1885-29-6Relevant articles and documents
Design, synthesis and evaluation of novel tacrine-multialkoxybenzene hybrids as multi-targeted compounds against Alzheimer's disease
Zhang, Chao,Du, Qiao-Yi,Chen, Lang-Di,Wu, Wen-Hao,Liao, Si-Yan,Yu, Li-Hong,Liang, Xin-Tong
, p. 200 - 209 (2016)
A series of benzoates (or phenylacetates or cinnamates) - tacrine hybrids (7a-o) were designed, synthesized and evaluated as multi-potent anti-Alzheimer drug candidates. The screening results showed that most of them exhibited a significant ability to inhibit ChEs, certain selectivity for AChE over BuChE and strong potency inhibitory of self-induced β-amyloid (Aβ) aggregation. All IC50 values of biological activity were at the nanomolar range. Especially, compound 7c displayed the greatest ability to inhibit AChE with an IC50 value of 5.63 nM and the highest selectivity with ratio of BuChE/AChE value of 64.6. Moreover, it also exhibited a potent inhibitory of Aβ aggregation with an IC50 value of 51.81 nM. A Lineweaver-Burk plot and molecular modeling study showed that compound 7c targeted both the CAS and PAS of ChEs. A structure-activity relationship analysis suggested that the electron density of aromatic ring which was linked with tacrine through acetyl group played a significant role in determining the inhibitory activity.
Biehl et al.
, p. 3674,3675-3677 (1979)
Ring-expansion reaction of cyano-substituted singlet phenyl nitrenes: Theoretical predictions and kinetic results from laser flash photolysis and chemical trapping experiments
Gritsan,Likhotvorik,Tsao,Celebi,Platz,Karney,Kemnitz,Borden
, p. 1425 - 1433 (2001)
On the basis of the open-shell electronic structure of the lowest-singlet state of phenylnitrene, it is predicted that substitution of a radical-stabilizing cyano group at an ortho carbon should facilitate cyclization at that carbon, whereas cyano substitution at the para carbon should retard the rate of cyclization. These qualitative predictions have been tested computationally by performing (8/8)CASSCF and CASPT2/6-31G* ab initio calculations and experimentally by carrying out laser flash photolysis and chemical trapping studies. The calculations and experiments both find that, unlike the case with ortho fluoro and ortho methyl substituents, the rate of cyclization at a substituted carbon is not retarded by an ortho cyano group. In contrast, a para cyano group is found, both computationally and experimentally, to raise the barrier to cyclization of singlet phenylnitrene by > 1 kcal/mol.
Transformations of 2-Ethyl-2-methyl-2,3-dihydro-1H-indole at the 3-Position
Abdrakhmanov, I. B.,Latypova, L. R.,Mustafin, A. G.,Salikhov, Sh. M.
, (2020)
The oxidation of N-acetyl-2-ethyl-2-methyl-2,3-dihydro-1H-indole with pyridinium chlorochromate, CrO3 · 2 Py, or CrO3 gave N-acetyl-2-ethyl-2-methyl-2,3-dihydro-1H-indol-3-one which was hydrolyzed to 2-ethyl-2-methyl-2,3-dihydro-1H-i
NaI/PPh3-Mediated Photochemical Reduction and Amination of Nitroarenes
Qu, Zhonghua,Chen, Xing,Zhong, Shuai,Deng, Guo-Jun,Huang, Huawen
supporting information, p. 5349 - 5353 (2021/07/21)
A mild transition-metal- and photosensitizer-free photoredox system based on the combination of NaI and PPh3 was found to enable highly selective reduction of nitroarenes. This protocol tolerates a broad range of reducible functional groups such as halogen (Cl, Br, and even I), aldehyde, ketone, carboxyl, and cyano. Moreover, the photoredox catalysis with NaI and stoichiometric PPh3 provides also an alternative entry to Cadogan-type reductive amination when o-nitrobiarenes were used.
Cu-Catalyzed Cross-Coupling of Nitroarenes with Aryl Boronic Acids to Construct Diarylamines
Guan, Xinyu,Zhu, Haoran,Driver, Tom G.
, p. 12417 - 12422 (2021/10/12)
The development and study of a simple copper-catalyzed reaction of nitroarenes with aryl boronic acids to form diarylamines that uses phenyl silane as the stoichiometric terminal reductant is described. This cross-coupling reaction requires as little as 2 mol % of CuX and 4 mol % of diphosphine for success and tolerates a broad range of functional groups on either the nitroarene or the aryl boronic acid to afford the amine in good yield. Mechanistic investigations established that the cross-coupling reaction proceeds via a nitrosoarene intermediate and that copper is required to catalyze both the deoxygenation of the nitroarene to afford the nitrosoarene and C-NAr bond formation of the nitrosoarene with the aryl boronic acid.