112775-09-4

Upstream product

• 2832-92-0 4-(4-phenylbutyl)morpholine 
• 960508-05-8 2-fluoro-1,3-dimethylimidazolinium p-toluenesulfonate 
• 3360-41-6 4-phenyl-butan-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 172147-80-7 (2R,3S,4R)-4-(4-Allyloxy-butoxy)-2-(4-phenyl-butoxymethyl)-tetrahydro-pyran-3-ol 
• 191926-15-5 (2R,3S,4R)-4-(5-Allyloxy-pentyloxy)-2-(4-phenyl-butoxymethyl)-tetrahydro-pyran-3-ol 
• 39686-51-6 1,5-diphenyl-1-pentanone 
• 36748-54-6 1,5-diphenyl-pentan-1-ol 
• 902757-49-7 N-(4-phenyl-1-butoxy)-5-(p-methoxyphenyl)-4-(methyl)thiazole-2(3H)-thione 
• 1215314-62-7 4-methyl-5-phenyl-3-(4-phenylbutoxy)-thiazole-2(3H)-thione 
• 1215314-63-8 4,5-dimethyl-3-(4-phenylbutoxy)-thiazole-2(3H)-thione 
• 1332887-18-9 1-phenyl-4-tosyloxybutyl nitrate 
• 2270-20-4 5-Phenylpentanoic acid 
• 150763-59-0 phenyl 1,2,3,4-tetrahydronaphthalen-1-yl sulfide 
• 67653-36-5 C₁₆H₁₆OS 
• 1232196-73-4 WMS-1405 

Relevant academic research and scientific papers

Nucleophilic substitution reactions of unbranched alkyl amines using triazine reagents

Since amines are present in many organic, biological, and drug molecules, a strategy of synthesizing desired compounds by nucleophilic substitution reactions of these amines is very attractive. By using triazine reagents, we have found that nucleophilic substitution reactions of unbranched alkyl amines via morpholine derivatives are feasible. This method can be performed under milder reaction conditions than those in previously reported methods.

Pummerer Cyclization Revisited: Unraveling of Acyl Oxonium Ion and Vinyl Sulfide Pathways

Two viable pathways (vinyl sulfide and acyl oxonium ion) for the Pummerer cyclization have been unraveled that expand the reaction scope and capabilities. Use of Br?nsted-enhanced Lewis acidity was key to realization of the vinyl sulfide pathway, whereas selective complexation of the sulfur lone pair facilitated the unprecedented acyl oxonium ion pathway. Preliminary mechanistic investigations support these hypotheses. A range of substrates have been explored to understand the reaction parameters.

Titania-catalyzed radiofluorination of tosylated precursors in highly aqueous medium

Nucleophilic radiofluorination is an efficient synthetic route to many positron-emission tomography (PET) probes, but removal of water to activate the cyclotron-produced [18F]fluoride has to be performed prior to reaction, which significantly increases overall radiolabeling time and causes radioactivity loss. In this report, we demonstrate the possibility of 18F-radiofluorination in highly aqueous medium. The method utilizes titania nanoparticles, 1:1 (v/v) acetonitrile-thexyl alcohol solvent mixture, and tetra-n-butylammonium bicarbonate as a phase-transfer agent. Efficient radiolabeling is directly performed with aqueous [18F]fluoride without the need for a drying/azeotroping step to significantly reduce radiosynthesis time. High radiochemical purity of the target compound is also achieved. The substrate scope of the synthetic strategy is demonstrated with a range of aromatic, aliphatic, and cycloaliphatic tosylated precursors.

Ni-catalyzed carboxylation of unactivated primary alkyl bromides and sulfonates with CO2

A Ni-catalyzed carboxylation of unactivated primary alkyl bromides and sulfonates with CO2 at atmospheric pressure is described. The method is characterized by its mild conditions and remarkably wide scope without the need for air- or moisture-sensitive reagents, which make it a user-friendly and operationally simple protocol en route to carboxylic acids.

Aspects of structural thiohydroxamate chemistry-on a systematic in the 5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione series

Bond angles at thiohydroxamate oxygen in crystal structures of 3-alkoxy-5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thiones gradually increased with the size of the 3-alkoxy substituent. This effect was attributed to strain on the basis of (i) a linear free energy relationship (Taft-Dubois correlation) and (ii) signal coalescence from resonances of diastereotopic CH3 groups in solution (O-cumyl substituent; DNMR). Substitution at oxygen along the sequence OR (R=prim-, sec-, and tert-alkyl), OH, and OLi was reflected in a gradual decrease of N,O distances and lengthening of associated C,S bonds. The responsivity for these changes was more pronounced in the thiazole-2(3H)-thione than in the pyridine-2(1H)-thione series.

PROCESS FOR PRODUCING ESTER OR ALCOHOL

Provided is a process for producing an ester or alcohol using a fluoroimidinium sulfonate derivative represented by the general formula (9) or a fluoroimidinium carboxylate derivative represented by the general formula (6) and using as a raw material alcohol involving inversion of steric configuration. Further provided are a fluoroimidinium sulfonate derivative represented by the general formula (9), and a process for producing the same.

NORVALINE DERIVATIVE AND METHOD FOR PREPARATION THEREOF

Norvaline derivative of the formula [I] or pharmaceutically acceptable salt thereof, method for preparing the same, pharmaceutical composition containing the same, and use of said compound for inhibiting transporting activity of glycine transporter type 2 (GlyT2). [wherein X is -CH2-, -O-, -S- or single bond; Ar is optionally substituted aryl or lower cycloalkyl; n is 0 to 2; R1 and R2 are (i) each is hydrogen or lower alkyl; (ii) R1 and R2 are combined to form lower alkylene; or (iii) R1 is hydrogen or lower alkyl and R2 is combined with R4 or R6 to form lower alkylene; R3 and R4 are (i) each is hydrogen or lower alkyl; (ii) R3 and R4 are combined to form lower alkylene; or (iii) R3 is hydrogen or lower alkyl and R4 is combined with R2 or R6 to form lower alkylene; R is or -OR7; R 5 and R6 are (i) each is optionally substituted lower alkyl, or hydrogen; (ii) R5 and R6 are combined to form aliphatic 5- to 6-membered heterocyclic group; or (iii) R5 is optionally substituted lower alkyl or hydrogen and R6 is combined with R2 or R4 to form lower alkylene; R7 is lower alkyl.

Simplified analogues of ritanserin and their affinity at 5-HT(2A), 5- HT(2B) and 5-HT(2C) serotonin receptors

The 5-HT2 serotonin antagonist ritanserin (6-(2-[4-[bis(4- fluorophenyl)methylene]-l-piperidinyl]ethyl)-7-methyl-5H-thiazole[3,2- a]pyrimidin-5-one, 2) binds with high affinity to 5-HT(2A), 5-HT(2B) and 5- HT(2C) serotonin receptors. With the aim of exploring how simplification of the thiazolepyrimidinone nucleus of 2 affects the affinity and selectivity for 5-HT(2A), 5-HT(2B) and 5-HT(2C) subtypes, some derivatives of 4-[bis(4- fluorophenyl)methylene]piperidine were synthesized, and their 5-HT(2A) and 5- HT(2C) receptor binding affinities and 5-HT(2B) antagonistic affinity evaluated. The new compounds bind the three 5-HT2 subtypes with lower affinity than did 2. Simplification of the thiazolepyrimidinone nucleus of ritanserin has only slight influence on the selectivity for 5-HT2 subtypes. The results suggest that the thiazolepyrimidinone moiety participates in key binding interactions and is determinant for high affinity at 5-HT2 receptor subtypes. Some derivatives showed antagonistic activity at 5-HT(2A) receptor.

THA analogs useful as cholinesterase inhibitors

The present invention provides cholinesterase inhibitors of general formula (I): STR1 wherein R is H or (C 1 -C 4)alkyl, Y is a linking group and Z is an alkyl or aryl group, including heteroaryl groups, and the pharmaceutically acceptable salts thereof.

Synthesis of alkylene linked bis-THA and alkylene linked benzyl-THA as highly potent and selective inhibitors and molecular probes of acetylcholinesterase

An efficient and economical synthesis of a series of rationally designed novel 9,9′-(alkane-1,-ω-diyldiimino)-1,2,3,4-tetrahydroacridines (ω = 7-10) and a second series of new analogues, 9-(ω-phenylalkylamino)-1,2,3,4-tetrahydroacridines (ω = 4-10), is re