359430-31-2Relevant academic research and scientific papers
Design and synthesis of novel sulphamide tethered quinazolinone hybrids as potential antitumor agents
Venkatesh, Ramineni,Kasaboina, Suresh,Jain, Nishant,Janardhan, Sridhara,Holagunda, Uma Devi,Nagarapu, Lingaiah
, p. 403 - 411 (2019)
In an attempt to develop potential and selective antitumor agents, a series of novel sulphamide tethered quinazolinone hybrids were efficiently synthesized and evaluated for antitumor activity against four cancer cell lines such as HeLa (cervical), MDA-MB-231 (breast), PANC-1 (pancreatic), and A549 (lung) in vitro. All the compounds (5a-j, 6a-g) exhibited significant anti-proliferative activity with GI50 values ranging from 0.045 to 6.94 μM, while compound 10c showed potent activity against all the cell lines (He La, MDA-MB-231, PANC-1 and A549) with GI50 values ranging from 0.09 to 0.21 μM. We have explored the binding mode and key active site interactions in HDAC8 and EHMT2 proteins. The docking results are complementary to the experimental results.
Probing the catalytic activity of highly efficient sulfonic acid fabricated cobalt ferrite magnetic nanoparticles for the clean and scalable synthesis of dihydro, spiro and bis quinazolinones
Awasthi, Satish K.,Yadav, Priyanka
supporting information, p. 15928 - 15941 (2021/09/22)
An exceptionally productive, rapid, simple, and eco-friendly approach for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been developed utilizing acidic magnetically retrievable cobalt ferrite nanoparticles (CFNP@SO3H). Herein, we have demonstrated the synthesis of these profoundly demanding N-heterocyclic molecules within 3-10 min in excellent yields at room temperature using the environmentally benign solvent ethanol. Outstanding catalytic performance, ease of retrievability, high turnover frequency (TOF) values (197.13-403.23 h?1), admirable green chemistry metrices, such as theEfactor (0.10), reaction mass efficiency (RME) value (90.9%), carbon efficiency (100%) and atom economy (AE) value (92.6%), and reusability for up to six runs without a significant loss of activity, make the current methodology advantageous from an environmental, as well as industrial perspective.
Praseodymium(iii) anchored on CoFe2O4 MNPs: An efficient heterogeneous magnetic nanocatalyst for one-pot, multi-component domino synthesis of polyhydroquinoline and 2,3-dihydroquinazolin-4(1: H)-one derivatives
Tamoradi, Taiebeh,Mousavi, Seyedeh Masoumeh,Mohammadi, Masoud
, p. 3012 - 3020 (2020/03/03)
In the present study, a facile technique to immobilize praseodymium(iii) complex on the surface of magnetic nanoparticles by using available materials is reported. The prepared samples were characterized by chemical and physical methods such as FTIR, SEM, XRD and EDX and were tested in the synthesis of polyhydroquinoline and 2,3-dihydroquinazolin-4(1H)-one derivatives. It was observed that the yields of the reactions in the presence of the prepared nanocatalyst were good to excellent. More importantly, the use of a recoverable and novel magnetic nanocatalyst in these reactions is the outstanding feature of this protocol.
Synthesis of 2,3-dihydroquinazolin-4(1H)-ones in the presence of Fe3O4@nano-cellulose–OPO3H as a bio-based magnetic nanocatalyst
Mirjalili, Bi Bi Fatemeh,Zaghaghi, Zahra,Monfared, Aazam
, p. 197 - 201 (2019/12/03)
In this research, we have used Fe3O4@nano-cellulose–OPO3H as magnetic bio-based nanocatalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones via condensation of 2-aminobenzamide and different aldehydes. The major advantages of the present methodology are good yields, ecofriendly catalyst, and easy workup.
Gemini basic ionic liquid as bi-functional catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones at room temperature
Dutta, Apurba,Damarla, Krishnaiah,Kumar, Arvind,Saikia, Prakash J.,Sarma, Diganta
, (2020/01/08)
A cascade synthesis of 2,3-dihydroquinazolin-4(1H)-ones has been developed from 2-aminobenzonitriles and carbonyl analogues using Gemini basic ionic liquid as green catalyst cum solvent at room temperature. Both aldehydes and ketones were condensed with 2-aminobenzonitriles affording good to excellent yields of products. Moreover, the ionic liquids can be reused up to 5th cycle without significant loss of catalytic activity.
KOH/DMSO: A basic suspension for transition metal-free Tandem synthesis of 2,3-dihydroquinazolin-4(1H)-ones
Dutta, Apurba,Damarla, Krishnaiah,Bordoloi, Ankur,Kumar, Arvind,Sarma, Diganta
supporting information, p. 1614 - 1619 (2019/05/24)
A novel protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones from 2-aminobenzamides and aldehyde derivatives catalyzed by KOH/DMSO suspension has been developed. The present transition metal free methodology is operationally simple, scalable and varieties of 2,3-dihydroquinazolin-4(1H)-one derivatives were obtained in good to excellent yields in short reaction times.
Efficient one-pot synthesis of 2,3-dihydroquinazoline-4(1H)-ones promoted by FeCl3/neutral Al2O3
Wu, Suo Juan,Zhao, Zi Qiang,Gao, Jing Shuo,Chen, Bao Hua,Chen, Guo Feng
, p. 2327 - 2339 (2019/02/01)
2,3-Dihydroquinazolin-4(1H)-one derivatives have been synthesized via one-pot reaction of isatoic anhydride, aromatic aldehyde, and ammonium acetate catalyzed by FeCl3/neutral Al2O3 in tert-butanol under reflux conditions.
SbCl3 as effective catalyst for the preparation of 2,3-Dihydroquinazolin-4(1H)-ones, spectroscopic investigation and DFT study
Pourmousavi, Seied Ali,Kanaani, Ayoob,Fatahi, Hamid Reza,Ghorbani, Fatemeh,Ajloo, Davood
, p. 82 - 93 (2017/03/20)
A simple and efficient method has been developed for the synthesis of Quinazolines using SbCl3 as a heterogeneous catalysis at room temperature. This method provides a good pathway for the synthesis of 2,3-Dihydroquinazolin-4(1H)-ones derivatives in the terms of excellent yields and short reaction times. Also we studied theoretically and experimentally on 2-phenyl-2,3-dihydroquinazolin-4(1H)-one (PDQ). Using density functional theory (DFT), the tautomerism of PDQ was also studied. Thermal stability of PDQ was studied by thermo gravimetric analysis (TGA). The spectroscopic results and theoretical calculations indicate that the strength of intramolecular hydrogen bonding (IHB) of PDQ is stronger than that in 2-methyl-4-quinolinol (2MQ). The absorption spectra of the PDQ in solvents with different polarity were obtained and the results show that PDQ exists in both keto-amine and enol-imine forms in THF, while it has keto-amine form in other solvents. Theoretical results show that the conductance of the two tautomers (keto-amine and enol-imine) varies greatly, which offers that the potential usage of this molecule is as a molecular device.
Glycerol assisted eco-friendly strategy for the facile synthesis of 4,4′-(arylmethylene)bis(3-methyl-1H-pyrazol-5-ols) and 2-aryl-2,3-dihydroquinazolin-4(1H)-ones under catalyst-free conditions
Ramesh, Rathinam,Nagasundaram, Nagarajan,Meignanasundar, Durairaj,Vadivel, Pullar,Lalitha, Appaswami
, p. 1767 - 1782 (2017/02/15)
Abstract: This article describes glycerol mediated eco-friendly approaches for the convenient access of structurally diverse 4,4′-(arylmethylene)bis(3-methyl-1H-pyrazol-5-ol) and 2-aryl-2,3-dihydroquinazolin-4(1H)-one motifs under catalyst-free conditions. Prominent advantages include clean processes, atom-efficiency, simplicity of the work-up, neutral conditions, low-cost reaction medium, excellent product yield and solvent reusability, in addition to relatively shorter reaction times. Graphical Abstract: [Figure not available: see fulltext.]
Synthesis and characterization of bromine source supported on magnetic Fe3O4 nanoparticles: A new, versatile and efficient magnetically separable catalyst for organic synthesis
Shiri, Lotfi,Ghorbani-Choghamarani, Arash,Kazemi, Mosstafa
, (2017/06/21)
Tribenzylammonium tribromide supported onto magnetic nanoparticles (Br3-TBA-Fe3O4) as a bromine source was successfully synthesized and characterized using Fourier transform infrared spectroscopy, thermogravimetric analysis, X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy and vibrating sample magnetometry. The synthesized catalyst is shown to be a versatile and highly efficient heterogeneous catalyst for the Knoevenagel condensation and synthesis of 2,3-dihydroquinazolin-4(1H)-one and polyhydroquinoline derivatives. To the best of the authors' knowledge, this is the first report of the use of a bromine source immobilized on Fe3O4 nanoparticles as a magnetically separable catalyst for these reactions. The nanosolid catalyst can be magnetically recovered and reused readily several times without significant loss in catalytic efficiency.
