232602-24-3

Upstream product

• 36404-88-3 2-chloro-3-carbaldehydepyridine 
• 62673-31-8 benzyl(bromo)zinc 
• 232602-09-4 2-Benzyl-nicotinic acid methyl ester 
• 128071-75-0 2-bromopyridine-3-carboxaldehyde 
• 1452-94-4 ethyl 2-chloronicotinate 
• 40134-18-7 methyl 2-chloropyridine-3-carboxylate 
• 232602-17-4 (2-benzyl-3-pyridyl)methanol 

Relevant academic research and scientific papers

Second Generation Grp94-Selective Inhibitors Provide Opportunities for the Inhibition of Metastatic Cancer

Glucose regulated protein 94 (Grp94) is the endoplasmic reticulum (ER) resident isoform of the 90 kDa heat shock protein (Hsp90) family and its inhibition represents a promising therapeutic target for the treatment of many diseases. Modification of the first generation cis-amide bioisostere imidazole to alter the angle between the resorcinol ring and the benzyl side chain via cis-amide replacements produced compounds with improved Grp94 affinity and selectivity. Structure–activity relationship studies led to the discovery of compound 30, which exhibits 540 nm affinity and 73-fold selectivity towards Grp94. Grp94 is responsible for the maturation and trafficking of proteins associated with cell signaling and motility, including select integrins. The Grp94-selective inhibitor 30 was shown to exhibit potent anti-migratory effects against multiple aggressive and metastatic cancers.

SECOND GENERATION GRP94-SELECTIVE INHIBITORS

The present technology provides compounds selective for the Grp94 isoform, as well as compositions including such compounds, that are useful for treatment of multiple myeloma, melanoma, lung cancer, hepatocellular carcinoma, breast cancer, prostate cancer

Herbicidal quinolines

The present invention relates to compounds of formula (I), or an agronomically acceptable salt of said compounds wherein A1a, A1b, R1, R2, R3, R4, R5 and R6 are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I), and to their use for controlling weeds, in particular in crops of useful plants.

Acetic Acid Promoted Redox Annulations with Dual C-H Functionalization

Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with 2-alkylquinoline-3-carbaldehydes as well as the corresponding 4-alkyl isomers and pyridine analogues. These processes involve dual C-H bond functionalization. Acetic acid

General preparative route to benzo[g]quinolines (1-azaanthracenes)

A convenient synthetic pathway to benzo[g]quinolines (1-azaanthracenes) has been developed. The nickel catalyzed coupling of methyl 2- chloronicotinate (3a) with benzylic organo zinc reagents 2a-e led to the methyl 2-benzylic substituted nicotinates 4a-e. Treatment of methyl 2- chloro-6-methylnicotinate (3b)with 2a in a similar manner led to methyl 2- benzyl-6-methylnicotinate (4f). The coupling of 2-chloro-3-acetylpyridine (5) with benzyl zinc bromide (2a) led to 2-benzyl-3-acetylpyridine (4g). The coupling of the 2,5-dichlorobenzylic organic zinc reagent (2f) with methyl 2- choronicotinate (3a) was unselective but readily coupled with methyl 2- bromonicotinate (6) to yield methyl 2-(2,5-dichlorobenzyl)nicotinate (4h). The esters 4a-f,h on reduction with lithium aluminum hydride led to the corresponding alcohols 7a-f,h which were subsequently oxidized with manganese dioxide to the respective 2-benzylic substituted pyridine-3-carboxaldehydes 8a-f,h. In one case the coupling of benzy] zinc bromide (2a) with 2- chloropyridine-3-carboxaldehyde (9) led directly to 2-benzylpyridine-3- carboxaldehyde (8a), but in poor yield. Cyclizations of the aldehydes 8a- d,f,h or the ketone 4g with polyphosphoric acid afforded the benzo[g]quinolines 10a-d,f-h in high yields. Aldehyde 8e was cyclized to 10e using a solution of sulfuric acid in methanol. Several of the benzo[g]quinolines 10c,d could be readly converted into the benzo[q]quinoline-5,10-diones 11c,d on treatment with ammonium ceric nitrate.