33451-54-6

Upstream product

• 29943-42-8 Tetrahydro-4H-pyran-4-one 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 80813-10-1 2-(4-phenyltetrahydro-2H-pyran-4-yl)acetic acid 
• 422280-49-7 2-(4-(4-chlorophenyl)tetrahydro-2H-pyran-4-yl)acetic acid 
• 117642-16-7 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid ethyl ester 
• 1581258-44-7 6-chloro-N-(2-(4-phenyltetrahydro-2H-pyran-4-yl)ethyl)pyrazin-2-amine 
• 1581258-43-6 2-chloro-6-(2-(4-phenyltetrahydro-2H-pyran-4-yl)ethoxy)pyrazine 
• 1542134-82-6 2-(4-phenyltetrahydro-2H-pyran-4-yl)ethanol 
• 1581258-24-3 3-(6-(2-(4-phenyltetrahydro-2H-pyran-4-yl)ethoxy)pyrazin-2-yl)benzonitrile 
• 1581258-12-9 6-(2,5-difluorophenyl)-N-(2-(4-phenyltetrahydro-2H-pyran-4-yl)ethyl)pyrazin-2-amine 
• 1581258-11-8 6-(3-methoxyphenyl)-N-(2-(4-phenyltetrahydro-2H-pyran-4-yl)ethyl)pyrazin-2-amine 
• 80813-09-8 cyano(4-phenyltetrahydropyran-4-yl)acetate d'ethyle 
• 1313603-18-7 3-chloro-N-[2-(4-phenyltetrahydro-2H-pyran-4-yl)ethyl]aniline 
• 1313603-17-6 3-methoxy-N-[2-(4-phenyltetrahydro-2H-pyran-4-yl)ethyl]aniline 

Relevant academic research and scientific papers

Distal γ-C(sp3)?H Olefination of Ketone Derivatives and Free Carboxylic Acids

Reported herein is the distal γ-C(sp3)?H olefination of ketone derivatives and free carboxylic acids. Fine tuning of a previously reported imino-acid directing group and using the ligand combination of a mono-N-protected amino acid (MPAA) and an electron-deficient 2-pyridone were critical for the γ-C(sp3)?H olefination of ketone substrates. In addition, MPAAs enabled the γ-C(sp3)?H olefination of free carboxylic acids to form diverse six-membered lactones. Besides alkyl carboxylic acids, benzylic C(sp3)?H bonds also could be functionalized to form 3,4-dihydroisocoumarin structures in a single step from 2-methyl benzoic acid derivatives. The utility of these protocols was demonstrated in large scale reactions and diversification of the γ-C(sp3)?H olefinated products.

Amide-Group-Directed Protonolysis of Cyclopropane: An Approach to 2,2-Disubstituted Pyrrolidines

Regioselective protonolytic C-C bond cleavage of acylated aminomethyl cyclopropanes can be achieved using trifluoroacetic acid. The intermediate tertiary carbenium ion undergoes an intramolecular amination to give 2,2-substituted pyrrolidines. The strength of the acid and the amine substituent are important factors to achieve high regioselectivity, suggesting intramolecular proton transfer from the protonated amide function. Preliminary mechanistic studies revealed that cyclopropane cleavage proceeds with retention of configuration at the carbon to which the proton is attached. This observation is consistent with the "edge" protonation trajectory of the C-C bond.

IDO INHIBITORS

There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the invention.

PIPERAZINE DERIVATIVES AS HIV PROTEASE INHIBITORS

The present invention is directed to piperazine derivatives, pharmaceutical compositions comprising the same, and their use in the inhibition of HIV protease, the inhibition of HIV replication, the prophylaxis of infection by HIV, the treatment of infection by HIV, and the prophylaxis, treatment, and delay in the onset or progression of AIDS.

PIPERAZINE DERIVATIVES AS HIV PROTEASE INHIBITORS

The present invention is directed to piperazine derivatives, pharmaceutical compositions comprising the same, and their use in the inhibition of HIV protease, the inhibition of HIV replication, the prophylaxis of infection by HIV, the treatment of infection by HIV, and the prophylaxis, treatment, and delay in the onset or progression of AIDS.

PIPERAZINE DERIVATIVES AS HIV PROTEASE INHIBITORS

The present invention is directed to compounds of Formula I pharmaceutical compositions comprising the same, and their use in the inhibition of HIV protease, the inhibition of HIV replication, the prophylaxis of infection by HIV, the treatment of infection by HIV, and the prophylaxis, treatment, and delay in the onset or progression of AIDS.

Aqueous DABCO, an efficient medium for rapid organocatalyzed Knoevenagel condensation and the Gewald reaction

In the presence of water and 1,4-diazabicyclo[2.2.2]octane, several aldehydes and cyclic ketones underwent efficient Knoevenagel condensation with malononitrile and ethyl cyanoacetate to produce the respective α.β-unsaturated systems within fairly short time periods. As a result, high yields of conjugated products were easily obtained. Products could be engaged in a Gewald reaction, either stepwise or in situ, to produce efficiently their respective 2-aminothiophenes within 4-7 h. TUeBITAK.

TETRAHYDROPYRAN-4-YLETHYLAMINO- OR TETRAHYDROPYRANYL-4-ETHYLOXY-PYRIMIDINES OR -PYRIDAZINES AS ISOPRENYLCYSTEINCARBOXYMETHYL TRANSFERASE INHIBITORS

A compound of formula (I): wherein: R1 is selected from: (i) phenyl, optionally substituted by one fluoro group; (ii) thienyl; (iii) furanyl; (iv) C1-4 alkyl; and (v) H; R2 is selected from: (II), R3 is selected from: (III), X is selected from NH and O; R4 is selected from phenyl, a 5-membered heteroaryl or a 6-membered heteroaryl, all of which are optionally substituted by one or more substituents selected from the group consisting of: methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano, fluoro, -OC2H4OMe, and pyrazolyl.

Improved synthesis of γ-lactones from cyclopropyl cyanoesters

Cyclopropyl cyanoesters 2 were reliably converted to c-lactones 4 on treatment with aqueous sulfuric acid. The cyanoesters could be easily prepared from ketones or aldehydes in two steps, making this process particularly attractive from an efficiency standpoint. Copyright

Discovery and SAR of methylated tetrahydropyranyl derivatives as inhibitors of isoprenylcysteine carboxyl methyltransferase (ICMT)

A series of tetrahydropyranyl (THP) derivatives has been developed as potent inhibitors of isoprenylcysteine carboxyl methyltransferase (ICMT) for use as anticancer agents. Structural modification of the submicromolar hit compound 3 led to the potent 3-methoxy substituted analogue 27. Further SAR development around the THP ring resulted in an additional 10-fold increase in potency, exemplified by analogue 75 with an IC50 of 1.3 nM. Active and potent compounds demonstrated a dose-dependent increase in Ras cytosolic protein. Potent ICMT inhibitors also reduced cell viability in several cancer cell lines with growth inhibition (GI50) values ranging from 0.3 to >100 μM. However, none of the cellular effects observed using ICMT inhibitors were as pronounced as those resulting from a farnesyltransferase inhibitor.