2528-01-0

Upstream product

• 6141-57-7 methyl 3-methylfuran-2-carboxylate 
• 99183-76-3 methyl 5,5-dimethoxy-3-methyl-2,3-epoxypentanoate 
• 5436-21-5 acetylacetaldehyde dimethyl acetal 

Downstream Products

• 1333376-27-4 C₁₅H₁₆O₃ 
• 1333376-29-6 C₂₂H₂₃NO₂ 
• 1333376-28-5 C₁₄H₁₄O₃ 
• 952710-73-5 3-methyl-5-(4-trifluoromethyl-phenyl)-furan-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthetic studies on pseudolaric acid B: Enantioselective synthesis of C4,C10-di-epi-trans-fused [5-7]-bicyclic skeleton

Studies on the synthesis of antifungal and anticancer natural product, pseudolaric acid B, have led to the enantioselective synthesis of di-epi-trans-fused [5–7]-bicyclic core skeleton. The synthesis was achieved in 10 linear steps, which features the Sharpless asymmetric epoxidation, cyanide-opening reaction of epoxide, and intramolecular [5 + 2] cycloaddition reaction as the key transformations. The stereochemistry was determined by the X-ray crystallographic analysis.

Bifunctional Furfuryl Cations Strategy: Three-Component Synthesis of Enamidyl Triazoles

A new multicomponent synthesis of functionalized enamidyl triazoles starting from simple and readily available starting materials is described. A simple treatment of a dichloromethane solution of an azide, amine, and 5-bromo-2-furylcarbinol with a Lewis acid provides the enamidyl triazole in good to high yield. A triple domino sequence, formal [3+2] cycloaddition/ring-opening/amidation, is involved in this new skeleton-generating reaction.

SAR analysis of innovative selective small molecule antagonists of sphingosine-1-phosphate 4 (S1P4) receptor

Recent evidence suggests an innovative application of chemical modulators targeting the S1P4 receptor as novel mechanism-based drugs for the treatment of influenza virus infection. Modulation of the S1P4 receptor may also represent an alternative therapeutic approach for clinical conditions where reactive thrombocytosis is an undesired effect or increased megakaryopoiesis is required. With the exception of our recent research program disclosure, we are not aware of any selective S1P4 antagonists reported in the literature to date. Herein, we describe complementary structure-activity relationships (SAR) of the high-throughput screening (HTS)-derived hit 5-(2,5-dichlorophenyl)-N-(2,6-dimethylphenyl)furan-2- carboxamide and its 2,5-dimethylphenyl analog. Systematic structural modifications of the furan ring showed that both steric and electronic factors in this region have a significant impact on the potency. The furan moiety was successfully replaced with a thiophene or phenyl ring maintaining potency in the low nanomolar range and high selectivity against the other S1P receptor subtypes. By expanding the molecular diversity within the hit-derived class, our SAR study provides innovative small molecule potent and selective S1P 4 antagonists suitable for in vivo pharmacological validation of the target receptor.

PYRROLONE MELANIN CONCENTRATING HORMONE RECEPTOR-1 ANTAGONISTS

The present application provides compounds, including all stereoisomers, solvates, prodrugs and pharmaceutically acceptable forms thereof according to Formula I wherein R1, Formula Ia, R4, R5, Formula Ib, R3, R3a, W, D, R2a, R2b and R2c are defined herein. Additionally, the present application provides pharmaceutical compositions containing at least one compound according to Formula I and optionally at least one additional therapeutic agent. Finally, the present application provides methods for treating a patient suffering from an MCHR-1 modulated disease or disorder such as, for example, obesity, diabetes, depression, anxiety or intestinal inflammation, by administration of a therapeutically effective dose of a compound according to Formula I.

HETEROCYCLIC COMPOUND

The present invention provides a heterocyclic compound represented by the following formula (I), which has a glucagon antagonistic action and is useful for the prophylaxis or treatment of diabetes and the like, a compound represented by wherein ring A is an optionally substituted benzene ring and the like; Y is a nitrogen atom and the like; X is -O- and the like; R4 is a hydrogen atom and the like; R5 and R6 are each independently a hydrogen atom and the like; R1 is an optionally substituted hydrocarbon group and the like; R2 is a hydrogen atom and the like; and R3 is -(CH2)3-COOH and the like, or a salt thereof.

3-Substituted-(5-arylfuran-2-ylcarbonyl)guanidines as NHE-1 inhibitors

The C-3 substituents effect on NHE-1 inhibitory activity of (5-arylfuran-2-ylcarbonyl)guanidines, previously identified as potent NHE-1 inhibitors, was investigated. The introduction of amine or alkyl groups at the 3-position of the furan ring, next to the acylguanidine moiety, remarkably improves NHE-1 inhibitory potency. Especially the important finding is that 5-(2,5-dichloro)phenyl and 5-(2-methoxy-5-chloro)phenyl derivatives exhibit high NHE-1 inhibitory activities (IC50 0.02 μM) that match those of 3-unsubstituted derivatives.

On the bromination of methyl 2-methyl-3-furoate

Methyl 2-methyl-3-furoate was subjected to bromination with N-bromosuccinimide (NBS), a milder brominating reagent, under different reaction conditions to obtain a variety of selective brominated products.

General Routes to 4-Methyl-2-substituted-furans: a Total Synthesis of Pleraplysillin-2, a Metabolite of the Sponge, Pleraplysilla spinifera

A general approach to 4-methyl-2-substituted-furans is described in which 4-methyl-2-furyl-lithium is the key intermediate.Using this method, pleraplysillin-2, a sesquiterpenoid ester from the sponge Pleraplysilla spinifera, has been synthesised.An alternative, less efficient, route to this type of furan, via acyclic keto-epoxides, is also discussed.