351-38-2

Usage

Uses

Used in Pharmaceutical Industry:
N-(CHLOROACETYL)-3-(TRIFLUOROMETHYL)ANILINE is used as a synthetic intermediate for the development of new drugs. Its unique functional groups allow for the creation of a variety of pharmaceutical compounds with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, N-(CHLOROACETYL)-3-(TRIFLUOROMETHYL)ANILINE is utilized as a building block in the synthesis of pesticides. Its reactivity and structural properties contribute to the development of effective and targeted agrochemicals for pest control and crop protection.
Used in Organic Chemistry Research:
N-(CHLOROACETYL)-3-(TRIFLUOROMETHYL)ANILINE is employed as a key compound in organic chemistry research. Its versatile reactivity makes it an important tool for exploring new reaction pathways and synthesizing novel organic molecules with potential applications in various fields.

InChI:InChI=1/C9H7ClF3NO/c10-5-8(15)14-7-3-1-2-6(4-7)9(11,12)13/h1-4H,5H2,(H,14,15)

Upstream product

• 98-16-8 3-trifluoromethylaniline 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 138129-20-1 ethyl 3-<2-<<3-(trifluoromethyl)phenyl>amino>-2-oxoethyl>-3,4-dihydro-4-oxo-1-phthalazineacetate 
• 596107-50-5 N-(3-trifluoromethylphenyl)-2-iodoacetamide 
• 138129-34-7 {4-Oxo-3-[(3-trifluoromethyl-phenylcarbamoyl)-methyl]-3,4-dihydro-phthalazin-1-yl}-acetic acid 
• 138129-43-8 {4-Oxo-3-[(3-trifluoromethyl-phenylthiocarbamoyl)-methyl]-3,4-dihydro-phthalazin-1-yl}-acetic acid 
• 138129-27-8 ethyl 3-<2-<<3-(trifluoromethyl)phenyl>amino>-2-thioxoethyl>-3,4-dihydro-4-oxo-1-phthalazineacetate 
• 5107-81-3 2-(diethylamino)-N-(3-trifluoromethyl-phenyl)acetamide 
• 339156-77-3 2-(2-amino-5-cyano-6-methylsulfanyl-pyrimidin-4-ylsulfanyl)-N-(3-trifluoromethyl-phenyl)-acetamide 
• 625078-81-1 2-(2-methyl-4-nitro-1H-imidazol-1-yl)-N-[3-(trifluoromethyl)phenyl]acetamide 
• 824944-77-6 2-(2,4-dioxo-imidazolidin-3-yl)-N-(3-trifluoromethyl-phenyl)-acetamide 
• 867041-26-7 2-[5-(4-chloro-benzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(3-trifluoromethyl-phenyl)-acetamide 
• 880796-49-6 2-[5-(4-methoxy-benzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(3-trifluoromethyl-phenyl)-acetamide 
• 867041-29-0 N-(4-chloro-phenyl)-2-{2,4-dioxo-3-[(3-trifluoromethyl-phenylcarbamoyl)-methyl]-thiazolidin-5-ylidene}-acetamide 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel thienylpyridyl-and thioether-containing acetamides and their derivatives as pesticidal agents

Referring to the structural information of the “hit” compound A from the reported pharmacophore-based virtual screening, a series of novel thienylpyridyl-and thioether/sulfoxide/ sulfone-containing acetamide derivatives have been designed and synthesized.

Novel selective ido1 inhibitors with isoxazolo[5,4-d]pyrimidin-4(5h)-one scaffold

Indoleamine 2,3-dioxygenase 1 (IDO1) is a promising target in immunomodulation of several pathological conditions, especially cancers. Here we present the synthesis of a series of IDO1 inhibitors with the novel isoxazolo[5,4-d]pyrimidin-4(5H)-one scaffold. A focused library was prepared using a 6-or 7-step synthetic procedure to allow a systematic investigation of the structure-activity relationships of the described scaffold. Chemistry-driven modifications lead us to the discovery of our best-in-class inhibitors possessing p-trifluoromethyl (23), p-cyclohexyl (32), or p-methoxycarbonyl (20, 39) substituted aniline moieties with IC50 values in the low micromolar range. In addition to hIDO1, compounds were tested for their inhibition of indoleamine 2,3-dioxygenase 2 and tryptophan dioxygenase, and found to be selective for hIDO1. Our results thus demon-strate a successful study on IDO1-selective isoxazolo[5,4-d]pyrimidin-4(5H)-one inhibitors, defining promising chemical probes with a novel scaffold for further development of potent small-molecule immunomodulators.

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.

PIPERIDINE-2,6-DIONES AS SMALL MOLECULE DEGRADERS OF HELIOS AND METHODS OF USE

Disclosed are compounds and pharmaceutically acceptable salts, hydrates, solvates, prodrugs, stereoisomers, and tautomers thereof that may cause degradation of various proteins e.g., IKZF2 (Helios). Also disclosed are pharmaceutical compositions containin

Design, synthesis and biological evaluation of novel naturally-inspired multifunctional molecules for the management of Alzheimer's disease

In our overall goal to overcome the limitations associated with natural products for the management of Alzheimer's disease and to develop in-vivo active multifunctional cholinergic inhibitors, we embarked on the development of ferulic acid analogs. A systematic SAR study to improve upon the cholinesterase inhibition of ferulic acid with analogs that also had lower logP was carried out. Enzyme inhibition and kinetic studies identified compound 7a as a lead molecule with preferential acetylcholinesterase inhibition (AChE IC50 = 5.74 ± 0.13 μM; BChE IC50 = 14.05 ± 0.10 μM) compared to the parent molecule ferulic acid (% inhibition of AChE and BChE at 20 μM, 15.19 ± 0.59 and 19.73 ± 0.91, respectively). Molecular docking and dynamics studies revealed that 7a fits well into the active sites of AChE and BChE, forming stable and strong interactions with key residues Asp74, Trp286, and Tyr337 in AChE and with Tyr128, Trp231, Leu286, Ala328, Phe329, and Tyr341 in BChE. Compound 7a was found to be an efficacious antioxidant in a DPPH assay (IC50 = 57.35 ± 0.27 μM), and it also was able to chelate iron. Data from atomic force microscopy images demonstrated that 7a was able to modulate aggregation of amyloid β1-42. Upon oral administration, 7a exhibited promising in-vivo activity in the scopolamine-induced AD animal model and was able to improve spatial memory in cognitive deficit mice in the Y-maze model. Analog 7a could effectively reverse the increased levels of AChE and BChE in scopolamine-treated animals and exhibited potent ex-vivo antioxidant properties. These findings suggest that 7a can act as a lead molecule for the development of naturally-inspired multifunctional molecules for the management of Alzheimer's and other neurodegenerative disorders.

Hydrophobic substituents on isatin derivatives enhance their inhibition against bacterial peptidoglycan glycosyltransferase activity

Moenomycin A, the well-known natural product inhibitor of peptidoglycan glycosyltransferase (PGT), is a large amphiphilic molecule of molecular mass of 1583 g/mol and its bioavailablity as a drug is relatively poor. In searching for small-molecule ligands

Discovery of novel N-substituted thiazolidinediones (TZDs) as HDAC8 inhibitors: in-silico studies, synthesis, and biological evaluation

Epigenetics plays a fundamental role in cancer progression, and developing agents that regulate epigenetics is crucial for cancer management. Among Class I and Class II HDACs, HDAC8 is one of the essential epigenetic players in cancer progression. Therefore, we designed, synthesized, purified, and structurally characterized novel compounds containing N-substituted TZD (P1-P25). Cell viability assay of all compounds on leukemic cell lines (CEM, K562, and KCL22) showed the cytotoxic potential of P8, P9, P10, P12, P19, and P25. In-vitro screening of different HDACs isoforms revealed that P19 was the most potent and selective inhibitor for HDAC8 (IC50 – 9.3 μM). Thermal shift analysis (TSA) confirmed the binding of P19 to HDAC8. In-vitro screening of all compounds on the transport activity of GLUT1, GLUT4, and GLUT5 indicated that P19 inhibited GLUT1 (IC50 – 28.2 μM). P10 and P19 induced apoptotic cell death in CEM cells (55.19% and 60.97% respectively) and P19 was less cytotoxic on normal WBCs (CC50 – 104.2 μM) and human fibroblasts (HS27) (CC50 – 105.0 μM). Thus, among this novel series of TZD derivatives, compound P19 was most promising HDAC8 inhibitor and cytotoxic on leukemic cells. Thus, P19 could serve as a lead for further development of optimized molecules with enhanced selectivity and potency.

Structure guided design and synthesis of furyl thiazolidinedione derivatives as inhibitors of GLUT 1 and GLUT 4, and evaluation of their anti-leukemic potential

Cancer cells increase their glucose uptake and glycolytic activity to meet the high energy requirements of proliferation. Glucose transporters (GLUTs), which facilitate the transport of glucose and related hexoses across the cell membrane, play a vital ro

Permuted 2,4-thiazolidinedione (TZD) analogs as GLUT inhibitors and their in-vitro evaluation in leukemic cells

Cancer is a heterogeneous disease, and its treatment requires the identification of new ways to thwart tumor cells. Amongst such emerging targets are glucose transporters (GLUTs, SLC2 family), which are overexpressed by almost all types of cancer cells; t

Benzylidene thiazolidinediones: Synthesis, in vitro investigations of antiproliferative mechanisms and in vivo efficacy determination in combination with Imatinib

Thiazolidinedione (TZD) has been an interesting scaffold due to its proven antidiabetic activity and encouraging findings in anticancer drug discovery. We synthesised benzylidene thiazolidinedione derivatives which exhibited excellent antiproliferative effects in chronic myeloid leukemic cells K562 and the most active compounds 3t and 3x had GI50 value of 0.9 and 0.23 μM respectively. Both the compound was found to arrest the growth of K562 cells in G0/G1 phase in a time and dose dependent manner. Further, western blot analysis revealed that 3t and 3x could also inhibit the expression of cell proliferation markers, PCNA and Cyclin D1 and compound 3x up-regulated apoptosis markers, cleaved PARP1 and activated caspase 3, which could be a possible mechanism for the excellent antiproliferative effects exhibited by these compounds. In vitro combination studies of 3t and 3x with Imatinib found to potentiate the antitumor effects of Imatinib. Further in vivo efficacy in K562 xenografts, of 3t and 3x alone and in combination with Imatinib was found to be promising and far better than control group and combination treatment was found to be more effective as compared to only Imatinib treated or test compound treated animals. Thus, our findings suggest that these compounds are promising antitumor agents and could help to enhance the anticancer effects of Imatinib and other tyrosine kinase inhibitors, when used in combination.