1198790-98-5

Basic information

• Product Name: sodium (1R,4S,5R)-1,4,5-trihydroxy-3-[(benzo[b]thiophen-5-yl)methoxy]cyclohex-2-en-1-carboxylate
• Synonyms: sodium (1R,4S,5R)-1,4,5-trihydroxy-3-[(benzo[b]thiophen-5-yl)methoxy]cyclohex-2-en-1-carboxylate
• CAS NO: 1198790-98-5
• Molecular Weight: 358.347
• Mol File: 1198790-98-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: sodium (1R,4S,5R)-1,4,5-trihydroxy-3-[(benzo[b]thiophen-5-yl)methoxy]cyclohex-2-en-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: sodium (1R,4S,5R)-1,4,5-trihydroxy-3-[(benzo[b]thiophen-5-yl)methoxy]cyclohex-2-en-1-carboxylate(1198790-98-5)
• EPA Substance Registry System: sodium (1R,4S,5R)-1,4,5-trihydroxy-3-[(benzo[b]thiophen-5-yl)methoxy]cyclohex-2-en-1-carboxylate(1198790-98-5)

Safety Data

• Hazardous Substances Data: 1198790-98-5(Hazardous Substances Data)

Upstream product

• 1198791-10-4 (1R,4S,5R)-3-(benzo[b]tiophen-5-yl)methoxy-1,4-dihydroxy-cyclohex-2-en-1,5-carbolactone 
• 862791-12-6 (1R,4S,5R)-1,4-bis(tert-butyldimethylsilyloxy)-3-oxocyclohexane-1,5-carbolactone 
• 1198791-03-5 (1R,4S,5R)-1,4-di(tert-butyldimethylsilyloxy)-3-(benzo[b]thiophen-5-yl)methoxycyclohex-2-en-1,5-carbolactone 
• 10133-22-9 5-bromomethyl-benzo[b]thiophene 

Downstream Products

• 1319745-61-3 ethyl (1R,4S,5R)-3-(benzo[b]thiophen-5-yl)methoxyl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylate 
• 1319745-73-7 ethyl (1R,4S,5R)-4,5-dibutyroxy-3-(benzo[b]thiophen-5-yl)methoxy-1-hydroxycyclohex-2-ene-1-carboxylate 
• 1319745-74-8 propyl (1R,4S,5R)-3-(benzo[b]thiophen-5-ylmethoxy)-4,5-dibutyroxy-1-hydroxycyclohex-2-ene-1-carboxylate 
• 1319745-75-9 propyl (1R,4S,5R)-3-(benzo[b]thiophen-5-ylmethoxy)-4-butyroxy-1,5-dihydroxycyclohex-2-ene-1-carboxylate 
• 1319745-65-7 propyl (1R,4S,5R)-3-(benzo[b]thiophen-5-yl)methoxy-1,4,5-trihydroxycyclohex-2-ene-1-carboxylate 

Relevant articles and documents

COMPETITIVE INHIBITORS OF TYPE II DEHYDROQUINASE ENZYME

The present invention is directed to a compound of formula (I), its diastereoisomers, its enantiomers or its pharmaceutically acceptable salts or solvates, formula (I), to procedures of obtaining the same, to intermediates thereof, and use as competitive inhibitors of the third enzyme of the shikimic acid pathway, the type II dehydroquinase.

Synthesis and biological evaluation of new nanomolar competitive inhibitors of Helicobacter pylori type II dehydroquinase. Structural details of the role of the aromatic moieties with essential residues

The shikimic acid pathway is essential to many pathogens but absent in mammals. Enzymes in its pathway are therefore appropriate targets for the development of novel antibiotics. Dehydroquinase is the third enzyme of the pathway, catalyzing the reversible dehydratation of 3-dehydroquinic acid to form 3-dehydroshikimic acid. Here we present the synthesis of novel inhibitors with high affinity for Helicobacter pylori type II dehydroquinase and efficient inhibition characteristics. The structure of Helicobacter pylori type II dehydroquinase in complex with the most potent inhibitor shows that the aromatic functional group interacts with the catalytic Tyr22 by π-stacking, expelling the Arg17 side chain, which is essential for catalysis, from the active site. The structure therefore explains the favorable properties of the inhibitor and will aid in design of improved antibiotics.