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Tricarbonyl complexes of transition metals with benzo-heterocyclic derivatives of the cyclopentadienyl anion

A transition metal, tricarbonylcyclopentadiene technology, applied in the field of therapeutic applications, can solve the problem of low cure rate and achieve the effect of high blood-brain barrier permeability

Active Publication Date: 2020-11-13
NAT CENT FOR SCI RES DEMOKRITOS +4
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the main treatment strategies used for brain tumors are radiotherapy and surgery, in both cases the cure rate is very low

Method used

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  • Tricarbonyl complexes of transition metals with benzo-heterocyclic derivatives of the cyclopentadienyl anion
  • Tricarbonyl complexes of transition metals with benzo-heterocyclic derivatives of the cyclopentadienyl anion
  • Tricarbonyl complexes of transition metals with benzo-heterocyclic derivatives of the cyclopentadienyl anion

Examples

Experimental program
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Embodiment 9

[0041] The use of the complex in Alzheimer's disease-related challenges, including the staining of amyloid plaques in brain tissue using the complex Re-2-Re-5 (Example 10), the complex 99m Tc-2-99m Determination of the affinity constant for the binding of Tc-4 to amyloid fibrils (Example 11), inhibition of amyloid fibril-induced toxicity in primary neuronal cells using the complex Re-2, Re-3 (Example 12), and the determination of the antioxidant activity of complexes Re-2 and Re-3 against ROS (Example 13).

Embodiment 1

[0044] Synthesis of Ferrocenyl-Benzothiazole (Fe-2)

[0045]

[0046] Ferroceneformaldehyde (1.1 g, 5 mmol) and 2-aminothiophenol (600 μL, 5.6 mmol, 1.1 eq) in ethanol (40 mL) were stirred at reflux for 16 hours. The reaction was brought back to r.t and a reddish brown solid precipitated. The final product was obtained by flash column chromatography of the precipitate eluting with hexane:ethyl acetate (98:2 to 96:4). Yield: 92%. NMR (DMSO-d 6 ,ppm): 1 Η(500MHz)8.03,7.92,7.47,7.39,5.02,4.60,4.16; 13 C(126MHz)153.43,126.24,124.52,121.96,121.80,70.82,70.13,68.50.MS(ESI)m / z:[M+H] + Calculated value C 17 h 14 NS 56 Fe, 320.0188; measured value, 320.0188.

Embodiment 2

[0048] Synthesis of Ferrocenyl-Benzimidazole (Fe-3)

[0049]

[0050] A mixture of ferroceneformaldehyde (0.76 g, 4 mmol) and sodium bisulfite (1.44 g, 1.4 mmol) was dissolved in a mixture of 20 mL of absolute ethanol and water (1:1). The reaction mixture was refluxed for 1 hour. o-Phenylenediamine (0.4 g, 4 mmol) was added at room temperature and the mixture was refluxed for another 1 hour. Then cool to room temperature and finally refrigerate. The formed precipitate was filtered and washed successively with ice cold water and cold absolute ethanol. The pure product was isolated by flash column chromatography of the precipitate eluting with dichloromethane:ethyl acetate (96:4). Yield: 62%. NMR (DMSO-d 6 ,ppm): 1 Η(500MHz) 12.35, 7.54, 7.44, 7.13, 5.04, 4.47, 4.10; 13 C NMR (126 MHz) 152.92, 120.86, 117.50, 110.15, 69.31, 68.91, 66.90.

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Abstract

Complex compounds of transition metals according to formula (1) wherein the M(CO)3<+> tricarbonyl-metal core forms a complex with the cyclopentadienyl anion linked to heterocyclic moieties of the benzothiazole, benzimidazole and benzoxazole families. The compounds exhibit high blood-brain barrier permeability and can be used in the diagnosis and / or treatment of diseases of the Central Nervous System.

Description

technical field [0001] The present invention relates to properly designed complexes of transition metals that exhibit high blood-brain barrier permeability and can be used as diagnostic / therapeutic agents for CNS diseases. More specifically, it relates to a) radiodiagnostics of common CNS diseases, including Alzheimer's disease and brain tumors, and b) therapeutic applications of these complexes. Background technique [0002] Blood Brain Barrier and CNS Drugs [0003] Penetration of the blood-brain barrier (BBB) ​​is a bottleneck in the development of drugs for the central nervous system (CNS) and especially for the brain [1]. The blood-brain barrier is characterized by the tight arrangement and dense junctions of endothelial cells in the CNS capillaries, and serves to maintain the stability of the microenvironment of the brain cavity and prevent the entry of toxic substances. The protection conferred by the BBB poses a large obstacle to the efficient delivery of drugs for...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K51/04A61P25/28A61P35/00A61K103/10
CPCA61K51/0453C07D277/66C07D263/57A61K51/04A61P25/28A61P35/00C07F13/005
Inventor 玛丽亚·佩莱卡纽赞帕拉玛丽娜·萨纽米纳斯·帕帕佐普洛斯扬尼斯·皮尔迈提斯芭芭拉·马夫罗迪安东尼奥·谢加尼
Owner NAT CENT FOR SCI RES DEMOKRITOS
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