94-32-6Relevant articles and documents
Folded-to-unfolded structural switching of a macrocyclic aromatic hexaamide based on conformation changes in the amide groups induced by N-alkylation and dealkylation reactions
Katagiri, Kosuke,Tohaya, Taichi,Shirai, Riwako,Kato, Takako,Masu, Hyuma,Tominaga, Masahide,Azumaya, Isao
, p. 23 - 28 (2014)
A macrocyclic compound has been designed and synthesized containing six para-phenylene groups and six alternate N-butyl and N-4-methoxybenzyl substituted amides. The three N-4-methoxybenzyl groups could be removed by N-dealkylation under acidic conditions to give the corresponding secondary amides, which underwent a switch in their conformation from cis to trans. Single crystal X-ray crystallographic analysis revealed that the macrocyclic compound containing six alternate N-butyl and N-4-methoxybenzyl substituted tertiary amide groups existed as the "folded" structure, whereas the macrocyclic compound with six alternate tertiary and secondary amide groups existed as the "unfolded" structure. Furthermore, these changes in the conformation of the hexaamide displayed reversible switching between the "folded" and "unfolded" states.
Production method of chemical product ethyl4-(butylamino)benzoate
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Paragraph 0006, (2019/10/02)
The invention relates to a production method of a chemical product ethyl4-(butylamino)benzoate, which is characterized in that ethyl p-aminobenzoate and n-butyraldehyde are selected as raw materials,palladium, platinum and other catalysts with high activity are selected, and hydrogen is used as reducing agent to synthesize target product in one step. The method has the advantages of simple production mode, friendly environment protection, high yield and low cost, and meets the requirements of large-scale production.
O -Phenylenediamine: A privileged pharmacophore of ferrostatins for radical-trapping reactivity in blocking ferroptosis
Sheng, Xie-Huang,Cui, Cheng-Cheng,Shan, Chao,Li, Yu-Zhen,Sheng, Duo-Hong,Sun, Bin,Chen, De-Zhan
, p. 3952 - 3960 (2018/06/11)
Ferroptosis is a non-apoptotic, iron dependent form of regulated cell death that is characterized by the accumulation of lipid hydroperoxides. It has drawn considerable attention owing to its putative involvement in diverse neurodegenerative diseases. Ferrostatins are the first identified inhibitors of ferroptosis and they inhibit ferroptosis by efficiently scavenging free radicals in lipid bilayers. However, their further medicinal application has been limited due to the deficient knowledge of the lipid peroxyl radical-trapping mechanism. In this study, experimental and theoretical methods were performed to illustrate the possible lipid hydroperoxide inhibition mechanism of ferrostatins. The results show that an ortho-amine (-NH) moiety from ferrostatins can simultaneously interact with lipid radicals, and then form a planar seven-membered ring in the transition state, and finally present greater reactivity. NBO analysis shows that the formed planar seven-membered ring forces ortho-amines into better alignment with the aromatic π-system. It significantly increases the magnitudes of amine conjugation and improves spin delocalization in the transition state. Additionally, a classical H-bond type interaction was discovered between a radical and an o-NH group as another transition state stabilizing effect. This type of radical-trapping mechanism is novel and has not been found in diphenylamine or traditional polyphenol antioxidants. It can be said that o-phenylenediamine is a privileged pharmacophore for the design and development of ferroptosis inhibitors.
