1700-29-4

Usage

Uses

Used in Pharmaceutical Industry:
4-BENZYLOXY-3-METHOXYPHENYLACETONITRILE is used as a key intermediate in the synthesis of various pharmaceuticals for its potential biological properties. It contributes to the development of new medicinal products, enhancing the range of treatments available in the healthcare sector.
Used in Agrochemical Industry:
In the agrochemical industry, 4-BENZYLOXY-3-METHOXYPHENYLACETONITRILE serves as a crucial component in the creation of agrochemicals. Its utilization aids in the development of effective products for agricultural applications, such as pesticides and herbicides, to improve crop protection and yield.
Used in Organic Compounds Production:
4-BENZYLOXY-3-METHOXYPHENYLACETONITRILE is used as an intermediate in the production of organic compounds. Its role is vital in creating a variety of chemical substances that find applications in different industries, including the synthesis of dyes, plastics, and other specialty chemicals.
Used in Research and Development:
4-BENZYLOXY-3-METHOXYPHENYLACETONITRILE is utilized in research and development initiatives to explore its potential applications and properties further. It serves as a building block for the preparation of other chemical substances, facilitating the discovery and innovation of new products in the fields of medicine and agriculture.

InChI:InChI=1/C16H15NO2/c1-18-16-11-13(9-10-17)7-8-15(16)19-12-14-5-3-2-4-6-14/h2-8,11H,9,12H2,1H3

Upstream product

• 72724-00-6 1-(benzyloxy)-4-(bromomethyl)-2-methoxybenzene 
• 143-33-9 sodium cyanide 
• 33688-50-5 1-(benzyloxy)-4-(chloromethyl)-2-methoxybenzene 
• 13435-20-6 tetraethylammoniumcyanide 
• 1700-28-3 β-(4-Benzyloxy-3-methoxy-benzyl)-α-thioxopropionsaeure 
• 121-33-5 vanillin 
• 100-39-0 benzyl bromide 
• 4468-59-1 4-hydroxy-3-methoxyphenylacetonitrile 
• 1860-54-4 5-(4-benzyloxy-3-methoxy-benzylidene)-2-thioxo-thiazolidin-4-one 
• 100-44-7 benzyl chloride 
• 498-00-0 4-hydroxymethyl-2-methoxyphenol 
• 33693-48-0 4-benzyloxy-3-methoxybenzyl alcohol 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 151-50-8 potassium cyanide 

Downstream Products

• 38171-33-4 2-(4-(benzyloxy)-3-methoxyphenyl)-N-methylethanamine 
• 65341-83-5 (4-Benzyloxy-2-bromo-5-methoxy-phenyl)-acetonitrile 
• 1527503-11-2 A-366 
• 29973-91-9 4-benzyloxy-3-methoxyphenylacetic acid 
• 13255-24-8 (3-benzyloxy-4-methoxy-phenyl)-acetic acid-(3,4-bis-benzyloxy-phenethylamide) 

Relevant academic research and scientific papers

Synthesis and biological evaluation of a D-ring-contracted analogue of lamellarin D

A D-ring contracted analogue of the strongly cytotoxic marine pyrrole alkaloid lamellarin D was synthesized and investigated for its antiproliferative action towards a wild type and a multidrug resistant (MDR) cancer cell line. The compound was found to inhibit tumor cell growth at submicromolar concentrations and showed a lower relative resistance in the MDR cell line than the antitumor drug camptothecin to which lamellarin D shows cross resistance and with which lamellarin D shares the same binding site.

Structure-based design, docking and binding free energy calculations of a366 derivatives as spindlin1 inhibitors

The chromatin reader protein Spindlin1 plays an important role in epigenetic regulation, through which it has been linked to several types of malignant tumors. In the current work, we report on the development of novel analogs of the previously published lead inhibitor A366. In an effort to improve the activity and explore the structure–activity relationship (SAR), a series of 21 derivatives was synthesized, tested in vitro, and investigated by means of molecular modeling tools. Docking studies and molecular dynamics (MD) simulations were performed to analyze and rationalize the structural differences responsible for the Spindlin1 activity. The analysis of MD simulations shed light on the important interactions. Our study highlighted the main structural features that are required for Spindlin1 inhibitory activity, which include a positively charged pyrrolidine moiety embedded into the aromatic cage connected via a propyloxy linker to the 2-aminoindole core. Of the latter, the amidine group anchor the compounds into the pocket through salt bridge interactions with Asp184. Different protocols were tested to identify a fast in silico method that could help to discriminate between active and inactive compounds within the A366 series. Rescoring the docking poses with MM-GBSA calculations was successful in this regard. Because A366 is known to be a G9a inhibitor, the most active developed Spindlin1 inhibitors were also tested over G9a and GLP to verify the selectivity profile of the A366 analogs. This resulted in the discovery of diverse selective compounds, among which 1s and 1t showed Spindlin1 activity in the nanomolar range and selectivity over G9a and GLP. Finally, future design hypotheses were suggested based on our findings.

AMIDE DERIVATIVES COMPRISING HETEROCYCLOALKYL RING

PROBLEM TO BE SOLVED: To provide compounds or pharmacologically acceptable salts thereof that have excellent EP300 and/or CREBBP histone acetyltransferase inhibitory activity. SOLUTION: The invention provides compounds represented by the formula (1) in the figure or pharmacologically acceptable salts thereof. (In the formula (1), ring Q1, ring Q2, ring Q3, X and L are as defined in the specification.) SELECTED DRAWING: None COPYRIGHT: (C)2020,JPO&INPIT

Designing new analogs for streamlining the structure of cytotoxic lamellarin natural products

Despite the therapeutic potential of marine-derived lamellarin natural products, their preclinical development has been hampered by their lipophilic nature, causing very poor aqueous solubility. In order to develop more drug-like analogs, their structure was streamlined in this study from both the cytotoxic activity and lipophilicity standpoints. First, a modified total synthetic route was successfully devised to construct a library of 59 systematically designed lamellarin analogs, which were then subjected to cytotoxicity and log P determinations. Along with the 25 first-generation lamellarins previously synthesized in our laboratory, the structure-activity and structure-lipophilicity relationships were extensively evaluated. Our results clearly indicated the additional structural requirements around the lamellarin skeleton which, when combined with those reported previously, can provide invaluable guidance for further modifications to increase the aqueous solubility of these compounds.

Facile and Divergent Synthesis of Lamellarins and Lactam-Containing Derivatives with Improved Drug Likeness and Biological Activities

With the goal to improve the aqueous solubility of lamellarins, the lactone ring in their skeleton was replaced with a lactam moiety in azalamellarins. However, the reported synthetic route produced such derivatives in very low yields. Hence, this study focused on developing an efficient simplified total synthetic scheme that could furnish both azalamellarins and the parent lamellarins from the same pyrrole ester intermediates. Subsequent comparative profiling revealed that the introduced lactone-to-lactam replacement rendered these molecules less lipophilic, whereas their cancer cytotoxicity remained equipotent to that of the parent compounds. Interestingly, their inhibitory activity was significantly enhanced towards the multifaceted GSK-3β enzyme. Our results clearly demonstrate the therapeutic potential of this promising class of marine-derived natural products and justify their further development, especially into anticancer agents.

A high-yielding modular access to the lamellarins: Synthesis of lamellarin G trimethyl ether, lamellarin η and dihydrolamellarin η

A deprotonated α-aminonitrile serves as a key intermediate in a highly efficient (95 % per step on average; see scheme) modular synthetic approach to the lamellarin alkaloids. Its reaction with an α,β- unsaturated aldehyde forms the central pyrrole ring in a one-pot procedure. The construction of the fused pentacyclic skeleton is completed by a microwave-assisted Ullmann-type lactone formation.

Design, synthesis and antiproliferative activity of tripentones: A new series of antitubulin agents

Structure-activity relationship studies of a new series of tripentones (thieno[2,3-b]pyrrolizin-8-ones), led us to prepare several derivatives with antiproliferative activities. The most promising 3-(3-hydroxy-4-methoxyphenyl)thieno[2,3-b]pyrrolizin-8-one 20 (leukemia L1210, IC50 = 15 nM) was shown to be a potent inhibitor of tubulin polymerization.

8H-thieno-[2,3-b]pyrrolizin-8-one compounds

A compound selected from those of formula (I): STR1 wherein: R1 represents hydrogen, halogen, alkyl, nitro, hydroxy, alkoxy, trihaloalkyl, trihaloalkoxy or optionally substituted amino, R2 represents optionally substituted aryl or heteroaryl, R3 represents hydrogen, halogen, alkyl, nitro, hydroxy, alkoxy, trihaloalkyl, trihaloalkoxy or optionally substituted amino, their isomers and addition pharmaceutically-acceptable acid or base salts thereof and medicinal products containing the same are useful in the treatment of cancer.

Incorporation of phenethylisoquinolines into colchicine in isolated seeds of Colchicum autumnale

The physiological parameters for application experiments using immature seeds of Colchicum autumnale were optimized, so that incorporation rates in the range of 10% and higher were consistently obtained with intermediate precursors. Application of tritium and 13C-labelled phenethylisoquinolines showed that N-methylation occurs prior to the substitution of ring C and that the free hydroxy group in position 13 of autumnaline is necessary for the phenolic coupling reaction. Autumnaline gives rise to a vast array of metabolites in seeds of this plant.

PHELLODENDRINE ANALOGS AND ALLERGY TYPE IV SUPPRESSOR CONTAINING THE SAME AS ACTIVE INGREDIENT

Phellodendrine analogs represented by general formula (I), wherein A represents the group (a); B represents hydrogen, lower alkyl or lower acyl, or alternatively A and B together with the adjacent nitrogen atom form a substituted 1,2,3,4-tetrahydroisoquinoline ring represented by general formula (II), R11, R12, R21, R22, R31 and R32 represent each hydrogen, hydroxyl or lower alkoxy; n1 represents a number of 0 to 2; n2 represents a number of 1 and 2; and m1 represents a number of 0 to 1, provided tsat when A represents the group (b), and n2 is 2, B is lower acyl, and that when A and B together form a substituted 1,2,3,4-tetrahydroisoquinoline ring, n1 is 1 and m1 is not 0. These analogs (I) and related compounds have an excellent activity of suppressing allergy type IV and hence are utilizable as a medicine efficacious against diseases wherein allergy type IV participates, such as chronic hepatitis, intractable asthma, nephrotic syndrome or rheumatism.