188817-13-2 Usage
Uses
Different sources of media describe the Uses of 188817-13-2 differently. You can refer to the following data:
1. 5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole is used as a cyclooxygenase inhibitors on the angiogenesis and apoptosis.
2. SC-560 has been used as a cyclooxygenase-1 (COX-1) inhibitor to study its effects on prostaglandin E-2 (PGE2) signaling in ciliogenesis in zebrafish embryos. It has also been used as a selective inhibitor of COX-1 to study its role in PM10-induced endothelial dysfunction.
Definition
ChEBI: A member of the class of pyrazoles that is 1H-pyrazole which is substituted at positions 1, 3 and 5 by 4-methoxyphenyl, trifluoromethyl and 4-chlorophenyl groups, respectively. Unlike many members of the diaryl heterocycle class of cyclo
xygenase (COX) inhibitors, SC-560 is selective for COX-1.
Biological Activity
Highly selective cyclooxygenase-1 (COX-1) inhibitor (IC 50 values are 0.009 and 6.3 μ M for COX-1 and COX-2 respectively). Inhibits COX-1-derived platelet thromboxane B 2 , gastric PGE 2 and dermal PDE 2 production. Significantly reduces ovarian surface epithelial tumor growth in vivo . Orally active.
Biochem/physiol Actions
SC-560 (5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole) is a non-steroidal anti-inflammatory drug (NSAID). It is a lipophilic, diaryl heterocyclic compound. SC-560 acts as an effective antiviral agent against hepatitis C virus (HCV). It also has a potential to hinder prostaglandin E2 synthesis in neurons at nanomolar concentrations.
in vitro
preincubation of cox-1 with sc-560 inhibited the conversion of arachidonic acid to pge2 in a concentration-dependent manner [1]. sc-560 was necessary to sustain a reduced basal level of pgi2 for an extended period. sc-560 inhibits cell proliferation and accelerates apoptosis which results in attenuated tumor growth [2].
in vivo
oral dosing with either 10 or 30 mg/kg sc-560 1 hr before assay completely inhibited cox-1-derived platelet thromboxane b2, gastric pge2, and dermal pge2 production [1]. sc-560 can suppress ovarian surface epithelial tumor growth. tumor growth was suppressed in allografted mice treated with sc-560 for a longer period, but the reduction in tumor growth was less dramatic than the short-term treated [2].
IC 50
0.009 μm for cox-1; 6.3 μm for cox-2
references
[1] daikoku t, wang d, tranguch s, morrow jd, orsulic s, dubois rn, dey sk. cyclooxygenase-1 is a potential target for prevention and treatment of ovarian epithelial cancer. cancer res. 2005 may 1;65(9):3735-44.[2] christopher j. smith, yan zhang, carol m. koboldt, jerry muhammad, ben s. zweifel, alex shaffer, john j. talley, jaime l. masferrer, karen seibert, peter c. isakson. pharmacological analysis of cyclooxygenase-1 in inflammation. proc natl acad sci u s a. 1998 oct 27; 95(22): 13313–13318.
Check Digit Verification of cas no
The CAS Registry Mumber 188817-13-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,8,8,8,1 and 7 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 188817-13:
(8*1)+(7*8)+(6*8)+(5*8)+(4*1)+(3*7)+(2*1)+(1*3)=182
182 % 10 = 2
So 188817-13-2 is a valid CAS Registry Number.
InChI:InChI=1/C17H12ClF3N2O/c1-24-14-8-6-13(7-9-14)23-15(10-16(22-23)17(19,20)21)11-2-4-12(18)5-3-11/h2-10H,1H3
188817-13-2Relevant articles and documents
Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters
Haydl, Alexander M.,Hartwig, John F.
supporting information, p. 1337 - 1341 (2019/02/26)
A method for the direct methylation of aryl, heteroaryl, and vinyl boronate esters is reported, involving the reaction of iodomethane with aryl-, heteroaryl-, and vinylboronate esters catalyzed by palladium and PtBu2Me. This transformation occurs with a remarkably broad scope and is suitable for late-stage derivatization of biologically active compounds via the boronate esters. The unique capabilities of this method are demonstrated by combining carbon-boron bond-forming reactions with palladium-catalyzed methylation in a tandem transformation.
Polysubstituted 3-trifluoromethylpyrazoles: Regioselective (3 + 2)-cycloaddition of trifluoroacetonitrile imines with enol ethers and functional group transformations
Utecht, Greta,Fruziński, Andrzej,Jasiński, Marcin
, p. 1252 - 1257 (2018/03/06)
Non-catalysed addition of trifluoroacetonitrile imines to enol ethers provided fully regioselectively (3 + 2)-cycloadducts, which either spontaneously or via Br?nsted acid-induced elimination of ROH molecules led to the formation of 3-trifluoromethylated
Synthesis of Celecoxib, Mavacoxib, SC-560, Fluxapyroxad, and Bixafen Enabled by Continuous Flow Reaction Modules
Britton, Joshua,Jamison, Timothy F.
supporting information, p. 6566 - 6574 (2017/12/02)
Multi-step continuous flow synthesis enables a parallel approach to obtain agrochemicals and pharmaceuticals containing 3-fluoroalkyl pyrazole cores. In this system, fluorinated amines are transformed into pyrazole cores through a telescoped in situ generation and consumption of diazoalkanes. Once synthesized, additional continuous flow and batch reactions add complexity to the pyrazole core via C–N arylation and methylation, TMS cleavage, and amidation. Using this modular assembly line approach, Bixafen and Fluxapyroxad were synthesized in 38 % yield over four continuous flow steps in an overall reaction time of 56 min. Finally, coupling selected continuous flow processes with an offline (batch) Ullmann coupling afforded Celecoxib, Mavacoxib, and SC-560 in 33–54 % yield over two to three steps.
