122-37-2Relevant articles and documents
The N-H and O-H bond dissociation energies in 4-hydroxydiphenylamine and its phenoxyl and aminyl radicals
Varlamov
, p. 306 - 312 (2004)
The N-H and O-H bond dissociation energies in 4-hydroxydiphenylamine Ph-NH-C6H4-OH (DNH= 353.4, DOH=339.3 kJ mol-1) and its semiquinone radicals DNH(Ph-NH-C 6H4-O.) = 273.6, DOH(Ph-N .-C6H4-OH) = 259.5 kJ mol-1 were first estimated using the parabolic model and experimental data (rate constants) on two elementary reactions with participation of N-phenyl-1,4- benzoquinonemonoimine (2). One of the reactions, namely, that of 2 with aromatic amines, was studied in this work using a specially developed method.
Construction of diaminobenzoquinone imines via ferrocene-initiated radical reaction of benzoquinone with amines
Feng, Yadong,Liu, Ying,Fu, Qi,Zou, Zhongai,Shen, Jinhai,Cui, Xiuling
, p. 733 - 735 (2020)
A ferrocene-initiated radical reaction of benzoquinone with amines has been successfully developed for the direct access to diaminobenzoquinone imines in high yields, in which the commercially available and cheap ferrocene was employed as a radical initiator and TBHP was used as an oxidant. Moreover, this reaction could be achieved with low loading of ferrocene (0.5 mol%). This protocol is highly efficient with good substrate tolerance and provides a new approach for the construction of benzoquinone imines with potential pharmaceutical interest.
Palladium-catalyzed carbonylation of iminoquinones and aryl iodides to access arylp-amino benzoates
Wang, Siqi,Wu, Xiao-Feng,Yao, Lingyun,Ying, Jun
supporting information, p. 8246 - 8249 (2021/10/12)
A palladium-catalyzed carbonylation of iminoquinones and aryl iodides has been developed for the construction of arylp-amino benzoates. Using benzene-1,3,5-triyl triformate (TFBen) as the CO source, the reaction proceeded well to give various arylp-amino benzoates in good to excellent yields. Additionally, control experiments were conducted to gain more insights into the reaction mechanism.
Discovery of 4-(3,5-dimethoxy-4-(((4-methoxyphenethyl)amino)methyl)phenoxy)-N-phenylaniline as a novel c-myc inhibitor against colorectal cancer in vitro and in vivo
Cao, Chaoguo,Lan, Suke,Li, Rui,Liu, Yuanyuan,Luo, Dan,Luo, Meng,Ma, Xinyu,Shan, Huifang,Yang, Jie,Yu, Su,Zhong, Xinxin
, (2020/05/08)
Proto-oncogene c-Myc plays an essential role in the development of colorectal cancer (CRC), since downregulation of c-Myc inhibits intestinal polyposis, which is the most cardinal pathological change in the development of CRC. Herein, a series of novel phenoxy-N-phenylaniline derivatives were designed and synthesized. The cytotoxicity activities of all the derivatives were measured by MTT assay in different colon cancer cells, 4-(3,5-dimethoxy-4-(((4-methoxyphenethyl)amino)methyl)phenoxy)-N-phenylaniline (42) was discovered, the lead compound 42 with excellent cytotoxicity activity of IC50 = 0.32 μM, IC50 = 0.51 μM, in HT29 and HCT 15 cells, respectively. Compound 42 had a good inhibitory activity of c-Myc/MAX dimerization and DNA binding. Besides, compound 42 could effectively induce apoptosis and induced G2/M arrest in low concentration and G0/G1 arrest in high concentration to prevent the proliferation and differentiation in colon cancer cells. Western blot analysis confirmed the 42 strongly down-regulated expression of c-Myc. Furthermore, during 30 days treatment 42 exhibited excellent efficacy in HT29 tumor xenograft model without causing significant weight loss and toxicity. Consequently, 42 could be a promising drug candidate for CRC therapy.
Pd-Catalyzed Redox-Neutral C-N Coupling Reaction of Iminoquinones with Electron-Deficient Alkenes without External Oxidants: Access of Tertiary (E)-Enamines and Application to the Synthesis of Indoles and Quinolin-4-ones
Jillella, Raveendra,Raju, Selvam,Hsiao, Huan-Chang,Hsu, Day-Shin,Chuang, Shih-Ching
supporting information, p. 6252 - 6256 (2020/08/12)
A novel and efficient reductive N-alkenylation of iminoquinones with electron-deficient olefins has been successfully developed by Pd(II)-catalyzed redox-neutral reactions, which provides a synthesis of tertiary (E)-enamines. We further demonstrate that the tertiary enamines can be converted to multifarious N-heterocyclic compounds, indoles, and quinolones in good yields.