98769-85-8Relevant academic research and scientific papers
Chromene, quinoline hybrids as potential anti-cancer agents: A novel and distinct approach for the synthesis of quinoline derivatives
Sultana, Rizuana,Tippanna, Ravinder Reddy
supporting information, p. 265 - 272 (2021/04/28)
A series of novel quinoline derivatives (6-phenyl-6H-chromeno[4,3-b]quinoline) have been prepared by using 4-chloro-2-phenyl-2H-chromene-3-carbaldehyde and various substituted isocyanides as starting materials in the presence of HClO4-SiO2 and Methanol. We screened eighteen compounds of this novel series (6a-r) in six different cancer cell lines (A549 (lung cancer cells), DU145 (prostate cancer cells), PC3 (prostate cancer cells), MCF7 (lung cancer cells), HT 29, HCT 116 (colon cancer cells). Most of the compounds showed anti-cancer activity and compound 6b showed good cytotoxicity IC50 = 2.61±0.34 μM against colon cancer on HT29 cell line among all. The key property of cell mi-gration was observed while treatment cells with 6b. Apoptosis in HT29 cells confirmed by annexin V staining, acridine orange/ethidium bromide (AO/EB), DAPI, induced by 6b. This method is operation-ally simple and works with a diverse range of substrates. These results indicate the anticancer potential of these series and warrants future investigations for further anticancer drug development.
Chromene- And quinoline-3-carbaldehydes: Useful intermediates in the synthesis of heterocyclic scaffolds
Rocha, Djenisa H.A.,Batista, Vasco F.,Balsa, Emanuel J.F.,Pinto, Diana C.G.A.,Silva, Artur M.S.
, (2020/10/02)
Chromenes and quinolines are recognized as important scaffolds in medicinal chemistry. Herein, the efficient use of chromene- and quinoline-3-carbaldehydes to synthesize other valuable heterocycles is described. These carbaldehydes are obtained in excelle
Facile synthesis of 6-phenyl-6h-chromeno [4, 3-b] quinoline derivatives using nahso4&at;sio2 re-usable catalyst and their antibacterial activity study correlated by molecular docking studies
Anuradha, Vejendla,Basaveswara Rao, Mandava Venkata,Prashanth, Jyothi,Rao, Koya Prabhakara,Subramanyam, Madala,Suman, Kancharla
, p. 929 - 938 (2020/07/10)
Background: Heterocyclic compounds containing heteroatoms (O, N and S) as part of five or six-membered cyclic moieties exhibited various potential applications, such as pharmaceutical drugs, agrochemical products and organic materials. Among many known heterocyclic moieties, quinoline and its derivatives are one of the privileged scaffolds found in many natural products. In general, quinoline derivatives could be prepared by utilizing ortho-substituted anilines and carbonyl compounds containing a reactive α-methylene group of well-known reaction routes like Friedlander synthesis, Niemantowski synthesis and Pfitzinger synthesis. Moreover, polysubstituted quinolones and their derivatives also had shown considerable interest in the fields of organic and pharmaceutical chemistry in recent years. Objectives: The main objective of our research work is towards the design and synthesis of divergent biological-oriented, proactive analogues with potential pharmacological value inspired by the anti-tubercular activity of 2-phenylquinoline analogues. In this study, we have been interested in the design and synthesis of bioactive, 2, 4-diphenyl, 8-arylated quinoline analogues. Methods: 6-phenyl-6h-chromeno [4, 3-b] quinoline derivatives were synthesized from 4-chloro-2phenyl-2H-chromene-3-carbaldehyde and various substituted aromatic anilines as starting materials using sodium bisulfate embedded SiO2 re-usable catalyst. All these fifteen new compound structures confirmed by spectral data1H &13C NMR, Mass, CHN analysis etc. Furthermore, all these new compounds antibacterial activity strains recorded using the paper disc method. The compound molecular structures were designed using molecular docking study by utilizing the crystallographic parameters of S. Areus Murb protein. Results: A series of fifteen new quinoline derivatives synthesized in moderate to good yields using sodium bisulfate embedded SiO2 re-usable catalyst. The molecular structures of these newly synthesized compounds elucidated by the combination of spectral data along with the elemental analysis. These compounds antibacterial activity study have shown moderate to good activity against, Escherichia coli (Gram-negative) and Staphylococcus aureus (gram-positive) organisms. These antibacterial activity results were also a very good correlation with molecular docking studies. Conclusion: In this study, fifteen new quinoline derivatives synthesized and structures confirmed by spectral data. In fact, all the compounds have shown moderate to good antibacterial activity. In general, the compounds containing the electron donor group at R1 position (R1 = OMe) and the acceptor group at R2 positions (R2 = F or Cl) had shown good antibacterial activity. These antibacterial activity results were also a very good correlation with molecular docking studies showing strong binding energies with the highest value being,-12.45 Kcal mol-1 with S. aureus MurB receptor.
Synthesis of pyrazole-substituted chromene analogues with selective anti-leukemic activity
Madhu,Sudhakar,Santosh Kumar,Rajashekher Reddy,Sravani,Ramakrishna,Prasad Rao, Ch.
, p. 2421 - 2428 (2017/11/24)
We report design and synthesis of a series of flavanone/chromene derivatives containing pyrazoles 6a–6h and 8a–8e with potent anti-leukemic activity. Anti-leukemic activity of novel flavanone derivatives was tested using the K562 cell line. The parental flavanone was selected as the reference compound in identification of analogues with superior anti-leukemic activity. More than two-thirds of the derivatives displayed higher activity than the initial flavanone. Positions of substituents that promoted anti-leukemic activity were identified on both the chromene and pyrazole fragments. Compounds 6b and 6c showed the highest activity against K562 cell line, with IC50 values 3.0 and 0.5 μM respectively. Notably, compounds 6b and 6c displayed very high selectivity in inhibition of leukemic cells (K562) but not of healthy HEK293 cells or solid cancer cell lines HeLa, MCF7 and BT474. Moreover, both the 6b and 6c compounds were predicted to have good ADME properties.
Asymmetric preparation of new N, N -dialkyl-2-amino-1,1,2-triphenylethanol catalysts and a kinetic resolution in the addition of diethylzinc to flavene-3-carbaldehydes
Kang, Seockyong,Baek, Jinho,Ko, Yikyung,Im, Chan,Park, Yongsun
supporting information, p. 630 - 634 (2013/04/23)
Enantiopure N,N-dialkyl-(S)-2-amino-1,1,2-triphenylethanols were prepared using a new synthetic methodology and tested for their ability to catalyze the enantioselective addition of diethylzinc to aldehydes. The structural modification of N-substituents of the catalysts led us to identify N-methyl-N-(S)-1-phenyl-ethyl-substituted 4d as an effective catalyst for the addition. Also disclosed is a kinetic resolution of racemic flavene-3- carbaldehydes with the chiral catalyst.
Synthesis and antitumour activity of a novel class of flavanones: 1,4-diaryl-1,4-dihydrochromeno[4,3-c]pyrazoles
Chen, Zhiwei,Wang, Zhihua,Su, Weike
experimental part, p. 45 - 48 (2012/04/04)
A new series of 1,4-diaryl-1,4-dihydrochromeno[4,3-c]pyrazoles have been synthesised. The target compounds and their analogues (2,4-diaryl-2,4- dihydrochromeno[4,3-c]pyrazoles) were tested for their antitumour activities in vitro against MCF-7 and HL-60 c
Synthesis of 5-aryl-2-piperidino-5H-chromeno[3,4-c]pyridine-1-carbonitriles
Venkati,Reddy, S. Satyanarayana,Swamy,Ravikumar,Krupadanam, G. L. David
experimental part, p. 355 - 364 (2012/06/29)
4-Chloro-2-aryl-2H-3-chromenecarbaldehydes 3a-g on reaction with malononitrile in ethanol in the presence of piperidine gave 5-aryl-2-piperidino- 5H-chromeno[3,4-c]pyridine-1-carbonitriles 4a-g in good yields. ARKAT-USA, Inc.
Flavene and thioflavene derivates, processes for their manufacture, pharmaceutical preparations that contain such compounds, and the use of the latter
-
, (2008/06/13)
Compounds of the formula I STR1 wherein rings A and B are each unsubstituted or substituted; Y is oxygen, sulfur, sulfinyl or sulfonyl; one of the symbols Z1 and Z2 is halogen and the other formyl; and pharmaceutically acceptable sal
