40914-13-4

Usage

Uses

Used in Pharmaceutical Industry:
2-chloro-N-(2-furylmethyl)acetamide is utilized as an intermediate in the synthesis of a range of pharmaceuticals. Its unique structure allows for the creation of diverse heterocyclic compounds, which are integral in the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 2-chloro-N-(2-furylmethyl)acetamide is employed as a precursor in the production of various agrochemicals. Its reactivity and structural features make it suitable for the synthesis of compounds with pesticidal or herbicidal activities, contributing to crop protection and yield enhancement.
Used in Medicinal Chemistry Research:
2-chloro-N-(2-furylmethyl)acetamide is also used as a building block in medicinal chemistry for the preparation of heterocyclic compounds. These compounds are often evaluated for their potential biological activities, such as antimicrobial, antiviral, or anticancer properties, and may lead to the discovery of novel therapeutic agents.
Used in Organic Synthesis:
As a reagent in organic synthesis, 2-chloro-N-(2-furylmethyl)acetamide facilitates the formation of a variety of chemical compounds. Its versatility in reactions makes it a valuable component in the synthesis of complex organic molecules for various applications, including the development of new materials and the improvement of existing chemical processes.
Used as a Starting Material:
2-chloro-N-(2-furylmethyl)acetamide serves as a starting material for the production of other chemical compounds. Its functional groups and structural attributes make it a suitable candidate for further chemical modifications, leading to the creation of new compounds with specific applications in various industries.

InChI:InChI=1/C7H8ClNO2/c8-4-7(10)9-5-6-2-1-3-11-6/h1-3H,4-5H2,(H,9,10)

Upstream product

• 617-89-0 furan-2-ylmethanamine 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 96731-89-4 triethyl-(furfurylcarbamoyl-methyl)-ammonium; iodide 
• 1207863-94-2 1-benzyl-3-[(2-furanylmethyl)aminocarbonylmethyl]imidazolium chloride 
• 1246541-25-2 C₂₅H₂₅NO₇ 
• 1164481-47-3 C₁₈H₁₉NO₆ 
• 347319-95-3 2-(3-formyl-indol-1-yl)-N-furan-2-ylmethyl-acetamide 
• 1215289-41-0 N-(furan-2-ylmethyl)-2-[4-oxo-2-(3-methoxyphenyl)pyrimido[1,2-a]benzimidazol-10(4H)-yl]-acetamide 

Relevant academic research and scientific papers

Synthesis, characterization and evaluation of novel ferrocenylmethylamine derivatives as cytotoxic agents

The present report describes a new series of amide functionalized 20- and 30-aminomethylferrocene derived from ferrocenylmethylamine. The compounds 1a-5a and 1b-5b were characterized by microanalysis, 1H, 13C NMR, UV–visible, fluorescence, FTIR, thermogravimetric and crystallographic techniques. The X-ray analysis demonstrated the ability of these molecules to form various intermolecular hydrogen bonding interactions, as verified by Hirshfeld surface analysis. All the compounds were evaluated against MCF 7, IMR 32, HepG2 and immortal L132 cell lines by MTT assay and the results were compared with cisplatin. Interestingly, many compounds were very active against all the investigated cell lines and proved to be more potent as cytotoxic agents than cisplatin. The western blot, gene expression, mitochondrial membrane potential and flow cytometry study were used to investigate the mode of action of these derivatives as antitumor agents. The results showed apoptotic property of the compounds by modulating inflammatory pathway against human tumor cells of different origin. We performed the density functional theory calculations and molecular docking to rationalize the experimental results.

Organocatalytic Cascade Reactions for the Diversification of Thiopyrano-Piperidone Fused Rings Utilizing Trienamine Activation

An aminocatalytic privileged diversity-oriented synthesis (ApDOS) strategy utilizing trienamine catalysis for the construction of diverse and complex thiopyrans-piperidone fused rings through a thia-Diels–Alder/nucleophilic ring-closing sequence by using dithioamides as activated heterodienophiles is reported. Following this strategy, a super cascade reaction to assemble nine fused rings can be achieved by employing a bis-dithioamide. Additionally, by linking an indole moiety on the dithioamide, a Pictet–Spengler type reaction can be promoted once the cascade sequence has been achieved, leading to more complex penta- hexa- and heptacyclic fused ring derivatives in a one-pot process. This investigation opens new perspectives for the synthesis of a new class of complex and diverse thiopyrans that contribute to populate new relevant regions in the chemical space.

Curcumenol derivatives and application of curcumenol derivatives in preparing antitumor drug

The invention relates to curcumenol derivatives and application of the curcumenol derivatives in preparing an antitumor drug. By performing structure modification on the curcumenol derivatives, aftera furfuryl amine fragment is introduced at a hydroxy group site of curcumenol, amine is further introduced through Mannich reaction to obtain a series of the curcumenol derivatives of a structure of aformula (I) as well as pharmaceutically acceptable salts, hydrates, solvates or prodrugs of the curcumenol derivatives which are not reported. Verified by an in vitro bioactivity experiment, the newcurcumenol derivatives have the inhibitory activity to a cervical cancer, a liver cancer, a lung cancer and the like, and the compound activity of most of the new curcumenol derivatives are remarkablyhigher than that of curcumenol as a parent of the new curcumenol derivatives. In addition, the polarity of the vast majority of the synthesized curcumenol derivatives is remarkably improved comparedwith the curcumenol; according to the similarity and intermiscibility principle, the phenomenon that the solubility of the synthesized curcumenol derivatives is higher than that of the curcumenol of aparent compound is proved to a certain degree, and a basic theoretical basis is provided for better performing preparation research and exerting efficacy. The formula (I) is shown in the description.

Structure-based design, synthesis, and biological evaluation of isatin derivatives as potential glycosyltransferase inhibitors

Peptidoglycan glycosyltransferase (PGT) has been shown to be an important pharmacological target for the inhibition of bacterial cell wall biosynthesis. Structure-based virtual screening of about 3 000 000 commercially available compounds against the crystal structure of the glycosyltransferase (GT) domain of the Staphylococcus aureus penicillin-binding protein 2 (S. aureus PBP2) resulted in identification of an isatin derivative, 2-(3-(2-carbamimidoylhydrazono)-2-oxoindolin-1-yl)-N-(m-tolyl)acetamide (4) as a novel potential GT inhibitor. A series of 4 derivatives were synthesized. Several compounds showed more active antimicrobial activity than the initial hit compound 4, in particular 2-(3-(2-carbamimidoylhydrazono)-2-oxoindolin-1-yl)-N-(3-nitrophenyl)acetamide (4l), against Gram-positive Bacillus subtilis and S. aureus with MIC values of 24 and 48 lg/mL, respectively. Saturation transfer difference (STD) NMR study revealed that there is a binding contact between 4l and the GT domain of S. aureus PBP2. Competitive STD-NMR further proved that 4l and moenomycin A bind to GT domain in a competitive manner. Molecular docking study suggests a potential binding pocket of 4l in the GT domain of S. aureus PBP2. Taken together, compound 4l would provide a new scaffold for further development of potent GT inhibitors.

Exploring DOXP-reductoisomerase binding limits using phosphonated N-aryl and N-heteroarylcarboxamides as DXR inhibitors

DOXP-reductoisomerase (DXR) is a validated target for the development of antimalarial drugs to address the increase in resistant strains of Plasmodium falciparum. Series of aryl- and heteroarylcarbamoylphosphonic acids, their diethyl esters and disodium salts have been prepared as analogues of the potent DXR inhibitor fosmidomycin. The effects of the carboxamide N-substituents and the length of the methylene linker have been explored using in silico docking studies, saturation transfer difference NMR spectroscopy and enzyme inhibition assays using both EcDXR and PfDXR. These studies indicate an optimal linker length of two methylene units and have confirmed the importance of an additional binding pocket in the PfDXR active site. Insights into the constraints of the PfDXR binding site provide additional scope for the rational design of DXR inhibitors with increased ligand-receptor interactions.

Synthesis and evaluation of phosphonated N-heteroarylcarboxamides as DOXP-reductoisomerase (DXR) inhibitors

The diethyl esters and disodium salts of a range of heteroarylcarbamoylphosphonic acids have been prepared and evaluated as analogues of the highly active DOXP-reductoisomerase (DXR) inhibitor, fosmidomycin. Computer-simulated docking studies, Saturation Transfer Difference (STD) NMR analysis and enzyme inhibition assays have been used to explore enzyme-binding and -inhibition potential, while in silico analysis of the DXR active site has highlighted the importance of including a well-parameterised metal co-factor in docking studies and has revealed the availability of an additional binding pocket to guide future drug design.

Synthesis, biological evaluation, and structure-activity relationship study of novel cytotoxic aza-caffeic acid derivatives

Three series of aza-caffeic acid derivatives with different linkers were designed and synthesized. Each of the synthesized derivatives was then used in cytotoxicity screening on either 8 or 12 human cancer cell lines. The structure-activity relationships on three structural regions A, B, and C are analyzed in detail, indicating that a nine bond linker B, containing a piperazine unit, is the most favorable linker leading to the generation of molecules with potent cytotoxicities. Compound (E)-1-(4-(3,4-dichlorobenzyl) piperazin-1-yl)-3-(4-(4-ethoxybenzyloxy)-3,5-dimethoxyphenyl)prop-2-en-1-one (80) exhibited the most significant and selective cytotoxicity to KB, BEL7404, K562, and Eca109 cell lines, with IC50 values of 0.2, 2.0, 1.7, and 1.1 μM, respectively, stronger than that seen for caffeic acid phenethyl ester (CAPE) and cisplatin (CDDP). Flow cytometric and western blot analysis indicate that compound 80 plays a role in mitochondria-dependent apoptosis activity by suppressing K562 cell proliferation in a concentration- and time-dependent manner.

Oxyacetamide compounds useful for stimulating or inducing the growth and/or retarding the loss of keratin fibers

Oxyacetamide compounds that are inhibitors of type-1 15-hydroxyprostaglandin dehydrogenase (15-PGDH) and which have the formula (I), or salts and/or solvates thereof: are useful for inducing and/or stimulating the growth of human keratin fibers, e.g., human head hair and/or eyelashes, and/or for retarding the loss and/or increasing the density thereof and/or for caring for and/or making up such keratin fibers.

USE OF-OXYACETAMIDE COMPOUNDS FOR PROMOTING AND/OR INDUCING AND/OR STIMULATING THE PIGMENTATION OF KERATIN MATERIALS AND/OR FOR LIMITING THEIR DEPIGMENTATION AND/OR BLEACHING

The present invention relates to the cosmetic use of at least one 2-oxyacetamide compound of formula (I) below, or a salt and/or solvate thereof, as an agent for promoting and/or inducing and/or stimulating the pigmentation of keratin materials and/or as an agent for preventing and/or limiting the depigmentation and/or bleaching of keratin materials and more particularly of human keratin fibres such as the hair, beard hair, moustache hair, the eyelashes and the eyebrows . The present invention more particularly relates to the cosmetic use of at least one 2-oxyacetamide compound of formula (I) , or a salt and/or solvate thereof , as an agent for preventing and/or limiting the canities of the said human keratin fibres.

Acetals useful for the preparation of polysaccharide derivatives

Polysaccharide aldehydes having the formula Sacch-O-CH2 -CH=CH-CHO, Sacch-O-CH2 -C C-CHO, STR1 such as starch, cellulose, and gum aldehydes, are useful for imparting wet, dry, or temporary wet strength to paper. They are prepared by a non-oxidative method which involves reacting the polysaccharide base, in the presence of alkali, with a derivatizing acetal reagent having the general structure STR2 and then hydrolyzing the acetal by adjusting the pH to less than 7, preferably 2-4. In the formulas, n is 1-3; R11 and R12 are independently an alkyl, aryl, aralkyl, or alkaryl group when n is 1, R11 or R12 is one of the groups when n is 2, or R11 and R12 are not present when n is 3; R13 is an alkyl group, optionally containing an ether linkage, or an aralkyl group; R14 and R15 are individually a hydrogen or a methyl group; R16, R17, and R18 are individually an alkyl group; Y- is an anion; Z is an organic group capable of reacting with the polysaccharide base to form an ether derivative and selected from the group consisting of an epoxide, ethylenically unsaturated group, halohydrin, and halogen; R19, if present, is a divalent organic group containing no reactive substiuents; and A and A' are lower alkyls or together form at least a 5-membered cyclic acetal.