3268-74-4

Basic information

• Product Name: 2-CHLORO-N-(6-ETHOXY-BENZOTHIAZOL-2-YL)-ACETAMIDE
• Synonyms: ASISCHEM C34529;2-CHLORO-N-(6-ETHOXY-BENZOTHIAZOL-2-YL)-ACETAMIDE;AKOS BBS-00005420;TIMTEC-BB SBB005217;2-chloro-N-(6-ethoxy-1,3-benzothiazol-2-yl)acetamide;2-chloro-N-(6-ethoxy-1,3-benzothiazol-2-yl)ethanamide;2-Chloro-N-(6-ethoxybenzo[d]thiazol-2-yl)acetamide
• CAS NO: 3268-74-4
• Molecular Formula: C₁₁H₁₁ClN₂O₂S
• Molecular Weight: 270.74
• Mol File: 3268-74-4.mol
• Article Data: 25

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.415g/cm³
• Refractive Index: 1.664
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-CHLORO-N-(6-ETHOXY-BENZOTHIAZOL-2-YL)-ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-N-(6-ETHOXY-BENZOTHIAZOL-2-YL)-ACETAMIDE(3268-74-4)
• EPA Substance Registry System: 2-CHLORO-N-(6-ETHOXY-BENZOTHIAZOL-2-YL)-ACETAMIDE(3268-74-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 3268-74-4(Hazardous Substances Data)

Usage

General Description

2-CHLORO-N-(6-ETHOXY-BENZOTHIAZOL-2-YL)-ACETAMIDE is a chemical compound with the molecular formula C11H10ClN2O2S. It is a chlorinated acetamide derivative with an ethoxybenzothiazolyl moiety. 2-CHLORO-N-(6-ETHOXY-BENZOTHIAZOL-2-YL)-ACETAMIDE has been studied for its potential use as a pharmaceutical intermediate in the synthesis of various drugs and bioactive compounds. Its structural features make it a valuable building block in organic synthesis, and it may also have potential applications in the development of new pharmaceuticals or agrochemicals. However, as with any chemical, proper handling and safety precautions should be observed when working with 2-CHLORO-N-(6-ETHOXY-BENZOTHIAZOL-2-YL)-ACETAMIDE.

InChI:InChI=1/C11H11ClN2O2S/c1-2-16-7-3-4-8-9(5-7)17-11(13-8)14-10(15)6-12/h3-5H,2,6H2,1H3,(H,13,14,15)

Upstream product

• 94-45-1 2-Amino-6-ethoxybenzothiazole 
• 541-88-8 Chloroacetic anhydride 
• 79-04-9 chloroacetyl chloride 
• 880-29-5 1-(4-ethoxyphenyl)thiourea 
• 156-43-4 4-Ethoxyaniline 
• 90180-69-1 C₉H₁₀N₂OS*BrH 

Downstream Products

• 3320-78-3 6-Ethoxy-2-(N-benzimidazolyl-acetylamino)-benzothiazole 
• 3320-61-4 6-Ethoxy-2--benzothiazole 
• 872057-69-7 C₂₁H₂₄N₄O₂S 
• 1276539-07-1 4-(6-ethoxy-1,3-benzothiazol-2-yl)amino-2-(4-hydroxyphenyl)amino-1,3-thiazole 
• 1276539-08-2 4-(6-ethoxy-1,3-benzothiazol-2-yl)amino-2-(4-methoxyphenyl)amino-1,3-thiazole 
• 1276539-05-9 4-(6-ethoxy-1,3-benzothiazol-2-yl)amino-2-phenylamino-1,3-thiazole 
• 1276539-06-0 4-(6-ethoxy-1,3-benzothiazol-2-yl)amino-2-(4-chlorophenyl)amino-1,3-thiazole 
• 1355611-88-9 N-(6-ethoxybenzothiazol-2-yl)-2-[[5-(2-cyclohexylethyl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide 
• 1355611-83-4 N-(6-ethoxybenzothiazol-2-yl)-2-[[5-(4-methoxyphenoxymethyl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide 
• 665024-59-9 2-(5-amino-1,3,4-thiadiazol-2-yl)thio-N-(6-ethoxybenzothiazol-2-yl)acetamide 
• 540513-50-6 C₁₈H₁₆N₆O₂S₂ 
• 1373946-43-0 2-((4-(4,6-bis(3,5-dimethylpiperidin-1-yl)-1,3,5-triazin-2-yl)phenyl)amino)-N-(6-ethoxybenzo[d]thiazol-2-yl)acetamide 

Relevant articles and documents

Thiazolidinedione "magic Bullets" Simultaneously Targeting PPARγand HDACs: Design, Synthesis, and Investigations of their in Vitro and in Vivo Antitumor Effects

Monotargeting anticancer agents suffer from resistance and target nonspecificity concerns, which can be tackled with a multitargeting approach. The combined treatment with HDAC inhibitors and PPARγagonists has displayed potential antitumor effects. Based on these observations, this work involves design and synthesis of molecules that can simultaneously target PPARγand HDAC. Several out of 25 compounds inhibited HDAC4, and six compounds acted as dual-targeting agents. Compound 7i was the most potent, with activity toward PPARγEC50 = 0.245 μM and HDAC4 IC50 = 1.1 μM. Additionally, compounds 7c and 7i were cytotoxic to CCRF-CEM cells (CC50 = 2.8 and 9.6 μM, respectively), induced apoptosis, and caused DNA fragmentation. Furthermore, compound 7c modulated the expression of c-Myc, cleaved caspase-3, and caused in vivo tumor regression in CCRF-CEM tumor xenografts. Thus, this study provides a basis for the rational design of dual/multitargeting agents that could be developed further as anticancer therapeutics.

Biological evaluation of a series of benzothiazole derivatives as mosquitocidal agents

Aedes aegypti is associated with the transmission of numerous human and animal diseases, such as yellow fever, dengue fever, chikungunya, and more recently Zika virus. Emerging insecticide resistance has created a need to develop new mosquitocidal agents for effective control operations. A series of benzothiazole-piperidine derivatives (1-24) were investigated for their larvicidal and adulticidal effects on Ae. aegypti It was observed that compounds 2, 4, 6, 7, 8, 11 and 13 showed notable larvicidal activity. Furthermore, compounds 6 and 10 showed promising adulticidal activity. Based on the mosquitocidal properties of these compounds, docking studies were also carried out in the active site of the AeSCP2 enzyme to explore any insights into further in vitro enzyme studies. Docking results indicated that all these active compounds showed reasonable interactions with critical residues in the active site of this enzyme. This outcome suggested that these compounds might show their larvicidal and adulticidal effects via the inhibition of AeSCP2. According to in vitro and in silico studies, compounds 2, 4, 6, 7, 8, 10, 11 and 13 stand out as candidates for further studies.

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.