22966-22-9Relevant articles and documents
Synthesis and structure elucidation of pyrimidobenzimidazoles and fused derivatives III [1,2]. Decahydropyrimido[1,2-a]benzimidazol-2-oles and octahydropyrimido[1,2-a]benzimida-zoles
Goessnitzer, Edith,Wendelin, Winfried
, p. 607 - 624 (2001)
The reaction of racemic trans-hexahydrobenzimidazol-2-amine with three vinylogous ketones under mild conditions was studied. Only in the case of 4-phenyl-3-buten-2-one cycloaddition products could be isolated. According to NMR spectroscopy they consist of mixtures of two of eight possible diastereomers: rac-2β-methyl-4β-phenyl-trans-5aα- and trans-5aβ-decahydropyrimido[1,2-a]benzimidazol-2α-ole. Reaction of the amine with the butenone at higher temperature and with, 2-methyl-1-phenyl-1-penten-3-one, and 4′-chlorochalcone afforded mixtures of two diastereomers each, which turned out as rac-4α-phenyl-trans-5aβ- and trans-5aα-octahydropyrimido[1,2-a]benzimidazoles. Complete structural and stereochemical assignments of the title compounds and their hydrochlorides were established by NMR spectroscopic investigations. The results showed that all investigated cyclization reactions proceeded regioselectively with equal orientation of the components, but not diastereoselectively. Variation of the reaction conditions did influence neither regionor diastereoselectivity.
Molecular recognition of synthesized halogenated chalcone by calf thymus DNA through multispectroscopic studies and analysis the anti-cancer, anti-bacterial activity of the compounds
Ghosh, Sudipta,Ghosh, Suvranil,Mahato, Sachinta,Majee, Adinath,Mukherjee, Abhijit,Pal, Mahadeb,Sen, Sukanta Kumar,Singh, Bula
, (2021/07/02)
The present study aims to elucidate the anti-cancer, antimicrobial activity of synthesized halogenated chalcones (1f, 1h, 1i) and their molecular interaction with calf thymus DNA. All the three compounds were characterized using different spectroscopic tools like FTIR, NMR. DFT and TDDFT computation were performed to support the structural and electronic parameter of the compounds. UV–vis absorbance, steady-state fluorescence, time-resolved fluorescence, circular dichroism, helix melting, molecular docking study reveals that the compounds (1f, 1h, 1i) actively interact with ctDNA via groove binding mode. The binding constants (Kb) were calculated to be 1.29 × 104, 0.54 × 104 and 0.45 × 104 M?1 respectively for compounds 1f, 1h, 1i. The compounds were cytotoxic to almost every cell line (PC3, HeLa, A549, HCT116) tested, having minimal toxicity in normal NKE cell line, among which PC3 cells were more sensitive with an IC50 value of 10 μM. The values were determined using dose response curve and found between 10 and 49 μM for cancer cells and 70 μM for normal cell. Compounds also cause apoptosis in PC3 cells, which was confirmed by Annexin V-FITC/PI assay. Results showed that 1f, 1h, 1i target DNA, to persuade DNA damage mediated cancer cell death. The inhibition zone was formed in the screening test indicating the anti-bacterial activity of 1f, 1h & 1i against model pathogenic bacteria. So the present communication provides quantitative insight of halo-chalcone based anti-cancerous and antimicrobial molecule involving relevant target nucleic acid, which holds future promise in the development of new therapeutic agents.
A new method for the synthesis of chalcone derivatives promoted by PPh3/I2under non-alkaline conditions
Xue, Kangsheng,Sun, Guoxiang,Zhang, Yanzhi,Chen, Xubing,Zhou, Yang,Hou, Jinjun,Long, Huali,Zhang, Zijia,Lei, Min,Wu, Wanying
supporting information, p. 625 - 634 (2020/11/23)
A straightforward and general method has been developed for the synthesis of chalcone derivatives by a Claisen-Schmidt reaction in the presence of PPh3/I2 in 1,4-dioxane under reflux temperatures. With the condensation of the aromatic ketone and aldehyde occurring at non-strongly alkaline conditions, our proposed method significantly expands the range of applicable substrates, especially for groups that are unstable under alkaline conditions.
