5391-30-0

Basic information

• Product Name: 1-(2-BROMOPHENYL)-2-THIOUREA
• Synonyms: 2-BROMOPHENYLTHIOUREA;1-(2-BROMOPHENYL)-2-THIOUREA;N-(2-BROMOPHENYL)THIOUREA;Thiourea,(2-bromophenyl)-;1-(2-Bromophenyl)thiourea;Thiourea, N-(2-broMophenyl)-
• CAS NO: 5391-30-0
• Molecular Formula: C₇H₇BrN₂S
• Molecular Weight: 231.11
• Product Categories: Organic Building Blocks;Sulfur Compounds;Thioureas
• Mol File: 5391-30-0.mol

Chemical Properties

• Melting Point: 125-129 °C(lit.)
• Boiling Point: 314.2 °C at 760 mmHg
• Flash Point: 143.8 °C
• Appearance: /
• Density: 1.728 g/cm³
• Vapor Pressure: 0.000474mmHg at 25°C
• Refractive Index: 1.748
• Storage Temp.: 2-8°C
• BRN: 2718427
• CAS DataBase Reference: 1-(2-BROMOPHENYL)-2-THIOUREA(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-BROMOPHENYL)-2-THIOUREA(5391-30-0)
• EPA Substance Registry System: 1-(2-BROMOPHENYL)-2-THIOUREA(5391-30-0)

Safety Data

• Hazard Codes: T
• Statements: 25-38-43
• Safety Statements: 22-28-36/37/39-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 5391-30-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
1-(2-BROMOPHENYL)-2-THIOUREA is used as a research compound for its potential biological activities, including anti-inflammatory and antioxidant properties. It is valued for its potential as an enzyme inhibitor, which can be significant in the development of new drugs.
Used in Enzyme Inhibition:
In the field of biochemistry, 1-(2-BROMOPHENYL)-2-THIOUREA is used as an enzyme inhibitor, targeting specific enzymes that may be implicated in various diseases, thereby offering therapeutic benefits.
Used in Antimicrobial Applications:
1-(2-BROMOPHENYL)-2-THIOUREA is used as an antibacterial and antifungal agent, leveraging its potential to combat microbial infections, which is crucial in the development of new antimicrobial drugs.
Used in Medicinal Chemistry:
In the realm of medicinal chemistry, 1-(2-BROMOPHENYL)-2-THIOUREA is utilized for its unique chemical structure, which allows for further research and development into its therapeutic applications and mechanisms of action.

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

Upstream product

• 1147550-11-5 ammonium thiocyanate 
• 94718-79-3 o-bromoaniline hydrochloride 
• 333-20-0 potassium thioacyanate 
• 615-36-1 2-bromoaniline 
• 5391-29-7 N-(2-bromophenyl)-N'-benzoylthiourea 
• 13037-60-0 1-bromo-2-isothiocyanatobenzene 

Downstream Products

• 1201683-08-0 N-(2-(phenylthio)phenyl)cyanamide 
• 343269-59-0 N-(2-bromophenyl)cyanamide 
• 1309261-86-6 C₂₁H₁₃BrN₄OS 
• 1309261-65-1 3-(4-bromo-1,3-benzothiazol-2-yl)-2-phenylquinazolin-4(3H)-one 

Relevant articles and documents

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.

Chiral Benzothiazole Monofluoroborate Featuring Chiroptical and Oxygen-Sensitizing Properties: Synthesis and Photophysical Studies

Advances in personalized medicine are prompting the development of multimodal agents, that is, molecules that combine properties promoting various diagnostic and therapeutic applications. General approaches exploit chemical conjugation of therapeutic agen

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.

Straightforward convergent access to 2-arylated polysubstituted benzothiazoles

A modular access to 2,4 disubstituted benzothiazoles has been achieved though the intermediacy of 4-bromo-2-iodobenzothiazole. The difference in reactivity of both halogens was advantageously exploited to achieve sequential Suzuki-Miyaura cross-coupling g

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.

Design and synthesis of N-Aryl isothioureas as a novel class of gastric H+/K+-ATPase inhibitors

To find new H+/K+-ATPase inhibitors for the treatment of peptic ulcer disease, a series of novel N-aryl isothiourea derivatives were synthesized and their structures were identified by 1H NMR and GC-MS. The effects of these compounds on inhibiting gastric acid secretion were evaluated by the guinea pig stomach mucous membrane study with pantoprazole magnesium as a positive control. The results showed that, of the 37 N-aryl isothiourea compounds synthesized, 20 compounds have comparable or stronger gastric acid inhibitory activities than that of pantoprazole magnesium. The quantitative structure-activity relationships (QSARs) of the N-aryl isothiourea compounds were also studied by comparative molecular field analysis (CoMFA) computation, and the model structure that was supposed to give more powerful bioactivities was finally predicted. A series of novel N-aryl isothiourea derivatives were synthesized and evaluated for their effects of inhibiting gastric acid secretion using the guinea pig stomach mucous membrane study with pantoprazole magnesium as a positive control. Compounds 2c, 2e, and 2k have higher bioactivity. The quantitative structure-activity relationships also defined these structural requirements.

QSAR modeling of synthesized 3-(1,3-benzothiazol-2-yl) 2-phenyl quinazolin-4(3H)-ones as potent antibacterial agents

Present communication elicits the designing and synthesis of 3-(1,3-benzothiazol-2-yl) 2-phenyl quinazolin-4(3H)-ones as potential antibacterial agents. A number of substituted 2-amino benzothiazoles, 2-amino-5-[(E)-phenyl diazenyl] benzoic acid, and 2-phenyl-4H benzo[d] [1,3] oxazin-4-one were synthesized as the precursor substrates. The compounds were synthesized in excellent yields and the structures were corroborated on the basis of IR, 1H NMR, Mass, and elemental analysis data. These compounds were screened in vitro for their antibacterial activity against a representative panel of Gram positive and Gram negative bacteria and models were generated through quantitative structure-activity relationship (QSAR).The activity contributions due to structural and substituent effects were determined using sequential regression procedure. The antimicrobial assay data show that the synthesized compounds are found to manifest profound antimicrobial activity. Springer Science+Business Media, LLC 2011.

SUBSTITUTED BENZIMIDAZOLES, BENZOTHIAZOLES AND BENZOXAZOLES

The present invention relates to substituted benzimidazoles, benzothiazoles and benzoxazoles, processes for their preparation, medicaments containing these compounds and the use of these compounds for the preparation of medicaments.

A one-pot preparation of cyanamide from dithiocarbamate using molecular iodine

An efficient one-pot method for the synthesis of cyanamides from dithiocarbamate salts via a double desulfurization strategy using molecular iodine is disclosed. Dithiocarbamates, by the action of iodine yield isothiocyanates in situ, which on treatment with aqueous NH3 give thioureas. The thioureas so generated undergo further oxidative desulfurization with I2 giving corresponding cyanamides in good yields. Environmental benignity, cost effectiveness and high yields are the important attributes of this one pot procedure. The Royal Society of Chemistry 2009.

Synthesis of some new 4-{2-[(aryl)amino]-1,3-thiazol-4-yl}benzene-1,2-diols as possible antibacterial and antifungal agents

Some new 4-{2-[(aryl) amino]-1,3-thiazol-4-yl}benzene-1,2-diols are prepared and characterized by spectral analysis. The newly prepared compounds are studied for their antibacterial and antifungal activity. Interestingly, almost all the compounds are found to possess promising antibacterial and antifungal activity against all tested microorganisms. Copyright Taylor & Francis Group, LLC.