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6-(4-Fluorophenyl)-2,3-dihydro-5-(4-pyridinyl)imidazo[2,1-b]thiazole dihydrochloride

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6-(4-Fluorophenyl)-2,3-dihydro-5-(4-pyridinyl)imidazo[2,1-b]thiazole dihydrochloride 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-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;5-(4-Pyridyl)-6-(4-fluorophenyl)-2,3-dihydroimidazo[2,1-b]thiazole
CAS:72873-74-6
MF:C16H12FN3S
MW:297.35
EINECS:
Product Categories:Inhibitors;Protein Kinase
Mol File:72873-74-6.mol
6-(4-Fluorophenyl)-2,3-dihydro-5-(4-pyridinyl)imidazo[2,1-b]thiazole dihydrochloride Structure
6-(4-Fluorophenyl)-2,3-dihydro-5-(4-pyridinyl)imidazo[2,1-b]thiazole dihydrochloride Chemical Properties
Melting point 189-190 °C(lit.)
Boiling point 476.1±55.0 °C(Predicted)
density 1.39±0.1 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,2-8°C
solubility DMSO: 9 mg/mL, soluble
form solid
pka4.36±0.10(Predicted)
color off-white
InChIInChI=1S/C16H12FN3S/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
InChIKeyYOELZIQOLWZLQC-UHFFFAOYSA-N
SMILESS1CCN2C(C3C=CN=CC=3)=C(C3=CC=C(F)C=C3)N=C12
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
HS Code 2934999090
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
SigmaAldrich English
6-(4-Fluorophenyl)-2,3-dihydro-5-(4-pyridinyl)imidazo[2,1-b]thiazole dihydrochloride Usage And Synthesis
DescriptionSKF 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.
UsesSKF 86002 is an inhibitor of p53, Cox, and 5-LO.
DefinitionChEBI: 6-(4-fluorophenyl)-5-pyridin-4-yl-2,3-dihydroimidazo[2,1-b]thiazole is a member of imidazoles.
Biological ActivityInhibitor 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 .
in vivo

SKF-86002 (10-90 mg/kg; p.o.; daily; for 22 days) has antiarthritic activity[5].

Animal Model:Lewis rats, with adjuvant-induced arthritis (AA)[5]
Dosage:10 mg/kg, 30 mg/kg, 90 mg/kg
Administration:Oral administration, daily, for 22 days
Result:Significantly decreased hindleg volumes after injection of adjuvant.
References[1] DON E. GRISWOLD. SK&F 86002: A structurally novel anti-inflammatory agent that inhibits lipoxygenase- and cyclooxygenase-mediated metabolism of arachidonic acid[J]. Biochemical pharmacology, 1987, 36 20: Pages 3463-3470. DOI: 10.1016/0006-2952(87)90327-3
[2] JOHN C. LEE. Inhibition of monocyte IL-1 production by the anti-inflammatory compound, SK&F 86002[J]. International journal of immunopharmacology, 1988, 10 7: Pages 835-843. DOI: 10.1016/0192-0561(88)90007-0
[3] M J DIMARTINO. Pharmacologic characterization of the antiinflammatory properties of a new dual inhibitor of lipoxygenase and cyclooxygenase.[J]. Agents and Actions, 1987, 20 1-2: 113-123. DOI: 10.1007/bf01965633
[4] A M BADGER. Protective effect of SK&F 86002, a novel dual inhibitor of arachidonic acid metabolism, in murine models of endotoxin shock: inhibition of tumor necrosis factor as a possible mechanism of action.[J]. Circulatory shock, 1989, 27 1: 51-61.
6-(4-Fluorophenyl)-2,3-dihydro-5-(4-pyridinyl)imidazo[2,1-b]thiazole dihydrochloride Preparation Products And Raw materials
Tag:6-(4-Fluorophenyl)-2,3-dihydro-5-(4-pyridinyl)imidazo[2,1-b]thiazole dihydrochloride(72873-74-6) Related Product Information
5-Chloro-2,3-difluoropyridine Pyridine 2-Chloro-5-trifluoromethylpyridine 6-(4-Fluorophenyl)-2,3-dihydro-5-(4-pyridinyl)imidazo[2,1-b]thiazole dihydrochloride 6-Phenyl-2,3-dihydroimidazo[2,1-b][1,3]thiazole 4-(3H-Imidazol-4-yl)-pyridine