26197-93-3

Usage

Uses

Used in Scientific Research:
4-BROMO-THIOBENZAMIDE is used as a chemical intermediate for the synthesis and modification of various derivatives in chemical reactions. Its unique properties, particularly due to the presence of Bromine, make it a valuable compound in the development of new chemical entities and processes.
Used in Chemical Synthesis:
4-BROMO-THIOBENZAMIDE is used as a precursor in the synthesis of new compounds, contributing to the advancement of chemical research and the discovery of novel applications in various fields.
Used in Environmental Protection:
4-BROMO-THIOBENZAMIDE is used in the development of methods and technologies aimed at preventing its release into the environment, due to its harmful effects on ecosystems and potential for causing environmental damage.
Used in Safety and Health Protocols:
4-BROMO-THIOBENZAMIDE is used in the establishment of safety and health protocols to ensure that its handling, storage, and disposal are conducted in a manner that minimizes risks to human health and the environment.

InChI:InChI=1/C7H6BrNS/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H2,9,10)

Upstream product

• 623-00-7 4-bromobenzenecarbonitrile 
• 25062-46-8 4-bromobenzaldehyde oxime 
• 45708-95-0 (4-bromophenyl)methanimine 
• 698-67-9 p-bromobenzamide 
• 1122-91-4 4-bromo-benzaldehyde 
• 4486-44-6 O,O-diisopropylphosphorothioic acid 

Downstream Products

• 96159-83-0 2-(4-bromophenyl)-4,5-dihydro-1,3-thiazole 
• 28599-60-2 2-(4-bromo-phenyl)-4,5-dimethyl-thiazole 
• 96819-31-7 2-(4-Bromo-phenyl)-[1,3]thiazine-6-thione 
• 96819-35-1 2-(4-Bromo-phenyl)-5-methyl-[1,3]thiazine-6-thione 
• 17969-17-4 ethyl 2-(4-Bromophenyl)-thiazol-4-ylacetate 
• 95642-53-8 4-hydroxy-2-p-(bromophenyl)-6H-1,3-thiazin-6-one 
• 533867-29-7 2-(4-bromo-phenyl)-4-(4-trifluoromethyl-phenyl)thiazole 
• 61291-89-2 ethyl 4-methyl-2-(4-bromophenyl)-1,3-thiazole-5-carboxylate 
• 501006-33-3 C₁₅H₉BrN₂O₂S 
• 910324-55-9 2-(4-bromophenyl)-6-cyclobutyl-5,6,7,8-tetrahydro-4H-[1,3]thiazolo[4,5-d]azepine 
• 1218818-13-3 2-(4-bromophenyl)-5-octyl-4,5-dihydrothiazol-4-ol 
• 1265800-79-0 C₁₆H₂₀BrNS 
• 187998-67-0 methyl 2-(4-bromophenyl)-4-methylthiazole-5-carboxylate 
• 1313711-70-4 methyl 2-(4-bromophenyl)-4-(dibromomethyl)thiazole-5-carboxylate 

Relevant academic research and scientific papers

Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions

Aerobic visible-light induced intermolecular S?N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4-thiadiazoles can be obtained from thioamides. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single-electron-transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4-thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S?N bonds.

Efficient Synthesis and Bioevaluation of Novel Dual Tubulin/Histone Deacetylase 3 Inhibitors as Potential Anticancer Agents

Novel dual HDAC3/tubulin inhibitors were designed and efficiently synthesized by combining the pharmacophores of SMART (tubulin inhibitor) and MS-275 (HDAC inhibitor), among which compound 15cwas found to be the most potent and balanced HDAC3/tubulin dual inhibitor with high HDAC3 activity (IC50= 30 nM) and selectivity (SI > 1000) as well as excellent antiproliferative potency against various cancer cell lines, including an HDAC-resistant gastric cancer cell line (YCC3/7) with IC50values in the range of 30-144 nM. Compound 15cinhibited B16-F10 cancer cell migration and colony formation. In addition, 15cdemonstrated significantin vivoantitumor efficacy in a B16-F10 melanoma tumor model with a better TGI (70.00%, 10 mg/kg) than that of the combination of MS-275 and SMART. Finally, 15cpresented a safe cardiotoxicity profile and did not cause nephro-/hepatotoxicity. Collectively, this work shows that compound 15crepresents a novel tubulin/HDAC3 dual-targeting agent deserving further investigation as a potential anticancer agent.

Synthesis of imidazo[1,2-: C] thiazoles through Pd-catalyzed bicyclization of tert-butyl isonitrile with thioamides

Building new biological molecules is challenging. Herein, imidazo[1,2-c]thiazoles were synthesized as a new class of heterobicyclic analogs through Pd-catalyzed cascade bicyclization from isonitriles with thioamides. The bicyclic scaffolds were constructed by inserting three molecules of isonitrile into two molecules of thioamide and then cyclizing them in a one-pot procedure. In vitro antitumor studies of these new compounds were conducted by using the MTT assay, and compound 3c showed excellent inhibitory effects against HepG2 at 7.06 ± 0.68 μM.

A efficient protocol for the synthesis of thioamides in [DBUH][OAc] at room temperature

A novel, simple and eco-friendly method to synthesize thioamides from aryl nitriles and sodium sulfide (Na2S·9H2O) catalyzed by 1,8-diazabicyclo[5,4,0]undec-7-enium acetate ([DBUH][OAc]) ionic liquid (IL) at room temperature was developed in this paper. In this reaction, readily available inorganic salt (Na2S·9H2O) serves as the sulfur source, and various functional groups of aryl nitriles were well tolerated at room temperature. In addition, the products were easily separated from the IL which could be reused at least five times without considerable loss of its activity and applied in the green, concise synthesis of ethionamide.

Synthesis, crystal structure, anti-HIV, and antiproliferative activity of new oxadiazole and thiazole analogs

A series of 2-adamantyl-5-arylthiazolyl-1,3,4-oxadiazoles 7a–x together with thiazoles 13 and 14 were synthesized. Compounds 7a–l, 13, and 14 were tested in vitro with the aim of identifying novel lead compounds active against human immunodeficiency virus type-1 and human immunodeficiency virus type-2 activity in MT-4 cells. Title compounds were also tested against representatives of Gram-positive and Gram-negative bacteria (Staphylococcus aureus, Salmonella spp.), various mycobacterial strains (Mycobacterium fortuitum and Mycobacterium smegmatis), yeast (Candida albicans), and mold (Aspergillus fumigatus). None of the compounds showed antiviral or antimicrobial activity, except compounds 13 and 14 exhibited anti-human immunodeficiency virus-1 activity with EC50 values of 1.79 and 2.39 μM with Selectivity index = 18 and 4, respectively. On the other hand, compounds 7a and 7j showed a marked cytotoxicity against the human CD4+ lymphocytes (MT-4). Therefore, 7a and 7j were evaluated for their antiproliferative activity against two solid tumor-derived cell lines, which exhibited IC50 values of 8.1 ± 0.10 μM and 4.8 ± 0.08 μM against Hep-G2 cell lines, respectively.

Design and optimization of hybrid of 2,4-diaminopyrimidine and arylthiazole scaffold as anticancer cell proliferation and migration agents

Therapeutics of metastatic or triple-negative breast cancer are still challenging in clinical. Herein we demonstrated the design and optimization of a series of hybrid of 2,4-diaminopyrimidine and arylthiazole derivatives for their anti-proliferative properties against two breast cancer cell lines (MCF-7 as human breast cancer and MDA-MB-231 as triple-negative breast cancer). More importantly, some of those compounds with potent antiproliferative activities also indicated excellent inhibitory activities against MDA-MB-231 cell migration. These results suggested that the new series of hybridation of aryl-thiazoles and aminopyrimidines could be identified and developed as novel highly potential anticancer agents against the triple-negative breast cancer as well as metastatic one in the future.

Powerful Antibacterial Activity of Phenyl-Thiolatobismuth(III) Complexes Derived from Oxadiazolethiones

Seven novel 5-substituted phenylthiazole oxadiazolethiones: [Me-PTOT(H)], [MeO-PTOT(H)], [MeS-PTOT(H)], [F-PTOT(H)], [Cl-PTOT(H)], [Br-PTOT(H)], and [CF3-PTOT(H)], {where X-PTOT(H) = 5-[2-(4-X)thiazol-4-yl]-1,3,4-oxadiazole-2(3H)-thione, 4-X = C6H4}, were synthesised from their corresponding thioamides. From these seven heteroleptic thiolatobismuth complexes: BiPh(Me-PTOT)2 6, BiPh(MeO-PTOT)2 7, BiPh(MeS-PTOT)2 8, BiPh(F-PTOT)2 9, BiPh(Cl-PTOT)2 10, BiPh(Br-PTOT)2 11 and BiPh(CF3-PTOT)2 12 were synthesised and characterised. Complexes [10(DMSO)2] and [11(DMSO)2] were structurally characterised using X-ray diffraction. Evaluation of the antibacterial properties of the thiones and their BiIII complexes against Mycobacterium smegmatis, Staphylococcus aureus (S. aureus), Methicillin-resistant Staphylococcus aureus (MRSA), Vancomycin-resistant Enterococcus (VRE), Enterococcus faecalis (E. faecalis) and Escherichia coli (E. coli) showed that all bismuth(III) complexes were highly effective against all the bacteria, as demonstrated by very low MIC values (1.1-2.1 μM). Complexes BiPh(Me-PTOT)2 6, BiPh(Cl-PTOT)2 10 and BiPh(Br-PTOT)2 11, showed best activity against the multi-drug resistant bacteria VRE and MRSA with an MIC value of 1.0 μM. All these complexes and their corresponding thiones failed to show any prominent activity against M. smegmatis and E. coli, even at high concentrations. These complexes showed little or no toxicity towards mammalian COS-7 cells at 20 μg/mL. Seven heteroleptic thiolatobismuth(III) complexes [BiPh(X-PTOT)2] derived from a series of 5-substituted phenylthiazole oxadiazolethiones [X-PTOT(H)] provide powerful antibacterial action against the multi-resistant bacteria MRSA and VRE.

Metal-free, one-pot oxidative conversion of aldehydes to primary thioamides in aqueous media

One-pot tandem reactions of a variety of aldehydes with aqueous ammonia, molecular iodine, and O,O-diethyl dithiophosphoric acid readily afford the corresponding primary thioamides. This is an inexpensive, practical, and metal-free way of accessing various thioamides from aldehydes in aqueous media. The pure products are obtained simply by filtration followed by successive washing with aqueous sodium thiosulfate and water. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Agonists for the adenosine A1 receptor with tunable residence time. a case for nonribose 4-amino-6-aryl-5-cyano-2-thiopyrimidines

We report the synthesis and evaluation of previously unreported 4-amino-6-aryl-5-cyano-2-thiopyrimidines as selective human adenosine A 1 receptor (hA1AR) agonists with tunable binding kinetics, this without affecting their nanomolar affinity for the target receptor. They show a very diverse range of kinetic profiles (from 1 min (compound 52) to 1 h (compound 43)), and their structure-affinity relationships (SAR) and structure-kinetics relationships (SKR) were established. When put in perspective with the increasing importance of binding kinetics in drug discovery, these results bring new evidence of the consequences of affinity-only driven selection of drug candidates, that is, the potential elimination of slightly less active compounds that may display preferable binding kinetics.

Novel and versatile synthesis of disubstituted 1,2-dihydro-1,2,4-triazol-3- ones

A novel method for the synthesis of a wide range of 1,5-disubstituted 1,2-dihydro-1,2,4-triazol-3-ones is described. The key step involves a reaction between a dilithiated BOC-hydrazine and a N-alkoxycarbonylcarboximidothioate. A broad range of aryl and a