1453-97-0

Usage

Chemical Properties

white to off-white fine crystalline powder

Synthesis Reference(s)

Journal of the American Chemical Society, 76, p. 5579, 1954 DOI: 10.1021/ja01651a001

InChI:InChI=1/C18H20N2O/c1-20(2)12-15-11-19-18-9-8-16(10-17(15)18)21-13-14-6-4-3-5-7-14/h3-11,19H,12-13H2,1-2H3/p+1

Upstream product

• 6640-09-1 5-benzyloxy-1H-indole-2-carboxylic acid 
• 92438-11-4 5-Benzyloxy-2,ω-dinitro-styrol 
• 22424-59-5 (5-benzyloxy-2-nitro-phenyl)-pyruvic acid 
• 50-00-0 formaldehyd 
• 1215-59-4 5-benzyloxy-1H-indole 
• 124-40-3 dimethyl amine 

Downstream Products

• 103401-68-9 1,4-bis-(5-benzyloxy-indol-3-ylmethyl)-piperazine 
• 103756-58-7 (5-benzyloxy-indol-3-ylmethyl)-dimethylamino-malonic acid diethyl ester 
• 112299-93-1 (5-benzyloxy-indol-3-ylmethyl)-hydroxy-malonic acid 
• 50469-23-3 acetylamino-(5-benzyloxy-indol-3-ylmethyl)-malonic acid diethyl ester 
• 1125-40-2 5-hydroxy-3-methylindole 
• 2436-15-9 NSC 73391 
• 4382-53-0 2-(5-benzyloxy-1H-indol-3-yl)acetic acid 
• 5933-28-8 5-benzyloxyindole-3-acetamide 
• 124563-53-7 2-Nitro-3-<5-benzyloxy-indolyl-(3)>-propionsaeure-ethylester 
• 131920-01-9 5-(5-benzyloxy-3-indolyl)-4-cyano-4-ethoxycarbonyl-1-(N-phthalimidyl)pentan-2-one 
• 131920-21-3 ethyl 3-(5-benzyloxy-3-indolyl)-2-cyanopropanoate 
• 113436-04-7 (5-benzyloxy-3-indolylmethyl)trimethylammonium iodide 
• 113626-30-5 L-5-(benzyloxy)tryptophan 
• 91164-52-2 ZK 91085 

Relevant academic research and scientific papers

BIOMARKER PANEL TARGETED TO DISEASES DUE TO MULTIFACTORIAL ONTOLOGY OF GLYCOCALYX DISRUPTION

The present disclosure provides biomarkers useful as companion diagnostics for detecting glycocalyx-based disease that is amenable to treatment using compounds designed for improving the condition of the glycocalyx and/or reducing inflammation and/or oxidative damage, as well as related compositions, kits, and methods.

General Synthesis of Unsymmetrical 3,3′-(Aza)diindolylmethane Derivatives

Diindolylmethane (DIM) and its derivatives have recently been in the focus of interest due to their significant biological activities, specifically in cancer prevention and therapy. Molecular targets of DIM have been identified, e.g., the immunostimulatory G protein-coupled receptor GPR84. However, most of the reported and investigated DIM derivatives are symmetrical because general methods for obtaining unsymmetrical DIMs have been lacking. To optimize the interaction of DIM derivatives with their protein targets, unsymmetrical substitution is required. In the present study we developed a new, mild and efficient access to unsymmetrically substituted 3,3′-DIMs by reaction of (3-indolylmethyl)trimethylammonium iodides with a wide range of substituted indole derivatives. 7-Azaindole also led to the 3,3′-connected DIM analogue, while 4- and 5-azaindoles reacted at the N1-nitrogen atom as confirmed by X-ray crystallography. The reactions were performed in water without the requirement of a catalyst or other additives. Wide substrate scope, operational simplicity, environmentally benign workup, and high yields are further advantages of the new method. The synthetic protocol proved to be suitable for upscaling to yield gram amounts for pharmacological studies. This procedure will allow the preparation of a broad range of novel, unsymmetrical DIM derivatives to exploit their potential as novel drugs.

SEPIAPTERIN REDUCTASE INHIBITORS FOR THE TREATMENT OF PAIN

Disclosed herein are small molecule heterocyclic inhibitors of sepiapterin reductase (SPR), and pro-drugs and pharmaceutically acceptable salts thereof. The Also featured are pharmaceutical compositions of the compounds and uses of these compounds for the treatment or prevention of pain (e.g., inflammatory pain, nociceptive pain, functional pain, and neuropathic pain)

Bicyclic derivatives of the potent dual aromatase-steroid sulfatase inhibitor 2-bromo-4-{[(4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino]methyl} phenylsulfamate: Synthesis, SAR, crystal structure, and in vitro and in vivo activities

The design and synthesis of a series of bicyclic ring containing dual aromatase-sulfatase inhibitors (DASIs) based on the aromatase inhibitor (AI) 4-[(4-bromobenzyl)(4H-1,2,4-triazol-4-yl)amino] benzonitrile are reported. Biological evaluation with JEG-3 cells revealed structure-activity relationships. The X-ray crystal structure of sulfamate 23 was determined, and selected compounds were docked into the aromatase and steroid sulfatase (STS) crystal structures. In the sulfamate-containing series, compounds containing a naphthalene ring are both the most potent AI (39, IC50AROM=0.25 nm) and the best STS inhibitor (31, IC50STS=26 nm). The most promising DASI is 39 (IC50AROM= 0.25 nm, IC50STS=205 nm), and this was evaluated orally in vivo at 10 mgkg-1, showing potent inhibition of aromatase (93%) and STS (93%) after 3 h. Potent aromatase and STS inhibition can thus be achieved with a DASI containing a bicyclic ring system; development of such a DASI could provide an attractive new option for the treatment of hormone-dependent breast cancer.

Enantioselective gold-catalyzed allylic alkylation of indoles with ALcohols: An efficient route to functionalized tetrahydrocarbazoles

[Chemical equation presented] Breaking the taboo: The direct use of allylic alcohols in catalytic and enantioselective Friedel-Crafts alkylation is described for the first time In the presence of chiral gold complexes. This intramolecular Friedel-Crafts reaction was used to prepare a broad range of functionalized tetrahydrocarbazoles (see scheme; X=Me, F, Br, Cl, OMe; R=Me, Et, tBu; R′=H, Me).

Brain-specific drug delivery

The subject compounds, which are adapted for the site-specific/sustained delivery of centrally acting drug species to the brain, are: (a) compounds of the formula wherein [D] is a centrally acting drug species, and [DHC] is the reduced, biooxidizable, blood-brain barrier penetrating lipoidal form of a dihydropyridine pyridinium salt redox carrier, with the proviso that when [DHC] is STR1 wherein R is lower alkyl or benzyl and [D] is a drug species containing a single NH2 or OH functional group, the single OH group when present being a primary or secondary OH group, said drug species being linked directly through said NH2 or OH function group to the carbonyl function of [DHC], then [D] must be other than a sympathetic stimulant, steroid sex hormone or long chain alkanol; and (b) non-toxic pharmaceutically acceptable salts of compounds of formula (I) wherein [D] is a centrally acting drug species and [DHC] is the reduced, biooxidizable, blood-brain barrier penetrating lipoidal form of a dihydropyridine pyridinium salt redox carrier. The corresponding ionic pyridinium salt type drug/carrier entitles [D--QC]+ X- are also disclosed.

Brain-specific drug delivery

The subject compounds, which are adapted for the site-specific/sustained delivery of centrally acting drug species to the brain, are: (a) compounds of the formula wherein [D] is a centrally acting drug species, and [DHC] is the reduced, biooxidizable, blood-brain barrier penetrating lipoidal form of a dihydropyridine pyridinium salt redox carrier, with the proviso that when [DHC] is STR1 wherein R is lower alkyl or benzyl and [D] is a drug species containing a single NH2 or OH functional group, the single OH group when present being a primary or secondary OH group, said drug species being linked directly through said NH2 or OH functional group to the carbonyl function of [DHC], then [D] must be other than a sympathetic stimulant, steroid sex hormone or long chain alkanol; and (b) non-toxic pharmaceutically acceptable salts of compounds of formula (I) wherein [D] is a centrally acting drug species and [DHC] is the reduced, biooxidizable, blood-brain barrier penetrating lipoidal form of a dihydropyridine pyridinium salt redox carrier. The corresponding ionic pyridinium salt type drug/carrier entities [D-QC]+ Y- are also disclosed.