24656-84-6

Upstream product

• 5470-96-2 quinoline 2-carbaldehyde 
• 104-94-9 4-methoxy-aniline 
• 67-56-1 methanol 
• 62-53-3 aniline 

Downstream Products

• 129239-53-8 2-[3-(4-Methoxy-phenyl)-3H-[1,2,3]triazol-4-yl]-quinoline 
• 129239-62-9 1-(4-methoxyphenyl)-5-(2-quinolyl)-1,2,3-triazoline 

Relevant academic research and scientific papers

Induction of the Endoplasmic Reticulum Stress Pathway by Highly Cytotoxic Organoruthenium Schiff-Base Complexes

Current anticancer drug discovery efforts focus on the identification of first-in-class compounds with a mode-of-action distinct from conventional DNA-targeting agents for chemotherapy. An emerging trend is the identification of endoplasmic reticulum (ER) targeting compounds that induce ER stress in cancer cells, leading to cell death. However, a limited pool of such compounds has been identified to date, and there are limited studies done on such compounds to allow for the rational design of ER stress-inducing agents. In our present study, we present a series of highly cytotoxic, ER stress-inducing Ru(II)-arene Schiff-Base (RAS) complexes, bearing iminoquinoline chelate ligands. We demonstrate that by structural modification to the iminoquinoline ligand, we could tune its -acidity and influence reactive oxygen species (ROS) induction, switching between a ROS-mediated ER stress pathway activation and one that is not mediated by ROS induction. Our current study adds to the available ER stress inducers and shows how structural tuning could be used as a means to modulate the mode-of-action of such compounds.

Structural tuning of organoruthenium compounds allows oxidative switch to control ER stress pathways and bypass multidrug resistance

Multidrug resistance (MDR) is a major impediment to the success of chemotherapy in many cancer types. One particular MDR mechanism is the inherent or acquired adaptation of the cellular survival pathways that render malignant cells resistant to apoptotic

New platinum(II)-based DNA intercalator: Synthesis, characterization and anticancer activity

Platinum agents with different action mechanisms from current platinum drugs can be effective candidates overcoming the resistance of platinum-based drugs. Platinum(II)-based DNA intercalators are potent candidate which act through mechanisms distinct fro

Structural determinants of p53-independence in anticancer ruthenium-arene Schiff-base complexes

p53 is a key tumor suppressor gene involved in key cellular processes and implicated in cancer therapy. However, it is inactivated in more than 50% of all cancers due to mutation or overexpression of its negative regulators. This leads to drug resistance

Iodine(III)-mediated C-H alkoxylation of aniline derivatives with alcohols under metal-free conditions

The development of a novel intermolecular oxidative C-H alkoxylation of aniline derivatives is described under metalfree conditions with high reaction rates at ambient temperature. In the presence of an I(III) oxidant, a range of aldehydes, anilines, and alcohol substrates undergo three-component coupling to produce synthetically useful alkoxyl-substituted N-arylimines. The preliminary mechanism investigations revealed that the transformation proceeds via imines as intermediates.

Chelated assisted metal-mediated N-H bond activation of β-lactams: Preparation of irida-, rhoda-, osma-, and ruthenatrinems

2-Azetidinones substituted with pyridine (2a), quinoline (2b), isoquinoline (2c), imidazole (2d), and benzimidazole (2e) at the 4-position of the four-membered ring have been prepared in order to synthesize tribactams containing a transition metal and its associated ligands, LnM, at the 2-position of the tricyclic skeleton. The developed procedure is compatible with a wide range of transition-metal starting complexes. Thus, the iridium and rhodium dimers [M(η5-C5Me5)Cl 2]2 react with 2a-e, in the presence of sodium acetate, to afford irida- and rhodatrinems (1a-j) containing the half-sandwich d 6 metal fragments M(η5-C5Me5)Cl (M = Ir, Rh). The reactions of [M(μ-OMe)(η4-COD)]2 (M = Ir, Rh) with 2a lead to irida- and rhodatrinems (1k,l) with the d 8 moieties M(η4-COD). The coordination sphere and oxidation state of the metal center in these compounds can be modified, without affecting the 2-azetidinone backbone, by means of substitution and oxidative addition reactions. As a proof of concept, metallatrinems with the M(CO) 2 (M = Ir (1m), Rh (1n)) and Ir(Me)I(CO)2 (1o) units are also reported. Osmatrinems 1p,q containing the d4 metal fragment OsH3(PiPr3)2 have been obtained starting from the d2 hexahydride OsH6(PiPr 3)2, by reaction with 2a,b, whereas the treatment of the tetrahydroborate complexes MH(η2-H2BH 2)(CO)(PiPr3)2 (M = Os, Ru) with 2a yields osma- and ruthenatrinems (1r,s) containing six-coordinate bis(phosphine) d6 metal fragments. The IR stretching frequency of the lactamic carbonyl, the bent angle between the five- and four-membered rings of the tricycle, and the N-CO bond length in the lactamic ring are clearly infuenced by the LnM fragment.

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.

Copper-catalyzed benzylic oxidation of C(sp3)-H bonds

A selective oxidation of benzylic C(sp3)-H bonds to C(sp 3)-O bonds catalyzed by copper complexes of quinoline-imine ligands was developed with peresters as oxidants under mild reaction conditions, which converted benzylic methylenes directly into benzylic alcohols and esters by means of direct C-H bond functionalization.