285991-71-1

Upstream product

• 145887-88-3 1,1-dimethyl-1H,5H-furo[3,4-c]pyridine-3,4-dione 
• 13332-71-3 4,5,5-trimethyl-2-oxo-2,5-dihydro-furan-3-carbonitrile 
• 1269593-14-7 4-(2-(dimethylamino)vinyl)-5,5-dimethyl-2-oxo-2,5-dihydrofuran-3-carbonitrile 
• 854930-11-3 C₉H₁₀ClNO₃ 
• 16498-81-0 2-methoxynicotinic acid 
• 67-64-1 acetone 
• 285991-68-6 4,6-dichloro-pyrimidine-5-carboxylic acid 1,1-dimethyl-prop-2-ynyl ester 

Downstream Products

• 1417819-01-2 4-(benzylamino)-1,1-dimethylfuro[3,4-c]pyridin-3(1H)-one 
• 1580537-51-4 4-(4-chlorophenylamino)-1,1-dimethyl-1H-furo[3,4-c]pyridin-3-one 
• 1580537-56-9 4-(1,1-dimethyl-3-oxo-1,3-dihydrofuro[3,4-c]pyridin-4-ylamino)benzenesulfonamide 

Relevant academic research and scientific papers

New C4- and C1-derivatives of furo[3,4-c]pyridine-3- ones and related compounds: Evidence for site-specific inhibition of the constitutive proteasome and its immunoisoform

A set of 18 new C4 and C1 derivatives of nor-cerpegin (1,1-dimethyl furo[3,4-c]pyridine-3-one), 6 model compounds (γ- and δ-lactones) and 20 furo- or thieno[2,3-d]-pyrimidine-4-one related compounds were designed and synthesized. Each compound was assayed for inhibition of CT-L, T-L and PA proteolytic activities of 20S constitutive proteasome (c20S). Most performant compounds were also assayed on 20S immunoproteasome (i20S). Compound 10 with a benzylamino group at C4 and dimethylated at C1 of the furopyridine ring was the most efficient PA site-specific inhibitor of the c20S (IC50cPA of 600 nM) without noticeable inhibition of the i20S PA site (iPA). In silico docking assays for 10 at the iPA catalytic site revealed the absence of poses normally observed for this compound and related ones at the constitutive PA site (cPA). The thieno[2,3-d]pyrimidine-4-one 40 was T-L site-specific with a mild inhibition of both c20S and i20S in vitro (IC50cT-L of 9.9 μM and IC50iT-L of 6.7 μM). In silico docking assays of 40 at T-L sites of c20S and i20S revealed almost identical first rank poses in the two types of sites with no possibility left for nucleophilic attack by Thr1 as observed for the fused furopyridine-3-one 10.

Synthesis of fused bicyclic pyridines with microwave-assisted intramolecular hetero-Diels-Alder cycloaddition of acetylenic pyrimidines

A series of acetylenic pyrimidines was synthesized and subjected to microwave irradiation. In contrast to conventional heating, the microwave irradiations generally gave clean conversion to fused bicyclic pyridines for all substrates reported with shorter reaction time. This method has been successfully applied to the synthesis of both fused lactones and lactams.

'One-pot' four-step synthesis of cerpegin

Cerpegin (1) was synthesized through a 'one-pot' reaction in 71% overall yield. Lithiation of commercially available 2-methoxynicotinic acid (2) as its lithium salt using LTMP, followed by addition of acetone at low temperature and a specific acidic treatment of the intermediate 3 thus obtained, gave the 1,1-dimethyl-3,4-dioxo-1,3,4,5-tetrahydrofuro[3,4-c]pyridine (4). The latter was finally selectively alkylated using methyl iodide and caesium carbonate to afford cerpegin (1).

THERAPEUTIC AGENTS USEFUL FOR TREATING PAIN

The Invention provides a compound of formula (I), (where A, X, Y, Z, R3, R4, R5, R6, m and n are disclosed herein) or a pharmaceutically acceptable salt thereof (the compound or pharmaceutically acceptable salt thereof being a "Piperazine Compound"); phar

A short total synthesis of cerpegin by intramolecular hetero Diels-Alder cycloaddition reaction of an acetylene tethered pyrimidine

The electron poor 4,6-dichloropyrimidine-5-carbaldehyde, which is readily available, is used as a starting material for the synthesis of fused 2-chloropyridines. Chlorination transforms the aldehyde into the corresponding acid chloride, which can be functionalized with acetylene tethers. Intramolecular hetero Diels-Alder reactions at elevated temperatures afford the fused pyridines in varying yield. This reaction sequence was applied to the total synthesis of cerpegin.