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oxazole-4-carboxylicacid structure, CAS 153259-65-5

oxazole-4-carboxylicacid

CAS Number153259-65-5

Synonymscis-4-(3-(Cyclopentyloxy)-4-methoxyphenyl)-4-cyanocyclohexane-1-carboxylic acid; 1xlx; cis-4-Cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexanecarboxylic acid; cis-4-Cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexanecarboxylic acid; S1455_Selleck; Ariflo; c-4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-r-1-cyclohexane carboxylic acid; 1xom; cilomilast; 4-Cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexanecarboxylic acid; SB-207499

Molecular FormulaC20H25NO4

Molecular Weight343.42

Purity≥95 (HPLC)%

Density1.2±0.1 g/cm3

Boiling Point549.1±50.0 °C at 760 mmHg

Melting Point157ºC

Flash Point

Appearancepowder

EINECS

MSDSChineseEnglish

Symbol

Signal Word

Cat. No.: 2A-9070528 Purity: ≥95 (HPLC)%
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Quality Control of [ 153259-65-5 ] Purity: ≥95 (HPLC)% SDS Specification MoL

COA NMR CNMR HPLC LC-MS
Chemical & Physical Properties
CAS Number153259-65-5
Catalog No.2A-9070528
Chinese Name西洛司特
Synonymscis-4-(3-(Cyclopentyloxy)-4-methoxyphenyl)-4-cyanocyclohexane-1-carboxylic acid; 1xlx; cis-4-Cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexanecarboxylic acid; cis-4-Cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexanecarboxylic acid; S1455_Selleck; Ariflo; c-4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-r-1-cyclohexane carboxylic acid; 1xom; cilomilast; 4-Cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexanecarboxylic acid; SB-207499
Molecular FormulaC20H25NO4
Molecular Weight343.42
Purity≥95 (HPLC)
Density1.2±0.1 g/cm3
Boiling Point549.1±50.0 °C at 760 mmHg
Melting Point157ºC
Appearancepowder
Water SolubilityDMSO: soluble15mg/mL, clear
Storage Condition?20°C
ApplicationCilomilast (SB 207499; Ariflo) is a PDE4 inhibitor with an IC50 of 110 nM and anti-inflammatory activity.
PubChem ID7848767
SMILESN#CC3(CCC(CC3)C(=O)O)c1cc(c(cc1)OC)OC2CCCC2
InChI1S/C20H25NO4/c1-24-17-7-6-15(12-18(17)25-16-4-2-3-5-16)20(13-21)10-8-14(9-11-20)19(22)23/h6-7,12,14,16H,2-5,8-11H2,1H3,(H,22,23)
InChI KeyCFBUZOUXXHZCFB-UHFFFAOYSA-N
NACRES CodeNA.77
UNSPSC41106305
MSDSmsds/70528_1_153259_65_5.pdf
BioactivityCilomilast(SB 207499; Ariflo) is a potent PDE4 inhibitor with IC50 of about 110 nM, has anti-inflammatory activity and low central nervous system activity.IC50 value: 110 nMTarget: PDE 4Cilomilast (SB-207499) inhibits HPDE4 and LPDE4 catalytic activity with equal potency (Ki ≈100 nM). SB-207499 and rolipram are equipotent against LPDE4, but Cilomilast (Ariflo, SB-207499) is 100-fold less potent against HPDE4. This profile suggests that Cilomilast (Ariflo, SB-207499) retain the anti-inflammatory activity of rolipram yet have a decreased tendency to produce side effects. Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE) Research Areas >> Inflammation/Immunology References [1]. MARY S. BARNETTE et al. SB 207499 (Ariflo), a Potent and Selective Second-Generation Phosphodiesterase 4 Inhibitor: In Vitro Anti-inflammatory Actions JPET 284:420 -426, 1998 [2]. Munisso MC, Kang JH, Tsurufuji M, Yamaoka T.Cilomilast enhances osteoblast differentiation of mesenchymal stem cells and bone formation induced by bone morphogenetic protein 2.Biochimie. 2012 Jun 15. [3]. Sadrai Z, Stevenson W, Okanobo A, Chen Y, Dohlman TH, Hua J, Amparo F, Chauhan SK, Dana R.PDE4 inhibition suppresses IL-17-associated immunity in dry eye disease.Invest Ophthalmol Vis Sci. 2012 Jun 14;53(7):3584-91. Print 2012 Jun. [4]. Pace E, Ferraro M, Uasuf CG, Giarratano A, La Grutta S, Liotta G, Johnson M, Gjomarkaj M.Cilomilast counteracts the effects of cigarette smoke in airway epithelial cells.Cell Immunol. 2011;268(1):47-53. Epub 2011 Feb 20. [5]. Barton AK, Niedorf F, Gruber AD, Kietzmann M, Ohnesorge B.Pharmacological studies of bronchial constriction inhibited by parasympatholytics and cilomilast using equine precision-cut lung slices.Berl Munch Tierarztl Wochenschr. 2010 May-Jun;123(5-6):229-35 Chemical & Physical Properties Density 1.2±0.1 g/cm3 Boiling Point 549.1±50.0 °C at 760 mmHg Melting Point 157ºC Molecular Formula C20H25NO4 Molecular Weight 343.417 Flash Point 285.9±30.1 °C Exact Mass 343.178345 PSA 79.55000 LogP 3.30 Vapour Pressure 0.0±1.6 mmHg at 25°C Index of Refraction 1.568 InChIKey CFBUZOUXXHZCFB-UHFFFAOYSA-N SMILES COc1ccc(C2(C#N)CCC(C(=O)O)CC2)cc1OC1CCCC1 Storage condition ?20°C Water Solubility DMSO: soluble15mg/mL, clear
Use ofProperties Name 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-1-carboxylic acid Synonym More Synonyms Cilomilast Biological Activity Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE) Research Areas >> Inflammation/Immunology References [1]. MARY S. BARNETTE et al. SB 207499 (Ariflo), a Potent and Selective Second-Generation Phosphodiesterase 4 Inhibitor: In Vitro Anti-inflammatory Actions JPET 284:420 -426, 1998 [2]. Munisso MC, Kang JH, Tsurufuji M, Yamaoka T.Cilomilast enhances osteoblast differentiation of mesenchymal stem cells and bone formation induced by bone morphogenetic protein 2.Biochimie. 2012 Jun 15. [3]. Sadrai Z, Stevenson W, Okanobo A, Chen Y, Dohlman TH, Hua J, Amparo F, Chauhan SK, Dana R.PDE4 inhibition suppresses IL-17-associated immunity in dry eye disease.Invest Ophthalmol Vis Sci. 2012 Jun 14;53(7):3584-91. Print 2012 Jun. [4]. Pace E, Ferraro M, Uasuf CG, Giarratano A, La Grutta S, Liotta G, Johnson M, Gjomarkaj M.Cilomilast counteracts the effects of cigarette smoke in airway epithelial cells.Cell Immunol. 2011;268(1):47-53. Epub 2011 Feb 20. [5]. Barton AK, Niedorf F, Gruber AD, Kietzmann M, Ohnesorge B.Pharmacological studies of bronchial constriction inhibited by parasympatholytics and cilomilast using equine precision-cut lung slices.Berl Munch Tierarztl Wochenschr. 2010 May-Jun;123(5-6):229-35 Chemical & Physical Properties Molecular Formula C20H25NO4 Exact Mass 343.178345 PSA 79.55000 Index of Refraction 1.568 InChIKey CFBUZOUXXHZCFB-UHFFFAOYSA-N
Transport InfoProduct Name: Cilomilast
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