57543-66-5Relevant articles and documents
One pot, three component 1,3 dipolar cycloaddition: Regio and diastereoselective synthesis of spiropyrrolidinyl indenoquinoxaline derivatives
Pattanaik, Priyabrata,Nayak, Sabita,Ranjan Mishra, Deepak,Panda, Pravati,Prasad Raiguru, Bishnu,Priyadarsini Mishra, Nilima,Mohapatra, Seetaram,Arjunreddy Mallampudi,Purohit, Chandra Shekhar
, p. 2688 - 2694 (2018)
A competent and highly discriminating one-pot synthesis of highly diversified novel functionalized indenoquinoxalone grafted spiropyrrolidine linked chromene-3-carbonitrile conjugates accumulating three pharmocophoric cores, heterocyclic indenoquinoxalone, pyrrolidines and chromene-3-carbonitrile in a single molecular framework by means of 1,3-dipolar cycloaddition reaction between indenoquinoxalone, proline/benzyl amine and chromene-3-carbonitrile in ethanol under classical and microwave conditions is described. The three component 1,3-dipolar cycloaddition reaction proceeds via in situ generation of azomethine ylides by the decarboxylative condensation of indenoquinoxalone with proline/benzyl amine and their selectivity towards the endo cyclic double bonds of dipolarophile (chromene-3-carbonitrile) leading to the formation of highly functionalised regio- and diastereoselective molecular hybrids. This methodology exemplifies the green chemistry protocol such as mild reaction conditions, high yields, one-pot procedure and operational simplicity.
A spectroscopic insight into the interaction of chromene 1,2,4-oxadiazole-based compounds with bovine serum albumin
Mishra, Nilima Priyadarsini,Satish, Lakoji,Mohapatra, Seetaram,Nayak, Sabita,Sahoo, Harekrushna
, p. 1181 - 1195 (2021)
Four synthesized 2H-chromene-based 1,2,4-oxadiazole compounds (6a-6d) were studied for binding with bovine serum albumin (BSA) by different spectroscopic and thermodynamic analyses. A molecular docking program was used to find out the possible binding sites and binding affinity of 2H-chromene based 1,2,4-oxadiazole compounds with bovine serum albumin (BSA). The intrinsic fluorescence of BSA was quenched by these compounds through static quenching mechanism, and the estimated binding constant (Kb) value was found to be 1.5 × 103–10 × 103. The conformational changes of BSA were monitored by circular dichroism analysis, and it was observed that BSA is structurally stable in the presence of these compounds. The thermodynamic results indicated that the interaction process is spontaneous and the binding between oxadiazole compounds and BSA is mainly driven by hydrogen bonding and van der Waals forces. This study would be helpful to understand the biological benefits of oxadiazole-based compounds as well as the nature of interactions with biomolecules. Graphic abstract: [Figure not available: see fulltext.].
Synthesis, characterization, and antifungal activity of novel chromene oxadiazole based dithiocarbamates
Bhoga, Srinivas,Gutam, Madhu,Konda, Santosh Kumar,Krupadanam, G. L. David,Mattela, Kutumbarao,Nayaki, Salva Reddy,Thalari, Gangadhar
supporting information, (2022/03/02)
A series of novel conjugated chromene oxadiazole-based dithiocarbamate (5a–i) derivatives have been synthesized from oxadiazole (4a–c) intermediates with carbon disulfide. The structures of all the newly synthesized compounds were established by IR, NMR, and Mass spectral analysis. The synthesized derivatives were screened for their antifungal activity against Aspergillus niger fungal strain and the results showed that some of the derivatives were found to exhibit good antifungal activity.
Synthesis, cytotoxicity, and molecular docking of substituted 3-(2-methylbenzofuran-3-yl)-5-(phenoxymethyl)-1,2,4-oxadiazoles
Mokenapelli, Sudhakar,Thalari, Gangadhar,Vadiyaala, Naveen,Yerrabelli, Jayaprakash R.,Irlapati, Vamshi K.,Gorityala, Neelima,Sagurthi, Someswar R.,Chitneni, Prasad R.
, (2020/04/27)
A series of new benzofuran/oxadiazole hybrids (8a–n) was synthesized from 2H-chromene-3-carbonitriles (3a–c) through the multistep synthetic methodology, and these hybrids are known to exhibit anticancer activities. All the compounds were evaluated for their in vitro cytotoxicity against the HCT116 and MIA PaCa2 cell lines. Compounds 6a (IC50: 9.71 ± 1.9 μM), 6b (IC50: 7.48 ± 0.6 μM), and 6c (IC50: 3.27 ± 1.1 μM) displayed a significant cytotoxic activity, whereas compounds 8d and 8e exhibited good activity against both cell lines. The depletion of glycogen synthase kinase-3β (GSK3β) induces apoptosis through the inhibition of basal NF-κB activity in HCT116 colon cancer cells and MIA PaCa2 pancreatic cancer cells. Molecular docking of compounds 6a, 6b, 6c, 8d, and 8e with GSK3β demonstrated the best binding affinity, correlating with the biological activity assay. Furthermore, the structure–activity relationship of these novel compounds reveals promising features for their use in anticancer therapy.
