6870-79-7Relevant articles and documents
Synthesis, characterization, and solid state dynamic studies of a hydrogen bond-hindered steroidal molecular rotor with a flexible axis
Mayorquín-Torres, Martha C.,Colin-Molina, Abraham,Pérez-Estrada, Salvador,Galano, Annia,Rodríguez-Molina, Braulio,Iglesias-Arteaga, Martín A.
, p. 3768 - 3779 (2018)
A novel steroid molecular rotor was obtained in four steps from the naturally occurring spirostane sapogenin diosgenin. The structural and dynamic characterization was carried out by solution NMR, VT X-ray diffraction, solid state 13C CPMAS, and solid state 2H NMR experiments. They allowed the identification of a fast dynamic process with a frequency of 14 MHz at room temperature, featuring a barrier to rotation Ea = 7.87 kcal mol-1. The gathered experimental evidence indicated the presence of a hydrogen bond that becomes stronger as the temperature lowers. This interaction was characterized using theoretical calculations, based on topological analyses of the electronic density and energies. In addition, combining theoretical calculations with experimental measurements, it was possible to propose a partition to Ea (～8 kcal/mol) into three contributions, that are the cost of the intrinsic rotation (～2 kcal/mol), the hydrogen bond interaction (～2 kcal/mol), and the packing effects (～2-3 kcal/mol). The findings from the present work highlight the relevance of the individual components in the function of molecular machines in the solid state.
Synthesis of diosgenin derivatives by A and B ring modifications and low-valent titanium (Ti0)-catalysed McMurry coupling reactions and designing to create novel biological agents
Ilkar Erdagi, Sevinc,Yildiz, Ufuk
, (2022/02/07)
Diosgenin is a steroidal sapogenin ((25R)-spirost-5-en-3β-ol) occurs abundantly in therapeutic herbs such as Dioscorea alata, Smilax China, and Trigonella foenum graecum. It demonstrates a wide range of pharmacological activities and medicinal properties in a large of experimental and theoretical studies. It also constitutes an important class of compounds for new drug development. In the current study, diosgenin derivatives were synthesized and designed, aiming to discover new steroid-based biological agents. In this work, new diosgenin derivatives were synthesized through low-valent titanium (Ti0)-catalyzed McMurry coupling reaction and structural modifications to the A- and B- rings in the diosgenin. McMurry reaction gave the A-nor and B-nor derivatives in by the intramolecular reductive dimerization of carbonyl compounds in the presence of low-valent titanium agents, in moderate yields (46–47%). The modification reactions on the A and B rings of diosgenin were accomplished by using efficient reagents to give three different series, in moderate to high yields (55–97%). The structures of all novel derivatives were confirmed by FTIR, 1H NMR, 13C NMR, and HRMS methods.
Design, synthesis, and biological evaluation of diosgenin-indole derivatives as dual-functional agents for the treatment of Alzheimer's disease
Zhou, Li-Cheng,Liang, Ying-Fan,Huang, Yi,Yang, Gui-Xiang,Zheng, Lu-Lu,Sun, Jia-Min,Li, Yang,Zhu, Fu-Li,Qian, He-Wen,Wang, Rui,Ma, Lei
, (2021/04/19)
The complex pathogenesis of Alzheimer's disease (AD) has become a major obstacle in its treatment. An effective approach is to develop multifunctional agents that simultaneously target multiple pathological processes. Here, a series of diosgenin-indole compounds were designed, synthesized and evaluated for their neuroprotective effects against H2O2 (hydrogen peroxide), 6-OHDA (6-hydroxydopamine) and Aβ (beta amyloid) damages. Preliminary structure-activities relationship revealed that the introduction of indole fragment and electron-donating group at C-5 on ring indole could be beneficial for neuroprotective activities. Results indicated that compound 5b was the most promising candidate against cellular damage induced by H2O2 (52.9 ± 1.9%), 6-OHDA (38.4 ± 2.4%) and Aβ1-42 (54.4 ± 2.7%). Molecular docking study suggested the affinity for 5b bound to Aβ1-42 was ?40.59 kcal/mol, which revealed the strong binding affinity of 5b to Aβ1-42. The predicted values of brain/blood partition coefficient (?0.733) and polar surface area (85.118 ?2) indicated the favorable abilities of BBB permeation and absorption of 5b. In addition, 5b significantly decreased ROS (reactive oxygen species) production induced by H2O2. In the following in vivo experiment, 5b obviously attenuated memory and learning impairments of Aβ-injected mice. In summary, compound 5b could be considered as a promising dual-functional neuroprotective agent against AD.
Ruthenium-Catalyzed Dehydrogenation of Alcohols with Carbodiimide via a Hydrogen Transfer Mechanism
Sueki, Shunsuke,Matsuyama, Mizuki,Watanabe, Azumi,Kanemaki, Arata,Katakawa, Kazuaki,Anada, Masahiro
, p. 4878 - 4885 (2020/06/02)
Ruthenium-catalyzed oxidative dehydrogenation of alcohols using carbodiimide as an efficient hydrogen acceptor has been developed. The protocol exhibits wide substrate scope with good to excellent yields. The results of the kinetic analysis indicated that the reaction mechanism includes the hydrogen transfer process and that the addition of carbodiimide is essential for the reaction system, and the resulting amidine also could react as a hydrogen acceptor.
