108618-27-5

Upstream product

• 408510-59-8 3-anilino-quinoline-4-carboxylic acid 
• 5332-24-1 3-bromoquinoline 
• 615-36-1 2-bromoaniline 
• 62-53-3 aniline 
• 591-50-4 iodobenzene 
• 580-17-6 3-aminoquinoline 
• 98-80-6 phenylboronic acid 
• 13669-42-6 3-quinolylcarboxaldehyde 
• 51934-46-4 3-Methylsulfenylquinoline 
• 139-66-2 diphenyl sulfide 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 603-33-8 triphenylbismuthane 
• 75353-47-8 acide amino-3-quinoleinecarboxylique-4 
• 848086-11-3 N-(2-bromophenyl)quinolin-3-amine 

Downstream Products

• 951647-76-0 1-methyl-3-(phenylamino)quinolin-1-ium iodide 
• 951647-77-1 1-(5-cyclohexylpentyl)-3-(phenylamino)quinolinium iodide 
• 951647-79-3 C₂₆H₂₇N₂⁽¹⁺⁾*I^(1-) 
• 480-26-2 cryptolepine 
• 109130-61-2 10-benzyl-10H-indolo[3,2-b]quinoline 
• 1268525-90-1 C₂₆H₃₂N₂ 
• 1342890-59-8 3,4-dimethoxy-N-phenyl-N-(quinolin-3-ylmethyl)benzenesulfonamide 

Relevant academic research and scientific papers

An Alternative Synthesis of 10H-Indolo[3,2-b]quinoline and its Selective N- Alkylation

A new and a more efficient synthesis of 10H-Indolo[3,2-b]quinoline (quindo line) is reported. The synthesis involved N-arylation of 3-aminoquinoline with triphenylbismuth diacet ate followed by oxidative cyclization using palladium (II) acetate. A selecti

Design, Synthesis, and Antifungal Evaluation of Cryptolepine Derivatives against Phytopathogenic Fungi

Inspired by the widely antiphytopathogenic application of diversified derivatives from natural sources, cryptolepine and its derivatives were subsequently designed, synthesized, and evaluated for their antifungal activities against four agriculturally important fungi Rhizoctonia solani, Botrytis cinerea, Fusarium graminearum, and Sclerotinia sclerotiorum. The results obtained from in vitro assay indicated that compounds a1-a24 showed great fungicidal property against B. cinerea (EC50 4 μg/mL); especially, a3 presented significantly prominent inhibitory activity with an EC50 of 0.027 μg/mL. In the pursuit of further expanding the antifungal spectrum of cryptolepine, ring-opened compound f1 produced better activity with an EC50 of 3.632 μg/mL against R. solani and an EC50 of 5.599 μg/mL against F. graminearum. Furthermore, a3 was selected to be a candidate to investigate its preliminary antifungal mechanism to B. cinerea, revealing that not only spore germination was effectively inhibited and the normal physiological structure of mycelium was severely undermined but also detrimental reactive oxygen was obviously accumulated and the normal function of the nucleus was fairly disordered. Besides, in vivo curative experiment against B. cinerea found that the therapeutic action of a3 was comparable to that of the positive control azoxystrobin. These results suggested that compound a3 could be regarded as a novel and promising agent against B. cinerea for its valuable potency.

Nickel-Catalyzed Amination of Aryl Thioethers: A Combined Synthetic and Mechanistic Study

Herein, we report a nickel-1,2-bis(dicyclohexylphosphino)ethane (dcype) complex for the catalytic Buchwald-Hartwig amination of aryl thioethers. The protocol shows broad applicability with a variety of different functional groups tolerated under the catalytic conditions. Extensive organometallic and kinetic studies support a nickel(0)-nickel(II) pathway for this transformation and revealed the oxidative addition complex as the resting state of the catalytic cycle. All the isolated intermediates have proven to be catalytically and kinetically competent catalysts for this transformation. The fleeting transmetalation intermediate has been successfully synthesized through an alternative synthetic organometallic pathway at lower temperature, allowing for in situ NMR study of the C-N bond reductive elimination step. This study addresses key factors governing the mechanism of the nickel-catalyzed Buchwald-Hartwig amination process, thus improving the understanding of this important class of reactions.

Palladium-Catalyzed Amination of Aryl Sulfides and Sulfoxides with Azaarylamines of Poor Nucleophilicity

The amination of aryl sulfides and sulfoxides with azaarylamines is investigated using a palladium-N-heterocyclic carbene (NHC) complex. Because azaarylamines are less nucleophilic than anilines, more reactive diaryl sulfides and sulfoxides are found to be suitable coupling partners that liberate better leaving arenethiolate or arenesulfenate anions, instead of aryl methyl sulfides as reported previously.

Structure-Activity Relationship for Small Molecule Inhibitors of Nicotinamide N-Methyltransferase

Nicotinamide N-methyltransferase (NNMT) is a fundamental cytosolic biotransforming enzyme that catalyzes the N-methylation of endogenous and exogenous xenobiotics. We have identified small molecule inhibitors of NNMT with >1000-fold range of activity and developed comprehensive structure-Activity relationships (SARs) for NNMT inhibitors. Screening of N-methylated quinolinium, isoquinolinium, pyrididium, and benzimidazolium/benzothiazolium analogues resulted in the identification of quinoliniums as a promising scaffold with very low micromolar (IC50 à 1 μM) NNMT inhibition. Computer-based docking of inhibitors to the NNMT substrate (nicotinamide)-binding site produced a robust correlation between ligand-enzyme interaction docking scores and experimentally calculated IC50 values. Predicted binding orientation of the quinolinium analogues revealed selective binding to the NNMT substrate-binding site residues and essential chemical features driving protein-ligand intermolecular interactions and NNMT inhibition. The development of this new series of small molecule NNMT inhibitors direct the future design of lead drug-like inhibitors to treat several metabolic and chronic disease conditions characterized by abnormal NNMT activity.

3-SUBSTITUTED QUINOLINIUM AND 7H-INDOLO[2,3-c]QUINOLINIUM SALTS AS NEW ANTIINFECTIVES

The present invention relates to quinolinium antiinfective agents in which the qunolinium nucleus is fused to an indole ring or the qunolinium nucleus is linked to a cyclic structure through an opened indole or a benzothiophene or benzofuran ring. The compound is further substituted with various substituent groups. The compounds are represented by formula (I), (II) and (III): Pharmaceutical compositions and methods of use are also included.

Design and synthesis of novel small-molecule inhibitors of the hypoxia inducible factor pathway

Hypoxia, a reduction in partial oxygen pressure, is a salient property of solid tumors. Hypoxia drives malignant progression and metastasis in tumors and participates in tumor resistance to radio- and chemotherapies. Hypoxia activates the hypoxia-inducible factor (HIF) family of transcription factors, which induce target genes that regulate adaptive biological processes such as anaerobic metabolism, cell motility, and angiogenesis. Clinical evidence has demonstrated that expression of HIF-1 is strongly associated with poor patient prognosis and activation of HIF-1 contributes to malignant behavior and therapeutic resistance. Consequently, HIF-1 has become an important therapeutic target for inhibition by small molecules. Herein, we describe the design and synthesis of small molecules that inhibit the HIF-1 signaling pathway. Many of these compounds exhibit inhibitory activity in the nanomolar range. Separate mechanistic studies indicate that these inhibitors do not alter HIF-1 levels but interfere with the ability of HIF-1α/HIF-1β to interact with cofactors p300/CBP to form an active transcriptional complex. (Figure presented)

A short and convenient synthesis and evaluation of the antiinfective properties of indoloquinoline alkaloids: 10H-indolo[3,2-b]quinoline and 7H-indolo[2,3-c]quinolines

(Chemical Equation Presented) 10H-Indolo[3,2-b]quinoline and 7H-indolo[2,3-c]quinoline have been synthesized in two steps using a modified approach to our previous reported method. Starting from commercially available 3-amino-quinoline and phenylboronic a

Antifungal and antiparasitic indoloquinoline derivates

A compound having the formula: wherein: R is an electron withdrawing or electron donating moiety; R5 and R10 may be the same or different and are a straight or branched 1-5 carbon or heteroatom chain substituted terminally by a cycloalkyl or aromatic ring, or other structural isomer or complex thereof; n is the position of substitution of R; Z is N—R10, O, S, S═O, CH2 or C═O; y is 1-5 and Q is Z or NH, with the proviso that, where Z is NH, N—CH3, S or O and Rn is H, R5 may not be CH3; as well as quaternary ammonium salts thereof and their use as pharmacological compositions and for methods of treatment.

Synthesis of 7H-indolo[2,3-c]quinolines: study of the Pd-catalyzed intramolecular arylation of 3-(2-bromophenylamino)quinolines under microwave irradiation

D-ring substituted 5-methyl-5H-indolo[2,3-c]quinolines (4) have been synthesized in three steps starting from commercially available 3-bromoquinoline (5) and 2-bromoanilines (6). The methodology consists of two consecutive palladium-catalyzed reactions: a