26893-15-2

Basic information

• Product Name: ethyl 4-chloro-6,7-dimethylquinoline-3-carboxylate
• Synonyms: ethyl 4-chloro-6,7-dimethylquinoline-3-carboxylate
• CAS NO: 26893-15-2
• Molecular Formula: C₁₄H₁₄ClNO₂
• Molecular Weight: 264
• Mol File: 26893-15-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 367.6±37.0 °C(Predicted)
• Appearance: /
• Density: 1.222±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 2.54±0.41(Predicted)
• CAS DataBase Reference: ethyl 4-chloro-6,7-dimethylquinoline-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4-chloro-6,7-dimethylquinoline-3-carboxylate(26893-15-2)
• EPA Substance Registry System: ethyl 4-chloro-6,7-dimethylquinoline-3-carboxylate(26893-15-2)

Safety Data

• Hazardous Substances Data: 26893-15-2(Hazardous Substances Data)

Upstream product

• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 95-64-7 4-amino-o-xylene 
• 26893-08-3 4-Hydroxy-6,7-dimethyl-quinoline-3-carboxylic acid ethyl ester 

Downstream Products

• 77792-58-6 2-(4'-bromophenyl)-pyrazoloquinolin-3-one 
• 236112-22-4 2-(4-trimethylsilanylethynyl-phenyl)-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one 

Relevant articles and documents

Studies in search of α2 selective ligands for GABA(A)/BzR receptor subtypes. Part I. Evidence for the conservation of pharmacophoric descriptors for DS subtypes

In an attempt to prepare selective ligands for α2 containing GABA(A)/BzR receptors, which may be involved in short term memory, several series of 4'-, 7- and 8-substituted pyrazoloquinolin-3-ones were synthesized and evaluated in vitro on recombinant BzR (receptor) subtypes to study their structure activity relationships. Single substitution at position-8 of the pyrazoloquinoline nucleus had little effect on affinity or selectivity, whereas substitution at position-7 resulted in loss of affinity by about one order of magnitude. The effect on selectivity was minimal. Substitution at position-4' had little effect on affinity but did enhance α2 selectivity. When the substituent at position-7 was a bromine atom and held constant, substitution at position-4' resulted in a decrease in affinity of about one order of magnitude, but ligands in this category did not exhibit higher affinity at α2 subtypes as compared to other subtypes. When the substituent at position-8 (such as a tert butyl group) was held constant, substitution at position-4' resulted in a similar effect on affinity to that of the 7-bromo series. However, among all isoforms, this decrease resulted in the least effect on the α2 subtype. The 2-(4-bromophenyl)-8-tert-butyl- pyrazoloquinolin-3-one (ligand 19 in Table 1) exhibited the highest affinity for α2-containing subtypes in vitro as compared to the other subtypes. This ligand also exhibited a 20 fold selectivity for α5-containing isoforms and a 4 fold selectivity for α3 isoforms, both of which exist in the hippocampus. Examination of these results suggests that simultaneous full occupation of both lipophilic pockets L2 and L(Di) may favor α2 selectivity. Since diindoles overlay well with pyrazoloquinolinones in the pharmacophore/receptor model, a series of rigid diindoles were tested in vitro on recombinant BzR isoforms. These ligands exhibited similar pharmacological profiles to β-carbolines for they did not fully interact with lipophilic pocket L2. Many rigid diindoles bound potently to all DS sites, which provides further evidence that pharmacophoric descriptors H1, H2 and L1 (two hydrogen bonding sites and a lipophilic pocket, see Figure 1) are well conserved in BzR subtypes.