5349-24-6

Usage

Uses

Used in Pharmaceutical Production:
N-BUTYL-2-CHLORO-ACETAMIDE is utilized as an intermediate in the synthesis of various pharmaceuticals, contributing to the development of new medications and enhancing existing ones.
Used in Agrochemical Synthesis:
In the agrochemical industry, N-BUTYL-2-CHLORO-ACETAMIDE serves as a key intermediate, playing a crucial role in the production of pesticides and other agricultural chemicals to improve crop protection and yield.
Used in Organic Synthesis:
As a reactant in organic synthesis, N-BUTYL-2-CHLORO-ACETAMIDE is employed to create a range of organic compounds, expanding the scope of chemical research and product development.
Used as a Solvent in Chemical Processes:
N-BUTYL-2-CHLORO-ACETAMIDE also functions as a solvent in various chemical processes, facilitating reactions and improving the efficiency of industrial chemical procedures.

InChI:InChI=1/C6H12ClNO/c1-2-3-4-8-6(9)5-7/h2-5H2,1H3,(H,8,9)

Upstream product

• 7572-29-4 dichloroethyne 
• 109-73-9 N-butylamine 
• 227945-00-8 diethyl 2-amino-6-[(hydroxycarbamoyl)-methyl]-azulene-1,3-dicarboxylate sodium 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 38766-10-8 N-(α-Chloroacetoxy)succinimide 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 76810-32-7 C₁₃H₁₈N₂O₂ 
• 37468-43-2 5-Chlormethyl-1-butyl-tetrazol 
• 93257-46-6 <2-Carbamoyl-4-chlor-phenylmercapto>-essigsaeure-butylamid 
• 92789-12-3 <2-Carbamoyl-phenylmercapto>-essigsaeure-butyl-amid 
• 93249-26-4 benzenesulfonyl-acetic acid butylamide 
• 97282-26-3 (toluene-4-sulfonyl)-acetic acid butylamide 
• 93405-63-1 (2-Acetamino-phenylmercapto)-essigsaeure-butylamid 

Relevant academic research and scientific papers

Effect on pKa of metal-bound water molecules in lanthanide ion-induced cyclen "cavities"

(Chemical Equation Presented) The macrocyclic cyclen conjugates 1-4 were synthesized with the aim of forming lanthanide ion-based macrocyclic conjugates possessing deep cavities, formed upon complexation to various lanthanide ions. These complexes all possess metal-bound water molecules, where the pK a of the water molecules depends on the nature of the cavity.

Liquid-liquid extraction process of amino acids by a new amide-based functionalized ionic liquid

The cost of separation and purification of amino acids accounts for more than 80% of their total production expenditure. Thus, investigation into new separation technology is of great importance. In this paper, a new hydrophobic amide-based functionalized ionic liquid ([EimCH2CONHBu]NTf 2) was designed and synthesized for the extraction of amino acids. From the preliminary experiments we found that the ionic liquid has a special selectivity for tryptophan (Trp) when pH = 0.5, and that its partition coefficient (PIL/W) can reach up to 10.02. Subsequently, important factors that affect the extraction process by [EimCH2CONHBu]NTf 2 were studied systematically. It was found that the extraction equilibrium could be achieved in 30 min. It was found that pH influences the PIL/W greatly; the smaller the pH value, the higher the P IL/W. When pH > pK2, the PIL/W is close to zero. With the increase of the volume ratio of the ionic liquid, extraction efficiency increases, while the PIL/W decreases. As for the effect of the initial concentration (C0) of tryptophan, PIL/W decreases with an increase of C0 when [EimCH2CONHBu] NTf2 is used as the extractant. From the investigation of the effect of temperature if was found that the extraction process of amino acid by functionalized ionic liquids is exothermic. Experiments on the recycling and reuse of [EimCH2CONHBu]NTf2 were also performed, and it was found that the extraction efficiency of [EimCH2CONHBu]NTf 2 does not change after four cycles. Finally, the mechanisms were probed and the results show that the hydrogen bond formed between the acetyl group of the ionic liquid and the NH2 group of tryptophan accounts for the higher extraction efficiency. The Royal Society of Chemistry.

Sequence-Defined Dithiocarbamate Oligomers via a Scalable, Support-free, Iterative Strategy

Precise control over the monomeric sequence on natural sequence-defined polymers (SDPs) leads to their structural diversity and functions. However, absolute control over the monomeric sequence on a synthetic polymer remains a challenging process. Herein, we describe a support-free, protection-deprotection-free, cost-effective, and fast iterative strategy for multigram production of a new class of SDP with a unique functional group, dithiocarbamate, a potential group for material and biomedical applications. The strategy is based on a unique monomer, named as amine-hydroxyl monomer, and a three-component reaction between the monomer, CS2, and terminal chloro group of the growing chain. The fast strategy allows us to synthesize a 5-mer sequence-defined oligomer in 6 h. For a proof of concept, a range of aliphatic and aromatic groups have been incorporated at different sequences in the sequence-defined oligomer. This SDP platform has further been advanced by two ways: (i) multiple approaches for postsynthetic modification of SDP and (ii) increasing the chain length in a single step.

Continuous-Flow Electrosynthesis of Benzofused S-Heterocycles by Dehydrogenative C?S Cross-Coupling

Reported herein is the synthesis of benzofused six-membered S-heterocycles by intramolecular dehydrogenative C?S coupling using a modular flow electrolysis cell. The continuous-flow electrosynthesis not only ensures efficient product formation, but also obviates the need for transition-metal catalysts, oxidizing reagents, and supporting electrolytes. Reaction scale-up is conveniently achieved through extended electrolysis without changing the reaction conditions and equipment.

Cink4T, a quinazolinone-based dual inhibitor of Cdk4 and tubulin polymerization, identified via ligand-based virtual screening, for efficient anticancer therapy

Inhibition of cyclin dependent kinase 4 (Cdk4) prevents cancer cells from entering the early G0/G1 phase of the cell division cycle whereas inhibiting tubulin polymerization blocks cancer cells’ ability to undergo mitosis (M) late in the cell cycle. We had reported earlier that two non-planar and relatively non-toxic fascaplysin derivatives, an indole and a tryptoline, inhibit Cdk4 with IC50 values of 6.2 and 10 μM, respectively. Serendipitously, we had also found that they inhibited tubulin polymerization. The molecules were efficacious in mouse tumor models. We have now identified Cink4T in a 59-compound quinazolinone library, designed on the basis of ligand-based virtual screening, as a compound that inhibits Cdk4 and tubulin. Its IC50 value for Cdk4 inhibition is 0.47 μM and >50 μM for inhibition of Cdk1, Cdk2, Cdk6, Cdk9. Cink4T inhibits tubulin polymerization with an IC50 of 0.6 μM. Molecular modelling studies on Cink4T with Cdk4 and tubulin crystal structures lend support to these observations. Cancer cell cycle analyses confirm that Cink4T blocks cells at both G0/G1 and M phases as it should if it were to inhibit both Cdk4 and tubulin polymerization. Our results show, for the very first time, that virtual screening can be used to design novel inhibitors that can potently block two crucial phases of the cell division cycle.

CYP enzymes, expressed within live human suspension cells, are superior to widely-used microsomal enzymes in identifying potent CYP1A1/CYP1B1 inhibitors: Identification of quinazolinones as CYP1A1/CYP1B1 inhibitors that efficiently reverse B[a]P toxicity and cisplatin resistance

Microsomal cytochrome P450 (CYP) enzymes, isolated from recombinant bacterial/insect/yeast cells, are extensively used for drug metabolism studies. However, they may not always portray how a developmental drug would behave in human cells with intact intracellular transport mechanisms. This study emphasizes the usefulness of human HEK293 kidney cells, grown in ‘suspension’ for expression of CYPs, in finding potent CYP1A1/CYP1B1 inhibitors, as possible anticancer agents. With live cell-based assays, quinazolinones 9i/9b were found to be selective CYP1A1/CYP1B1 inhibitors with IC50 values of 30/21 nM, and > 150-fold selectivity over CYP2/3 enzymes, whereas they were far less active using commercially-available CYP1A1/CYP1B1 microsomal enzymes (IC50, >10/1.3–1.7 μM). Compound 9i prevented CYP1A1-mediated benzo[a]pyrene-toxicity in normal fibroblasts whereas 9b completely reversed cisplatin resistance in PC-3/prostate, COR-L23/lung, MIAPaCa-2/pancreatic and LS174T/colon cancer cells, underlining the human-cell-assays’ potential. Our results indicate that the most potent CYP1A1/CYP1B1 inhibitors would not have been identified if one had relied merely on microsomal enzymes.

Synthesis of E/Z N-(1-Chlorovinyl)formamide Using Vilsmeier–Haack Reaction

Synthesis of a variety of novel Z/E N-(1-chlorovinyl)formamides through Vilsmeier–Haack reaction starting from 2-phenoxyethanamides with POCl3/DMF has been accomplished. The reactions introduced chlorine atom to the Cα-position and p

Design, Synthesis, and SAR Studies of Heteroarylpyrimidines and Heteroaryltriazines as CB2R Ligands

Herein we describe the design and synthesis of a new series of heteroarylpyrimidine/heteroaryltriazine derivatives on the basis of quinazoline-2,4(1H,3H)-diones as CB2R-selective ligands using a bioisosterism strategy. An acetamide group was explored to displace the enamine linker of the lead compound for the purpose of stereoisomerism elimination and hydrophilicity increase. As a result, some of the synthesized compounds showed high bioactivity and selectivity for CB2R in calcium mobilization assays, and four displayed CB2R agonist activity, with EC50 values below 30 nm. The compound exhibiting the highest agonist activity toward CB2R (EC50=7.53±3.15 nm) had a selectivity over CB1R of more than 1328-fold. Moreover, structure–activity relationship (SAR) studies indicated that the substituents on the nucleus play key roles in the functionality of a ligand, with one such example demonstrating CB2R antagonist activity. Additionally, molecular docking simulations were conducted with the aim of better understanding of these new derivatives in relation to the structural requirements for agonists/antagonists binding to CB2R.

Rational Design, Synthesis, and Biological Activity of N-(1,4-Benzoxazinone)Acetamide Derivatives as Potent Platelet Aggregation Inhibitors

Inappropriate thrombus formation within blood vessels is the leading cause of mortality in the industrialized world. Platelet aggregation activated by thrombin may have close relationship with thrombosis. Based on our studies on the pharmacophoric role of 1,4-benzoxazine-3(4H)-one for desirable platelet aggregation inhibitory activity, we identified N-(4-ethyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-2-(4-methylpiperazin-1-yl)acetamide (BOAP-AM6) and N-(4-butyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-2-(4-(4-fluorophenyl)piperazin-1-yl)acetamide (BOAP-AM21) as platelet aggregation inhibitors with an IC50 of 8.93 and 8.67 μM, respectively, as potent as the positive control aspirin. A combination of structure–activity relationships studies and molecular modeling revealed that the molecule BOAP-AM6 interacted with the amino acid residue TYR166 and ARG214 in the binding site of GPIIb/IIIa receptor through hydrogen bond and compound BOAP-AM21 acted on the amino acid residue ASN215 and ALA218, both through the same approach as the reported potent molecules 7a and 7b.

N-alkyl-N-substitute vinyl formamide compound and synthesis method thereof

The invention discloses an N-alkyl-N-substitute vinyl formamide compound and a synthesis method thereof. A 2-aryloxycarboxylic acetamide compound structured by a formula III as shown in the specification reacts with POCl3, thus preparing the N-alkyl-N-sub