120681-05-2Relevant articles and documents
Solution phase preparation of highly pure amide mixtures via in-situ chlorotrimethylsilane protection and activation
Ho, Koc-Kan,Wang, Nai Fang,Lercara, Christine,O'Toole, Doris C.,Achan, Douglas M.,Vuocolo, Edmund A.,Leone-Bay, Andrea
, p. 883 - 895 (1997)
Coupling of 4-(4-aminophenyl)butyric acid 1 with acyl halides in both organic and aqueous media were found to produce large amount of oligomeric materials. By using an in situ chlorotrimethylsilane protection/activation procedure, these oligomers were sup
Investigating the Role of Weak Interactions to Explore the Polymorphic Diversity in Difluorinated Isomeric N-Phenylcinnamamides
Bhowal, Rohit,Chopra, Deepak
, p. 4162 - 4177 (2021)
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.
Antifungal Exploration of Quinoline Derivatives against Phytopathogenic Fungi Inspired by Quinine Alkaloids
Chen, Yong-Jia,Ma, Kun-Yuan,Du, Sha-Sha,Zhang, Zhi-Jun,Wu, Tian-Lin,Sun, Yu,Liu, Ying-Qian,Yin, Xiao-Dan,Zhou, Rui,Yan, Yin-Fang,Wang, Ren-Xuan,He, Ying-Hui,Chu, Qing-Ru,Tang, Chen
, p. 12156 - 12170 (2021/10/26)
Enlightened from our previous work of structural simplification of quinine and innovative application of natural products against phytopathogenic fungi, lead structure 2,8-bis(trifluoromethyl)-4-quinolinol (3) was selected to be a candidate and its diversified design, synthesis, and antifungal evaluation were carried out. All of the synthesized compounds Aa1-Db1 were evaluated for their antifungal activity against four agriculturally important fungi, Botrytis cinerea, Fusarium graminearum, Rhizoctonia solani, and Sclerotinia sclerotiorum. Results showed that compounds Ac3, Ac4, Ac7, Ac9, Ac12, Bb1, Bb10, Bb11, Bb13, Cb1. and Cb3 exhibited a good antifungal effect, especially Ac12 had the most potent activity with EC50 values of 0.52 and 0.50 μg/mL against S. sclerotiorum and B. cinerea, respectively, which were more potent than those of the lead compound 3 (1.72 and 1.89 μg/mL) and commercial fungicides azoxystrobin (both >30 μg/mL) and 8-hydroxyquinoline (2.12 and 5.28 μg/mL). Moreover, compound Ac12 displayed excellent in vivo antifungal activity, which was comparable in activity to the commercial fungicide boscalid. The preliminary mechanism revealed that compound Ac12 might cause an abnormal morphology of cell membranes, an increase in membrane permeability, and release of cellular contents. These results indicated that compound Ac12 displayed superior in vitro and in vivo fungicidal activities and could be a potential fungicidal candidate against plant fungal diseases.
Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives
Li, Peng-Xiao,Liu, Guo-Yun,Liu, Ren-Min,Liu, Yue,Mu, Wen-Wen,Sun, Ya-Lei,Yang, Jie
, (2022/01/13)
This work deals with the design and synthesis of 18 barbituric acid derivatives bearing 1,3-dimethylbarbituric acid and cinnamic acid scaffolds to find potent anticancer agents. The target molecules were obtained through Knoevenagel condensation and acylation reaction. The cytotoxicity was assessed by the MTT assay. Flowcytometry was performed to determine the cell cycle arrest, apoptosis, ROS levels and the loss of MMP. The ratios of GSH/GSSG and the MDA levels were determined by using UV spectrophotometry. The results revealed that introducing substitutions (CF3, OCF3, F) on the meta- of the benzyl ring of barbituric acid derivatives led to a considerable increase in the antiproliferative activities compared with that of corresponding ortho- and para-substituted barbituric acid derivatives. Mechanism investigation implied that the 1c could increase the ROS and MDA level, decrease the ratio of GSH/GSSG and MMP, and lead to cell cycle arrest. Further research is needed for structural optimization to enhance hydrophilicity, thereby improve the biological activity of these compounds.