55728-89-7

Upstream product

• 100-52-7 benzaldehyde 
• 55728-88-6 penta-N-Cbz-paromomycin 

Downstream Products

• 942304-67-8 C₇₆H₉₃N₅O₂₄Si 
• 1221493-35-1 4,6-O-benzylidene-penta-O-tert-butyldimethylsilanyloxy-penta-N-benzyloxycarbonyl paromomycin 
• 1284216-81-4 6,3',2'',5'',3''', 4'''-hexa-O-methoxycarbonyl-4',6'-benzylidene-per-N-Cbz-paromomycin 
• 68405-95-8 O⁴-(O⁴,O⁶-(R)-benzylidene-2-benzyloxycarbonylamino-α-D-2-deoxy-glucopyranosyl)-O⁵-[O³-(N⁶,O⁴-(Ξ)-benzylidene-2,6-bis-benzyloxycarbonylamino-β-L-2,6-dideoxy-idopyranosyl)-β-D-ribofuranosyl]-N,N'-bis-benzyloxycarbonyl-1D-2-deoxy-streptamine 

Relevant academic research and scientific papers

ANTIBACTERIAL AMINOGLYCOSIDE ANALOGS

Compounds having antibacterial activity are disclosed. The compounds have one of the following structures (I) or (II): including stereoisomers, pharmaceutically acceptable salts and prodrugs thereof, wherein Q1, Q2, R1, R2, R3 and Z1 are as defined herein. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.

Hybrid aminoglycoside antibiotics via tsuji palladium-catalyzed allylic deoxygenation

Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an R,β-unsaturated 6′- aldehyde and an allylic 3′-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd2(dba)3 and Bu3P granted access to a novel series of 3′,4′-dideoxy- 4′,5′-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin.

ANTIBACTERIAL AMINOGLYCOSIDE ANALOGS

Compounds having antibacterial activity are disclosed. The compounds have the following structure (I): (I) including stereoisomers, pharmaceutically acceptable salts and prodrugs thereof, wherein Ql, Q2, Rl, R2 and R3 are as defined herein. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.

ANTIBACTERIAL AMINOGLYCOSIDE ANALOGS

Compounds having antibacterial activity are disclosed. The compounds have the following structure (I): (I) including stereoisomers, pharmaceutically acceptable salts and prodrugs thereof, wherein Q1, Q2, R1, R2 and R3 are as defined herein. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.

ANTIBACTERIAL 1,4,5-SUBSTITUTED AMINOGLYCOSIDE ANALOGS

The present invention is directed to analogs of aminoglycoside compounds as well as their preparation and use as prophylactic or therapeutics against microbial infection.

Structure-based design, synthesis, and A-site rRNA cocrystal complexes of functionally novel aminoglycoside antibiotics: C2″ ether analogues of paromomycin

A series of 2″-O-substituted ether analogues of paromomycin were prepared based on new site-selective functionalizations. X-ray cocrystal complexes of several such analogues revealed a new mode of binding in the A-site rRNA, whereby rings I and II adopted the familiar orientation and position previously observed with paromomycin, but rings III and IV were oriented differently. With few exceptions, all of the new analogues showed potent inhibitory activity equal or better than paromomycin against a sensitive strain of S. aureus. Single digit μM MIC values were obtained against E. coli, with some of the ether appendages containing polar or basic end groups. Two analogues showed excellent survival rate in a mouse septicemia protection assay. Preliminary histopathological analysis of the kidney showed no overt signs of toxicity, while controls with neomycin and kanamycin were toxic at lower doses.