Convenient and Scalable Synthesis of 2,3-Dihydroquinazolin-4(1<i>H</i>)-one Derivatives and Their Anticancer Activities

Lingayya, Rajaka; Penumati, Nageshwar Rao; Nagaiah, K.; Poornachandra, Y.; Kumar, C. Ganesh

doi:10.1080/00397911.2015.1046555

Cited by 20 publications

(7 citation statements)

References 18 publications

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“…1 H NMR (400 MHz, CDCl3) δ 8.01 (dd, J = 7.8, 1.3 Hz, 1H), 7.32 -7.24 (m, 5H), 7.20 -7.11 (m, 3H), 6.91 -6.85 (m, 1H), 6.79 -6.72 (m, 2H), 6.62 (d, J = 8.0 Hz, 1H), 6.06 (s, 1H), 4.74 (s, 1H), 3.74 (s, 3H). 13 13 C NMR spectra are consistent with the literature [4] .…”

Section: S7supporting

confidence: 88%

5,5’-Indigodisulfonic acid as an efficient catalyst for the synthesis of 2,3-dihydroquinazolinone derivatives

Liu

Wang

et al. 2022

Synthetic Communications

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Section: S7supporting

confidence: 88%

5,5’-Indigodisulfonic acid as an efficient catalyst for the synthesis of 2,3-dihydroquinazolinone derivatives

Liu

Wang

et al. 2022

Synthetic Communications

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“…Due to their application in biology [2], they attracted the interest of many researchers. Many protocols related to the synthesis of dihydroquinazolinones [3], with great biological significance, are reported [4]. For instance, substituted dihydroquinazolinones are reported as cell multiplication inhibitors [5], anti-fibrillatory and choleretic agents [6], anti-inflammatory agents [7], gastrointestinal motility improving and antiemetic agents, [8] IMPDH inhibitors [9], having H1/H2-antihistaminic actions [10], as PARP-1 inhibitors [11] and having anticancer activity [12,13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Piperidine Conjugated Dihydroquinazolin-4(1H)-ones and their Antiproliferative Activity, Molecular Docking Studies and DFT Calculations

Narasimhamurthy

Chandra²,

Swaroop

et al. 2019

LDDD

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Background: Xanthatin, fluoropyrimidine and thienopyrimidine, pyrazolopyrimidine, pyrimidine carboxamides, and SKLB1002 are reported as VEGFR2 tyrosine kinase inhibitors. Recently, many studies related to different heterocycles conjugated with dihydroquinazolinones are known to have very good biological activities. In this study, we are intended to explore the cytotoxic studies of piperidine conjugated dihydroquinazolinones against colorectal/colon cancer cell lines and along with molecular docking studies and DFT calculations. Methods: The colorectal/colon cell lines HCT116 and A549 cell lines were treated with these compounds and cytotoxic activities were evaluated by MTT dye uptake method. We performed molecular modelling for compound 3d using the Auto Dock software. The binding of compound 3d with target proteins was studied with the collection of experimentally determined PDB database. Optimized geometry by DFT calculations was performed with B3LYP/6-31G (d) basis set. Results: Piperidine-conjugated dihydroquinazolinone analogues displayed anticancer activity. Particularly, the compound 3d with electron-withdrawing substituents on a phenyl ring showed significant cytotoxicity against HCT116 and A549 cell lines. Molecular docking studies proved that the compound 3d has good fitting by forming hydrogen bonds with amino acid residues at the active sites of VEGFR2. The HOMO, LUMO, their energies and UV visible spectrum were predicted using DFT calculations. Conclusion: Four piperidine-conjugated dihydroquinazolinones were synthesized and evaluated against colorectal and colon cancer cell lines. Compound 3d significantly inhibited the growth of HCT116 and A549. Molecular docking studies displayed good fitting of compound 3d by forming different H-bonds with the amino acid at the active sites of the VEGFR2 target. Using a theoretical approach, we optimized HOMO and LUMO plots for the compound 3d.

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“…However, the use of suitable catalysts makes the process easier. The catalytic methods involve use of tetrabutylammonium bromide in the presence of CuCl 2 , cyanuric chloride in anhydrous CH 3 CN at room temperature (RT), β‐cyclodextrin in water at 60°C, β‐cyclodextrine‐SO 3 H in water in RT, Amberlyst‐15 ® in CH 3 CN at 20°C, graphene oxide nanosheets in aqueous medium at RT, InBr 3 in CH 3 CN at RT, SbCl 3 in MeOH, molecular iodine under solvent‐free condition, silica‐supported preyssler nanoparticles heteropolyacid, and CuI/L‐proline/Cs 2 CO 3 /100°C . Catalyst‐free conditions have been also reported; under heating in PEG‐400 at 110°C, in water at 90°C, and in acetic acid under irradiation of visible light (hv >390 nm) .…”

Section: Introductionmentioning

confidence: 99%

Yttrium nitrate catalyzed synthesis, photophysical study, and TD‐DFT calculation of 2,3‐dihydroquinazolin‐4(1H)‐ones

Khan

Mitra

Mandal

et al. 2017

Heteroatom Chemistry

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We have developed an efficient method of the synthesis of 2,3‐dihydroquinazolin‐4(1H)‐one (DHQ) using yttrium nitrate catalyst at room temperature. The synthetic method is simple, convenient, and easy product isolation. Best results obtained in CH3CN, DMF, or water. The synthesized DHQ derivatives are found to be good fluorophores, and their characteristic photoluminescence properties are measured. Absorption and emission spectra of DHQ derivatives were recorded in CH3CN. Calculated emission and absorption bands are in excellent agreement with experimentally observed values.

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Convenient and Scalable Synthesis of 2,3-Dihydroquinazolin-4(1H)-one Derivatives and Their Anticancer Activities

Cited by 20 publications

References 18 publications

5,5’-Indigodisulfonic acid as an efficient catalyst for the synthesis of 2,3-dihydroquinazolinone derivatives

5,5’-Indigodisulfonic acid as an efficient catalyst for the synthesis of 2,3-dihydroquinazolinone derivatives

Synthesis of Piperidine Conjugated Dihydroquinazolin-4(1H)-ones and their Antiproliferative Activity, Molecular Docking Studies and DFT Calculations

Yttrium nitrate catalyzed synthesis, photophysical study, and TD‐DFT calculation of 2,3‐dihydroquinazolin‐4(1H)‐ones

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