112396-13-1

Upstream product

• 67-56-1 methanol 
• 2039-88-5 2-bromostyrene 
• 96557-30-1 2-bromophenylacetaldehyde 
• 6630-33-7 ortho-bromobenzaldehyde 
• 130089-19-9 1-bromo-2-(2-methoxyethenyl)benzene 

Downstream Products

• 131271-03-9 2-<2-<1-Hydroxy-3-(2-oxanyloxy)-propyl>-phenyl>-acetaldehyd-dimethylacetal 
• 131271-02-8 2-<2-(1-Hydroxy-4,6,9-trioxadecyl)-phenyl>-acetaldehyd-dimethylacetal 
• 131271-06-2 2-<2-<α-Hydroxy-2-(1,3,6-trioxaheptyl)-benzyl>-phenyl>-acetaldehyd-dimethylacetal 
• 148919-54-4 (2S,4R)-(-)-Methyl 4-<(S)-2-(2,2-dimethoxyethyl)-α-hydroxybenzyl>-2-(1,1-dimethylethyl)-3-oxazolidincarboxylat 
• 148919-57-7 (2R,4S)-(+)-Methyl 4-<(R)-2-(2,2-dimethoxyethyl)-α-hydroxybenzyl>-2-(1,1-dimethylethyl)-3-oxazolidincarboxylat 
• 148919-58-8 (2R,4S)-Methyl 4-<(S)-2-(2,2-dimethoxyethyl)-α-hydroxybenzyl>-2-(1,1-dimethylethyl)-3-oxazolidincarboxylat 
• 112396-12-0 Homophthalaldehyd-monodimethylacetal 
• 198978-43-7 2-[2-(2-nitro-1-phenylethyl)phenyl]acetaldehyde dimethyl acetal 
• 96557-30-1 2-bromophenylacetaldehyde 
• 172794-68-2 (4R,5R)-2-(2-Bromo-benzyl)-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester 
• 130089-28-0 2-<2-(α-Hydroxy-4-methoxybenzyl)-phenyl>-acetaldehyddimethylacetal 
• 130089-27-9 2-<2-(α-Hydroxybenzyl)-phenyl>-acetaldehyddimethylacetal 
• 153899-52-6 2-<2-(1-Hydroxycyclohexyl)-phenyl>-acetaldehyd-dimethylacetal 
• 129812-03-9 (+/-)-3-<2-(2,2-Dimethoxyethyl)phenyl>-3-hydroxy-3-phenylpropionaldehyd-dimethylacetal 

Relevant academic research and scientific papers

Synthesis and Structure-Affinity Relationships of Spirocyclic Benzopyrans with Exocyclic Amino Moiety

σ1 and/or σ2 receptors play a crucial role in pathological conditions such as pain, neurodegenerative disorders, and cancer. A set of spirocyclic cyclohexanes with diverse O-heterocycles and amino moieties (general structure III) was prepared and pharmacologically evaluated. In structure-activity relationships studies, the σ1 receptor affinity and σ1:σ2 selectivity were correlated with the stereochemistry, the kind and substitution pattern of the O-heterocycle, and the substituents at the exocyclic amino moiety. cis-configured 2-benzopyran cis-11b bearing a methoxy group and a tertiary cyclohexylmethylamino moiety showed the highest σ1 affinity (Ki = 1.9 nM) of this series of compounds. In a Ca2+ influx assay, cis-11b behaved as a σ1 antagonist. cis-11b reveals high selectivity over σ2 and opioid receptors. The interactions of the novel σ1 ligands were analyzed on the molecular level using the recently reported X-ray crystal structure of the σ1 receptor protein. The protonated amino moiety forms a persistent salt bridge with E172. The spiro[benzopyran-1,1′-cyclohexane] scaffold and the cyclohexylmethyl moiety occupy two hydrophobic pockets. Exchange of the N-cyclohexylmethyl moiety by a benzyl group led unexpectedly to potent and selective μ-opioid receptor ligands.

A generalized approach for iron catalyzed chemo- and regioselective formation of anti-Markovnikov acetals from styrene derivatives

Fe(BF4)2·6H2O in the presence of pyridine-2,6-dicarboxylic acid and PhI(OAc)2 can efficiently catalyze the formation of chemoselective dialkyl acetals from styrene derivatives with anti-Markovnikov regioselectivity in good to high yields under mild and benign reaction conditions.

Design, synthesis and pharmacological evaluation of spirocyclic σ1 receptor ligands with exocyclic amino moiety (increased distance 1)

Various pharmacophore models for potent σ1 ligands specify a basic amino group flanked by two different hydrophobic regions in defined distances to the basic amine (distance 1 and distance 2, respectively). According to these models distance 1 of the potent spirocyclic σ1 ligand 1 is too short. In order to find a new class of more potent σ1 ligands and to verify the distance hypothesis of the pharmacophore models spirocyclic compounds 2 with an exocyclic amino group were designed and synthesized. The secondary amines 8 and 9 with N-benzyl residues are >100-fold less potent than the spirocyclic piperidine 1. However, the tertiary methylamines trans-11 and cis-11 represent potent σ1 ligands with Ki-values of 43 and 24 nM, respectively. Whereas one large benzyl moiety is required for high σ1 receptor binding, a second large N-substituent is not tolerated by the σ1 receptor protein. As a rule, cis-configured diastereomers with a longer distance 1 (predominantly 7.16-7.23 ) show higher σ1 affinities than their trans-configured counterparts (distance 1 is predominantly 5.88-6.26 ).

Molecular clefts 2. An analogue of Kagan's ether as a molecular cleft: Synthesis and clathrate formation with ethyl acetate

A convenient synthesis of 5α,8α, 14α, 17α-5,6,8,9,14,15,17,18 - octahydro-5,17:8,14-diepoxydibenzo[e,e′]benzo[1,2-a:4,5-a′ dicyclooctene (2) is described. This molecular cleft represents the parent of a new class of chiral molecular tweezers. It forms a clathrate with ethyl acetate which is stable even after 12 hours at 0.1 Tort. The structure of 2 was established by spectral and X-ray data. A convenient synthesis of 5a,8a,14a,17a-5,6,8,9,14,15,17,18-octahydro-5,17:8,14-diepoxydibenzo[e, e′]benzo[1,2-a:4,5-a′]icyclooctene (2) is described. It forms a clathrate with ethyl acetate which is stable even after 12 hours at .1 Torr. (Chemical Equation Presented).

Benzo(f)isoquinoline compounds useful as calcium entry blockers

Benzo(f)isoquinoline compounds, particularly, penta- and tetrahydrobenzo(f)isoquinoline dicarboxylic acid compounds, their preparation and their use as calcium entry blockers are disclosed.