1636-33-5

Usage

Uses

Used in Chemical Synthesis:
2-Naphthylisothiocyanate is used as a reagent in chemical synthesis for the preparation of thiourea derivatives. Its high reactivity with nucleophiles allows for the formation of stable adducts, which are essential in the creation of various organic compounds.
Used in Fluorescent Dye Synthesis:
In the field of fluorescent dyes, 2-Naphthylisothiocyanate is utilized for the synthesis of dyes that have specific applications in research and industry. The dyes can be used for labeling and visualizing molecules in various scientific studies.
Used in Pharmaceutical Industry:
2-Naphthylisothiocyanate is employed in the pharmaceutical industry for the synthesis of certain drugs. Its ability to form stable adducts with nucleophiles is crucial in the development of new pharmaceutical compounds.
Used in Agrochemicals:
2-naphthylisothiocyanate also finds use in the agrochemical sector, where it is involved in the synthesis of various agrochemical products. Its reactivity and ability to form stable adducts contribute to the development of effective agrochemicals.
Used in Amino Acid and Protein Analysis:
2-Naphthylisothiocyanate is used as a labeling agent in the analysis of amino acids and proteins. It can modify functional groups within these molecules, allowing for their detection and analysis in various biological assays.
Safety Considerations:
While 2-Naphthylisothiocyanate is not classified as highly toxic, it can cause irritation to the skin, eyes, and respiratory system upon contact or inhalation. Proper handling and safety measures are essential when working with 2-naphthylisothiocyanate.

InChI:InChI=1/C11H7NS/c13-8-12-11-6-5-9-3-1-2-4-10(9)7-11/h1-7H

Upstream product

• 6335-93-9 1-naphthalen-2-yl-3-phenyl-thiourea 
• 7647-01-0 hydrogenchloride 
• 479232-11-6 1-naphthalen-2-yl-3-o-tolyl-thiourea 
• 3674-54-2 tetrabutylammonium thiocyanate 
• 463-71-8 thiophosgene 
• 91-59-8 naphthalen-2-ylamine 
• 10124-78-4 2-napthylisocyanide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 110378-01-3 Naphthalen-2-yl-dithiocarbamic acid; compound with triethyl-amine 
• 81286-47-7 N-p-Tolyl-N'-β-naphthyl thiourea 
• 506-77-4 cyanogen chloride 
• 541-41-3 chloroformic acid ethyl ester 
• 75-15-0 carbon disulfide 
• 398-48-1 N-(2-naphthyl)-2,2,2-trifluoroacetamide 

Downstream Products

• 17931-25-8 2-chloronaphtho<2,1-d>thiazole 
• 17931-26-9 naphtho[2,1-d]thiazole-2(3H)-thione 
• 38560-12-2 1-[2]naphthyl-1,4-dihydro-tetrazolethione 
• 135-64-8 3-hydroxy-N-(2-naphthyl)-naphthamide 
• 30087-88-8 biphenyl-4-yl-(3-cyclohexyl-5-naphthalen-2-ylamino-2-thiophen-2-yl-2,3-dihydro-thiazol-4-yl)-methanone 
• 56914-07-9 1-naphthalen-2-yl-3-pyridin-2-ylmethyl-thiourea 
• 79009-30-6 1-Naphthalen-2-yl-3-thiobenzoyl-thiourea 
• 14938-75-1 benzaldehyde-(4-[2]naphthyl thiosemicarbazone) 
• 109806-13-5 4-methoxy-benzaldehyde-(4-[2]naphthyl thiosemicarbazone) 
• 1029234-53-4 C₁₈H₁₅N₃S 
• 77510-04-4 Naphthalen-2-yl-(3-phenyl-[1,2,4]thiadiazol-5-yl)-amine 
• 1238148-57-6 N-(5-methylisoxazol-3-yl)-4-(3-naphthalen-2-ylthioureido)benzenesulfonamide 

Relevant academic research and scientific papers

A more sustainable isothiocyanate synthesis by amine catalyzed sulfurization of isocyanides with elemental sulfur

Isothiocyanates (ITCs) are typically prepared using amines and highly toxic reagents such as thiophosgene, its derivatives, or CS2. In this work, an investigation of a multicomponent reaction (MCR) using isocyanides, elemental sulfur and amines revealed that isocyanides can be converted to isothiocyanates using sulfur and catalytic amounts of amine bases, especially DBU (down to 2 mol%). This new catalytic reaction was optimized in terms of sustainability, especially considering benign solvents such as Cyrene or γ-butyrolactone (GBL) under moderate heating (40 °C). Purification by column chromatography was further optimized to generate less waste by maintaining high purity of the product. Thus, E-factors as low as 0.989 were achieved and the versatility of this straightforward procedure was shown by converting 20 different isocyanides under catalytic conditions, while obtaining moderate to high yields (34-95%). This journal is

Organophosphine-free copper-catalyzed isothiocyanation of amines with sodium bromodifluoroacetate and sulfur

A copper-catalyzed isothiocyanation of amines with sodium bromodifluoroacetate and sulfur in the absence of organophosphine has been established. This approach represents a simple and efficient one-pot synthesis of isothiocyanates, and features excellent functional group tolerance and the use of a cheap, safe and odorless sulfur source. Moreover, this process could directly provide isothiocyanate analogous bioactive molecules, thiocarbonyl-containing pesticides and facile construction of benzoxazole and benzimidazole frames.

Isothiocyanate synthesized by three components and preparation method of isothiocyanate

The invention discloses isothiocyanate and a preparation method thereof. The method comprises the steps that primary amine, sodium difluorobromoacetate and elemental sulfur are taken as reactants forreaction; the reaction is carried out under the action of a copper catalyst, wherein the copper catalyst is any one of cuprous chloride, copper bromide, cuprous iodide, copper chloride and copper trifluoromethanesulfonate; an alkali is also added, wherein the alkali is any one of sodium bicarbonate, potassium carbonate, cesium carbonate, potassium phosphate, DABCO and sodium tert-butoxide; the whole reaction is carried out in a solvent, wherein the solvent is acetonitrile or dimethyl sulfoxide, the reaction temperature is 80-120 DEG C, and the reaction time is 10-14 hours. The method can directly synthesize the target product, does not need to separate intermediate products and only needs stirring and heating reaction under normal pressure to obtain the target product, and the yield can beup to 87%; a waste solution is fewer during the reaction, and the method protects the environment and ensures the health of an operator; in addition, a series of isothiocyanate derivatives can be prepared, and the method has a stronger substrate universality.

Synthesis, anti-proliferative activity, SAR, and kinase inhibition studies of thiazol-2-yl- substituted sulfonamide derivatives

A series of novel thiazol-2-yl substituted-1-sulfonamide derivatives were synthesized from anilines. This involved the coupling of sulfonyl chlorides with thiazol amine to obtain the final compounds 7a–7j and 8a–8j. All synthesized compounds were screened for anticancer activity against MCF-7, HeLa, A-549, and Du-145 cancer cell lines by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Preliminary bioassay suggests that most of the compounds show anti-proliferation to different degrees, with doxorubicin used as positive control. The synthesized compounds show IC50 values in the range 2.74–8.17 μM in the different cell lines. The compounds 7d, 7e, 8a, 8d, and 8e were active compared to doxorubicin. The compounds having butyl and pantyl chains were more active than their lower and higher carbon chains and also their ring counterparts.

Synthesis, structure-activity relationship and binding mode analysis of 4-thiazolidinone derivatives as novel inhibitors of human dihydroorotate dehydrogenase

A series of 4-thiazolidinone derivatives were synthesized and evaluated as novel human dihydroorotate dehydrogenase (hDHODH) inhibitors. Compounds 26 and 31 displayed IC50 values of 1.75 and 1.12 μM, respectively. The structure-activity relationship was summarized. Further binding mode analysis revealed that compound 31 could form a hydrogen bond with Tyr38 and a water-mediated hydrogen bond with Ala55, which may be necessary for maintaining the bioactivities of the compounds in this series. Further structural optimization of the para- or meta-position of the phenyl group at R will lead to the identification of more potent hDHODH inhibitors.

A metal-free synthesis of 2-aminobenzothiazoles through aminyl radical addition to aryl isothiocyanates

A convenient synthesis of 2-aminobenzothiazoles, starting from aryl isothiocyanates and formamides under metal-free conditions, is described. Various secondary and tertiary amine- and even α-amino acid-derived formamides can be used as amino sources in this process. Mechanistic studies suggest that the reaction is initiated by decarbonylative aminyl radical formation in the presence of n-Bu4NI and TBHP, followed by aminyl radical addition to isothiocyanates and cyclization via sulfur centred radical intermediates.

Design, synthesis, X-ray crystallographic analysis, and biological evaluation of thiazole derivatives as potent and selective inhibitors of human dihydroorotate dehydrogenase

Human dihydroorotate dehydrogenase (HsDHODH) is a flavin-dependent mitochondrial enzyme that has been certified as a potential therapeutic target for the treatment of rheumatoid arthritis and other autoimmune diseases. On the basis of lead compound 4, which was previously identified as potential HsDHODH inhibitor, a novel series of thiazole derivatives were designed and synthesized. The X-ray complex structures of the promising analogues 12 and 33 confirmed that these inhibitors bind at the putative ubiquinone binding tunnel and guided us to explore more potent inhibitors, such as compounds 44, 46, and 47 which showed double digit nanomolar activities of 26, 18, and 29 nM, respectively. Moreover, 44 presented considerable anti-inflammation effect in vivo and significantly alleviated foot swelling in a dose-dependent manner, which disclosed that thiazole-scaffold analogues can be developed into the drug candidates for the treatment of rheumatoid arthritis by suppressing the bioactivity of HsDHODH.

Novel selective and potent inhibitors of malaria parasite dihydroorotate dehydrogenase: Discovery and optimization of dihydrothiophenone derivatives

Taking the emergence of drug resistance and lack of effective antimalarial vaccines into consideration, it is of significant importance to develop novel antimalarial agents for the treatment of malaria. Herein, we elucidated the discovery and structure-activity relationships of a series of dihydrothiophenone derivatives as novel specific inhibitors of Plasmodium falciparum dihydroorotate dehydrogenase (PfDHODH). The most promising compound, 50, selectively inhibited PfDHODH (IC50 = 6 nM, with >14 000-fold species-selectivity over hDHODH) and parasite growth in vitro (IC50 = 15 and 18 nM against 3D7 and Dd2 cells, respectively). Moreover, an oral bioavailability of 40% for compound 50 was determined from in vivo pharmacokinetic studies. These results further indicate that PfDHODH is an effective target for antimalarial chemotherapy, and the novel scaffolds reported in this work might lead to the discovery of new antimalarial agents.

NOVEL BICYCLIC THIAZOLE COMPOUNDS

The present invention relates to novel bicyclic thiazole compounds that inhibit Traf2- and Nck-interacting kinase (TNIK), and as such are useful as TNIK inhibitors administered to cancer patients, especially to solid cancer patients such as colorectal cancer, pancreatic cancer, non-small cell lung cancer, prostate cancer or breast cancer. The bicyclic thiazole compounds are showed by a next formula (I). (wherein R1, R2, R3 and Q are as defined in the specification), or a pharmaceutically acceptable salt thereof.

Diversity-orientated synthesis of 3,5-bis(arylamino)pyrazoles

The synthesis of differentially-substituted 3,5-bis(arylamino)pyrazoles has not yet been documented. During our investigation, we managed to develop a novel, entirely combinatorial synthesis of 3,5-bis(arylamino)pyrazoles relying on a simple one-pot two-step operation.