123453-95-2

Upstream product

• 79644-03-4 (1S,5S)-6-oxabicyclo<3.2.1>oct-3-en-7-one 
• 4720-83-6 6-oxabicyclo<3.2.1>-oct-3-en-7-one 
• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 
• 4720-83-6 6-oxabicyclo[3.2.1]oct-3-en-7-one 
• 108-05-4 vinyl acetate 
• 54911-89-6 cis-methyl 5-hydroxycyclohex-3-enecarboxylate 
• 68295-80-7 (1S,5S)-5-Hydroxy-cyclohex-3-enecarboxylic acid methyl ester 
• 19914-92-2 (+/-)-4-iodo-6-oxabicyclo[3.2.1]octan-7-one 
• 123536-66-3 (1S,4S,5S)-4-iodo-6-oxabicyclo<3.2.1>octan-7-one 
• 5708-19-0 (1S)-3-cyclohexenecarboxylic acid 
• 6493-77-2 methyl cyclohex-3-ene-1-carboxylate 

Downstream Products

• 123536-65-2 (5S)-5-hydroxymethyl-2-cyclohexen-1-one 

Relevant academic research and scientific papers

Synthesis and antiviral evaluation of cis-substituted cyclohexenyl and cyclohexanyl nucleosides

Starting from commercially available (rac)-3-cyclohexene-1-carboxylic acid, a series of purine and pyrimidine cis-substituted cyclohexenyl and cyclohexanyl nucleosides were synthesized through a key Mitsunobu reaction. Antiviral evaluations were performed

Enzyme catalyzed reverse enantiomeric separation of methyl (±)-3-cyclohexene-1-carboxylate

We describe the differences of hydrolase-type enzymes pig liver esterase (PLE), horse liver esterase (HLE), and porcine pancreatic lipase (PPL) on the hydrolysis of methyl (±)-3-cyclohexene-1-carboxylate to afford both enantiomers with 89% to the resultant enantiomerically pure (S)-(-)-3- cyclohexene-1-carboxylic acid was transformed into (1S,5S)-(-)-5-(hydroxymethyl) -2-cyclohexen-1-ol via iodolactonization, subsequent elimination of iodine with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and reduction with lithium aluminum hydride (LAH).

Palladium-Catalyzed Allylic Alkylation of 2-Aryl-1,3-Dithianes, an Umpolung Synthesis of β,γ-Unsaturated Ketones

Palladium-catalyzed allylic alkylation of 2-aryl-1,3-dithianes at room temperature is described. A variety of cyclic and acyclic electrophiles successfully coupled with in-situ generated 2-sodio-1,3-dithiane nucleophiles to afford the allylated products in good to excellent yields (25 examples). Deprotection of these products leads to valuable β,γ-unsaturated ketones. Direct synthesis of such β,γ-unsaturated ketones via a one-pot allylation-oxidation protocol is also presented. Investigation into the stereochemistry of the allylation reaction revealed that the 2-sodio-1,3-dithiane nucleophile behaves as a “soft” nucleophile, which underwent external attack on the π-allyl palladium complex to provide retention of stereochemistry (double inversion pathway). Additionally, the utility of this method was demonstrated through a sequential one-pot allylation-Heck cyclization to produce asterogynin derivatives, which are important bioactive compounds in medicinal chemistry. (Figure presented.).

Catalytic sp3–sp3Functionalisation of Sulfonamides: Late-Stage Modification of Drug-Like Molecules

A new application of Pd-catalysed allylation is reported that enables the synthesis of a range of branched sp3-functionalised sulfonamides, a compound class for which few reported methods exist. By reacting benzyl sulfonamides with allylic acetates in the presence of Pd0catalysts and base at room temperature, direct allylation was efficiently performed, yielding products that are analogues of structural motifs seen in biologically active small molecules. The reaction was performed under mild conditions and could be applied to nanomolar sigma-receptor binders, thus enabling a late-stage functionalisation and efficient expansion of drug-like chemical space.

ADENINE DERIVATIVES AS PROTEIN KINASE INHIBITORS

The present invention relates to a compound suitable for use as a kinase inhibitor according to general formula (I) [compound (C), herein after], or the N- oxide, pharmaceutically acceptable salt, pharmaceutically acceptable solvate, or stereoisomer thereof, formula (I) wherein A, R1, R2, R3, R3', R4, R4', X, Y, Z, T are as defined in the claims. The invention further relates to an in vitro method of inhibiting protein kinase activity which comprises contacting a protein kinase with a compound of formula (I), or the N-oxide, pharmaceutically acceptable salt, pharmaceutically acceptable solvate, or stereoisomer thereof. The invention further relates to the compounds of formula (I) per se, as well as to their use as a medicament, and for use or in a method of treatment of a disease mediated by a protein kinase selected from cancer, inflammatory disorders, cardiovascular diseases, viral induced diseases, circulatory diseases, fibro-proliferative diseases and pain sensitization disorders.

A-ring hydroxymethyl 19-nor analogs of the natural hormone 1α,25-dihydroxyvitamin D3: Synthesis and preliminary biological evaluation

A series 5-8 of 1- and 3-CH2OH 19-nor analogs of the hormone calcitriol (1) has been prepared. Surprisingly, 19-nor 1α-CH2OH analog 5a is more antiproliferative at 100 nM concentration than the corresponding regioisomeric analog 6a w

Practical syntheses of enantiopure carbasugars: Carba-β-altrose, carba-β-mannose, carba-β-idose, and carba-β-talose derivatives

D and L forms of carba-β-altrose 8, carba-β-mannose 10a, carba-β-idose 12, carba-β-talose 14 derivatives were prepared from (±)-3-cyclohexene-1-carboxylic acid 1. Homochiral diol compounds D-5a and L-5a, which were prepared from 1 via enzyme resolution of

Synthesis of (±) cis-substituted cyclohexenyl and cyclohexanyl nucleosides via a double Mitsunobu-type reaction

This letter describes the synthesis of (±) cis-substituted cyclohexenyl and cyclohexanyl nucleosides. The synthesis of cis isomers was successfully achieved by the use of two consecutive Mitsunobu reactions involving an inversion of configuration and a sugar-base condensation.

Synthesis of (-)-periplanone-B, a sex pheromone component of the American cockroach (Periplaneta americana)

The naturally occurring (-)-enantiomer of periplanone-B was synthesized stereoselectively starting from (S)-3-cyclohexene-1-carboxylic acid. The crystalline pheromone was obtained in 12% overall yield through 18 steps.