39089-62-8

Usage

Uses

Used in Pharmaceutical Industry:
2-CHLORO-N-(TETRAHYDROFURAN-2-YLMETHYL)ACETAMIDE is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 2-CHLORO-N-(TETRAHYDROFURAN-2-YLMETHYL)ACETAMIDE serves as a precursor for the production of various agrochemicals, including pesticides and herbicides. Its incorporation into these products can enhance their effectiveness in controlling pests and weeds.
Used in Chemical Research:
2-CHLORO-N-(TETRAHYDROFURAN-2-YLMETHYL)ACETAMIDE is utilized in chemical research as a building block for the preparation of complex organic molecules. Its unique functional groups and structural features make it a valuable tool for exploring new chemical reactions and synthesizing novel compounds.
Safety Considerations:
Due to the potential hazards associated with 2-CHLORO-N-(TETRAHYDROFURAN-2-YLMETHYL)ACETAMIDE, it is crucial to handle 2-CHLORO-N-(TETRAHYDROFURAN-2-YLMETHYL)ACETAMIDE with care and follow proper safety protocols. This includes using appropriate personal protective equipment, working in a well-ventilated area, and disposing of the compound according to local regulations.

InChI:InChI=1/C7H12ClNO2/c8-4-7(10)9-5-6-2-1-3-11-6/h6H,1-5H2,(H,9,10)

Upstream product

• 4795-29-3 TETRAHYDROFURFURYLAMINE 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 324546-10-3 C₁₃H₁₅Cl₂NO₃ 
• 430452-27-0 C₁₃H₁₅BrClNO₃ 
• 919207-69-5 C₁₃H₁₅ClFNO₃ 
• 1214193-03-9 2-(2,6-dichlorophenylthio)-N-((tetrahydrofuran-2-yl)methyl)acetamide 
• 1214193-24-4 2-(2,3-dichlorophenylthio)-N-((tetrahydrofuran-2-yl)methyl)acetamide 
• 1214193-14-2 2-(2,4-dichlorophenylthio)-N-((tetrahydrofuran-2-yl)methyl)acetamide 
• 849129-97-1 2-(2,5-dichlorophenylthio)-N-((tetrahydrofuran-2-yl)methyl)acetamide 

Relevant academic research and scientific papers

Dual targeting of cholinesterase and amyloid beta with pyridinium/isoquinolium derivatives

With the surge in the cases of Alzheimer's disease (AD) over the years, several targets have been explored to curb the disease. Cholinesterases, namely acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), remain to be the available targets that are amendable to currently approved treatments. In this study, a series of novel compounds based on tramiprosate, a highly specific amyloid beta (Aβ) inhibitor, was designed to inhibit AChE, BuChE, and Aβ aggregation. In particular, the addition of a pyridinium/isoquinolinium ring to the tramiprosate moiety (to give compounds 3a–j) led to an increase in the binding affinity for the catalytic active site of cholinesterase, which was hampered by the presence of sulfonic acid. Exclusion of the sulfonic acid moiety led to a novel but effective class of cholinesterase inhibitors (9a–w). in vitro Aβ aggregation inhibition assay indicated that compounds 3a–j, 9e–f, 9i–l, 9q, 9r, 9u–w, and 12 could inhibit over 10% Aβ aggregation at 1 mM concentration. Cholinesterase inhibition assay suggested that compounds 9g, 9h, 9o, and 9q–t exhibit over 70% inhibition on both AChE and BuChE at a concentration of 100 μM. Amongst the designed molecules, compound 9r (ca 18% at 1 mM) showed comparable inhibitory effect on the inhibition of Aβ aggregation with tramiprosate (ca 20% at 1 mM), along with impressive cholinesterase inhibitory potential (AChE IC50 = 13 μM and BuChE IC50 = 12 μM), acceptable toxicity and ability to pass through blood brain barrier, which could be used to ameliorate the phenotypes of AD in preclinical models.

Synthesis and anticancer potential of novel xanthone derivatives with 3,6-substituted chains

In an effort to develop new drug candidates with enhanced anticancer activity, our team synthesized and assessed the cytotoxicity of a series of novel xanthone derivatives with two longer 3,6-disubstituted amine carbonyl methoxy side chains on either benzene ring in selected human cancer cell lines. An MTT assay revealed that a set of compounds with lower IC50values than the positive control, 5-FU, exhibited greater anticancer effects. The most potent derivative (XD8) exhibited anticancer activity in MDA-MB-231, PC-3, A549, AsPC-1, and HCT116 cells lines with IC50values of 8.06, 6.18, 4.59, 4.76, and 6.09?μM, respectively. Cell cycle analysis and apoptosis activation suggested that the mechanism of action of these derivatives includes cell cycle regulation and apoptosis induction.

Synthesis and in vitro antimicrobial activity of benzo[b][1,4]thiazin-3(4H) -ones via smiles rearrangement

New benzo[b][1,4]thiazin-3(4H)-one derivatives (compounds 12a-p) were synthesized via Smiles rearrangement and assayed in vitro for their antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. The antimicrobial activity of the benzo[b][1,4]thiazin-3(4H)-ones showed, on the whole, potent toward all tested Gram-positive and Gram-negative microorganism (minimal inhibitory concentration ranging from 16 to 64 lg/ml), whereas weak effectiveness was exhibited against fungi. Data obtained suggested that 12g, 12i, and 12o exerted the best antibacterial activity against Gram-positive bacteria and compound 12b demonstrated the best inhibition of Gram-negative bacteria. These observations provide some predictions to design further antimicrobial active compounds prior to their synthesis following with molecular modeling studies. Springer Science+Business Media, LLC 2010.

Synthesis of benzo[b][1,4]oxazin-3(4H)-ones via smiles rearrangement for antimicrobial activity

The benzo[b][1,4]oxazin-3(4H)-one derivatives, 1a-p, carrying F, Br, and Cl on the benzene ring, or benzyl, cyclohexyl, n-hexyl, and tetrafuryl methylene groups attached to nitrogen atom were synthesized via Smiles rearrangement and assayed in vitro for their antimicrobial activity against Gram-positive, Gram-negative bacteria, and fungi. The antimicrobial activity of the benzo[b][1,4]oxazin-3(4H)-ones showed, on the whole, potency toward all the tested Gram-positive and Gramnegative microorganism (MIC ranging from 16 to 64 lg/ ml), whereas weak effectiveness was exhibited against fungi. Data obtained suggest that fluorine atom in the compounds, 1c, 1f, 1i plays an important role in enhancing the antimicrobial properties of this class of compounds. These observations provide some predictions to design further antimicrobial active compounds prior to their synthesis according to molecular modeling studies.

NEW PYRIDOTHIENOPYRIMIDINE DERIVATIVES

Use of a pyridothienopyrimidine derivative of formula (I), and the pharmaceutically acceptable salts and N-oxides thereof, wherein G1 represents a group selected from -CR6R7- or -NR6 being R6 and R7 independently selected from hydrogen atoms and C1-4 alkyl groups m and n are integers selected from 0 or 1 R1 and R2 are independently selected from hydrogen atoms and C1-4 alkyl groups R3 represents a group selected from alkyl, amino, monoalkylamino, dialkylamino, aryl, heteroaryl and saturated N-containing heterocyclyl groups bound through the nitrogen atom to the piridine ring, all of them being optionally substituted by one or more substituents selected from the group consisting of halogen atoms and alkyl, alkoxyalkyl, arylalkyl, R8OCO-, alkoxy, R8R9N-CO-, -CN, -CF3, -NR8R9, -SR8 and - SO2NH2 groups wherein R8 and R9 are independently selected from hydrogen atoms and C1-4alkyl groups R4 and R5 are independently selected from the group consisting of hydrogen atoms alkyl groups and groups of formula (II), wherein p and q are integers selected from 1, 2 and 3; A is either a direct bond or a group selected from -CONR14-, -NR14CO-, -O-, -COO-, -OCO-, -NR 14OCO-, - OCONR14-, -NR14CONR15-, -S-, -SO-, -SO2-, -COS- and -SCO-; and G2 is a group selected from aryl, heteroaryl or heterocyclyl; wherein the alkyl groups and the group G2 are optionally substituted by one or more substituents selected from group consisting of halogen atoms and alkyl, alkoxyalkyl, arylalkyl, R16OCO-, hydroxy, alkoxy, oxo, R16R17NCO-, -CN, -CF3, -NR16R17,-SR16 and -SO2NH2 groups; wherein R10 to R17 are independently selected from hydrogen atoms and C1-4 alkyl groups; in the manufacture of a medicament for the treatment or prevention of a pathological condition or disease susceptible to amelioration by inhibition of phosphodiesterase 4.

One-pot synthesis of pyridazino[1,4]oxazin-3-ones

Pyridazino[1,4]oxazin-3-ones were conveniently prepared in a one-pot condensation of N-substituted 2-chloroacetamides with various 5-chloro-pyridazin-6-ones via rearrangement of a spiro-aminoketal intermediate.

Novel synthesis of pyridazino[4,5-b][1,4]oxazin-3,8-diones

A novel and effective synthesis of pyridazino[4,5-b][1,4]oxazin-3,8-diones via Smiles rearrangement is presented. Treatment of N-substituted 2-chloro(or hydroxy)acetamide, 2-tetrahydropyranyl-4-chloro-5-hydroxy(or chloro)pyridazin-3-one and cesium carbonate in refluxing acetonitrile was afforded the corresponding pyridazino[4,5-b][1,4]oxazin-3,8-diones in excellent yield.

A one-pot synthesis of pyrido[2,3.b][1,4]oxazin-2-ones

Pyrido[2,3-b][1,4]oxazin-2-ones are conveniently prepared in excellent yields by a one-pot annulation of N-substituted-2-chloroacetamides with 2-halo-3-hydroxypyridines with use of cesium carbonate in refluxing acetonitrile. The key transformation features a Smiles rearrangement of the initial O-alkylation product and subsequent cyclization.