87393-53-1

Upstream product

• 5332-24-1 3-bromoquinoline 
• 13133-62-5 thiophenolate 
• 930-69-8 sodium thiophenolate 
• 108-98-5 thiophenol 
• 79476-07-6 3-Iodoquinoline 
• 882-33-7 diphenyldisulfane 
• 91-22-5 quinoline 
• 591-50-4 iodobenzene 
• 5219-64-7 2-methyl-2-(phenylthio)propanoic acid 
• 10490-07-0 2-phenyl-2-(phenylthio)acetic acid 
• 103-04-8 (phenylthio)acetic acid 
• 580-17-6 3-aminoquinoline 

Downstream Products

• 1265087-27-1 3-(phenylsulfanyl)-1-(5-cyclohexylpentyl)quinolin-1-ium iodide 
• 1265087-24-8 3-(phenylsulfanyl)-1-(5-phenylpentyl)quinolin-1-ium iodide 
• 1265087-21-5 1-methyl-3-(phenylthio)quinolinium iodide 

Relevant academic research and scientific papers

Generation of Thiyl Radicals from Air-Stable, Odorless Thiophenol Surrogates: Application to Visible-Light-Promoted C-S Cross-Coupling

The synthetic versatility of thiophenols is offset by their airsensitivity and foul odor. It is demonstrated that S-aryl isothiouronium salts can be used as precursors to thiyl radicals, extending the practical benefits of these air-stable, odorless salts from ionic to single electron manifolds. The isothiouronium salts are accessed via Ni-catalyzed crosscoupling of (hetero)aryl iodides and thiourea and are isolated as freeflowing solids following anion exchange. Judicious choice of a redox-innocent counteranion enables use of these convenient thiophenol surrogates in radical processes, as is exemplified by the synthesis of nonsymmetrical diaryl thioethers via light-promoted S-arylation.

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.

Metallaphotoredox-Catalyzed C-S Cross-Coupling between Heteroaryl Bromides and α-Thioacetic Acids to Access Biaryl Thioethers

Metallaphotoredox-catalyzed C-S cross-coupling between heteroaryl bromides and α-thioacetic acids to form biaryl thioethers is described herein. This transformation allows for cross-coupling between building blocks containing reactive functional groups, nitrogen heterocycles, and pharmaceutically relevant scaffolds. Mechanistic experiments indicate a unique means by which this C-S cross-coupling occurs.

Visible-Light-Driven Halogen-Bond-Assisted Direct Synthesis of Heteroaryl Thioethers Using Transition-Metal-Free One-Pot C-I Bond Formation/C-S Cross-Coupling Reaction

An efficient protocol for the synthesis of thioether directly from heteroarenes has been developed in the presence of visible light in a one-pot manner at room temperature. This method involves two sequential reactions in a single pot where the formation of the iodinated heteroarene is followed by a transition-metal-free C-S coupling reaction. A wide range of heteroarene and thiol partners (including aliphatic thiols) have been used for the synthesis of thioethers. NMR studies and DFT calculations revealed the presence of a halogen bond between the thiolate anion (halogen bond acceptor) and iodoheteroarene (halogen bond donor). This halogen bonded complex on photoexcitation facilitates the electron transfer from the thiolate anion to the iodoheteroarene at room temperature.

Iron(0) nanoparticles mediated direct conversion of aryl/heteroaryl amines to chalcogenides via in situ diazotization

A simple procedure for the synthesis of organo-chalcogenides has been developed by the reaction of aryl/heteroaryl amines with di-aryl/heteroaryl dichalcogenides in the presence of tBuONO and Fe(0) nanoparticles. The reaction proceeds via in situ diazotization followed by chalcogenation. A series of functionalized diaryl/aryl heteroaryl/diheteroaryl/aryl-alkyl selenides, sulfides and tellurides have been obtained by this procedure. Significantly, using this procedure 2,4-dinitroaniline is converted to (2,4-dinitrophenyl)(phenyl)selane which is known as thioredoxin reductase (TR) and glutathione reductase (GR) inhibitor. The reaction goes by a radical pathway and a plausible mechanism has been suggested.

Benzothieno[3,2-b]quinolinium and 3-(phenylthio)quinolinium compounds: Synthesis and evaluation against opportunistic fungal pathogens

Substitution around 5-methyl benzothieno[3,2-b]quinolinium (2) ring system was explored in order to identify positions of substitution that could improve its antifungal profile. The 3-methoxy (10b) was active against C. albicans, C. neoformans, and A. fum

Optimization of 3-(phenylthio)quinolinium compounds against opportunistic fungal pathogens

Ring-opened benzothieno[3,2-b]quinolinium salts (3) were designed and synthesized with substitution on the thiophene moiety. In vitro screenings were carried out against fungal pathogens including Cryptococcus neoformans, Candida albicans, Candida glabrat

Microwave-assisted synthesis of quinoline, isoquinoline, quinoxaline and quinazoline derivatives as CB2 receptor agonists

Quinoline, isoquinoline, quinoxaline, and quinazoline derivatives were synthesized using microwave-assisted synthesis and their CB1/CB2 receptor activities were determined using the [35S]GTPγS binding assay. Most of the prepared quinoline, isoquinoline, and quinoxalinyl phenyl amines showed low-potency partial CB2 receptor agonists activity. The most potent CB2 ligand was the 4-morpholinylmethanone derivative (compound 40e) (-log EC 50 = 7.8; Emax = 75%). The isoquinolin-1-yl(3- trifluoromethyl-phenyl)amine (compound 26c) was a high efficacy CB2 agonist (-log EC50 = 5.8; Emax = 128%). No significant CB1 receptor activation or inactivation was shown in these studies, except 40e, which showed weak CB1 agonist activity (CB1 -log EC50 = 5.0). These ligands serve as novel templates for the development of selective CB2 receptor agonist.

Palladium-catalyzed carbon-sulfur cross-coupling reactions with indium tri(organothiolate) and its application to sequential one-pot processes

(Chemical Equation Presented) It was found that indium tri(organothiolate) is an effective nucleophilic coupling partner in Pd-catalyzed C-S cross-coupling reactions to produce the functionalized sulfides in excellent yields with high atom efficiency and

Tributylmagnesium ate complex-mediated bromine-magnesium exchange of bromoquinolines: A convenient access to functionalized quinolines

2-, 3- and 4-bromoquinolines were converted to the corresponding lithium tri(quinolyl)magnesates at -10°C by treatment with Bu3MgLi in THF or toluene. The resulting organomagnesium derivatives were quenched by various electrophiles to afford functionalized quinolines.