1450-74-4Relevant academic research and scientific papers
Bioactivity study of thiophene and pyrazole containing heterocycles
Athare, Anil E.,Dare, Sushama B.,Kale, Nitin V.,Karale, Bhausaheb K.,Mhaske, Sadhana D.,Salve, Supriya P.,Takate, Sushama J.
, p. 891 - 899 (2021/09/08)
Chalcones 3a-f were prepared by reacting thiophene containing pyrazolyl aldehyde (2) with different 2-hydroxy acetophenones 1a-f. The compounds 3a-f were transformed into different Pyrazolines 4a-f. The formation of chromene derivatives 5a-f occurred from the cyclization of 3a-f, which were then transformed into pyrazole derivatives 6a-f. Newly synthesized compounds have promising antibacterial activity against S. typhii and S. aureus, while weak activity against B. subtilis and E. coli. Compounds 5d and 6d had significant antifungal action towards A. niger, while most of the compounds were moderately active towards T. viride. Some of the synthesized compounds showed promising α-amylase inhibitory activity at 1 mg/mL concentration.
Chromone dioxadiazole compound as well as preparation method and application thereof
-
Paragraph 0021-0023, (2021/10/30)
The preparation method comprises the following steps: adding an intermediate F and bis (acetoxy) iodobenzene to dichloromethane for reaction to obtain the chromone compound. The invention provides a novel chromone dioxadiazole compound and a preparation method thereof, and overcomes the defects of large toxicity and high preparation cost of the traditional method.
Novel p-functionalized chromen-4-on-3-yl chalcones bearing astonishing boronic acid moiety as MDM2 inhibitor: Synthesis, cytotoxic evaluation and simulation studies
Bhatia, Richa Kaur,Coutinho, Evans C.,Garg, Ruchika,Kancherla, Satyavathi,Kaur, Maninder,Madan, Jitender,Pissurlenkar, Raghuvir R. S.,Singh, Lakhwinder,Yadav, Manmohan
, p. 212 - 228 (2020/03/10)
Background: Novel 4-[3-(6/7/8-Substituted 4-Oxo-4H-chromen-3-yl)acryloyl]phenyl-boronic acid derivatives (5a-h) as well as other 6/7/8-substituted-3-(3-oxo-3-(4-substituted-phenyl)prop-1-enyl)-4H-chromen-4-one derivatives (3a-u) have been designed as p53-MDM2 pathway inhibitors and reported to possess significant cytotoxic properties against several cancer cell lines. Objectives: The current project aims to frame the structure-anticancer activity relationship of chromen-4-on-3-yl chalcones (3a-u/5a-h). In addition, docking studies were performed on these chromeno-chalcones in order to have an insight into their interaction possibilities with MDM2 pro-tein. Methods: Twenty-nine chromen-4-on-3-yl chalcone derivatives (3a-u/5a-h) were prepared by utilizing silica supported-HClO4 (green route with magnificent yield) and tested against four cancer cell lines (HCT116, MCF-7, THP-1, NCIH322). Results: Among the series 3a-u, compound 3b exhibited the highest anticancer activity (with IC50 values ranging from 8.6 to 28.4 μM) overall against tested cancer cell lines. Interestingly, para-Boronic acid derivative (5b) showed selective inhibition against colon cancer cell line, HCT-116 with an IC50 value of 2.35 μM. Besides the emblematic hydrophobic interactions of MDM2 inhibi-tors, derivative 5b was found to exhibit extra hydrogen bonding with GLN59 and GLN72 residues of MDM2 in molecular dynamics (MD) simulation. All the compounds were virtually nontoxic against normal fibroblast cells. Conclusion: Novel compounds were obtained with good anticancer activity especially 6-Chlorochromen-4-one substituted boronic acid derivative 5b. The molecular docking study proposed good activity as a MDM-2 inhibitor suggesting hydrophobic as well as hydrogen bonding interactions with MDM2.
Synthesis and anti-inflammatory activity of 2-oxo-2H-chromenyl and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates
Bhimapaka, China Raju,Karri, Shailaja,Kuncha, Madhusudana,Kurma, Siva Hariprasad,Sistla, Ramakrishna
, (2020/06/22)
Cycloaddition reaction of 4-chloro-2-oxo-2H-chromene-3-carbaldehydes (3a-g) and 4-chloro-2H-chromene-3-carbaldehydes (7a-h) with activated alkynes (4a-b) provided the 2-oxo-2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (5a-n) and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (8a-p). All the prepared compounds were screened for anti-inflammatory activity. In vitro anti-inflammatory activity data demonstrated that the compounds 5g, 5i, 5k-l and 8f are effective among the tested compounds against TNF-α (1.108 ± 0.002, 0.423 ± 0.022, 0.047 ± 0.001, 0.070 ± 0.002 and 0.142 ± 0.001 μM) in comparison with standard compound Prednisolone (0.033 ± 0.002 μM). Based on in vitro results, three compounds (5i, 5k and 8f) have been selected for in vivo experiments and these compounds are identified as better compounds with respect to anti-inflammatory activity in LPS induced mice model. Compound 5i was identified as potent and showed significant reduction in TNF-α and IL-6.
Synthesis and Antibacterial Screening of Some New Pyrazolylchromones and Pyrazolylcoumaran-3-ones
Takate, Sushama J.,Salve, Supriya P.,Dare, Sushama B.,Karale, Bhausaheb K.,Akolkar, Hemantkumar N.,Falke, Dnyaneshwar B.,Ghungurde, Rahul B.,Mhaske, Sadhana D.
, p. 525 - 530 (2021/02/02)
Some new pyrazolylchromones 4a-e (flavone analogs) and pyrazolylcoumaran-3-ones 5a-e (aurone analogs) were synthesized by refluxing chalcones 3a-e in dimethyl sulfoxide/I2 and Pyridine/ Hg(OAc)2, respectively. Spectral techniques such as infrared, proton nuclear magnetic resonance, and mass spectrometry were used to confirm the structures of newly synthesized compounds. These compounds were studied for their antibacterial activities toward Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Salmonella typhi. Some of these compounds showed promising activity against test organisms.
Synthesis, characterization and biological activity of mixed ligands complexes of quinolin-8-ol and substituted chromones with Mn(II), Co(II), Ni(II) and Cu(II) metal ions
Kolhe, Nitin H.,Jadhav, Shridhar S.
, p. 973 - 996 (2018/11/23)
The mixed ligand complexes were synthesized using quinolin-8-ol and substituted chromone derivative with transition metals like Mn(II), Cu(II), Ni(II) and Co(II). These complexes were characterized using elemental analysis by electron dispersive spectroscopy, Fourier transforms infrared, ultraviolet–visible, proton nuclear magnetic resonance, liquid chromatography coupled with mass spectrometry, electron spin resonance spectra, magnetic susceptibility, powder X-ray diffraction, thermogravimetric analysis and scanning electron microscopy. The complexes were screened by biological activities such as antioxidant activity by 2, 2-Diphenyl-1-picrylhydrazyl, antimicrobial activity by the agar well-diffusion method and anticancer activity by yellow tetrazolium (3-(4, 5-dimethylthiazolyl-2)-2,5-diphenyltetrazolium bromide methods. The synthesis of mixed ligand complexes were synthesized by using homoleptic complexes of respective metal complexes of chromones. The FTIR spectra show νM–O the νM–N frequencies are obtained at 515–645?cm?1 and 431–496?cm? 1 respectively. The NMR spectra of Ni(II) complexes were indicating the complexes are paramagnetic in nature. The ESR spectra of copper complexes shows singlet signal, and they indicate that the copper has 2 + oxidation state in complexes. The complexes showed a well-defined crystal system indicated by powder-X-ray diffraction patterns. The thermogram studies show formation of metal oxides residues at the end product of decomposition of complexes. The scanning electron microscope showed complexes were nanocrystalline in nature. The mixed ligand complex of Ni(II) shows 80.73% antioxidant activity as compared to both the ligands and other metal complexes. The antibacterial activity result obtained clearly showed that all complexes were effective against all the microorganisms of Staphylococcus aures, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginos. The inhibition of the cancerous cell is more the case of Ni (II) complexes as compared with other complexes.
5-Chlorobenzofuran-2-carboxamides: From allosteric CB1 modulators to potential apoptotic antitumor agents
Youssif, Bahaa G.M.,Mohamed, Ashraf M.,Osman, Essam Eldin A.,Abou-Ghadir, Ola F.,Elnaggar, Dina H.,Abdelrahman, Mostafa H.,Treamblu, Laurent,Gomaa, Hesham A.M.
, p. 1 - 11 (2019/05/27)
Cannabinoids as THC and the CB1 allosteric modulator CBD were reported to have antiproliferative activities with no reports for other CB1 allosteric modulators as the 5-chloroindole-2-carboxamide derivatives and their furan congeners. Based on the antiproliferative activity of two 5-chlorobenzofuran-2-carboxamide allosteric CB1 modulators, a series of novel derivatives was designed and synthesized. The synthesized compounds were tested in a cell viability assay using human mammary gland epithelial cell line (MCF-10A) where all the compounds exhibited no cytotoxic effects and more than 85% cell viability at a concentration of 50 μM. Some derivatives showed good antiproliferative activities against tumor cells as compounds 8, 15, 21 and 22. The most active compound 15 showed equipotent activity to doxorubicin. Compounds 7, 9, 15, 16, 21 and 22 increased the level of active caspase 3 by 4–8 folds, compared to the control cells in MCF-7 cell line and doxorubicin as a reference drug. Compounds 15 and 21, the most activecaspase-3 inducers, increase the levels of caspase 8 and 9 indicating activation of both intrinsic and extrinsic pathways and showed potent induction of Bax, down-regulation of Bcl-2 protein levels and over-expression of Cytochrome C levels in MCF-7 cell lines. Compound 15 exhibited cell cycle arrest at the Pre-G1 and G2/M phases in the cell cycle analysis of MCF-7 cell line. The drug Likeness profile of the synthesized compounds showed that all the compounds were predicted to have high oral absorption complying with different pharmacokinetics filters.
Practical and efficient synthesis of hydroxyaryl ketones catalyzed by HF@SiO2 under solvent-free condition
Paghandeh, Hossein,Saeidian, Hamid,Ghaffarzadeh, Mohammad
, p. 809 - 814 (2018/09/26)
A wide variety of hydroxyaryl ketones bearing different motifs was successfully synthesized with good yields and excellent selectivities in the presence of HF@SiO2 as an environmental friendly acid under solvent-free condition. Mild and green reaction conditions and excellent yields (50-91%) make this method an attractive method for the efficient synthesis of hydroxyaryl ketones. Fries rearrangement of phenyl benzoate in the presence of HF@SiO2 led to p-hydroxybenzophenone, while phenyl acetate in the same conditions produced o-hydroxyacetophenone as a single isomer.
Ultrasound-assisted synthesis and antimicrobial activity of tetrazole-based pyrazole and pyrimidine derivatives
Dofe, Vidya S.,Sarkate, Aniket P.,Shaikh, Zarina M.,Gill, Charansingh H.
, p. 59 - 65 (2018/01/18)
New tetrazole-based pyrazole and pyrimidine derivatives were synthesized by an ultrasound irradiation method. All compounds were characterized by infrared spectroscopy (IR), 1H nuclear magnetic resonance (NMR), 13C NMR, mass spectrometry (MS) and elemental analysis and assessed in vitro for their efficacy as antimicrobial agents against four bacteria (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa) and two fungi (Candida albicans, Aspergillus Niger). Compounds 8a, 8e, 9a, 9b and 9e show potent activity against the tested strains compared to the reference drugs chloramphenicol and clotrimazole.
Synthesis, antimicrobial activity and anti-biofilm activity of novel tetrazole derivatives
Dofe, Vidya S.,Sarkate, Aniket P.,Kathwate, Santosh H.,Gill, Charansingh H.
, p. 325 - 330 (2017/08/18)
In the development of antimicrobial agents, we designed and synthesized novel tetrazole derivatives. The structures of compounds 6a-f and 7a-f were characterized by IR, 1H NMR, 13C NMR, MS and elemental analysis. These compounds were tested for their antimicrobial activity against a series of strains Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa and for antifungal activity against the strains Candida albicans, Candida glabrata, and Candida tropicalis. Compounds 6e, 6f, 7a, and 7f exhibit potent antimicrobial activities compared to the reference drugs streptomycin and miconazole. Tetrazole derivatives 7a-f also inhibit biofilm formation and compound 7f exhibits best anti-biofilm activity with a biofilm inhibitory concentration (BIC) as low as 0.9 μm.
