1253799-65-3

Upstream product

• 100-51-6 benzyl alcohol 
• 13958-93-5 3,5-dichloropyridine-4-carboxylic acid 
• 1253799-61-9 3-(benzyloxy)-5-chloroisonicotinic acid 
• 13061-96-6 dihydroxy-methyl-borane 
• 1253799-63-1 phenyl 3-(benzyloxy)-5-chloroisonicotinate 

Downstream Products

• 1253799-67-5 C₄₁H₄₇N₃O₇Si 
• 1254367-42-4 phenyl 3-(benzyloxy)-2-bromo-6-chloro-5-methylisonicotinate 
• 1254367-50-4 phenyl 5-(benzyloxy)-2-methoxy-3-methylisonicotinate 
• 1254367-39-9 phenyl 5-(benzyloxy)-2-(dimethylamino)-3-methylisonicotinate 
• 1254367-63-9 phenyl 5-benzyloxy-2-(dimethylamino)-3-methyl-6-(propylamino)isonicotinate 
• 1254367-58-2 (4aS,11aR,12aS,13S)-10-chloro-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8-(ethylamino)11a,12,12a,13-tetrahydro-5-hydroxy-3,7-bis(phenylmethoxy)-isoxazolo[5',4':6,7]naphth[2,3-g]-isoquinoline-4,6(4aH,11H)-dione 
• 1268248-39-0 N-[(4aS,11aR,12aS,13S)-10-chloro-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,4a,6,11,11a,12,12a,13-octahydro-5-hydroxy-4,6-dioxo-3,7-bis(phenylmethoxy)isoxazolo[50,40:6,7]naphth[2,3-g]isoquinolin-8-yl]-2-[(1,1-dimethylethyl)amino]-acetamide 
• 1254367-67-3 C₂₅H₂₅BrN₂O₅ 
• 1254367-66-2 phenyl 3-(benzyloxy)-2-bromo-6-[(t-butoxycarbonyl)-amino]-5-methylisonicotinate 
• 1254367-38-8 phenyl 5-(benzyloxy)-2-bromo-3-methylisonicotinate 
• 1254367-94-6 (4aS,11aR,12aS,13S)-10,13-bis(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11a,12,12a,13-tetrahydro-5-hydroxy-3,7-bis(phenylmethoxy)-8-(2-propen-1yl)-isoxazolo[5',4':6,7]naphth[2,3-g]isoquinoline-4,6(4aH,11H)-dione 
• 1254367-65-1 N-[(4aS,11aR,12aS,13S)-10,13-bis(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-10-fluoro-4,4a,6,11,11a,12,12a,13-octahydro-5-hydroxy-4,6-dioxo-3,7-bis(phenylmethoxy)isoxazolo[5',4';6,7]naphth[2,3-g]isoquinolin-8-yl]-N-propyl-carbamic acid 1,1-dimethylethyl ester 
• 1254367-74-2 N-[(4aS,11aR,12aS,13S)-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-10-fluoro-4,4a,6,11,11a,12,12a,13-octahydro-5-hydroxy-4,6-dioxo-3,7-bis(phenylmethoxy)isoxazolo[5',4';6,7]naphth[2,3-g]isoquinolin-8-yl]-N-[3-(dimethylamino)-2,2-dimethylpropyl]-carbamic acid phenylmethyl ester 
• 1254367-64-0 phenyl 5-benzyloxy-6-[(t-butoxycarbonyl)(propyl)amino]-2-(dimethylamino)-3-methylisonicotinate 

Relevant academic research and scientific papers

8-azatetracyclines: Synthesis and evaluation of a novel class of tetracycline antibacterial agents

A novel series of fully synthetic 8-azatetracyclines was prepared and evaluated for antibacterial activity. Compounds were identified that overcome both efflux (tet(K)) and ribosomal protection (tet(M)) tetracycline resistance mechanisms and are active against Gram-positive and Gram-negative organisms. Two compounds were identified that exhibit comparable efficacy to marketed tetracyclines in in vivo models of bacterial infection.

SYNTHESIS OF TETRACYCLINES AND INTERMEDIATES THERETO

The tetracycline class of antibiotics has played a major role in the treatment of infectious diseases for the past 50 years. However, the increased use of the tetracyclines in human and veterinary medicine has led to resistance among many organisms previously susceptible to tetracycline antibiotics. The recent development of a modular synthesis of tetracycline analogs through a chiral enone intermediate has allowed for the efficient synthesis of novel tetracycline analogs never prepared before. The present invention provides more efficient routes for preparing the enone intermediate and allows for substituents at positions 4a, 5, 5a, and 12a of the tetracycline ring system.

8-AZA TETRACYCLINE COMPOUNDS

The present invention is directed to a compound represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof. The variables for Structural Formula I are defined herein. Also described is a pharmaceutical composition comprising the compound of Structural Formula I and its therapeutic use.