21327-14-0

Usage

Uses

Used in Pharmaceutical Research:
1-(3-Bromophenyl)-2-thiourea is used as a research compound for the development of new pharmaceuticals. Its unique chemical properties and reactivity make it a promising candidate for the synthesis of bioactive molecules and drug candidates.
Used in Organic Synthesis:
1-(3-Bromophenyl)-2-thiourea is used as an intermediate in the synthesis of other organic compounds. Its reactivity and the presence of the bromine atom allow for further functionalization and the creation of a variety of chemical entities.
Used in Analytical Chemistry:
1-(3-Bromophenyl)-2-thiourea is used as a reagent in analytical chemistry. Its unique properties can be leveraged for the development of new analytical methods and techniques.
Used in the Preparation of Novel Materials:
1-(3-Bromophenyl)-2-thiourea is used as a building block in the preparation of novel materials for various applications. Its unique structure and reactivity can contribute to the development of new materials with specific properties and functions.
Used in Halogenation Reactions:
1-(3-Bromophenyl)-2-thiourea is used as a reagent for halogenation reactions in organic synthesis. The presence of the bromine atom allows for the introduction of other halogens, expanding the synthetic potential of the compound.

InChI:InChI=1/C7H7BrN2S/c8-5-2-1-3-6(4-5)10-7(9)11/h1-4H,(H3,9,10,11)

Upstream product

• 89069-93-2 N-((3-bromophenyl)carbamothioyl)benzamide 
• 1147550-11-5 ammonium thiocyanate 
• 591-19-5 m-Bromoaniline 
• 463-56-9 thiocyanic acid 
• 333-20-0 potassium thioacyanate 
• 540-72-7 sodium thiocyanide 
• 56967-17-0 m-bromoaniline hydrochloride 
• 2131-59-1 3-bromophenyl isothiocyanate 

Downstream Products

• 98948-12-0 2-bromo-4-thioureido-phenylmercury ⁽¹⁺⁾; acetate 
• 67241-20-7 (3-bromo-phenyl)-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-amine 
• 67241-37-6 (3-bromo-phenyl)-[4-(2-chloro-5-methyl-phenyl)-thiazol-2-yl]-amine 
• 67241-45-6 [4-(2-bromo-5-methyl-phenyl)-thiazol-2-yl]-(3-bromo-phenyl)-amine 
• 88352-41-4 N-(3-Bromophenyl)-S-methyl isothiourea 
• 708997-95-9 N-(3-bromophenyl)-4-(4-pyridinyl)-1,3-thiazol-2-amine 
• 1309261-76-4 C₂₁H₁₃BrN₄OS 
• 1309261-87-7 C₂₁H₁₃BrN₄OS 
• 1309261-61-7 3-(5-bromo-1,3-benzothiazol-2-yl)-2-phenylquinazolin-4(3H)-one 
• 1309261-67-3 3-(7-bromo-1,3-benzothiazol-2-yl)-2-phenylquinazolin-4(3H)-one 
• 20358-05-8 7-bromo-1,3-benzothiazol-2-amine 

Relevant academic research and scientific papers

Cu(II)-N-benzyl-amino-1H-tetrazole complex immobilized on magnetic chitosan as a highly effective nanocatalyst for C-N coupling reactions

Herein, the synthesis of a novel catalytic nanosystem with high activity and easy recoverability through immobilization of Cu(II)-N-benzyl-amino-1H-tetrazole complex on magnetic chitosan (MCS-BAT-Cu(II)) is reported. The catalytic potential of MCS-BAT-Cu(II) catalyst has been assessed in C-N coupling reaction of 5-amino-1H-tetrazole with aryl halides. Various aryl iodides/bromides were successfully coupled using MCS-BAT-Cu(II) catalyst for the synthesis of 1-aryl-5-amino-1H-tetrazoles with excellent reaction yields. In addition, the magnetic catalyst was easily and effectively separated from the reaction mixture using an external magnet and reused five times without notable loss of catalytic activity.

Optimization of Benzothiazole and Thiazole Hydrazones as Inhibitors of Schistosome BCL-2

Limited therapeutic options are available for the treatment of human schistosomiasis caused by the parasitic Schistosoma flatworm. The B cell lymphoma-2 (BCL-2)-regulated apoptotic cell death pathway in schistosomes was recently characterized and shown to share similarities with the intrinsic apoptosis pathway in humans. Here, we exploit structural differences in the human and schistosome BCL-2 (sBCL-2) pro-survival proteins toward a novel treatment strategy for schistosomiasis. The benzothiazole hydrazone scaffold previously employed to target human BCL-XL was repurposed as a starting point to target sBCL-2. We utilized X-ray structural data to inform optimization and then applied a scaffold-hop strategy to identify the 5-carboxamide thiazole hydrazone scaffold (43) with potent sBCL-2 activity (IC50 30 nM). Human BCL-XL potency (IC50 13 nM) was inadvertently preserved during the optimization process. The lead analogues from this study exhibit on-target activity in model fibroblast cell lines dependent on either sBCL-2 or human BCL-XL for survival. Further optimization of the thiazole hydrazone class is required to exhibit activity in schistosomes and enhance the potential of this strategy for treating schistosomiasis.

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.

Chemical screening of novel strigolactone agonists that specifically interact with DWARF14 protein

Strigolactones (SLs) are a class of plant hormones that regulate shoot branching as well as being known as root-derived signals for parasitic and symbiotic interactions. The physical interaction between SLs and the DWARF14 (D14) receptor family can be examined by differential scanning fluorimetry (DSF) that monitors the changes in protein melting temperature (Tm). The Tm of D14 is lowered by bioactive SLs in DSF analysis. In this report, we screened the compounds that lower the Tm of Arabidopsis D14 (AtD14) as potential candidates for SL agonists using DSF analysis. Subsequent physiological analyzes revealed that 113D10 acts as a novel SL agonist in a D14-dependent manner. Intriguingly, 113D10 has a chemical structure different from natural SLs in that it does not possess an enol ether bond that connects to a methylbutenolide moiety. Moreover, 113D10 does not stimulate seed germination of root parasitic plants. Accordingly, 113D10 can be a useful tool for SL studies and agricultural applications.

Fe3O4@SiO2 nanoparticle supported ionic liquid for green synthesis of antibacterially active 1-carbamoyl-1-phenylureas in water

In the present work, we have designed a novel, heterogeneous and recyclable magnetic Br?nsted acidic ionic liquid based on 5-phenyl-1H-tetrazole. The {Fe3O4@SiO2@CH2)35-phenyl-1H-tetrazole-SO3H/Cl} ([FSTet-SO3H]Cl) was prepared via the immobilization of 5-phenyl-1H-tetrazole-bonded sulfonic acid onto the surface of silica-coated magnetic nanoparticles using 3-chloropropyltriethoxysilane as a linker. The catalyst was characterized by XRD, TEM, FESEM, EDS, TG-DTA, and FT-IR. The ability and high activity of this catalyst were demonstrated in the synthesis of 1-carbamoyl-1-phenylureas with good to excellent yields via a new, simple and one-pot procedure in aqueous media under reflux conditions. This procedure has advantages such as high yields, short reaction times, a simple methodology and work-up process, green reaction conditions, high stability, catalytic activity, and easy preparation, separation and reusability of the catalyst. The synthesis of these compounds was confirmed by FT-IR, 1H NMR, 13C NMR and CHN. In addition, we investigated the biological properties of the 1-carbamoyl-1-phenylureas as newly synthesized compounds. The described catalyst could be easily separated from the reaction mixture by additional magnetic force and reused several times without a remarkable loss of its catalytic activity and any considerable changes in the product yield and the reaction time.

JAK INHIBITORS

Disclosed is a series of JAK inhibitors, which specifically relates to a compound shown in formula (I) or pharmaceutically acceptable salts thereof.

Synergism of fused bicyclic 2-aminothiazolyl compounds with polymyxin B against: Klebsiella pneumoniae

A series of fused bicyclic 2-aminothiazolyl compounds were synthesized and evaluated for their synergistic effects with polymyxin B (PB) against Klebsiella pneumoniae (SIPI-KPN-1712). Some of the synthesized compounds exhibited synergistic activity. When 4 μg ml-1 compound B1 was combined with PB, it showed potent antibacterial activity, achieving 64-fold reduction of the MIC of PB. Furthermore, compound B1 showed prominent synergistic efficacy in both concentration gradient and time-kill curves in vitro. In addition, B1 combined with PB also exhibited synergistic and partial synergistic effect against E. coli (ATCC25922 and its clinical isolates), Acinetobacter baumannii (ATCC19606 and its clinical isolates), and Pseudomonas aeruginosa (Pae-1399).

Probing the ATP-Binding Pocket of Protein Kinase DYRK1A with Benzothiazole Fragment Molecules

DYRK1A has emerged as a potential target for therapies of Alzheimer's disease using small molecules. On the basis of the observation of selective DYRK1A inhibition by firefly d-luciferin, we have explored static and dynamic structural properties of fragment sized variants of the benzothiazole scaffold with respect to DYRK1A using X-ray crystallography and NMR techniques. The compounds have excellent ligand efficiencies and show a remarkable diversity of binding modes in dynamic equilibrium. Binding geometries are determined in part by interactions often considered "weak", including "orthogonal multipolar" types represented by, for example, F-CO, sulfur-aromatic, and halogen-aromatic interactions, together with hydrogen bonds that are modulated by variation of electron withdrawing groups. These studies show how the benzothiazole scaffold is highly promising for the development of therapeutic DYRK1A inhibitors. In addition, the subtleties of the binding interactions, including dynamics, show how full structural studies are required to fully interpret the essential physical determinants of binding.

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.

METALLO-BETA-LACTAMASE INHIBITORS

The present invention relates to compounds of formula I that are metallo-β-lactamase inhibitors, the synthesis of such compounds, and the use of such compounds for use with β-lactam antibiotics for overcoming resistance.