| Identification | Back Directory | [Name]
1-naphthyl 3,5-dinitrobenzoate | [CAS]
93261-39-3 | [Synonyms]
JMC-4
1-naphthyl 3,5-dinitrobenzoate
napthalen-1-yl 3,5-dinitrobenzoate
naphthalen-1-yl 3,5-dinitrobenzoate
1-(3,5-DINITROBENZOATE) 1-NAPHTHALENOL | [Molecular Formula]
C17H10N2O6 | [MOL File]
93261-39-3.mol | [Molecular Weight]
338.27 |
| Chemical Properties | Back Directory | [Melting point ]
217-219 °C(Solv: toluene (108-88-3)) | [Boiling point ]
541.4±40.0 °C(Predicted) | [density ]
1.466±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
≤0.1mg/ml in methanol;0.5mg/ml in DMSO | [form ]
crystalline solid | [color ]
Off-white to light yellow |
| Hazard Information | Back Directory | [Biological Activity]
1-naphthyl 3,5-dinitrobenzoate is a dual 5-lipoxygenase and microsomal prostaglandin e synthase-1 inhibitor.human 5-lipoxygenase (5-lox), a target for antiinflammation drug design, catalyzes the first two reactions in the production of leukotrienes from arachidonic acid (aa): oxygenation of aa to 5-hpete and further dehydration to leukotriene a4 (lta4). then lta4 is metabolized to other leukotrienes. furthermore, 5-lox is also found to play key roles in tumor formation and cancer metastasis and thus is considered as a potential target for anticancer drugs. | [in vitro]
a previous study built a comparative model for the human 5-lox closed conformation and successfully used it in virtual screening. out of around 200 000 compounds, 105 compounds were selected for experimental test. in cell-free assay, 30 compounds were found to have ic50 values less than 100 μm and 11 with ic50 values less than 10 μm. eventually, 1-naphthyl 3,5-dinitrobenzoate was screened out to have inhibition activity in the human whole blood assay with ic50 values less than 10 μm. 1-naphthyl 3,5-dinitrobenzoate was also identified as efficient dualfunctional inhibitors of 5-lox and mpges-1 in both cell-free assay and cell-based assay. in addition, 1-naphthyl 3,5-dinitrobenzoate was able to simultaneously suppress the production of ltb4 and pge2 in human whole blood, and its targets was verified as 5-lox and mpges-1, not lta4h, cox-1, cox-2 [1]. | [IC 50]
1 and 3.6 μm for 5-lipoxygenase and microsomal prostaglandin e synthase-1, respectively | [References]
[1] wu, y. ,he, c.,gao, y., et al. dynamic modeling of human 5-lipoxygenase-inhibitor interactions helps to discover novel inhibitors. journal of medicinal chemistry 55, 2597-2605 (2012). |
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