brassica campestris) as model plants by a Petri dish culture method. Most target compounds were found to possess moderate to good inhibitory activities against the plant growth at 100 μg mL?1. Among them, the compounds10qand10nshowed the highest herbicidal activities against the roots of barnyard grass and rape seedlings with the corresponding inhibition rates of 65.6% and 84.0%, respectively. This result indicated that pyrrolidine-2,4-dione derivatives incorporating a substituted phenoxyethyl moiety are worthy of further structural optimization.

Synthesis and Antichlamydial Activity of Molecules Based on Dysregulators of Cylindrical Proteases

Chlamydia trachomatis is the most common sexually transmitted bacterial disease globally and the leading cause of infertility and preventable infectious blindness (trachoma) in the world. Unfortunately, there is no FDA-approved treatment specific for chlamydial infections. We recently reported two sulfonylpyridines that halt the growth of the pathogen. Herein, we present a SAR of the sulfonylpyridine molecule by introducing substituents on the aromatic regions. Biological evaluation studies showed that several analogues can impair the growth of C. trachomatis without affecting host cell viability. The compounds did not kill other bacteria, indicating selectivity for Chlamydia. The compounds presented mild toxicity toward mammalian cell lines. The compounds were found to be nonmutagenic in a Drosophila melanogaster assay and exhibited a promising stability in both plasma and gastric fluid. The presented results indicate this scaffold is a promising starting point for the development of selective antichlamydial drugs.

PYRIDIN-3-YL ACETIC ACID DERIVATIVES AS INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION

Disclosed are compounds of Formula I, including pharmaceutically acceptable salts, pharmaceutical compositions comprising the compounds, methods for making the compounds and their use in inhibiting HIV integrase and treating those infected with HIV or AIDS.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.

Activity of Fluorine-Containing Analogues of WC-9 and Structurally Related Analogues against Two Intracellular Parasites: Trypanosoma cruzi and Toxoplasma gondii

Two obligate intracellular parasites, Trypanosoma cruzi, the agent of Chagas disease, and Toxoplasma gondii, an agent of toxoplasmosis, upregulate the mevalonate pathway of their host cells upon infection, which suggests that this host pathway could be a potential drug target. In this work, a number of compounds structurally related to WC-9 (4-phenoxyphenoxyethyl thiocyanate), a known squalene synthase inhibitor, were designed, synthesized, and evaluated for their effect on T. cruzi and T. gondii growth in tissue culture cells. Two fluorine-containing derivatives, the 3-(3-fluorophenoxy)- and 3-(4-fluorophenoxy)phenoxyethyl thiocyanates, exhibited half-maximal effective concentration (EC50) values of 1.6 and 4.9 μm, respectively, against tachyzoites of T. gondii, whereas they showed similar potency to WC-9 against intracellular T. cruzi (EC50values of 5.4 and 5.7 μm, respectively). In addition, 2-[3- (phenoxy)phenoxyethylthio]ethyl-1,1-bisphosphonate, which is a hybrid inhibitor containing 3-phenoxyphenoxy and bisphosphonate groups, has activity against T. gondii proliferation at sub-micromolar levels (EC50=0.7 μm), which suggests a combined inhibitory effect of the two functional groups.

Identification of N-(2-Phenoxyethyl)imidazo[1,2-a]pyridine-3-carboxamides as New Antituberculosis Agents

A series of imidazo[1,2-a]pyridine carboxamides (IPAs) bearing an N-(2-phenoxyethyl) moiety was designed and synthesized as new antitubercular agents. Seven 2,6-dimethyl IPAs demonstrated excellent in vitro activity (MIC: 0.025-0.054 μg/mL) against the drug susceptive H37Rv strain and two clinically isolated multidrug-resistant Mycobacterium tuberculosisstrains. Compound 10j displayed acceptable safety and pharmacokinetic properties, opening a new direction for further development.

HIV INTEGRASE INHIBITORS

The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.