27069-16-5

Usage

Chemical Properties

White solid

InChI:InChI=1/C11H10N2O3/c1-16-8-4-2-7(3-5-8)9-6-10(11(14)15)13-12-9/h2-6H,1H3,(H,12,13)(H,14,15)

Upstream product

• 938182-54-8 ethyl 5-(4-methoxyphenyl)-1H-pyrazole-3-carboxylate 
• 35322-20-4 ethyl 3-(4-methoxybenzoyl)pyruvate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 39757-31-8 methyl (4-methoxybenzoyl)pyruvate 
• 192701-83-0 methyl 5-(4-methoxyphenyl)-1H-pyrazole-3-carboxylate 
• 100-66-3 methoxybenzene 
• 938182-54-8 ethyl 5-(4-methoxyphenyl)-1H-pyrazole-3-carboxylate 
• 192701-83-0 C₁₂H₁₂N₂O₃ 

Downstream Products

• 1093649-88-7 5-(4-hydroxyphenyl)-1H-pyrazole-3-carboxylic acid 
• 1316754-40-1 C₂₄H₂₉N₅O₂ 
• 1609174-04-0 N-(2-butoxy-4-(3-(diethylamino)propoxy)phenyl)-3-(4-methoxyphenyl)-1H-pyrazole-5-carboxamide 

Relevant academic research and scientific papers

Design, synthesis, biological evaluation and in silico studies of pyrazole‐based nh2‐acyl oseltamivir analogues as potent neuraminidase inhibitors

Oseltamivir represents one of the most successful neuraminidase (NA) inhibitors in the current anti‐influenza therapy. The 150‐cavity of NA was identified as an additional binding pocket, and novel NA inhibitors have been designed to occupy the 150‐cavity

Synthesis, biological evaluation and molecular modeling studies of psammaplin A and its analogs as potent histone deacetylases inhibitors and cytotoxic agents

In this study, a concise synthetic method of psammaplin A was achieved from 3-bromo-4-hydroxybenzaldahyde and hydantoin through a four-step synthesis via Knoevenagel condensation, hydrolysis, oximation and amidation in 37% overall yield. A collection of novel psammaplin A analogs focused on the variations of substituents at the benzene ring and modifications at the oxime moiety were synthesized. Among all the synthesized compounds, 5d and 5e showed better HDAC inhibition than psammaplin A and comparable cytotoxicity against four cancer cell lines (PC-3, MCF-7, A549 and HL-60). Molecular docking and dynamics simulation revealed that (i) hydrogen atom of the oxime group interacts with Asp99 of HDAC1 through a water bridged hydrogen bond and (ii) a hydroxyl group is optimal attached on the para-position of benzene, interacting with Glu203 at the entrance to the active site tunnel.

5-Aryl-1H-pyrazole-3-carboxylic acids as selective inhibitors of human carbonic anhydrases IX and XII

Inhibitory activity of a congeneric set of 23 phenyl-substituted 5-phenyl-pyrazole-3-carboxylic acids toward human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms I, II, IX and XII was evaluated by a stopped-flow CO2 hydrase assay. These compounds exerted a clear, selective inhibition of hCA IX and XII over hCAI and II, with Ki in two to one digit micromolar concentrations (4-50 μM). Derivatives bearing bulkier substituents in para-position of the phenyl ring inhibited hCA XII at one-digit micromolar concentrations, while derivatives having alkyl substituents in both ortho- and meta-positions inhibited hCA IX with Kis ranging between 5 and 25 μM. Results of docking experiments offered a rational explanation on the selectivity of these compounds toward CA IX and XII, as well as on the substitution patterns leading to best CA IX or CA XII inhibitors. By examining the active sites of these four isoforms with GRID generated molecular-interaction fields, striking differences between hCA XII and the other three isoforms were observed. The field of hydrophobic probe (DRY) appeared significantly different in CA XII active site, comparing to other three isoforms studied. To the best of our knowledge such an observation was not reported in literature so far. Considering the selectivity of these carboxylates towards membrane-associated over cytosolic CA isoforms, the title compounds could be useful for the development of isoform-specific non-sulfonamide CA inhibitors.

Novel heteroarylcarboxamide derivative or pharmacutically acceptable salt thereof, process for the preparation thereof and pharmaceutical composition for prevention or treatment of RAGE receptor related diseases containing the same as an active ingredient

The present invention refers to novel heterocyclic biting Carbox probably the id derivative acceptable salt, and manufacturing method thereof including RAGE associated active acetylcholinesterase receptor or pharmaceutical composition for preventing or treating disease is directed to. Heterocycle by the present invention a derivative biting Carbox probably the id RAGE receptor antagonism in by, nerve cells with the beta loss oh with wheat id RAGE conjunction with receptor, inhibiting moving into brain, the resulting beta Amyloid plaque formed 21 is known to effectively inhibit generation.. Furthermore, memory a chemicals that are important in the acetylcholine for decomposing an aromatic thus inhibiting acetylcholine s reel sacrifice , RAGE disease associated active acetylcholinesterase receptor or Alzheimer's disease, cerebrovascular dementia, dementia due to damage bean curd, multi blockade dementia, Alzheimer's disease or the like dementia alcoholic or mixed dementia multi blockade and including dementia, pick (pick) bottle, a smartcrew [...] -Jakob (Creutzfeldt-jakob) bottle, that thyroid gland symptoms , bean curd a blade Parkinson (Parkinson) bottle, Huntington's disease (Huntington) which is useful in preventing or treating, can be used.

Pyrazole-5-carboxamides, novel inhibitors of receptor for advanced glycation end products (RAGE)

In an effort to develop novel inhibitors of receptor for advanced glycation end products (RAGE) for the treatment of Alzheimer's disease, a series of pyrazole-5-carboxamides were designed, synthesized and biologically evaluated. Analyses of the extensive

Synthesis and anticancer activity of heteroaromatic linked 4β-amido podophyllotoxins as apoptotic inducing agents

A series of different heteroaromatic linked 4β-amidopodophyllotoxin conjugates (16a-i, 17a-i and 18a-d) were synthesized and evaluated for anticancer activity against five human cancer cell lines. Among the series, one of the compound 17g showed significant antiproliferative activity in A549 (lung cancer) cell line. Flow cytometric analysis showed that 17g arrested the cell cycle in the G2/M phase leading to caspase-3 dependent apoptotic cell death. Further, Hoechst 33258 staining and DNA fragmentation assay also suggests that 17g induces cell death by apoptosis.

Synthesis and anti-inflammatory activity of some novel 3-phenyl-N-[3-(4- phenylpiperazin-1yl)propyl]-1H-pyrazole-5-carboxamide derivatives

A new series of 3-phenyl-N-[3-(4-phenylpiperazin-1yl)propyl]-1H-pyrazole-5- carboxamide derivatives were synthesized and investigated their anti-inflammatory activities using carrageenan-induced rat paw edema model in vivo. All the synthesized compounds were found to be potent anti-inflammatory agents.

Synthesis and structural characterisation of the isotypic complexes MIIL2(py)2·2H2O (M = Cu, Zn); the interplay of lattice imposed ligand disposition and Jahn-Teller distortions [HL = 5-(4-methoxyphenyl)pyrazole-3-carboxylic acid]

The mononuclear complexes of general formula ML2(H2O)2 (M = Zn, Cu, Ni, Co) and ML2(py)2?2H2O (M = Zn, Cu, Co) have been prepared [HL = 5-(4-methoxyphenyl)pyrazole-3-carboxylic acid, py = pyridine]. The crystal structures of ZnL2(py)2·2H2O and CuL2(py)2·2H2O have been determined and are isotypic. Two independent molecules are present in the structures, both of which are pseudo-octahedral with mutually trans stereochemistries. In the zinc case the two metal coordination environments differ only slightly and these differences are probably due to packing forces, but for copper the differences are greater and indicate that the direction of the Jahn-Teller distortion observed is dependent upon the subtle constraints imposed by the lattice. The occurrence of such molecular forms is unique for such donor sets and allows a special opportunity to observe the interplay of Jahn-Teller effects and packing forces.