622-52-6

Usage

Uses

Used in Organic Synthesis:
4-METHYLPHENYLTHIOUREA is used as a reagent in organic synthesis for the production of heterocyclic compounds, which are important building blocks in the creation of various pharmaceuticals and chemical products.
Used in Pharmaceutical Industry:
4-METHYLPHENYLTHIOUREA is used as a precursor to pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Dye and Pigment Production:
In the dye and pigment industry, 4-METHYLPHENYLTHIOUREA is used as an intermediate in the production of various dyes and pigments, enhancing the color properties and stability of these products.
Used in Rubber Chemicals:
4-METHYLPHENYLTHIOUREA is utilized in the synthesis of rubber chemicals, improving the performance and durability of rubber products.
Used in Pesticide and Herbicide Production:
4-METHYLPHENYLTHIOUREA is also used as a component in the production of pesticides and herbicides, helping to control and manage pests and weeds in agricultural settings.
Used in Anti-Cancer Therapy Research:
4-METHYLPHENYLTHIOUREA has been studied for its potential use in anti-cancer therapy, exploring its ability to target and inhibit the growth of cancer cells.
Used in Anti-Diabetic Research:
Additionally, it has been investigated for its potential as an anti-diabetic agent, examining its capacity to manage and treat diabetes-related conditions.
Used as a Catalyst in Chemical Reactions:
4-METHYLPHENYLTHIOUREA is employed as a catalyst in various chemical reactions, facilitating and enhancing the efficiency of these processes.

InChI:InChI=1/C8H10N2S/c1-6-2-4-7(5-3-6)10-8(9)11/h2-5H,1H3,(H3,9,10,11)

Upstream product

• 13037-22-4 methyl (N-(4-methylphenyl))dithiocarbamate 
• 540-23-8 p-toluidine hydrochloride 
• 1147550-11-5 ammonium thiocyanate 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 333-20-0 potassium thioacyanate 
• 106-49-0 p-toluidine 
• 17356-08-0 thiourea 
• 6281-61-4 1-benzoyl-3-(4-methylphenyl)thiourea 
• 124-41-4 sodium methylate 
• 2941-78-8 2-Amino-5-methylbenzoic acid 
• 64-17-5 ethanol 
• 7664-41-7 ammonia 
• 7732-18-5 water 
• 106-43-4 para-chlorotoluene 

Downstream Products

• 99982-53-3 3-p-tolylcarbamimidoylmercapto-propane-1-sulfonic acid 
• 112584-15-3 N-(p-tolyl)thiazol-2-amine 
• 2536-91-6 6-methylbenzothiazol-2-ylamine 
• 39889-77-5 1-p-tolyl-1H-tetrazol-5-ylamine 
• 109497-76-9 N,N''-di-p-tolyl-μ-disulfido-dicarboxamidine; dihydrobromide 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 10532-64-6 N-(4-methylphenyl)cyanamide 
• 17385-68-1 2-(4-tolylamino)thiazol-4-one 
• 100061-42-5 (4-methyl-thiazol-2-yl)-p-tolyl-amine 
• 73318-36-2 N-(4-methylphenyl)-S-methylisothiourea 
• 16240-04-3 3-(4-methylphenyl)thiazolidine-2,4-dione 
• 20765-47-3 (N-p-tolyl-carbamimidoylmercapto)-acetic acid 
• 16098-04-7 2-[N-(p-methylphenylamino)]-4-phenyl-thiazole 
• 21261-92-7 6-Methyl-3-butyl-benzothiazolin-2-thion 

Relevant academic research and scientific papers

Retinoic acid derivative with multiple target points and preparation method and application thereof

The invention provides a retinoic acid derivative with multiple targets and a preparation method and application thereof A series of novel multi-target retinoic acid derivatives are designed and synthesized by taking a multi-target drug theory as guidance, taking Am580 as a parent nucleus and combining structural characteristics of Am580 to select N-hydroxyguanidine NO donors as NO sources, performing chemical modification on the NO donors to obtain a series of different donors, and coupling ester or amido bonds with the parent nucleus. Experiments prove that the derivative has the characteristics of higher activity, lower toxic and side effects and better anti-tumor effect. The structural general formula of the retinoic acid derivative with multiple target points is shown as the followingformula (I),.

Design, synthesis, and antipoliferative activities of novel substituted imidazole-thione linked benzotriazole derivatives

A new series of benzotriazole moiety bearing substituted imidazol-2-thiones at N1 has been designed, synthesized and evaluated for in vitro anticancer activity against the different cancer cell lines MCF-7(breast cancer), HL-60 (Human promyelocytic leukemia), and HCT-116 (colon cancer). Most of the benzotriazole analogues exhibited promising antiproliferative activity against tested cancer cell lines. Among all the synthesized compounds, BI9 showed potent activity against the cancer cell lines such as MCF-7, HL-60 and HCT-116 with IC50 3.57, 0.40 and 2.63 μM, respectively. Compound BI9 was taken up for elaborate biological studies and the HL-60 cells in the cell cycle were arrested in G2/M phase. Compound BI9 showed remarkable inhibition of tubulin polymerization with the colchicine binding site of tubulin. In addition, compound BI9 promoted apoptosis by regulating the expression of pro-apoptotic protein BAX and anti-apoptotic proteins Bcl-2. These results provide guidance for further rational development of potent tubulin polymerization inhibitors for the treatment of cancer.

Green and efficient synthesis of thioureas, ureas, primary: O -thiocarbamates, and carbamates in deep eutectic solvent/catalyst systems using thiourea and urea

An efficient and general catalysis process was developed for the direct preparation of various primary O-thiocarbamates/carbamates as well as monosubstituted thioureas/ureas by using thiourea/urea as biocompatible thiocarbonyl (carbonyl) sources. This procedure used choline chloride/tin(ii) chloride [ChCl][SnCl2]2 with a dual role as a green catalyst and reaction medium to afford the desired products in moderate to excellent yields. Moreover, the DES can be easily recovered and reused for seven cycles with no significant loss in its activity. Besides, the method shows very good performance for synthesizing the desired products on a large scale.

Eco-efficient one-pot tandem synthesis of 1-aryl-1H-tetrazol-5-amine by CAN via in situ generated 1-phenylthiourea and heterocumulene

A simple, cost-effective, environmentally benign, and efficient one-pot tandem approach to the synthesis of pharmaceutically important 1-aryl-1H-tetrazole-5-amines 3a-k and 4a-k has been described. The reaction utilized 1-phenyl thiourea, which was generated in situ from aqueous ammonia and isocyanates 1a-k, for the formation of heterocumenes using sodium azide, triethylamine, and ceric ammonium nitrate (CAN) to obtain various aryl-substituted 1H-tetrazole-5-amines (3a-k) in good to excellent yields.

Synthesis and biological evaluation of 3-amino-1,2,4-triazole derivatives as potential anticancer compounds

Two series of compounds carrying 3-amino-1,2,4-triazole scaffold were synthesized and evaluated for their anticancer activity against a panel of cancer cell lines using XTT assay. The 1,2,4-triazole synthesis was revisited for the first series of pyridyl derivatives. The biological results revealed the efficiency of the 3-amino-1,2,4-triazole core that could not be replaced and a clear beneficial effect of a 3-bromophenylamino moiety in position 3 of the triazole for both series (compounds 2.6 and 4.6) on several cell lines tested. Moreover, our results point out an antiangiogenic activity of these compounds. Overall, the 5-aryl-3-phenylamino-1,2,4-triazole structure has promising dual anticancer activity.

Synthetic (E)-3-phenyl-5-(phenylamino)-2-styryl-1,3,4-thiadiazol-3-ium chloride derivatives as promising chemotherapy agents on cell lines infected with HTLV-1

Synthesis of four compounds belonging to mesoionic class, (E)-3-phenyl-5-(phenylamino)-2-styryl-1,3,4-thiadiazol-3-ium chloride derivatives (5a-d) and their biological evaluation against MT2 and C92 cell lines infected with human T-cell lymphotropic virus type-1 (HTLV-1), which causes adult T-cell leukemia/lymphoma (ATLL), and non-infected cell lines (Jurkat) are reported. The compounds were obtained by convergent synthesis under microwave irradiation and the cytotoxicity was evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assays. Results showed IC50 values of all compounds in the range of 1.51-7.70 μM in HTLV-1-infected and non-infected cells. Furthermore, it was observed that 5b could induce necrosis after 24 h for Jurkat and MT2 cell lines. The experimental (fluorimetric method) and theoretical (molecular docking) results suggested that the mechanism of action for 5b could be related to its capacity to intercalate into DNA. Moreover, the preliminary pharmacokinetic profile of the studied compounds (5a-d) was obtained through human serum albumin (HSA) binding affinity using multiple spectroscopic techniques (circular dichroism, steady-state and time-resolved fluorescence), zeta potential and molecular docking calculations. The interaction HSA:5a-d is spontaneous and moderate (Ka ～ 104 M-1) via a ground-state association, without significantly perturbing both the secondary and surface structures of the albumin in the subdomain IIA (site I), indicating feasible biodistribution in the human bloodstream.

CuBr2 mediated synthesis of 2-Aminothiazoles from dithiocarbamic acid salts and ketones

In a one-pot procedure, CuBr2 has been used as a efficient desulfurizing agent in the synthesis of 2-aminothiazoles by the condensation of in situ-generated 1-substituted thioureas from their dithiocarbamic acid salts, with in situ-generated α-bromoketones from ketones. All reactions were carried out under optimized reaction conditions and gave the target products in 61–95% yield.

Discovery of novel pyrimidine-based benzothiazole derivatives as potent cyclin-dependent kinase 2 inhibitors with anticancer activity

To develop novel CDK2 inhibitors as anticancer agents, a series of novel pyrimidine-based benzothiazole derivatives were designed and synthesized. Initial biological evaluation demonstrated some of target compounds displayed potent antitumor activity in vitro against five cancer cell lines. Especially, the analogue 10s exhibited approximately potency with AZD5438 toward four cells including HeLa, HCT116, PC-3, and MDA-MB-231 with IC50 values of 0.45, 0.70, 0.92, 1.80 μM, respectively. More interestingly, the most highly active compound 10s in this study also possessed promising CDK2/cyclin A2 inhibitory activities with IC50 values of 15.4 nM, which was almost 3-fold potent than positive control AZD5438, and molecular docking studies revealed that the analogue bound efficiently with the CDK2 binding site. Further studies indicated that compound 10s could induce cell cycle arrest and apoptosis in a concentration-dependent manner. These observations suggest that pyrimidine-benzothiazole hybrids represent a new class of CDK2 inhibitors and well worth further investigation aiming to generate potential anticancer agents.

Design, synthesis and biological evaluation of novel semicarbazone-selenochroman-4-ones hybrids as potent antifungal agents

A series of novel 2,3-dihydro-4H-1-benzoselenin-4-one (thio)semicarbazone derivatives were designed and synthesized by using molecular hybridization approach. All the target compounds were characterized by HRMS and NMR and evaluated in vitro antifungal activity against five pathogenic strains. In comparison with precursor selenochroman-4-ones, the hybrid molecules in this study showed significant improvement in antifungal activities. Notably, compound B8 showed significant antifungal activity against other strains excluding Aspergillus fumigatus (0.25 μg/mL on Candida albicans, 2 μg/mL on Cryptococcus neoformans, 8 μg/mL on Candida zeylanoides and 2 μg/mL on fluconazole-sensitive strains of Candida albicans). Moreover, compounds B8, B9 and C2 also displayed most potent activities against four fluconazole-resistance strains. Especially the MIC values of the hybrid molecule B8 against fluconazole-resistant strains were in the range of 0.5–2 μg/mL. Therefore, the molecular hybridization approach in this study provided new ideas for the development of antifungal drug.

Phthaloyl Dichloride–DMF Mediated Synthesis of Benzothiazole-based 4-Formylpyrazole Derivatives: Studies on Their Antimicrobial and Antioxidant Activities

Benzothiazole-based pyrazole derivatives prepared by a molecular hybridization approach with an aim to influence the biological activity significantly. Efficient conversion of hydrazones 3a–k derived from their corresponding methyl ketones to 4-formylpyrazoles 4a–k was carried out at 60°C in dioxane, using the Vilsmeier–Haack reagent isolated from phthaloyl dichloride and N,N-dimethylformamide. The newly synthesized compounds 4a–k and hydrazones 3a–k were screened in vitro for their antimicrobial activities using the broth macrodilution method. The compounds 4a–k were also screened for their antioxidant activities using the DPPH radical scavenging assay. Some of the synthesized compounds showed significant antibacterial and antifungal activities as evident from their minimum inhibitory concentrations. Compound 4d showed remarkable antioxidant activity.