13565-05-4Relevant articles and documents
Hybrids of aurantiamide acetate and isopropylated genipin as potential anti-inflammatory agents: The design, synthesis, and biological evaluation
Wang, Hongwei,Gao, Sufan,Li, Jiaming,Ma, Xiaodong,Liu, Wandong,Qian, Shihu
, p. 797 - 808 (2020/12/03)
A novel series of hybrids designed on the basis of aurantiamide acetate and isopropylated genipin were synthesized and biologically evaluated as anti-inflammatory agents. Among them, compound 7o exhibited the best inhibitory activity against TNF-α secretion (IC50?=?16.90?μM) and was selected for further in vitro and in vivo functional study. The results demonstrated that 7o was capable of suppressing the expression of LPS-induced iNOS and COX-2, as well as reducing the production of NO at the concentration of 5?μM, which may be resulted from its regulation of NF-κB signaling and MAPK signaling. Moreover, compound 7o exhibited favorable in vivo anti-inflammatory activity with an inhibition rate of 53.32% against xylene-induced ear swelling in mice at the dose of 5?mg/kg.
Investigating the Role of Weak Interactions to Explore the Polymorphic Diversity in Difluorinated Isomeric N-Phenylcinnamamides
Bhowal, Rohit,Chopra, Deepak
, p. 4162 - 4177 (2021/07/26)
A total of nine difluoro derivatives of N-phenylcinnamamides have been synthesized from fluoro-substituted cinnamic acids and anilines in order to investigate the formation of polymorphs arising due to the conformational flexibility around the amide and vinyl group. Among them, four compounds have been found to exist in multiple polymorphic forms, which includes concomitant polymorphism, solvatomorphism, and packing polymorphism, while the remaining five compounds display monomorphic behavior. Crystal structure analyses of all the forms belonging to these four compounds reveal that, although the molecules are primarily held by strong N-H?O hydrogen bonds, the relative interplay of weak C-H?F, C-H?O, C-H?π, and π?πinteractions allows the flexible molecules to adopt different orientations and exhibit polymorphism. These forms interestingly also display different thermal stabilities, and they have been quantified by intermolecular interaction topological analyses. The occurrence of different primary packing motifs in these crystal structures has been further investigated by the crystal structure prediction (CSP) computational method, wherein an energy landscape of an unsubstituted N-phenylcinnamamide was generated and a number of hypothetical structures were accessed with experimentally obtained crystal structures of its difluoro-substituted derivatives.
Design, Synthesis, Structure-Activity Relationship, Molecular Docking, and Herbicidal Evaluation of 2-Cinnamoyl-3-Hydroxycyclohex-2-en-1-one Derivatives as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors
Song, Hao-Min,Zhao, Li-Xia,Zhang, Shuai-Qi,Ye, Tong,Fu, Ying,Ye, Fei
, p. 12621 - 12633 (2021/11/13)
Cinnamic acid, isolated from cinnamon bark, is a natural product with excellent bioactivity, and it effectively binds with cyclohexanedione to form novel 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors. According to the active sub-structure combinat
