5603-15-6

Basic information

• Product Name: 4-[(quinolin-2(1H)-ylidenemethyl)imino]cyclohexa-2,5-dien-1-one
• CAS NO: 5603-15-6
• Molecular Formula: C₁₆H₁₂N₂O
• Molecular Weight: 248.2793
• Mol File: 5603-15-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 403.9°C at 760 mmHg
• Flash Point: 198.1°C
• Density: 1.17g/cm³
• Vapor Pressure: 9.85E-07mmHg at 25°C
• Refractive Index: 1.634
• CAS DataBase Reference: 4-[(quinolin-2(1H)-ylidenemethyl)imino]cyclohexa-2,5-dien-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(quinolin-2(1H)-ylidenemethyl)imino]cyclohexa-2,5-dien-1-one(5603-15-6)
• EPA Substance Registry System: 4-[(quinolin-2(1H)-ylidenemethyl)imino]cyclohexa-2,5-dien-1-one(5603-15-6)

Safety Data

• Hazardous Substances Data: 5603-15-6(Hazardous Substances Data)

Upstream product

• 5470-96-2 quinoline 2-carbaldehyde 
• 123-30-8 4-amino-phenol 

Downstream Products

• 477935-08-3 [(Z)-4-Hydroxy-phenylimino]-quinolin-2-yl-acetonitrile 

Relevant articles and documents

Discovery and investigation of anticancer ruthenium-arene Schiff-base complexes via water-promoted combinatorial three-component assembly

The structural diversity of metal scaffolds makes them a viable alternative to traditional organic scaffolds for drug design. Combinatorial chemistry and multicomponent reactions, coupled with high-throughput screening, are useful techniques in drug discovery, but they are rarely used in metal-based drug design. We report the optimization and validation of a new combinatorial, metal-based, three-component assembly reaction for the synthesis of a library of 442 Ru-arene Schiff-base (RAS) complexes. These RAS complexes were synthesized in a one-pot, on-a-plate format using commercially available starting materials under aqueous conditions. The library was screened for their anticancer activity, and several cytotoxic lead compounds were identified. In particular, [(η6-1,3,5-triisopropylbenzene)RuCl(4-methoxy-N-(2- quinolinylmethylene)aniline)]Cl (4) displayed low micromolar IC50 values in ovarian cancers (A2780, A2780cisR), breast cancer (MCF7), and colorectal cancer (HCT116, SW480). The absence of p53 activation or changes in IC50 value between p53+/+ and p53-/- cells suggests that 4 and possibly the other lead compounds may act independently of the p53 tumor suppressor gene frequently mutated in cancer.

A new facile method for preparation of heterocyclic α-iminonitriles and α-oxoacetic acid from heterocyclic aldehydes, p-aminophenol, and sodium cyanide

Very efficient, simple, and high yield procedures for the transformation of heterocyclic aldehydes into heterocyclic methylidene-p-hydroxyanilines, heterocyclic α-iminonitriles, and finally into heterocyclic α-oxoacetic acids were described. Considering that many of these compounds have biological activity, the synthetic methodology was optimized using readily available, inexpensive starting materials, and the purification of the product involved only simple crystallization.