17184-19-9Relevant articles and documents
Metabolic activation of deferiprone mediated by CYP2A6
Zheng, Xiaojiao,Wang, Xu,Ding, Zifang,Li, Wei,Peng, Ying,Zheng, Jiang
, p. 1282 - 1291 (2021)
Deferiprone (DFP) is a metal chelating agent generally used to treat patients with thalassaemia, due to iron overload in clinical settings. Studies have revealed that long-term use of DFP can induce hepatotoxicity, however, mechanisms of its toxic action remain unclear. The present studies are aimed to characterize the reactive metabolite of DFP, to define the metabolic pathway, and to determine the P450 enzymes participating in the bioactivation. A demethylation metabolite (M1) was observed in rat liver microsomal incubations. Additionally, a glutathione (GSH) conjugate (M2) and an N-acetylcysteine (NAC) conjugate (M3) were detected in microsomal incubations fortified with DFP and GSH/NAC. Biliary M2 and urinary M3 were respectively found in animals administered DFP. CYP2A6 enzyme dominated the catalysis to bioactivate DFP.
Lanthanide containing compounds for therapeutic care in bone resorption disorders
Barta, Cheri A.,Sachs-Barrable, Kristina,Jia, Jessica,Thompson, Katherine H.,Wasan, Kishor M.,Orvig, Chris
, p. 5019 - 5030 (2007)
Lanthanide ions, Ln(iii), are known functional mimics of Ca(ii) ions and have been shown to affect the bone remodeling cycle. Exploiting this disruption to the bone remodeling cycle has potential for the treatment of bone density disorders, such as osteoporosis. In an effort to find new orally active agents for these disorders, a series of Ln(iii) containing complexes incorporating small, non-toxic, bidentate pyrone and pyridinone ligands have been synthesized and characterized (LnL3, Ln = La, Eu, Gd, Tb, Yb, L = 3-oxy-2-methyl-4-pyrone (ma-), 3-oxy-2-ethyl-4-pyrone (ema -), 3-oxy-1,2-dimethyl-4-pyridinone (dpp-) and 3-oxy-2-methyl-4(1H)-pyridinone (mpp-)). Preliminary biological analysis included cytotoxicity, cell uptake and bidirectional transport studies in Caco-2 cells and in vitro hydroxyapatite (HA) binding studies. The proportion of intact compounds bound to HA was calculated based on determination of Ln(iii) concentration by ICP-MS and by UV-vis spectrophotometric assay of the proligand in solution. The LnL3 species were found to have IC 50 values at least 6 times greater than that of cisplatin, ≥ 98% HA-binding capacity, and permeability coefficients in the moderate range. La(dpp)3 was ascertained to be the lead compound for the treatment of bone density disorders with the highest percentage cell uptake of 9.07 ± 2.33% and the highest preliminary Papp value of 3.54 ± 2.86 × 10-6 cm s-1 compared to the other LnL3 complexes tested. This journal is The Royal Society of Chemistry.
Discovery of N-Aryl-pyridine-4-ones as Novel Potential Agrochemical Fungicides and Bactericides
Yu, Xiuqiang,Zhu, Xinyue,Zhou, Yang,Li, Qinglin,Hu, Zhan,Li, Ting,Tao, Jun,Dou, Menglan,Zhang, Meng,Shao, Yu,Sun, Ranfeng
, p. 13904 - 13913 (2019/12/24)
A series of N-aryl-pyridine-4-one derivatives were designed and synthesized using maltol and antidesmone as lead compounds, and then their fungicidal/bactericidal activities and possible mechanism of action against Colletotrichum musae were explored. Most of these compounds exhibited significant fungicidal activity in vitro. Especially, compound 23 has more than 90% inhibitory activity against nine plant pathogenic fungi at 50 μg mL-1, which is superior to azoxystrobin. Moreover, an in vivo bioassay also demonstrated that compound 23 exhibited high-efficiency broad-spectrum antifungal activity and can effectively control postharvest diseases of mango. In addition, it was found that compounds 22 and 23 can also effectively control rice bacterial leaf blight in pot experiments, which was even more effective than zhongshengmycin. Preliminary mechanism studies revealed that compound 23 may cause cell membrane and mitochondria destruction. These findings indicate that compound 23 can be used to develop potential agrochemical fungicides and bactericides.
Application of 1-aryl-4-pyridone compound
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Paragraph 0071-0072, (2020/01/12)
The invention discloses application of a 1-aryl-4-pyridone compound, and provides application of a compound of a structure of a formula (I) shown in the description in inhibiting activity of plant pathogenic bacteria. The compound of the structure of the formula (I) shown in the description has outstanding broad-spectrum antifungal activity upon plant pathogenic bacteria in agricultural production, and meanwhile, has a prevention and treatment effect on bacterial disease of crops. In-vivo biological assay shows that the compound of the structure of the formula (I) shown in the description hasa prevention and control effect greater than 95% on cucumber downy mildew, cucumber target leaf spot, wheat scab and tomato gray mold. Meanwhile, results of postharvest fresh-keeping tests of mangos show that the compound is capable of effectively controlling postharvest diseases of mangos and in addition, prolonging the fresh-keeping time of the mangos. In addition, results show that the compoundis also capable of effectively controlling bacterial leaf blight of rice in pot experiments, and is more effective than a commercial fungicide zhongshengmycin. In conclusion, the 1-aryl-4-pyridone derivative of the formula (I) shown in the description has broad-spectrum plant pathogenic fungus resistance and bacterial activity, and is a type of lead compounds with wide bioactivity.
A pantoprazole intermediate 2 - chloromethyl - 3, 4 - dimethoxy pyridine hydrochloride preparation method
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Paragraph 0022-0029, (2018/09/08)
The invention belongs to the technical field of medicine, and particularly relates to a preparation method of a pantoprazole intermediate 2-chloromethyl-3,4-dimethoxy pyridine hydrochloride. The preparation method comprises the following steps: using 3-hydroxyl-2-methyl-4-pyrone as a starting raw material, and then only performing five-step reaction to obtain the pantoprazole intermediate 2-chloromethyl-3,4-dimethoxy pyridine hydrochloride. The preparation method reduces the reaction steps, shortens the reaction cycle, improves the working efficiency, and increases the yield coefficient.
Fluorinated derivatives of deferiprone
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Page/Page column 32-33, (2008/12/07)
The present invention relates to novel derivatives of deferiprone. In particular, the present invention relates to fluorinated derivatives of deferiprone or pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising same, processes for the manufacture thereof and their use in the treatment of neurodegenerative diseases caused by the presence of free iron or iron accumulation in neural tissues and in diseases wherein excess iron must be removed or redistributed.
A New Microwave Reactor for Batchwise Organic Synthesis
Raner, Kevin D.,Strauss, Christopher R.,Trainor, Robert W.,Thorn, John S.
, p. 2456 - 2460 (2007/10/02)
A laboratory-scale microwave batch reactor (MBR) has been developed for organic synthesis or kinetic studies on the 20-100 mL scale, with upper operating limits of 260 deg C and 10 MPa (100 atm).The MBR complements a continuous microwave reactor which was the subject of a previous report from the author's laboratory.Microwave-assisted organic reactions were conducted safely and conveniently in the MBR, for lengthy periods when required, and in volatile organic solvents.The use of water as a solvent for organic reactions was also explored.Examples include oxidation, elimination, esterifications, hydrolysis of a tertiary amide, etherification, isomerization, Hofmann elimination, α-iodination of a carboxylic acid, Claisen rearrangement, aminoreductone formation, and Willgerodt reactions.Advantages of the new MBR include the capability for rapid heating and quenching of reaction mixtures, minimal temperature gradients within the sample, and elimination of wall effects.Safety aspects have been discussed.
Process for producing pyrid-4-ones
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, (2008/06/13)
Substituted-3-hydroxy-pyrid-4-ones, derivatives thereof, and salts thereof are produced by reacting subsituted-3-hydroxypyr-4-one with ammonia or a non-sterically hindered primary amine usually in the presence of a solvent such as water. Also disclosed are novel derivatives of 2-ethyl-3-hydroxypyrid-4-one.
Physical and structural studies of N-substituted-3-hydroxy-2-methyl-4(1H)-pyridinones
Nelson, William O.,Karpishin,Timothy B.,Rettig, Steven J.,Orvig, Cris
, p. 123 - 131 (2007/10/02)
A series of 3-hydroxy-2-methyl-4(1H)-pyridinones has been prepared with the sunstituents H, CH3, n-C6H11, and CH2CH2NH2 at the ring N.The dipyridinone 1,6-bis(3-hydroxy-2-methyl-4(1H)-pyridinon-1-yl)hexane has also been synthesized.The products with H and CH3 subtituents have been studied by single crystal X-ray diffraction.Crystals of 3-hydroxy-2-methyl-4-pyridinone are monoclinic, a=6.8351(4), b=10.2249(4), c=8.6525(4) Angstroem, β=105.215(4) deg, Z=4,space group P21/n and those of 3-hydroxy-1,2-dimethyl-4-pyridinone are orthorhombic, a=7.3036(4), b=13.0490(6), c=13.7681(7) Angstroem, Z=8, space group Pbca.Both structures were solved by direct methods and were refined by full-matrix least-squares procedures to R=0.037 and 0.044 for 914 and 857 reflections with I>/=3?(I), respectively.Bond lengths and angles in the compounds were normal.All the compounds have been studies by mass spectrometry, and by infrared and proton nmr spectroscopies.The importance of hydrogen bonding to both the solution and solid state properties of these compounds has been confirmed by these techniques.
Pyridones as potential antitumor agents II: 4-pyridones and bioisosteres of 3-acetoxy-2-pyridone
Hwang,Proctor,Driscoll
, p. 1074 - 1076 (2007/10/02)
Pyridone structural requirements for activity against murine P-388 leukemia have been extended to isosteric analogs of 3-hydroxy-4-pyridone, a compound previously found to have activity. An amino group can be substituted for the 3-hydroxyl function with retention of activity. A sulfur, but not an amino function, can replace the lactam oxygen in the 2-position. Relocation of the lactam oxygen from the 2- to the 4-position in the pyridine ring also produces active pyridones, including 2-methyl-3-acetoxy-4-pyridone. This compound, which has a T/C value of 179%, is the most active material discovered thus far in the pyridone studies.
