263239-23-2

Basic information

• Product Name: 2-CHLORO-N-(6-FLUORO-1,3-BENZOTHIAZOL-2-YL)ACETAMIDE
• Synonyms: Acetamide, 2-chloro-N-(6-fluoro-2-benzothiazolyl)-;2-Chloro-N-(6-fluorobenzo[d]thiazol-2-yl)acetamide
• CAS NO: 263239-23-2
• Molecular Formula: C₉H₆ClFN₂OS
• Molecular Weight: 244.68
• Mol File: 263239-23-2.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• Density: 1.579±0.06 g/cm3(Predicted)
• PKA: 8.24±0.70(Predicted)
• CAS DataBase Reference: 2-CHLORO-N-(6-FLUORO-1,3-BENZOTHIAZOL-2-YL)ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-N-(6-FLUORO-1,3-BENZOTHIAZOL-2-YL)ACETAMIDE(263239-23-2)
• EPA Substance Registry System: 2-CHLORO-N-(6-FLUORO-1,3-BENZOTHIAZOL-2-YL)ACETAMIDE(263239-23-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 263239-23-2(Hazardous Substances Data)

Usage

Description

2-Chloro-N-(6-fluoro-1,3-benzothiazol-2-yl)acetamide is a chemical compound with the molecular formula C10H7ClFN2OS. It is an acetamide derivative featuring a chloro and fluoro substitution on the benzothiazole ring. 2-CHLORO-N-(6-FLUORO-1,3-BENZOTHIAZOL-2-YL)ACETAMIDE is recognized for its potential medicinal properties, particularly in the treatment of neurological disorders and cancer. Moreover, it exhibits antibacterial and antifungal activities, highlighting its value in medicine and drug development.

Uses

Used in Pharmaceutical Industry:
2-Chloro-N-(6-fluoro-1,3-benzothiazol-2-yl)acetamide is utilized as a pharmaceutical intermediate for the synthesis of various drugs. Its unique structure and functional groups contribute to the development of new therapeutic agents.
Used in Neurological Disorder Treatment:
In the medical field, this compound serves as a potential treatment for neurological disorders due to its specific interactions with biological targets and mechanisms of action.
Used in Cancer Therapy:
2-Chloro-N-(6-fluoro-1,3-benzothiazol-2-yl)acetamide is also considered for cancer therapy, where it may exhibit anticancer properties and contribute to the development of novel cancer treatments.
Used in Antibacterial Applications:
2-CHLORO-N-(6-FLUORO-1,3-BENZOTHIAZOL-2-YL)ACETAMIDE's antibacterial activity makes it a candidate for use in the development of new antibiotics, addressing the need for effective treatments against bacterial infections.
Used in Antifungal Applications:
Similarly, its antifungal properties position 2-chloro-N-(6-fluoro-1,3-benzothiazol-2-yl)acetamide as a potential agent in the creation of antifungal medications, combating fungal infections effectively.

Upstream product

• 348-40-3 2-amino-6-fluoro-1,3-benzothiazole 
• 79-04-9 chloroacetyl chloride 
• 371-40-4 4-fluoroaniline 

Downstream Products

• 872057-68-6 C₁₉H₁₉FN₄OS 
• 1276539-03-7 4-(6-fluoro-1,3-benzothiazol-2-yl)amino-2-(4-hydroxyphenyl)amino-1,3-thiazole 
• 1276539-04-8 4-(6-fluoro-1,3-benzothiazol-2-yl)amino-2-(4-methoxyphenyl)amino-1,3-thiazole 
• 1276539-01-5 4-(6-fluoro-1,3-benzothiazol-2-yl)amino-2-phenylamino-1,3-thiazole 
• 1276539-02-6 4-(6-fluoro-1,3-benzothiazol-2-yl)amino-2-(4-chlorophenyl)amino-1,3-thiazole 
• 1373946-37-2 2-((4-(4,6-bis(3,5-dimethylpiperidin-1-yl)-1,3,5-triazin-2-yl)phenyl)amino)-N-(6-fluorobenzo[d]thiazol-2-yl)acetamide 

Relevant articles and documents

Design, synthesis, in vitro and in silico evaluation of a new series of oxadiazole-based anticancer agents as potential Akt and FAK inhibitors

In the current work, new 1,3,4-oxadiazole derivatives were synthesized and investigated for their cytotoxic effects on A549 human lung adenocarcinoma, C6 rat glioma and NIH/3T3 mouse embryonic fibroblast cell lines. Compounds 2, 6 and 9 were found to be the most potent anticancer agents against A549 and C6 cell lines and therefore their effects on apoptosis, caspase-3 activation, Akt, FAK, mitochondrial membrane potential and ultrastructural morphological changes were evaluated. N-(5-Nitrothiazol-2-yl)-2-[[5-[((5,6,7,8-tetrahydronaphthalen-2-yl)oxy)methyl]-1,3,4-oxadiazol-2-yl]thio]acetamide (9) increased early and late apoptotic cell population in A549 and C6 cells more than cisplatin and caused more mitochondrial membrane depolarization in both cell lines than cisplatin. On the other hand, N-(6-methoxybenzothiazol-2-yl)-2-[[5-[((5,6,7,8-tetrahydronaphthalen-2-yl)oxy)methyl]-1,3,4-oxadiazol-2-yl]thio]acetamide (6) caused higher caspase-3 activation than cisplatin in both cell lines. Compound 6 showed significant Akt inhibitory activity in both cell lines. Moreover, compound 6 significantly inhibited FAK (Phospho-Tyr397) activity in C6 cell line. Molecular docking simulations demonstrated that compound 6 fitted into the active sites of Akt and FAK with high affinity and substrate-specific interactions. Furthermore, compounds 2, 6 and 9 caused apoptotic morphological changes in both cell lines obtained from micrographs by transmission electron microscopy. A computational study for the prediction of ADME properties of all compounds was also performed. These compounds did not violate Lipinski's rule, making them potential orally bioavailable anticancer agents.

Design, synthesis, and biological evaluation of novel 1,3,4-thiadiazole derivatives as potential antitumor agents against chronic myelogenous leukemia: Striking effect of nitrothiazole moiety

In an attempt to develop potent antitumor agents, new 1,3,4-thiadiazole derivatives were synthesized and evaluated for their cytotoxic effects on multiple human cancer cell lines, including the K562 chronic myelogenous leukemia cell line that expresses the Bcr-Abl tyrosine kinase. N-(5-Nitrothiazol-2-yl)-2-((5-((4-(trifluoromethyl)phenyl)amino)-1,3,4-thiadiazol-2-yl)thio)acetamide (2) inhibited the Abl protein kinase with an IC50 value of 7.4 μM and showed selective activity against the Bcr-Abl positive K562 cell line. Furthermore, a Bcr-Abl-compound 2 molecular modelling simulation highlighted the anchoring role of the nitrothiazole moiety in bonding and hydrophobic interaction with the key amino acid residues. These results provide promising starting points for further development of novel kinase inhibitors.

Fighting against alzheimer’s disease: Synthesis of new pyrazoline and benzothiazole derivatives as new acetylcholinesterase and MAO inhibitors

Background: Alzheimer’s Disease (AD) is a complicated neurodegenerative disorder with a multifaceted pathogenesis.AD, characterized by gradual memory loss, falling in language ability and other cognitive deterioration, and has been a prominent risk to ageing population. This means that there is an urgent need to find new lead compounds for controlling and fighting against (AD). In this way, a new thiophene-2-pyrazoline derivatives (A1-A5) and benzothiazole derivatives (A6-A13) have been synthesized to give beneficial compounds to controlling and battling against (AD). Results: Compounds A5 and A13 showed the most remarkable activity with an 18.53 μM and 15.26 μM IC50 values against AChE enzyme. In like manner, compound A4 was active with a 20.34 μM IC50 value against MAO-A. These active compounds are in fact non-toxic making them very attractive for additional future studies. Enzyme kinetic was analyzed and the Lineweaver-Burk plot reveals that compound A13 was typically mixed AChE inhibitors, which showed significant similarity to donepezil. In addition, the best docking pose was done by analyzing the docking pattern of the most active compound A13 which was very compatible with the gorge and in interaction with both CAS and PAS. Conclusion: The synthesis of new thiophene-2-pyrazoline and benzothiazole derivatives targeting AChE/(MAO-A)/(MAO-B) enzymes was described. The selection of enzyme-kinetic analysis, molecular docking and toxicity test was led to good understanding to the therapeutic potential for the active derivatives. Therefore, these compounds may be accepted as promising leads for future research efforts in fighting against AD.