128472-97-9

Upstream product

• 105-13-5 4-Methoxybenzyl alcohol 
• 693-13-0 diisopropyl-carbodiimide 

Downstream Products

• 128472-55-9 (6R,7S)-3-Acetoxymethyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 128472-56-0 (6R,7S)-3-Acetoxymethyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 128472-64-0 (6R,7S)-3-Acetoxymethyl-7-methoxy-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 214976-42-8 6-Chloro-9-fluoro-4-(4-methoxy-benzyloxy)-benzo[g]isoquinoline-5,10-dione 
• 172779-21-4 9-chloro-6-fluoro-4-(p-methoxybenzyloxy)benzo[g]isoquinoline-5,10-dione 
• 102-17-0 4-methoxybenzyl 2-phenylacetate 
• 24318-41-0 p-methoxybenzyl benzoate 
• 72845-81-9 p-methoxybenzyl salicylate 
• 172779-27-0 10-(p-methoxybenzyloxy)-5-chloro-2-methylisoquino[5,6,7-cd]indazole-6(2H)-one 
• 214976-43-9 5-Chloro-2-(2-dimethylamino-ethyl)-7-(4-methoxy-benzyloxy)-2H-1,2,9-triaza-aceanthrylen-6-one 
• 172779-28-1 5-chloro-2-[2-(dimethylamino)ethyl]-10-(p-methoxybenzyloxy)isoquino[5,6,7-cd]indazole-6(2H)-one 
• 172779-00-9 10-(p-methoxybenzyloxy)-5-[[2-(dimethylamino)ethyl]amino]-2-methylisoquino[5,6,7-cd]indazole-6(2H)-one 
• 214976-46-2 5-Chloro-2-[2-(2-hydroxy-ethylamino)-ethyl]-7-(4-methoxy-benzyloxy)-2H-1,2,9-triaza-aceanthrylen-6-one 
• 214976-44-0 2-(2-Dimethylamino-ethyl)-5-(2-dimethylamino-ethylamino)-7-(4-methoxy-benzyloxy)-2H-1,2,9-triaza-aceanthrylen-6-one 

Relevant academic research and scientific papers

A convenient preparation of p-methoxybenzyl esters

Carboxylic acids are conveniently and efficiently protected as their p-methoxybenzyl esters under very mild conditions using the pre-formed reagent N,N'-diisopropyl-O-(4-methoxybenzyl)isourea, and this method allows selective protection of carboxylic acids in the presence of other functionalities such as enolisable ketones and alcohol groups.

PRODRUG INHIBITORS

Provided herein are compounds useful as metallo-β-lactamase (MBL) inhibitors. The compounds have a formula A–B, where A is a β-lactam antibiotic moiety comprising a bridging methylene (-CH2-) covalently attached to -B; and B is a latent MBL inhibitor. Also provided are formulations comprising such compounds; as well as such compounds or formulations for use as a medicament. The compounds and formulations may be used in the treatment of antibiotic resistance, bacterial infection. The compounds and formulations may be used in the inhibition of a bacterial MBL.

Synthesis of 4-hydroxy-6,9-difluorobenz[g]isoquinoline-5,10-diones and conversions to 4-hydroxy-6,9-bis[(aminoalkyl)amino]-benz[g]isoquinoline-5,10-diones

Synthetic procedures have been developed which lead to 4-hydroxy-6,9-difluorobenz[g]isoquinoline-5,10-dione (4a) and its 3-methyl analogue 4b. Attempts to displace the fluorides from 4a with N,N-dimethylethylenediamine were unsuccessful. Analogue 4a on treatment with N-(t-butoxycarbonyl)ethylene diamine led to 15, formed from addition of the nucleophilic amine to C-3. On the other hand, analogue 4b, on treatment with N,N-dimethylethylenediamine led to the anticipated difluoride displacement product 3c. The protection of the hydroxy group of 4a by benzylation with phenyldiazomethane led to 4c which on treatment with N-(t-butoxycarbonyl)ethylene diamine or N,N-dimethylethylenediamine led to the corresponding 6,9-bis-substituted analogues 18a and 18b, respectively. Reductive debenzylations of 18a and 18b by hydrogenation over Pearlman's catalyst also effected partial reductions of the quinone. However, air oxidation of the over reduced products led to 3a and 3b, respectively. Treatment of 3a with hydrogen chloride gas led to the hydrochloride salt of 3d. Addition of O-p-Methoxybenzyl-N,N'-diisopropylurea to 4a led to the p-methoxybenzyl analogue 4d. Treatment of 4d with N,N-dimethylethylene diamine or N-(t-butoxycarbonyl)ethylene diamine led to displacements of the fluorides to yield 18c and 18d, respectively. Deprotection of 18c to 3b was accomplished using methanesulfonic acid. Treatment of 18d with trifluoroacetic acid followed by addition of maleic acid led to dimaleate salt of 3d.

Inhibition of Human Leukocyte Elastase. 2. Inhibition by Substituted Cephalosporin Esters and Amides

A variety of 7α-methoxycephalosporin ester and amide sulfones were prepared and tested to determine the structure-activity relations for inhibition of human leukocyte elastase (HLE), a serine protease which has been implicated in several degenerative lung