22415-60-7

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 87324-01-4 (S)-(+)-methyl tetrahydrofuran-2-carboxylate 
• 58879-34-8 (S)-5-tosyloxypentan-4-olide 
• 87324-00-3 (R)-(-)-methyl tetrahydrofuran-2-carboxylate 
• 97-99-4 (R)-(tetrahydrofuran-2-yl)methanol 
• 87392-05-0 (R)-tetrahydro-2-furoic acid 
• 87392-07-2 (S)-tetrahydro-2-furoic acid 

Downstream Products

• 58879-33-7 (R)-(-)-γ-<(tosyloxy)methyl>-γ-butyrolactone 
• 1140917-34-5 N-[5-tert-butyl-2-[(2R)-tetrahydrofuran-2-ylmethyl]isoxazol-3(2H)-ylidene]-5-chloro-2-methoxybenzamide 
• 1140917-19-6 N-[(2Z)-5-tert-butyl-3-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3,4-thiadiazol-2(3H)-ylidene]-5-chloro-2-methoxybenzamide 
• 1140917-22-1 5-chloro-N-[(2Z)-5-(1,1-dimethylprop-2-ynyl)-3-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3,4-thiadiazol-2(3H)-ylidene]-2-methoxybenzamide 
• 3200-06-4 (S)-3-Naphthalen-1-yl-2-[(S)-1-(tetrahydro-furan-2-yl)methyl]-propionic acid 2-diethylamino-ethyl ester; compound with oxalic acid 
• 3200-06-4 (R)-3-Naphthalen-1-yl-2-[(S)-1-(tetrahydro-furan-2-yl)methyl]-propionic acid 2-diethylamino-ethyl ester; compound with oxalic acid 
• 1376220-34-6 (S)-diethyl 2-[(naphthalen-1-yl)methyl]-3-(tetrahydrofuran-2-yl)malonate 
• 1376220-35-7 C₁₉H₂₀O₅ 

Relevant academic research and scientific papers

The discovery of a potent and selective pyrazolo-[2,3-e]-[1,2,4]-triazine cannabinoid type 2 receptor agonist

The development of selective CB2 receptor agonists is a promising therapeutic approach for the treatment of inflammatory diseases, without CB1 receptor mediated psychoactive side effects. Preliminary structure-activity relationship studies on pyrazoylidene benzamide agonists revealed the -ylidene benzamide moiety was crucial for functional activity at the CB2 receptor. A small library of compounds with varying linkage moieties between the pyrazole and substituted phenyl group has culminated in the discovery of a potent and selective pyrazolo-[2,3-e]-[1,2,4]-triazine agonist 19 (CB2R EC50 = 19 nM, CB1R EC50 > 10 μM). Docking studies have revealed key structural features of the linkage group that are important for potent functional activity.

5-OXA-2-AZASPIRO[3.4]OCTANE DERIVATIVES AS M4 AGONISTS

Provided herein are compounds according to Formula (I) or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R5, and R7 are defined herein. Also provided herein are pharmaceutical compositions comprising a compound of Formula (I) as well as the use of such compounds as M4 receptor agonists.

5-AMINO-8-(4-PYRIDYL)-[1,2,4]TRIAZOLO[4,3-C]PYRIMIDIN-3-ONE COMPOUNDS FOR USE AGAINST CANCER

Described herein are triazalone compounds of Formula (I) and pharmaceutically acceptable salts thereof. Methods of making and using compounds of Formula (I) are also described. Compounds of Formula (I) and pharmaceutically acceptable salts thereof can be

C-2 auxiliaries for stereoselective glycosylation based on common additive functional groups

The stereoselective introduction of the glycosidic bond is one of the main challenges in chemical oligosaccharide synthesis. Stereoselective glycosylation can be achieved using neighbouring group participation of a C-2 auxiliary or using additives, for example. Both methods aim to generate a defined reactive intermediate that reacts in a stereoselective manner with alcohol nucleophiles. This inspired us to develop new C-2 auxiliaries based on commonly used additive functionalities such as ethers, phosphine oxides and tertiary amides. Good 1,2-trans-selectivity was observed for the phosphine oxide and amide-based auxiliaries expanding the toolbox with new auxiliaries for stereoselective glycosylation reactions.

Anti-Selective Catalytic Asymmetric Nitroaldol Reaction of α-Keto Esters: Intriguing Solvent Effect, Flow Reaction, and Synthesis of Active Pharmaceutical Ingredients

A rare-earth metal/alkali metal bimetallic catalyst proved particularly effective for enantioselectively coupling nitroalkanes and α-keto esters in an anti-selective manner to afford synthetically versatile, densely functionalized, and optically active α-nitro tertiary alcohols. A chiral diamide ligand captured two distinct metal cations, giving rise to a catalytically competent solid-phase heterobimetallic catalyst by simple mixing via self-assembly. The advantage of the solid-phase asymmetric catalyst was realized by successful application to the enantio- and diastereoselective reaction in a continuous-flow platform. The use of closely related solvents in terms of structures and polarity parameters, THF and its methylated congener 2-Me-THF, had an unexpectedly large solvent effect both on the reaction rate and the stereoselectivity. The nitroaldol products share a privileged unit for active pharmaceutical ingredients, as demonstrated by the streamlined enantioselective synthesis of the marketed antifungal agents efinaconazole and albaconazole.

NOVEL DIHYDROPYRIDINONE AND DIHYDROPYRIMIDINONE COMPOUNDS AND THEIR USE

The present invention is directed to novel compounds of Formula I; pharmaceutically acceptable salts or solvates thereof, and their use.

COMPOUNDS THAT INHIBIT MCL-1 PROTEIN

Provided herein are myeloid cell leukemia 1 protein (Mcl-1) inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula I, and pharmaceutically acceptable salts thereof and pharmaceutical compositions containing the compounds. The compounds and compositions provided herein may be used, for example, in the treatment of diseases or conditions, such as cancer.

2-OXO-3,4-DIHYDROPYRIDINE-5-CARBOXYLATES AND THEIR USE

The present invention is directed to novel compounds of Formula (I), pharmaceutically acceptable salts or solvates thereof, and their use.

1,3-THIAZOL-2-YL SUBSTITUTED BENZAMIDES

The present invention relates to 1,3-thiazol-2-yl substituted benzamide compounds of general formula (I) as described and defined herein, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of neurogenic disorder, as a sole agent or in combination with other active ingredients.

Practical access to four stereoisomers of naftidrofuryl and their binding affinity towards 5-hydroxytryptamine 2A receptor

Naftidrofuryl oxalate (Praxilene, 1) has been used for the treatment of intermittent claudication for more than 30 years. It selectively blocks vascular and platelet 5-hydroxytryptamine 2 (5-HT2) receptors. This drug is marketed as a mixture of four stereoisomers, and so far there is no individual biological evaluation on the single isomers. The purpose of this study is to provide an improved method for the preparation of all four stereoisomers of naftidrofuryl, and more importantly, to distinguish them in terms of their binding affinity to 5-hydroxytryptamine 2A (5-HT2A) receptor. The bioassay results revealed that the C-2S configuration of naftidrofuryl was crucial for the binding affinity with 5-HT2A receptor, and the C-2′ configuration was less important for binding. In conclusion, our study may pave the way to develop single naftidrofuryl isomers with C-2S configuration as inhibitors of 5-HT2A receptor that have clinical significance as vasodilators and CNS agents.