ML
1-(5-Iodonaphthalene-1-sulfonyl)-1H-hexahydro-1,4 -diazepine, hydrochloride
CAS: 110448-33-4
Molecular Formula: C15H18ClIN2O2S
ML - Names and Identifiers
ML - Physico-chemical Properties
| Molecular Formula | C15H18ClIN2O2S |
| Molar Mass | 452.74 |
| Melting Point | 246-249°C dec. |
| Boling Point | 542.7℃ at 760 mmHg |
| Appearance | White to light brown powder |
| Color | white |
| Storage Condition | -20°C |
| MDL | MFCD00065524 |
| In vitro study | In the adherent MCF-10A and MCF-10A Ras transformed cells, ML-7 inhibited MLCK, resulting in the activation of caspase-3. ML-7 caused a dose-dependent decrease in MLC20 phosphorylation and an increase in cell death of smooth muscle cells. The inhibition of MLCK by ML-7 was very specific with a Ki value of 0.3 μm, whereas the Ki for PKA by ML-7 was 21 μm and the Ki for PKC was 42 μm. Overexpression of Bcl-2 protects cells from ML-7-induced apoptosis. |
| In vivo study | ML7 was able to modulate tight junction protein ZO-1 and occludin by phosphorylation of MLCK and MLC, thereby improving vascular endothelial dysfunction and atherosclerosis in rabbits on a high fat diet. ML7 reduces the expression of phosphorylated MLCK and MLC in arterial walls of high fat diet rabbits; In a rabbit model of atherosclerosis, lipid deposition lesions are reduced. |
ML - Risk and Safety
| WGK Germany | 3 |
ML - Reference Information
| introduction | 1-(5-iodonaphthalene-1-sulfonyl) -1H-hexahydro-1, 4-diazepine hydrochloride can be used as an intermediate in pharmaceutical synthesis and as an inhibitor of selective catalytic activity myosin light chain kinase (MLCK). |
| preparation | 1) add 1.2 liters of perpiperazine (89.7g,896mmol)(15 volumes relative to the expected weight) dissolved in toluene to a three-necked round bottom flask, stir, cool the mixture in an ice bath, and within 30 minutes (T0=7 ℃, tfinaie = 140 ℃) 5-iodo-1-naphthalenesulfonyl chloride (224mmol,800mL) solution was added, and then the reaction was stirred at 18±2 ℃ for 16 hours. The mixture was filtered under vacuum on sintered glass (diameter = 10cm, porosity = 3, thickness = 1cm), the solid was washed with 80mL(1 volume) of toluene, the filtrate was washed 6 times with 800mL of water (10 volumes), the organic phase was purified on a silicone pad (2 parts, diameter = 8cm, thickness of silica = 6.5cm), and eluted with the following solvent:-1 liter of toluene/iPrOH(90/10):Fl-1 liter of toluene/iPrOH(70/30):F2-2 liter of toluene/iPrOH(60/40):F3-1 liter of toluene/iPrOH(50/50):F4 vacuum evaporation The resulting fraction is 1 to 4, and the resulting solid is crystallized with 320ml of isopropanol (4 volumes), and after cooling to 5±2°C, the solid was filtered out and washed with 80mL(1 volume) of cold isopropanol, and the compound was vacuum-dried to give 57.2g of beige solid 1-(5-iodonaphthalene-1-sulfonyl) -1H-hexahydro-1, 4-diazepines in 61% yield. 2) Add 1-(5-iodonaphthalene-1-sulfonyl) -1H-hexahydro-1, 4-diazepine ((57.2g,137mmol) and 286mL(5 volumes) isopropyl alcohol to a three-necked round bottom flask, reflux the suspension until the mixture becomes uniform, cool to 20±2°C, and then add 6NHCl(22.9mL,137mmol) through a funnel, the mixture is cooled to 5±2°C, filtered, the solid is washed with cold isopropanol (57mL,1 volume), the resulting solid is crystallized with 114mL of water (2 volumes), cooled to 5±2°C, the solid is filtered out and washed with 57mL(1 volume) cold water, the compound is vacuum dried at 70°C, 52.7g of 1-(5-iodonaphthalene-1-sulfonyl) -1H-hexahydro-1, 4-diazepine hydrochloride in white solid form was obtained with 84% yields. |
| biological activity | ML-7 is a smooth muscle myosin light chain kinase MLCK inhibitor with a Ki value of 0.3 μM. It has reversible and ATP competitive inhibitory effect on calcium ion-calmodulin-dependent or non-dependent smooth muscle MLCKs. ML-7 can also inhibit PKA and PKC, and the corresponding Ki values are 21 μM and 42 μM respectively. |
| target | TargetValue MLCK (Cell-free say) 0.3 μM(Ki) PKA (in Ehrlich cells) 21 μM PKC (in Ehrlich cells) 42 μM |
| Target | Value |
| MLCK (Cell-free assay) | 0.3 μM(Ki) |
| PKA (in Ehrlich cells) | 21 μM |
| PKC (in Ehrlich cells) | 42 μM |
| in vitro study | in adherent MCF-10A and MCF-10A Ras transformed cells, ML-7 inhibit MLCK and cause caspase-3 activation. ML-7 can cause a dose-dependent decrease in MLC20 phosphorylation and an increase in cell death of smooth muscle cells. The inhibitory effect of ML-7 on MLCK is very specific, Ki value is 0.3 μM; However, the Ki value of ML-7 to PKA is 21 μM and the Ki value to PKC is 42 μM. Over-expression of Bcl-2 can protect cells from apoptosis induced by ML-7. |
| In vivo studies | ML7 in rabbits fed a high-fat diet can regulate tight junction protein ZO-1 and closure protein through phosphorylation of MLCK and MLC, thereby improving vascular endothelial dysfunction and atherosclerosis. ML7 reduces the expression of phosphorylated MLCK and MLC in the arterial wall of rabbits fed a high-fat diet; in a rabbit model of atherosclerosis, it reduces lipid deposition lesions. |
Last Update：2024-04-10 22:29:15
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Tel: 18301782025
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