50882-68-3

Usage

Chemical structure

A naphthyl group attached to an ethanamine molecule.

Form

Salt form with hydrochloric acid as the counter ion.

Applications

Pharmaceutical and research purposes, used as a building block for the synthesis of other organic compounds or as a reagent in chemical reactions.

Handling precautions

Potential hazards and should be handled with care.

Upstream product

• 118868-72-7 2-(2-(naphthalen-1-yloxy)ethyl)isoindoline-1,3-dione 
• 86-86-2 1-Naphthylacetamide 
• 136918-14-4 phthalimide 
• 711-82-0 2-(1-naphthyloxy)-1-ethanol 
• 1972-28-7 diethylazodicarboxylate 
• 13247-79-5 1-(2-bromoethoxy)naphthalene 
• 60225-63-0 2-(naphthalen-1-yloxy)ethyl 4-toluenesulfonate 
• 90-15-3 α-naphthol 
• 753022-51-4 1-(2-azidoethoxy)naphthalene 

Relevant academic research and scientific papers

IRREVERSIBLE COVALENT INHIBITORS OF THE GTPASE K-RAS G12C

Irreversible inhibitors of K-Ras, H-Ras or N-ras protein comprising a G12C mutation are provided. Also disclosed are methods to regulate the activity of K-Ras, H-Ras or N-ras protein comprising G12C mutation and methods to disease mediated by K-Ras, H-Ras or N-ras G12C.

New serotonin 5-HT1A receptor agonists endowed with antinociceptive activity in vivo

We report the synthesis of new compounds 4-35 based on two different openings (A and B) of the chromane ring present in the previously identified 5-HT1A receptor (5-HT1AR) ligand 3. The synthesized compounds were assessed for binding affinity, selectivity, and functional activity at the 5-HT1AR. Selected candidates resulting from B opening were also evaluated for their potential antinociceptive effect in vivo and pharmacokinetic properties in vitro. Analogue 19 [2-(4-{[2-(2-ethoxyphenoxy) ethyl]amino}butyl)tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione] has been characterized as a high-affinity and potent 5-HT1AR agonist (K i = 2.3 nM; EC50 = 19 nM). Pharmacokinetic studies indicated that compound 19 displays a good metabolic stability in human liver microsomes (t1/2 ～ 3 h and CLint = 3.5 mL/min/kg, at 5 μM), and a low level of protein binding (25%, at 5 μM). Interestingly, 19 (3 mg/kg, ip, and 30 mg/kg, po) caused significant attenuation of formalin-induced behavior in early and late phases of the mouse intradermal formalin test of pain, and this in vivo effect was reversed by the selective 5-HT1AR antagonist WAY-100635. Thus, the new 5-HT1AR agonist identified in this work, 19, exhibits oral analgesic activity, and the results herein represent a step toward identifying new therapeutics for the control of pain.

Chiral aryloxyalkylamines: Selective 5-HT1B/1D activation and analgesic activity

A series of chiral 2,3-dichlorophenoxy and 1-naphthyloxy alkylamines were synthesized, and their binding affinities towards 5-HT1D and h5-HT1B receptors were evaluated. In the naphthyloxy series, the (R)-prolinol derivative was the most selective 5-HT1D ligand, while (S)-N-methyl-2-(1-naphthyloxy)propan-1-amine showed the highest selectivity for h5-HT1B. Both compounds performed as 5-HT1D agonists in the isolated guinea pig assay and showed higher analgesic activity than both sumatriptan and the achiral analogue 20b in the mouse hotplate test. Neither ligand displayed any affinity for nicotinic ACh receptors present in mouse brain membranes, thus indicating that their analgesic activity does not arise through interaction with these receptors.

Structure-affinity studies for a novel series of homochiral naphtho and tetrahydronaphtho analogues of α1 antagonist WB-4101

A number of enantiomeric pairs of naphthodioxane, tetrahydronaphthodioxane and naphthoxy analogues of WB-4101 (1) were designed and synthesized in order to improve the selectivity profile of the parent compound, hopefully in favour of the α1a-AR with respect to the other two α1 subtypes and the 5-HT1A receptor. The new compounds 2-8 and, in addition, the two enantiomers of 1 were tested in binding assays on the α1a-AR, α1b-AR, α1d-AR, and the 5-HT1A receptor. Two of them, namely the naphtho- and tetrahydronaphthodioxane derivatives (S)-2 and (S)-3, showed lower, but significantly more specific α1a affinity than (S)-1, while the two enantiomers of the 2-methoxy-1-naphthoxy analogue 6 maintained most of the very high α1a affinity of (S)-1 and its α1a versus α1b selectivity slightly increasing the α1a/α1d and α1a/5HT 1A affinity ratios. The SAR data were evaluated in the light of known α1 subtype pharmacophores and of the α1a-AR binding mode of WB-4101 resultant from literature mutagenesis studies disclosing some interesting consonances with these models.

Pyridinium derivatives, their production and use

Novel pyridinium derivatives represented by the formula (I): STR1 wherein STR2 is an optionally substituted pyridinium ring; R1 is a lower alkyl group or aralkyl group; R7 and R10 are independently hydrogen, a lower alkyl group, aryl group or aralkyl group; l is 0 or 1; R5 is a phenylene group or an alkylene group which may be substituted; R11 is an alkyl group or aryl group; X is a group of the formula: --CH2 OCH2 -- or a group of the formula: STR3 wherein R6 is hydrogen, a lower alkyl or a lower alkoxy, and m is an integer of 0 to 3; U is a group of the formula: STR4 wherein R4 is hydrogen, a lower alkyl group, aryl group or aralkyl group; Y and Z are independently a divalent chain group consisting of one to six members which is selected from the class consisting of groups of the formulae: STR5 wherein R is hydrogen, a lower alkyl group, acyl group or aryl group and at least one of which is a group of the formula: STR6 with the proviso that R may be the same or different from each other, or may form a ring together when two or more groups of the formula: STR7 are present, that R may be bonded to R4 when Y contains a group of the formula: STR8 and that R may be bonded to R11 when Z contains a group of the formula: STR9 and W? is a counter anion; are useful as a platelet activating factor antagonist.

Design and Synthesis of Propranolol Analogues as Serotonergic Agents

Serotonin (5-HT) binds with nearly identical affinity at the various central 5-HT binding sites.Few agents bind with selectivity for 5-HT1A sites.The β-adrenergic antagonist propranolol binds stereoselectively both at 5-HT1A and 5-HT