21258-04-8

Basic information

• Product Name: N-Benzoyl-N'-(m-chlorophenyl)thiourea
• Synonyms: N-Benzoyl-N'-(m-chlorophenyl)thiourea;USAF K-1476
• CAS NO: 21258-04-8
• Molecular Formula: C₁₄H₁₁ClN₂OS
• Molecular Weight: 290.77
• Mol File: 21258-04-8.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• Density: 1.38g/cm³
• Refractive Index: 1.698
• CAS DataBase Reference: N-Benzoyl-N'-(m-chlorophenyl)thiourea(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzoyl-N'-(m-chlorophenyl)thiourea(21258-04-8)
• EPA Substance Registry System: N-Benzoyl-N'-(m-chlorophenyl)thiourea(21258-04-8)

Safety Data

• Hazardous Substances Data: 21258-04-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H11ClN2OS/c15-11-7-4-8-12(9-11)16-14(19)17-13(18)10-5-2-1-3-6-10/h1-9H,(H2,16,17,18,19)

Upstream product

• 1147550-11-5 ammonium thiocyanate 
• 98-88-4 benzoyl chloride 
• 108-42-9 3-chloro-aniline 
• 333-20-0 potassium thioacyanate 
• 65-85-0 benzoic acid 
• 532-55-8 Benzoyl isothiocyanate 

Downstream Products

• 1391013-06-1 N-(4-amino-3-(2-chloro-phenyl)-5-phenyl-3H-thiazol-ylidine)-benzamide 
• 3083-97-4 N-(5-chlorobenzo[d]oxazol-2-yl)benzamide 
• 56721-60-9 1-(3-Chloro-phenyl)-2-methyl-isothiourea; hydriodide 
• 1269603-78-2 (4S)-4-(N-benzyloxycarbonyl-2-aminoethyl)-2-[(3-chlorophenyl)amino]imidazoline 
• 1269487-68-4 (4S)-4-(N-benzyloxycarbonyl-2-aminoethyl)-2-[(3-chlorophenyl)amino]imidazoline hydrochloride 
• 88445-56-1 Pt(C₈H₄O₂N)2(C₁₄H₁₁N₂OSCl) 
• 88445-70-9 Pd(C₈H₄O₂N)2(C₁₄H₁₁N₂OSCl) 
• 88445-60-7 Co(C₈H₄O₂N)2(C₁₄H₁₁N₂OSCl) 
• 88445-62-9 Ni(C₈H₄O₂N)2(C₁₄H₁₁N₂OSCl)(H₂O)2 
• 88726-87-8 Cu(C₈H₄O₂N)2(C₁₄H₁₁N₂OSCl) 
• 324008-18-6 2-{2-[2-(3-chloro-phenylamino)-thiazol-4-yl]-ethyl}-isoindole-1,3-dione 
• 4947-89-1 1-(3-chlorophenyl)-2-thiourea 

Relevant articles and documents

Benzoylthioureas: Design, synthesis and antimycobacterial evaluation

Background: New drugs and strategies to treat tuberculosis (TB) are urgently needed. In this context, thiourea derivatives have a wide range of biological activities, including anti-TB. This fact can be illustrated with the structure of isoxyl, an old anti-TB drug, which has a thiourea as a pharmacophore group. Objective: The aim of this study is to describe the synthesis and the antimycobacterial activity of fifty-nine benzoylthioureas derivatives. Methods: Benzoylthiourea derivatives have been synthesized and evaluated for their activity against Mycobacterium tuberculosis using the MABA assay. After that, a structure-activity relationship study of this series of compounds has been performed. Results and Discussion: Nineteen compounds exhibited antimycobacterial activity between 423.1 and 9.6 μM. In general, we observed that the presence of bromine, chlorine and t-Bu group at the para-position in benzene ring plays an important role in the antitubercular activity of Series A. These substituents were fixed at this position in benzene ring and other groups such as Cl, Br, NO2 and OMe were introduced in the benzoyl ring, leading to the derivatives of Series B. In general, Series B was less cytotoxic than Series A, which indicates that the presence of a substituent at benzoyl ring contributes to an improvement in both antimycobacterial activity and toxicity profiles. Conclusion: Compound 4c could be considered a good prototype to be submitted to further structural modifications in the search for new anti-TB drugs, since it is 1.8 times more active than the first line anti-TB drug ethambutol and 0.65 times less active than isoxyl.

Effect of N-1 arylation of monastrol on kinesin Eg5 inhibition in glioma cell lines

An original and focused library of two sets of dihydropyrimidin-2-thiones (DHPMs) substituted with N-1 aryl groups derived from monastrol was designed and synthesized in order to discover a more effective Eg5 ligand than the template. Based on molecular docking studies, four ligands were selected to perform pharmacological investigations against two glioma cell lines. The results led to the discovery of two original compounds, called 20h and 20e, with an anti-proliferative effects, achieving IC50 values of about half that of the IC50 of monastrol in both cell lines. As with monastrol, flow cytometry analyses showed that the 20e and 20h compounds induced cell cycle arrest in the G2/M phase, and immunocytochemistry essays revealed the formation of monopolar spindles due to Eg5 inhibition without any toxicity to Caenorhabditis elegans.

Synthesis and antitumor evaluation of 5-(benzo[: D] [1,3]dioxol-5-ylmethyl)-4-(tert -butyl)- N -arylthiazol-2-amines

A series of novel N-aryl-5-(benzo[d][1,3]dioxol-5-ylmethyl)-4-(tert-butyl)thiazol-2-amines (C1-C31) were synthesized and evaluated for their antitumor activities against HeLa, A549 and MCF-7 cell lines. Some tested compounds showed potent growth inhibition properties with IC50 values generally below 5 μM against the three human cancer cells lines. Compound C27 showed potent activities against HeLa and A549 cell lines with IC50 values of 2.07 ± 0.88 μM and 3.52 ± 0.49 μM, respectively. Compound C7 (IC50 = 2.06 ± 0.09 μM) was the most active compound against A549 cell line, while compound C16 (IC50 = 2.55 ± 0.34 μM) showed the best inhibitory activity against the MCF-7 cell line. The preliminary mechanism of the inhibitory effect was investigated via further experiments, such as morphological analysis by dual AO/EB staining and Hoechst 33342 staining, and cell apoptosis and cycle assessment by FACS analysis. The results illustrated that compound C27 could induce apoptosis and cause both S-phase and G2/M-phase arrests in HeLa cell line. Therefore, compound C27 could be developed as a potential antitumor agent.