66739-90-0

Basic information

• Product Name: 4-Methoxyiminocarbonylbenzaldehyd-Hydrochlorid
• CAS NO: 66739-90-0
• Molecular Weight: 199.637
• Mol File: 66739-90-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 4-Methoxyiminocarbonylbenzaldehyd-Hydrochlorid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxyiminocarbonylbenzaldehyd-Hydrochlorid(66739-90-0)
• EPA Substance Registry System: 4-Methoxyiminocarbonylbenzaldehyd-Hydrochlorid(66739-90-0)

Safety Data

• Hazardous Substances Data: 66739-90-0(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 105-07-7 4-cyanobenzaldehyde 

Downstream Products

• 55514-20-0 4-amidinobenzaldehyde 
• 785035-50-9 3,5-Bis-[1-(4-carbamimidoyl-phenyl)-meth-(E)-ylidene]-4-oxo-piperidine-1-carboxylic acid ethyl ester 
• 258519-35-6 (E,E)-2,10-bis(4-amidinobenzylidene)cyclodecan-1-one 
• 258519-29-8 C₂₅H₂₈N₄O 
• 750558-22-6 C₂₈H₂₆N₄O 
• 756805-43-3 3,5-Bis-[1-(4-carbamimidoyl-phenyl)-meth-(E)-ylidene]-4-oxo-cyclohexanecarboxylic acid methyl ester 
• 258519-44-7 3,5-Bis-[1-(4-carbamimidoyl-phenyl)-meth-(Z)-ylidene]-4-oxo-cyclohexanecarboxylic acid methyl ester 
• 191732-42-0 Z,E-1,3-bis[(4'-(amino(imino)methyl)phenyl)methylene]-2-oxocyclooctane 
• 741239-08-7 3,5-Bis-[1-(4-carbamimidoyl-phenyl)-meth-(E)-ylidene]-4-oxo-cyclohexanecarboxylic acid 
• 258519-56-1 C₂₄H₂₆N₄O 

Relevant articles and documents

Synthesis, characterization, and structure-activity relationships of amidine-substituted (bis)benzylidene-cycloketone olefin isomers as potent and selective factor Xa inhibitors

Factor Xa (FXa) is a trypsin-like serine protease that plays a key role in blood coagulation linking the intrinsic and extrinsic pathways to the final common pathway of the coagulation cascade. During our initial studies, we observed facile photochemical conversion of the known FXa/tPA inhibitor, BABCH [(E,E)-2,7-bis(4-amidinobenzylidene)cycloheptan-1-one, 1a], to the corresponding (Z,Z) olefin isomer, 1c (FXa K(i) = 0.66 nM), which was over 25 000 times more potent than the corresponding (E,E) isomer (1a, FXa K(i) = 17 000 nM). In order to determine the scope of this observation, we expanded on our initial investigation through the preparation of the olefin isomers in a homologous series of cycloalkanone rings, 4-substituted cyclohexanone analogues, and modified amidine derivatives. In most cases the order of potency of the olefin isomers was (Z,Z) > (E,Z) > (E,E) with the cycloheptanone analogue (1c) showing the most potent factor Xa inhibitory activity. In addition, we found that selectivity versus thrombin (FIIa) can be dramatically improved by the addition of a carboxylic acid group to the cycloalkanone ring as seen with 8c (FXa K(i) = 6.9 nM, FIIa K(i) > 50 000 nM). Compounds with one or both of the amidine groups substituted with N-alkyl substituents or replaced with amide groups led to a significant loss of activity. In this report we have demonstrated the importance of the two amidine groups, the cycloheptanone ring, and the (Z,Z) olefin configuration for maximum inhibition of FXa within the BABCH template. The results from this study provided the foundation for the discovery of potent, selective, and orally active FXa inhibitors.