| Identification | More | [Name]
Irsogladine | [CAS]
57381-26-7 | [Synonyms]
rsogladin
IRSOGLADINE
Dicloguamine
Irsogladine free base
2',5'-Dichlorobenzoguanamine
5-triazine-2,4-diamine,6-(2,5-dichlorophenyl)-3
6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine
2,4-diamino-6-(2,5-dichlorophenyl)-1,3,5-triazine
Irsogladine,2,4-DiaMino-6-(2,5-dichlorophenyl)-1,3,5-triazine | [Molecular Formula]
C9H7Cl2N5 | [MDL Number]
MFCD00866871 | [Molecular Weight]
256.09 | [MOL File]
57381-26-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
268-269°C | [Boiling point ]
552.2±60.0 °C(Predicted) | [density ]
1.572 | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
insoluble in H2O; insoluble in EtOH; ≥12.80 mg/mL in DMSO | [form ]
solid | [pka]
3.88±0.10(Predicted) | [color ]
White to off-white | [CAS DataBase Reference]
57381-26-7(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
Irsogladine is a PDE4 inhibitor and muscarinic acetylcholine receptor binder.
Target: PDE4; mACHR
Irsogladine treatment (300 and 500 mg/kg/day) resulted in a dose-dependent reduction of angiogenesis in wild-type mice by 21 and 45.3% (P < 0.02, P < 0.001), in tPA-deficient mice by 42.6 and 46% (P < 0.001, P < 0.001), and in uPA-deficient mice by 27.2 and 46% (P < 0.05, p < 0.001), respectively. Irsogladine inhibits bFGF-induced angiogenesis in wild-type, tPA-knockout, and uPA-knockout mice [1]. Irsogladine up-regulates GJIC between PC cells via regulation of the PKA pathway. It also suggests a useful adjuvant of Irsogladine to pancreatic cancer therapy [2]. irsogladine produces the increase of intracellular cAMP content via non-selective inhibition of PDE isozymes, which may be a key mechanism involved in its gastroprotective actions [3]. | [Definition]
ChEBI: 6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine is a dichlorobenzene. | [Biological Activity]
irsogladine is a pde4 inhibitor and muscarinic acetylcholine receptor binder.irsogladine treatment (300 and 500 mg/kg/day) resulted in a dose-dependent reduction of angiogenesis in wild-type mice by 21 and 45.3% (p < 0.02, p < 0.001), in tpa-deficient mic | [Synthesis]
General procedure for the synthesis of 6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine x maleate from 6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine: 6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine x maleate (0.3 g, 0.80 mmol) was dissolved in ethyl acetate ( 50 mL) and the reaction was stirred with saturated NaHCO3 solution (50 mL) for 1 hour at room temperature. After completion of the reaction, the organic layer was separated and washed with distilled water. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the target product 6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine in 70% yield. | [IC 50]
PDE4 | [References]
[1] Ren, C.J., et al., Irsogladine maleate inhibits angiogenesis in wild-type and plasminogen activator-deficient mice. J Surg Res, 1998. 77(2): p. 126-31. DOI:10.1006/jsre.1998.5381
[2] Kawasaki, Y., et al., Irsogladine malate up-regulates gap junctional intercellular communication between pancreatic cancer cells via PKA pathway. Pancreas, 2002. 25(4): p. 373-7. DOI:10.1097/00006676-200211000-00009
[3] Kyoi, T., et al., Phosphodiesterase inhibition by a gastroprotective agent irsogladine: preferential blockade of cAMP hydrolysis. Life Sci, 2004. 75(15): p. 1833-42. DOI:10.1016/j.lfs.2004.03.022 |
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