1780-17-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Quinolinylmethyl is used as an intermediate in the synthesis of aminopiperidines and related compounds. These compounds act as MCH receptor modulators, which are useful in the treatment of metabolic, feeding, and sexual disorders in humans. The modulation of MCH receptors by these compounds can help regulate various physiological processes and provide therapeutic benefits for patients suffering from these disorders.

InChI:InChI=1/C10H9NO/c12-7-9-6-5-8-3-1-2-4-10(8)11-9/h1-6,12H,7H2

Upstream product

• 5470-96-2 quinoline 2-carbaldehyde 
• 4377-41-7 2-Chloromethylquinoline 
• 60483-07-0 acetic acid quinolin-2-ylmethyl ether 
• 83798-34-9 2-Pyrrolidinomethylchinolin-1-oxid 
• 91850-85-0 <1,2,3>triazolo<1,5-a>quinoline-3-carboxylic acid 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 65094-35-1 2-[(trimethylsilyl)methyl]quinoline 
• 91850-86-1 3-(N,N-diethylcarbamoyl)<1,2,3>triazolo<1,5-a>quinoline 
• 76253-74-2 2-(chloromethyl)quinoline N-oxide 
• 91-63-4 2-methylquinoline 
• 163733-96-8 3,4,5-trifluoro aniline 
• 63430-79-5 1,2,3,4-tetrahydro-quinoline-2-carboxylic acid methyl ester 
• 63430-96-6 1,2,3,4-tetrahydroquinolin-2-ylmethanol 
• 93-10-7 quinoline-2-carboxylic acid 

Downstream Products

• 61831-29-6 quinolin-2-ylmethyl benzoate 
• 5470-96-2 quinoline 2-carbaldehyde 
• 4377-41-7 2-Chloromethylquinoline 
• 13425-28-0 phenyl-carbamic acid-[2]quinolylmethyl ester 
• 91-63-4 2-methylquinoline 
• 5760-20-3 2-aminomethylquinoline 
• 18004-62-1 quinolin-2-ylmethanamine bischlorohydrate 
• 110490-58-9 Ν-(4-methylphenyl)quinoline-2-carboxamide 
• 22765-54-4 N-(3-chlorophenyl)quinoline-2-carboxamide 

Relevant academic research and scientific papers

Synthesis of new chiral 2-functionalized-1,2,3,4-tetrahydroquinoline derivatives via asymmetric hydrogenation of substituted quinolines

The asymmetric hydrogenation of a series of quinolines substituted by a variety of functionalized groups linked to the C2 carbon atom is providing access to optically enriched 2-functionalized 1,2,3,4-tetrahydroquinolines in the presence of in situ generated catalysts from [Ir(cod)Cl]2, a bisphosphine, and iodine. The enantioselectivity levels were as high as 96% ee.

Highly enantioselective hydrogenation of new 2-functionalized quinoline derivatives

The asymmetric hydrogenation of a new series of 2-functionalized quinolines has been developed in the presence of in situ generated catalysts obtained from [Ir(cod)Cl]2/(R)-bisphosphine/I2 combinations. The enantioselectivity levels

A new, convenient, highly selective free-radical hydroxymethylation of heteroaromatic bases by persulfate oxidation of ethylene glycol and glycerol, catalysed by AgNO3

A new, convenient and selective source of hydroxymethyl ( .CH2OH) radical has been developed by persulfate oxidation of ethylene glycol with AgNO3 catalysis. The .CH 2OH radical is selectively trapped

Unprecedented Reaction Pathway of Sterically Crowded Calcium Complexes: Sequential C?N Bond Cleavage Reactions Induced by C?H Bond Activations

Five bis(quinolylmethyl)-(1H-indolylmethyl)amine (BQIA) compounds, that is, {(quinol-8-yl-CH2)2NCH2(3-Br-1H-indol-2-yl)} (L1H) and {[(8-R3-quinol-2-yl)CH2]2NCH(R2)[3-R1-1H-indol-2-yl]} (L2–5H) (L2H: R1=Br, R2=H, R3=H; L3H: R1=Br, R2=H, R3=iPr; L4H: R1=H, R2=CH3, R3=iPr; L5H: R1=H, R2=nBu, R3=iPr) were synthesized and used to prepare calcium complexes. The reactions of L1–5H with silylamido calcium precursors (Ca[N(SiMe2R)2]2(THF)2, R=Me or H) at room temperature gave heteroleptic products (L1, 2)CaN(SiMe3)2 (1, 2), (L3, 4)CaN(SiHMe2)2 (3 a, 4 a) and homoleptic complexes (L3, 5)2Ca (D3, D5). NMR and X-ray analyses proved that these calcium complexes were stabilized through Ca???C?Si, Ca???H?Si or Ca???H?C agostic interactions. Unexpectedly, calcium complexes ((L3–5)CaN(SiMe3)2) bearing more sterically encumbered ligands of the same type were extremely unstable and underwent C?N bond cleavage processes as a consequence of intramolecular C?H bond activation, leading to the exclusive formation of (E)-1,2-bis(8-isopropylquinol-2-yl)ethane.

Structural Basis for Developing Multitarget Compounds Acting on Cysteinyl Leukotriene Receptor 1 and G-Protein-Coupled Bile Acid Receptor 1

G-protein-coupled receptors (GPCRs) are the molecular target of 40% of marketed drugs and the most investigated structures to develop novel therapeutics. Different members of the GPCRs superfamily can modulate the same cellular process acting on diverse pathways, thus representing an attractive opportunity to achieve multitarget drugs with synergic pharmacological effects. Here, we present a series of compounds with dual activity toward cysteinyl leukotriene receptor 1 (CysLT1R) and G-protein-coupled bile acid receptor 1 (GPBAR1). They are derivatives of REV5901-the first reported dual compound-with therapeutic potential in the treatment of colitis and other inflammatory processes. We report the binding mode of the most active compounds in the two GPCRs, revealing unprecedented structural basis for future drug design studies, including the presence of a polar group opportunely spaced from an aromatic ring in the ligand to interact with Arg792.60 of CysLT1R and achieve dual activity.

STIMULI - OR BIO- RESPONSIVE COPOLYMERS, THE POLYMERSOMES COMPRISING THE SAME AND THEIR USE IN DRUG DELIVERY

The present invention concerns amphiphilic copolymers that may be photo- or redox-cleavable and that may assemble into polymersomes. It also concerns their process of preparation and their use as drug carriers.

Visible Light Induced Reduction and Pinacol Coupling of Aldehydes and Ketones Catalyzed by Core/Shell Quantum Dots

We present an efficient and versatile visible light-driven methodology to transform aryl aldehydes and ketones chemoselectively either to alcohols or to pinacol products with CdSe/CdS core/shell quantum dots as photocatalysts. Thiophenols were used as proton and hydrogen atom donors and as hole traps for the excited quantum dots (QDs) in these reactions. The two products can be switched from one to the other simply by changing the amount of thiophenol in the reaction system. The core/shell QD catalysts are highly efficient with a turn over number (TON) larger than 4 × 104 and 4 × 105 for the reduction to alcohol and pinacol formation, respectively, and are very stable so that they can be recycled for at least 10 times in the reactions without significant loss of catalytic activity. The additional advantages of this method include good functional group tolerance, mild reaction conditions, the allowance of selectively reducing aldehydes in the presence of ketones, and easiness for large scale reactions. Reaction mechanisms were studied by quenching experiments and a radical capture experiment, and the reasons for the switchover of the reaction pathways upon the change of reaction conditions are provided.

Hydroxymethylation of quinolinesviairon promoted oxidative C-H functionalization: synthesis of arsindoline-A and its derivatives

Herein, we report a mild and efficient hydroxymethylation of quinolinesviaan iron promoted cross-dehydrogenative coupling reaction under external acid free conditions. Various hydroxyalkyl substituted quinolines were achieved in excellent yields with well tolerated functional groups. Importantly, a few of the hydroxylmethylated quinolines were further transformed into respective aldehydes, and were successfully utilized for the synthesis of alkaloid arsindoline-A and its derivatives.

Multikilogram Synthesis of a Potent Dual Bcl-2/Bcl-xL Antagonist. 1. Manufacture of the Acid Moiety and Development of Some Key Reactions

Our efforts toward the process development of drug candidate 1 are described in a series of two papers. This manuscript focuses on the synthesis of kilogram quantities of acid precursor 2 to provide batches of material for preclinical studies and first-in

Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols

We have developed robust in vivo and in vitro biocatalytic systems that enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad substrate tolerance and provided information on the reactivity patterns of these substrates. E. coli cells expressing a heterologous CAR were employed as a multi-step hydrogenation catalyst to convert a variety of α,β-unsaturated carboxylic acids to the corresponding saturated primary alcohols, affording up to >99percent conversion. This was supported by the broad substrate scope of E. coli endogenous alcohol dehydrogenase (ADH), as well as the unexpected CC bond reducing activity of E. coli cells. In addition, a broad range of benzofused (hetero)aromatic carboxylic acids were converted to the corresponding primary alcohols by the recombinant E. coli cells. An alternative one-pot in vitro two-enzyme system, consisting of CAR and glucose dehydrogenase (GDH), demonstrates promiscuous carbonyl reductase activity of GDH towards a wide range of unsaturated aldehydes. Hence, coupling CAR with a GDH-driven NADP(H) recycling system provides access to a variety of (hetero)aromatic primary alcohols and allylic alcohols from the parent carboxylates, in up to >99percent conversion. To demonstrate the applicability of these systems in preparative synthesis, we performed 100 mg scale biotransformations for the preparation of indole-3-aldehyde and 3-(naphthalen-1-yl)propan-1-ol using the whole-cell system, and cinnamyl alcohol using the in vitro system, affording up to 85percent isolated yield.