769901-73-7

Usage

Chemical category

diacetic acids

Common use

precursor in the synthesis of pharmaceutical drugs

Specific applications

production of certain anti-tumor and anti-cancer agents

Synthesis method

condensation reaction between 4-piperidone monohydrate and benzyl bromide

Resulting structure

piperidine ring with a benzyl substituent

Potential applications

therapeutic applications in medicinal chemistry research

Unique features

structural features and functional groups valuable for the development of new drugs with improved biological activities.

Upstream product

• 160133-32-4 ethyl 2-[1-benzyl-4-(2-ethoxy-2-oxoethyl)-4-piperidyl]acetate 
• 3612-20-2 1-phenylmethyl-4-piperidone 
• 189333-46-8 9-benzyl-2,4-dioxo-3,9-diazaspiro[5,5]undecane-1,5-dicarbonitrile 

Downstream Products

• 189333-48-0 9-benzyl-3,9-diazaspiro[5.5]undecane-2,4-dione 

Relevant academic research and scientific papers

Substituted Spiroamine Compounds

Substituted spiroamine compounds corresponding to the formula (I) In which m, n, o, p, Q, r, s, t, R1, R2, R3, R4a, R4b, R5a, R5b, R6a, R6b, R7, R8, R9, R10 and R11 have defined meanings; a process for the preparation of such compounds, pharmaceutical compositions containing such compounds and the use of substituted spiroamines for the treatment or inhibition of pain and/or other conditions mediated by the bradykinin 1 receptor.

CGRP RECEPTOR ANTAGONISTS

Compounds of Formula (I): and Formula (II): (where variables R2, R4, A, B, D, W, X, Y and Z are as defined herein) useful as antagonists of CGRP receptors and useful in the treatment or prevention of diseases in which the CGRP is involved, such as headache, migraine and cluster headache. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

Synthesis, Screening, and Molecular Modeling of New Potent and Selective Antagonists at the α1d Adrenergic Receptor

In the present study, more than 75 compounds structurally related to BMY 7378 have been designed and synthesized. Structural variations of each part of the reference molecule have been introduced, obtaining highly selective ligands for the α1d adrenergic receptor. The molecular determinants for selectivity at this receptor are essentially held by the phenyl substituent in the phenylpiperazine moiety. The integration of an extensive SAR analysis with docking simulations using the rhodopsin-based models of the three α1-AR subtypes and of the 5-HT1A receptor provides significant insights into the characterization of the receptor binding sites as well as into the molecular determinants of ligand selectivity at the α1d-AR and the 5-HT1A receptors. The results of multiple copies simultaneous search (MCSS) on the substituted phenylpiperazines together with those of manual docking of compounds BMY 7378 and 69 into the putative binding sites of the α1a-AR, α1b-AR, α1d-AR, and the 5-HT1A receptors suggest that the phenylpiperazine moiety would dock into a site formed by amino acids in helices 3, 4, 5, 6 and extracellular loop 2 (E2), whereas the spirocyclic ring of the ligand docks into a site formed by amino acids of helices 1, 2, 3, and 7. This docking mode is consistent with the SAR data produced in this work. Furthermore, the binding site of the imide moiety does not allow for the simultaneous involvement of the two carbonyl oxygen atoms in H-bonding interactions, consistent with the SAR data, in particular with the results obtained with the lactam derivative 128. The results of docking simulations also suggest that the second and third extracellular loops may act as selectivity filters for the substituted phenylpiperazines. The most potent and selective compounds for α1d adrenergic receptor, i.e., 69 (Rec 26D/038) and 128 (Rec 26D/073), are characterized by the presence of the 2,5-dichlorophenylpiperazine moiety.