3608-86-4

Usage

Uses

Used in Pharmaceutical Research:
2-CHLORO-N-(1,5-DIMETHYL-3-OXO-2-PHENYL-2,3-DIHYDRO-1H-PYRAZOL-4-YL)ACETAMIDE is used as a building block for the development of new drugs due to its potential biological activity. It can be utilized in the synthesis of various pharmaceutical compounds, contributing to the advancement of drug discovery and therapeutic applications.
Used in Chemical Synthesis:
In the chemical industry, 2-CHLORO-N-(1,5-DIMETHYL-3-OXO-2-PHENYL-2,3-DIHYDRO-1H-PYRAZOL-4-YL)ACETAMIDE can be used as an intermediate in the synthesis of other complex organic compounds. Its unique structure, featuring a chloro group and a pyrazole ring, makes it a valuable component in the creation of specialty chemicals and materials.

InChI:InChI=1/C13H14ClN3O2/c1-9-12(15-11(18)8-14)13(19)17(16(9)2)10-6-4-3-5-7-10/h3-7H,8H2,1-2H3,(H,15,18)

Upstream product

• 83-07-8 4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 58965-86-9 N,N-dimethyl-glycine 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylamide 
• 100549-90-4 3,3-Diphenyl-5-ethoxycarbonyl-2-oxoindoline-1-acet-4-antipyrylamide 
• 100549-89-1 3,3-Diphenyl-4-ethoxycarbonyl-2-oxoindoline-1-acet-4-antipyrylamide 

Relevant academic research and scientific papers

Anti-hepatic fibrosis compound, preparation, preparation method and application

The invention belongs to the technical field of medicines, in particular to an anti-hepatic fibrosis compound, a preparation, a preparation method and application, and the structural formula of the anti-hepatic fibrosis compound is shown in the specification. The anti-hepatic fibrosis compound can obviously improve hepatic fibrosis, improve liver function indexes, reduce extracellular matrix accumulation of collagen and the like in extracellular interstitial substances, reduce the degree of hepatic fibrosis and inhibit the formation and development of hepatic fibrosis.

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

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.

Anti-hepatic fibrosis compound and preparation as well as preparation method and application of compound

The invention belongs to the technical field of medicines, and in particular relates to an anti-hepatic fibrosis compound and a preparation as well as a preparation method and application of the compound. A structural formula of the anti-hepatic fibrosis compound is shown in the specification. The anti-hepatic fibrosis compound can obviously improve hepatic fibrosis, improve liver function indexes, reduce accumulation of extracellular matrixes such as collagen in extracellular interstitial substances, reduce the degree of the hepatic fibrosis and inhibit the formation and development of the hepatic fibrosis.

Synthesis and primary cytotoxicity evaluation of new 5-benzylidene-2,4- thiazolidinedione derivatives

In the present work, ten novel derivatives (3a-3j) of 5-benzylidene-2,4- thiazolidinediones were synthesized and their structures were determined by analytical and spectral (FTIR, 1H NMR, 13C NMR) methods. The newly synthesized compounds were evaluated for their antiproliferative activity at Tata Memorial's Advanced Center for Treatment, Research and Education in Cancer (ACTREC), India, in a panel of 7 cancer cell lines using four concentrations at 10-fold dilutions. Sulforhodamine B (SRB) protein assay was used to estimate cell stability or growth. Though the compounds showed varying degrees of cytotoxicity in the tested cell lines, most marked effect was observed by compound 3e in MCF7 (breast cancer), K562 (leukemia) and GURAV (nasopharyngeal cancer) cell lines with log10 GI50 values of -6.7, -6.72 and -6.73 respectively.

Design and synthesis of some thiazolyl and thiadiazolyl derivatives of antipyrine as potential non-acidic anti-inflammatory, analgesic and antimicrobial agents

The synthesis of two groups of structure hybrids comprising basically the antipyrine moiety attached to either polysubstituted thiazole or 2,5-disubstituted-1,3,4-thiadiazole counterparts through various linkages is described. Twelve out of the newly synt

Synthesis of some triazolyl-antipyrine derivatives and investigation of analgesic activity

The synthesis of some triazolyl-antipyrine derivatives starting from 4-chloroacetamidoantipyrine and 3-(aryloxyalkyl)-4-ethyl/phenyl-5-mercapto-1,2,4-triazoles is described. The chemical structures of the compounds were elucidated by IR, 1H-NMR and mass spectral studies. These compounds were tested for analgesic activity.