122-37-2Relevant academic research and scientific papers
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.
N-H bond dissociation energies in N,N′-diphenyl-1,4-phenylenediamine and its aminyl radical
Varlamov,Krisyuk
, p. 1609 - 1614 (2004)
The N-H bond dissociation energy (DNH) in the 4-anilinodiphenylaminyl radical formed from N,N′-diphenyl-1,4- phenylenediamine was experimentally determined and calculated by the quantum-chemical method. The experimental DNH value was found from the enthalpy of the reaction of N,N′-diphenyl-1,4-benzoquinonediimine with 4-hydroxydiphenylamine taking into account the bond dissociation energies in 4-hydroxydiphenylamine and its aminyl and phenoxyl radicals, which were determined by the intersecting parabolas method from the kinetic data. The quantum-chemical calculations of DNH used several semiempirical methods by the MOPAC program and the ab initio and DFT methods by the GAUSSIAN 94/98 program. The DNH values, which were closest to the experimental values, were obtained by the B3LYP/6-31+G*method. The results of quantum-chemical calculations of the N-H and O-H bond dissociation energies in 4-hydroxydiphenylamine and its radicals are presented.
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.
Phenoxy-N-phenylaniline derivative and application thereof
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Paragraph 0064; 0067; 0069; 0071; 0110-0113, (2020/06/05)
The invention relates to a phenoxy-N-phenylaniline derivative and an application thereof, and belongs to the technical field of novel colorectal cancer drugs. The present invention addresses the problem of providing some novel compounds having c-Myc inhibitory activity. The structural formula of the compound is shown as a formula I in the specification. According to the invention, a series of novel phenoxy-N-phenylaniline derivatives are designed and synthesized, and the compounds can be used as c-Myc inhibitors, have a good inhibition effect on the proliferation of colorectal cancer cells, and provide a new choice for colorectal cancer drugs.
Substituted anilino-benzothiazole-2-thioketone compound as well as preparation method and application thereof
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Paragraph 0071-0072, (2020/06/05)
The invention discloses a substituted anilino-benzothiazole-2-thioketone compound and a preparation method thereof. In addition, the invention also relates to an application of the compound in rubberproducts. The substituted anilino-benzothiazole-2-thioketone compound disclosed by the invention not only can promote rubber vulcanization, but also can prolong the service life of the rubber products.
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.
Ni/Pd-catalyzed Suzuki-Miyaura cross-coupling of alcohols and aldehydes and C-N cross-coupling of nitro and amines: via domino redox reactions: base-free, hydride acceptor-free
Ahmed, Rebin Omer,Kazemnejadi, Milad,Mahmoudi, Boshra
, p. 43962 - 43974 (2020/12/25)
Domino oxidation-Suzuki-Miyaura cross-coupling of benzyl alcohols with phenylboronic acid and domino reduction-C-N cross-coupling of the nitro compounds with aryl halides were carried out using a strong Ni/Pd bimetallic redox catalyst. The catalyst bearing a copolymer with two Ni/Pd coordinated metals in porphyrin (derived from demetalated chlorophyll b) and salen-type ligands, and pyridine moiety as a base functionality all immobilized on magnetite NPs was synthesised and characterized. The domino oxidation cross-coupling reaction was accomplished under molecular O2 in the absence of any hydride acceptor or/and base. Also, the domino reduction C-N cross-coupling reaction was performed in the presence of NaBH4 without the need for any base and co-reductant. This multifunctional catalyst gave moderate to good yields for both coupling reactions with high chemoselectivity. A wide investigation was conducted to determine its mechanism and chemoselectivity.
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.
Enolizable Ketones as Activators of Palladium(II) Precatalysts in Amine Arylation Reactions
Hu, Huaiyuan,Gilliam, Ashley M.,Qu, Fengrui,Shaughnessy, Kevin H.
, p. 4127 - 4135 (2020/05/05)
Enolizable ketones have been identified as effective activators for palladium(II) precatalysts in the coupling of aryl bromides and aniline. N-arylation reactions catalyzed by [(DTBNpP)PdCl2]2 (DTBNpP = (bis(tert-butyl)neopentylphosphine) and PEPPSI-IPr precatalysts are activated by the addition of acetone, mesityl oxide, and 3-pentanone. 3-Pentanone was the most effective activator. Mechanistic studies show that acetone, 3-pentanone, and mesityl oxide reduce [(DTBNpP)PdCl2]2 in the presence of NaO-t-Bu to Pd0(DTBNpP)2
