448224-88-2

Basic information

• Product Name: 2-[(Bromoacetyl)amino]-4-(4-chlorophenyl)-1,3-thiazole, N-(Bromoacetyl)-4-(4-chlorophenyl)-1,3-thiazol-2-amine
• Synonyms: 2-[(Bromoacetyl)amino]-4-(4-chlorophenyl)-1,3-thiazole, N-(Bromoacetyl)-4-(4-chlorophenyl)-1,3-thiazol-2-amine;2-Bromo-N-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]acetamide
• CAS NO: 448224-88-2
• Molecular Formula: C₁₁H₈BrClN₂OS
• Molecular Weight: 331.61602
• Mol File: 448224-88-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-[(Bromoacetyl)amino]-4-(4-chlorophenyl)-1,3-thiazole, N-(Bromoacetyl)-4-(4-chlorophenyl)-1,3-thiazol-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(Bromoacetyl)amino]-4-(4-chlorophenyl)-1,3-thiazole, N-(Bromoacetyl)-4-(4-chlorophenyl)-1,3-thiazol-2-amine(448224-88-2)
• EPA Substance Registry System: 2-[(Bromoacetyl)amino]-4-(4-chlorophenyl)-1,3-thiazole, N-(Bromoacetyl)-4-(4-chlorophenyl)-1,3-thiazol-2-amine(448224-88-2)

Safety Data

• Hazardous Substances Data: 448224-88-2(Hazardous Substances Data)

Usage

2-[(Bromoacetyl)amino]-4-(4-chlorophenyl)-1,3-thiazole

A 1,3-thiazole ring with a bromoacetyl group attached to the amino group.

N-(Bromoacetyl)-4-(4-chlorophenyl)-1,3-thiazol-2-amine

A 1,3-thiazole ring with a bromoacetyl group attached to the nitrogen atom.

Amino derivative

In the first compound, the 1,3-thiazole ring has an amino group (-NH2) functional group.

Amine derivative

In the second compound, the 1,3-thiazole ring has an amine group (-NH) functional group.

Bromine

Both compounds have a bromoacetyl group (BrCH2CO-) attached to the nitrogen atom.

Chlorine

Both compounds have a 4-(4-chlorophenyl) group attached to the thiazole ring.

Thiazole derivatives

Both compounds are derivatives of the 1,3-thiazole ring, which is a five-membered heterocyclic ring containing sulfur and nitrogen atoms.

Biological activities and therapeutic applications

Thiazole derivatives are known for their diverse biological activities and potential therapeutic applications in pharmaceutical and agrochemical research.

Reactivity

Due to the presence of the amino and amine functional groups, both compounds may undergo various chemical reactions such as nucleophilic substitution, acylation, and condensation.

Stability

The presence of the halogen atoms and the aromatic 4-(4-chlorophenyl) group may contribute to the stability of the compounds.

Upstream product

• 2103-99-3 4-(4-chlorophenyl)-2-thiazolamine 
• 598-21-0 2-Bromoacetyl bromide 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 99-91-2 para-chloroacetophenone 

Relevant articles and documents

Novel 4-(piperazin-1-yl)quinolin-2(1H)-one bearing thiazoles with antiproliferative activity through VEGFR-2-TK inhibition

A new series of 2-(4-(2-oxo-1,2-dihydroquinolin-4-yl)piperazin-1-yl)-N-(4-phenylthiazol-2-yl)acetamide derivatives were synthesized and evaluated for anticancer activity. All target compounds showed anticancer activity higher than that of their 2-oxo-4-piperazinyl-1,2-dihydroquinolin-2(1H)-one precursors. Multidose testing of target compounds was performed against breast cancer T-47D cell line. Five compounds showed higher cytotoxic activity than Staurosporine. The dihalogenated derivative showed the best cytotoxic activity with IC50 2.73 ± 0.16 μM. In addition, the VEGFR-2 inhibitory activity of all synthetic compounds was evaluated. Two compounds of 6-fluoro-4-(piperazin-1-yl)quinolin-2(1H)-ones showed inhibitory activity comparable to sorafenib with IC50 46.83 ± 2.4, 51.09 ± 2.6 and 51.41 ± 2.3 nM, respectively. The cell cycle analysis of two compounds namely, 2-(4-(6-fluoro-2-oxo-1,2-dihydroquinolin-4-yl)piperazin-1-yl)-N-(4-phenylthiazol-2-yl)acetamide and N-(4-(4-chlorophenyl)thiazol-2-yl)-2-(4-(2-oxo-1-phenyl-1,2-dihydroquinolin-4-yl)piperazin-1-yl)acetamide revealed that the arrest of cell cycle occurred at S phase. In apoptosis assay, the same two compounds were able to induce significant levels of early and late apoptosis. In a similar manner to Sorafenib, docking of target compounds with VEGFR-2 protein 4ASD showed HB with Cys919 in hinge region of enzyme and HB with both Glu885 and Asp1046 in gate area. Using SwissADME, all target compounds were predicted to be highly absorbed from gastrointestinal tract with no BBB permeability. It is clear that the two compounds are promising antiproliferative candidates that require further optimization.

Synthesis and evaluation of 5,6-disubstituted thiopyrimidine aryl aminothiazoles as inhibitors of the calcium-activated chloride channel TMEM16A/Ano1

Transmembrane protein 16A (TMEM16A), also called Ano1, is a Ca2+ activated Cl? channel expressed widely in mammalian epithelia, as well as in vascular smooth muscle and some tumors and electrically excitable cells. TMEM16A inhibitors have potential utility for treatment of disorders of epithelial fluid and mucus secretion, hypertension, some cancers and other diseases. 4-Aryl-2-amino thiazole T16Ainh-01 was previously identified by high-throughput screening. Here, a library of 47 compounds were prepared that explored the 5,6-disubstituted pyrimidine scaffold found in T16Ainh-01. TMEM16A inhibition activity was measured using fluorescence plate reader and short-circuit current assays. We found that very little structural variation of T16Ainh-01 was tolerated, with most compounds showing no activity at 10 μM. The most potent compound in the series, 9bo, which substitutes 4-methoxyphenyl in T16Ainh-01 with 2-thiophene, had IC50 ～1 μM for inhibition of TMEM16A chloride conductance.

FUSED PYRIMIDINE-DIONE DERIVATIVES AS TRPA1 MODULATORS

The invention described herein relates to novel fused pyrimidinediones derivatives of formula (I) which are TRPA (Transient Receptor Potential subfamily A) modulators. In particular, compounds described herein are useful for treating or preventing diseases, conditions and/or disorders modulated by TRPAl (Transient Receptor Potential subfamily A, member 1). This invention also provides processes for preparing compounds described herein, intermediates used in their synthesis, pharmaceutical compositions thereof, and methods for treating or preventing diseases, conditions and/or disorders modulated by TRPAl. Formula (I)

IMIDAZO [2,1-B] PURINE DERIVATIVES AS TRPA1 MODULATORS

The present invention provides TRPA (Transient Receptor Potential subfamily A) modulators. In particular, compounds described herein are useful for treating or preventing diseases, conditions and/or disorders modulated by TRPAl (Transient Receptor Potenti