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Usage

Uses

Used in Chemical Industry:
1-naphthalen-1-yl-3-phenylthiourea is used as a catalyst in the synthesis of organic compounds, facilitating various chemical reactions that are crucial for the production of a wide array of products.
Used in Rubber Chemicals Production:
In the rubber industry, 1-naphthalen-1-yl-3-phenylthiourea serves as a key component in the formulation of rubber chemicals, contributing to the enhancement of rubber properties such as durability and elasticity.
Used in Agriculture:
1-naphthalen-1-yl-3-phenylthiourea is utilized as a pesticide and herbicide in agricultural applications, helping to control pests and weeds that can damage crops and reduce yields.
Used in Pharmaceutical Research:
1-naphthalen-1-yl-3-phenylthiourea has been studied for its potential anti-inflammatory and anti-cancer properties, indicating its use as a subject of research in the development of new pharmaceuticals for the treatment of various diseases.

Upstream product

• 134-32-7 1-amino-naphthalene 
• 103-72-0 phenyl isothiocyanate 
• 62-53-3 aniline 
• 551-06-4 1-isothiocyanatonaphthalene 
• 67-66-3 chloroform 
• 29647-76-5 (naphth-1-ylamino)phenoxymethane-1-thione 
• 1240-37-5 N,N'-bis(1-naphthyl)thiourea 

Downstream Products

• 7669-41-2 (3-naphthalen-1-yl-4-oxo-2-phenylimino-thiazolidin-5-yl)-acetic acid 
• 14236-75-0 5-benzylidene-2-naphthalen-1-ylimino-3-phenyl-thiazolidin-4-one 
• 14230-07-0 (2-naphthalen-1-ylimino-4-oxo-3-phenyl-thiazolidin-5-ylidene)-acetic acid methyl ester 
• 111022-27-6 1-Naphthalen-1-yl-3-phenyl-thiourea; compound with 2,3-dicyano-but-2-enedinitrile 
• 134-32-7 1-amino-naphthalene 
• 103-72-0 phenyl isothiocyanate 
• 62-53-3 aniline 
• 551-06-4 1-isothiocyanatonaphthalene 
• 111089-71-5 methyl-naphtho[1,2-d]thiazol-2-yl-phenyl-amine 
• 101601-72-3 1-(1-naphthyl)-N--phenyl-1H-tetrazol-5-amine 
• 65672-98-2 naphthalen-1-yl-(3-phenyl-[1,3]thiazetidin-2-ylidene)-amine 
• 65672-97-1 (3-naphthalen-1-yl-[1,3]thiazetidin-2-ylidene)-phenyl-amine 
• 42135-78-4 4-(1-naphthyl)-3-thiosemicarbazide 
• 21431-44-7 naphtho[1,2-d]thiazol-2-yl-phenyl-amine 

Relevant academic research and scientific papers

A facile method for the preparation of carbodiimides from thioureas and (Boc)2O

A concise method for the preparation of carbodiimides from thioureas using di-tert-butyl dicarbonate [(Boc)2O] as the dehydrosulfurizative reagent has been developed. Using DMAP as the catalyst, a variety of symmetric and asymmetric 1,3-diaryl thioureas were converted into the corresponding carbodiimides efficiently in a short time.

Palladium catalyzed carbonylative annulation of the C(sp2)-H bond of N,1-diaryl-1H-tetrazol-5-amines and N,4-diaryl-4H-triazol-3-amines to quinazolinones

Pd(ii) catalyzed direct C-H carbonylative annulation of N,1-diaryl-1H-tetrazol-5-amines and N,4-diaryl-4H-1,2,4-triazol-3-amines gave the corresponding triazole and tetrazole fused quinazolinones in good yields. This methodology offers a convenient method for the synthesis of these important heterocyclic scaffolds in a highly atom economical process. On the mechanistic aspect weakly nucleophilic triazole and tetrazole moieties function as both directing as well as intramolecular nucleophiles. The catalytically active C-H activated intermediate dimeric Pd complex was isolated and characterized which on exposure to CO gas gave the corresponding tetrazole fused quinazolinone derivative. On the basis of isolation of the intermediate and observed kinetic isotope effects, a mechanism has been proposed for the C-H activated direct carbonylative annulation reaction.

Antileishmanial thioureas: Synthesis, biological activity and in Silico evaluations of new promising derivatives

Leishmaniasis is a neglected tropical disease caused by protozoan parasites belonging to the genus Leishmania. Currently, the drugs available for treatment of this disease present high toxicity, along with development of parasite resistance. In order to overcome these problems, efforts have been made to search for new and more effective leishmanicidal drugs. The aim of this study was to synthesize and investigate the leishmanicidal effect of N,N′-disubstituted thioureas against Leishmania amazonensis, with evaluation of their in silico pharmacokinetics and toxicity profiles. Our results showed that different thioureas could be obtained in high to moderate yields using simple reaction conditions. Nine thiourea derivatives (3e, 3i, 3k, 3l, 3p, 3q, 3v, 3x and 3z) were active against parasite promastigotes (IC50 21.48–189.10μM), with low cytotoxicity on mice peritoneal macrophages (CC50>200μM), except for thiourea 3e (CC50=49.22μM). After that, the most promising thioureas (3k, 3l, 3p, 3q and 3v) showed IC50 ranging from 70 to 150μM against L. amazonensis amastigotes in infected macrophages. Except for thiourea 3p, the leishmanicidal activity of the derivatives were independent of nitric oxide (NO) production. Thioureas 3q and 3v affected promastigotes cell cycle without disturbing the mitochondrial membrane potential. Furthermore, our derivatives showed satisfactory theoretical absorption, distribution, metabolism, excretion, toxicity (ADMET) properties. These data indicate that thiourea derivatives are good candidates as leading compounds for the development of new leishmanicidal drugs.

Thiocarbonyl Surrogate via Combination of Sulfur and Chloroform for Thiocarbamide and Oxazolidinethione Construction

An efficient and practical thiocarbonyl surrogate via combination of sulfur and chloroform has been developed. A variety of thiocarbamides and oxazolidinethiones have been established, including chiral thiourea catalysts and chiral oxazolidinethione auxiliaries with high selectivity. Meanwhile, pesticides Diafenthiuron (an acaricide), ANTU (a rodenticide), and Chloromethiuron (an insecticide) were practically synthesized through this method in gram scale. Dicholorocarbene, as the key intermediate, was further confirmed via a carbene-trapping control experiment.

Convenient synthesis of unsymmetrical N,N′-disubstituted thioureas in water

A simple and convenient two-step method has been developed and used to synthesise 25 (4 of which are novel) unsymmetrical N,N′-disubstituted thioureas in water. Alkylamines or variously substituted arylamines reacted smoothly with phenyl chlorothionoformate at room temperature to form thiocarbamates, which were then reacted with another alkyl- or arylamine in water at reflux to afford the unsymmetrical N,N′-disubstituted thioureas in good to excellent yields. Mild conditions, simple work-up, high yields as well as using water as solvent are the major advantages of the method.

Synthesis and antiplatelet activity of antithrombotic thiourea compounds: Biological and structure-activity relationship studies

The incidence of hematological disorders has increased steadily in Western countries despite the advances in drug development. The high expression of the multi-resistance protein 4 in patients with transitory aspirin resistance, points to the importance of finding new molecules, including those that are not affected by these proteins. In this work, we describe the synthesis and biological evaluation of a series of N,N′-disubstituted thioureas derivatives using in vitro and in silico approaches. New designed compounds inhibit the arachidonic acid pathway in human platelets. The most active thioureas (compounds 3d, 3i, 3m and 3p) displayed IC50 values ranging from 29 to 84 μM with direct influence over in vitro PGE2 and TXA2 formation. In silico evaluation of these compounds suggests that direct blockage of the tyrosyl-radical at the COX-1 active site is achieved by strong hydrophobic contacts as well as electrostatic interactions. A low toxicity profile of this series was observed through hemolytic, genotoxic and mutagenic assays. The most active thioureas were able to reduce both PGE2 and TXB2 production in human platelets, suggesting a direct inhibition of COX-1. These results reinforce their promising profile as lead antiplatelet agents for further in vivo experimental investigations.

Synthesis, phytotoxic, cytotoxic, acetylcholinesterase and butrylcholinesterase activities of N,N-diaryl unsymmetrically substituted thioureas

Fourteen N,N-diaryl unsymmetrically substituted thioureas were synthesised and their cytotoxic (in vitro), phytotoxic (in vitro), acetylcholinesterase and butrylcholinesterase activities were determined. Thiourea 16 exhibited high, and 1 and 3 showed significant phytotoxic activity. Thioureas 1, 3, 4, 6 and 10 showed significant activity and 2, 6 and 7 indicated moderate cytotoxic activities. Compound 12 exhibited butrylcholinesterase activity higher than a standard reference.

Ultrasound-promoted scavenging: A rapid parallel purification for solution phase combinatorial synthesis

Ultrasound irradiation enhances the mass transfer and reaction rate in scavenging, avoiding the trouble of time-consuming purification procedure in solution-phase parallel synthesis. An application of this technique is demonstrated in the scavenging of excess isothiocyanates from reaction mixtures.