574-17-4Relevant articles and documents
Comprehensive spectroscopic (FT-IR, FT-Raman, 1H and 13C NMR) identification and computational studies on 1-acetyl-1H-indole-2,3-dione
Almutairi, Maha S.,Muthu,Prasana, Johanan C.,Chandralekha,Al-Ghamdi, Alwah R.,Attia, Mohamed I.
, p. 225 - 237 (2017)
Fourier transform infrared (FT-IR) and FT-Raman spectra of 1-acetyl-1H-indole-2,3-dione (N-acetylisatin) were recorded in the solid phase and analyzed. The molecular geometry, vibrational frequencies, infrared intensities, Raman activities and atomic charges were calculated using density functional theory (DFT/B3LYP) calculations with a standard 6-311++G(d,p) basis set. The fundamental vibrational modes of N-acetylisatin were analyzed and fully assigned with the aid of the recorded FT-IR and FT-Raman spectra. The simulated FT-IR and FT-Raman spectra showed good agreement with the experimental spectra. The stability of the molecule, arising from hyper-conjugative interactions and charge delocalization, was analyzed using natural bond orbital (NBO) analysis. The dipole moment (μ), polarization (α) and hyperpolarization (β) values of N-acetylisatin were also computed. The potential energy distribution (PED) was computed for the assignment of unambiguous vibrational fundamental modes. The HOMO and LUMO energy gap illustrated the chemical activity of N-acetylisatin. The energy and oscillator strength were calculated by DFT. Gauge-including atomic orbital NMR (1H and 13C) chemical shift calculations were performed and compared with the experimental values. Thermodynamic properties (heat capacity, entropy and enthalpy) of the compound at different temperatures were also calculated.
Imatinib derivatives as inhibitors of K562 cells in chronic myeloid leukemia
Azevedo, Liviane D.,Bastos, M?nica M.,Vasconcelos, Flávia C.,Hoelz, Lucas V. B.,Junior, Floriano P. S.,Dantas, Rafael F.,de Almeida, Ana C. M.,de Oliveira, Andressa Paula,Gomes, Larissa C.,Maia, Raquel C.,Boechat, Nubia
, p. 2929 - 2941 (2017)
Imatinib was the first representative of the class of Breakpoint cluster region-Abelson murine leukemia viral oncogene homolog (BCR-ABL) tyrosine kinase inhibitors used for the treatment of chronic myeloid leukemia. Second-generation and third-generation drugs have been introduced in this therapy, affording increased patient survival. However, all BCR-ABL tyrosine kinase inhibitors have been shown to induce resistance, necessitating a search for new therapeutic options. The sunitinib, another tyrosine kinase inhibitor used in the treatment of renal cell carcinoma and gastrointestinal stromal tumors is an isatin derivative. Isatin nucleus is highly versatile for the preparation of new substances, and several tyrosine kinase inhibitors examples have been obtained using it. This work aimed to design, synthesize, and biological evaluation of new compounds using the K562 cell line, which constitutively expresses the active BCR-ABL enzyme. Three new series of imatinib derivatives have been planned from the imatinib, and all have a phenylaminopyrimidine group as the main pharmacophore. Sunitinib was used as a structural prototype to planning the series 1 (8a–e) of hybrids between sunitinib and imatinib. Series 2 and 3 are 2-oxo-2-phenyacetamide and 2,2-difluoro-2-phenylacetamide derivatives, respectively. Isatins were used as the starting materials for all series. Compounds were synthesized using simple methodologies and were obtained in high purities. The compounds were tested against K562 cells, and four showed a reduction in cell viability, with EC50 values ranging from 0.37 to 2.02 μM, some of which are close to the imatinib standard (0.21 μM).
Lanthanide Silylamide-Catalyzed Synthesis of Pyrano[2,3- b]indol-2-ones
Chen, Qifa,Teng, Yue,Xu, Fan
supporting information, p. 4785 - 4790 (2021/06/28)
A lanthanide silylamide-catalyzed tandem reaction of isatins, diethyl phosphite, and 2,3-diarylcyclopropenones has been developed. A series of pyrano[2,3-b]indol-2-ones were synthesized in high yields. The cooperation of the Lewis acidity of the lanthanide center and the Bronsted basicity of the N(SiMe3)2 anion may be the key factor affecting the catalytic activity of lanthanide amides.
Dynamic Kinetic Asymmetric Transformation of Racemic Diastereomers: Diastereo- and Enantioconvergent Michael–Henry Reactions to Afford Spirooxindoles Bearing Furan-Fused Rings
Sohail, Muhammad,Tanaka, Fujie
supporting information, p. 21256 - 21260 (2021/08/23)
Dynamic kinetic asymmetric transformation (DYKAT) reactions of racemic diastereomer mixtures that afford the products as essentially single diastereomers with high enantioselectivities are described. We demonstrated the DYKAT in the diastereo- and enantio
