72873-74-6

Basic information

• Product Name: 6-(4-FLUOROPHENYL)-2,3-DIHYDRO-5-(4-PYRIDINYL)IMIDAZO[2,1-B]THIAZOLE DIHYDROCHLORIDE
• Synonyms: 6-(4-FLUOROPHENYL)-5-(4-PYRIDYL)-2,3-DIHYDROIMIDAZO[2,1-B]-THIAZOLE;6-(4-FLUOROPHENYL)-2,3-DIHYDRO-5-(4-PRIDYL)IMIDAZO-[2,1,B]-THAIZOLE;6-(4-FLUOROPHENYL)-2,3-DIHYDRO-5-(4-PYRIDINYL)IMIDAZO[2,1-B]THIAZOLE DIHYDROCHLORIDE;6-(4-FLUOROPHENYL)-2,3-DIHYDRO-5-(4-PYRIDYL)IMIDAZO[2,1-B]THIAZOLE;SKF-86002;SKF 86002 DIHYDROCHLORIDE;6-(4-fluorophenyl)-2,3-dihydro-5-(4-pyridinyl)imidazo(2,1-b)thiazole;4-(4-Pyridyl)-5-(4-fluorophenyl)-2,3-dihydro-1-thia-3a,6-diazapentalene
• CAS NO: 72873-74-6
• Molecular Formula: C₁₆H₁₂FN₃S
• Molecular Weight: 297.36
• Product Categories: Protein Kinase;Inhibitors
• Mol File: 72873-74-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 189-190 °C(lit.)
• Boiling Point: 476.1°C at 760 mmHg
• Flash Point: 241.7°C
• Appearance: off-white/solid
• Density: 1.39±0.1 g/cm3(Predicted)
• Vapor Pressure: 3.14E-09mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: DMSO: 9 mg/mL, soluble
• PKA: 4.36±0.10(Predicted)
• CAS DataBase Reference: 6-(4-FLUOROPHENYL)-2,3-DIHYDRO-5-(4-PYRIDINYL)IMIDAZO[2,1-B]THIAZOLE DIHYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(4-FLUOROPHENYL)-2,3-DIHYDRO-5-(4-PYRIDINYL)IMIDAZO[2,1-B]THIAZOLE DIHYDROCHLORIDE(72873-74-6)
• EPA Substance Registry System: 6-(4-FLUOROPHENYL)-2,3-DIHYDRO-5-(4-PYRIDINYL)IMIDAZO[2,1-B]THIAZOLE DIHYDROCHLORIDE(72873-74-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 72873-74-6(Hazardous Substances Data)

Usage

Description

SKF 86002 is an anti-inflammatory agent. It inhibits rat seminal vesicle prostaglandin H2 (PGH2) synthase (IC50 = 120 μM), as well as prostanoid production by rat basophilic leukemia (RBL-1) cells and human monocytes (IC50s = 70 and 1 μM, respectively). SKF 86002 inhibits leukotriene B4 (LTB4) and LTC4 production induced by A23187 in human neutrophils and monocytes, respectively (IC50 = 20 μM for both). It also inhibits LPS-induced IL-1 production in human monocytes (IC50 = 1.3 μM). SKF 86002 (10, 30, and 90 mg/kg) reduces hindleg volume in rat models of adjuvant- or collagen-induced arthritis. It also decreases serum levels of TNF-α and increases survival in a mouse model of LPS and galactosamine-induced endotoxic shock when administered at a dose of 100 mg/kg.

Uses

SKF 86002 is an inhibitor of p53, Cox, and 5-LO.

Biological Activity

Inhibitor of p38 MAP kinase (IC 50 = 0.1-1 μ M). Potently inhibits LPS-induced IL-1 and TNF- α production in human monocytes (IC 50 = 1 μ M). Also inhibits 5-lipoxygenase- and cyclooxygenase-mediated arachidonic acid metabolism in RBL-1 cells (IC 50 values are 10 and 100 μ M respectively). Anti-inflammatory following oral administration in vivo .

InChI:InChI=1/C16H12FN3S.2ClH/c17-13-3-1-11(2-4-13)14-15(12-5-7-18-8-6-12)20-9-10-21-16(20)19-14;;/h1-8H,9-10H2;2*1H

Upstream product

• 106465-78-5 6-(4-fluorophenyl)-2,3-dihydroimidazo<2,1-b>thiazole 
• 110-86-1 pyridine 
• 87532-41-0 1-(4-Fluoro-phenyl)-2-hydroxy-2-pyridin-4-yl-ethanone 
• 72882-75-8 4-(4-fluorophenyl)-5-(pyridin-4-yl)-1,3-dihydro-imidazole-2-thione 
• 106-93-4 ethylene dibromide 
• 106465-75-2 5-(N-ethoxycarbonyl-1,4-dihydro-pyridin-4-yl)-6-(4-fluorophenyl)-2,3-dihydroimidazo[2,1-b]-thiazole 

Downstream Products

• 72873-77-9 6-(4-Fluorophenyl)-5-(4-Pyridyl)-2,3-Dihydroimidazo-[2,1-b]Thiazole-1-Oxide 

Relevant articles and documents

Synthetic and Mechanistic Studies on the Preparation of Pyridyl-Substituted Imidazothiazoles

A new method is presented for the introduction of the 4'-pyridyl substituent into 6-aryl-2,3-dihydroimidazothiazoles.The method involves treatment of the imidazothiazolines with the reactive complex of pyridine and ethyl chloroformate and oxidative deethyl carboxylation of the dihydropyridine adducts formed.Sulfur in refluxing mesitylene was found most suitable for the latter reaction, but chromium trioxide in pyridine or KtBuO and air were also effective.