Synthesis of 1,8-dioxooctahydroxanthene derivatives using ionic liquids, quantum chemical studies and anticancer activity

Sangwan, Reetu; Saini, Monika; Verma, Ruchi; Kumar, Saurabh; Banerjee, Monisha; Jain, Sudha

doi:10.1016/j.molstruc.2020.127786

Cited by 7 publications

(5 citation statements)

References 46 publications

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“…This fact substantially restricts the experimental study of the ED in practically significant compounds. A compromise solution is to obtain the ED distribution in compounds from theoretical calculations by the density functional (DFT) method [5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Application of the Molecular Invariom Model for the Study of Interactions Involving Fluorine Atoms in the {$${\text{Yb}}_{{\text{2}}}^{{{\text{II}}}}$$(μ2-OCH(CF3)2)3(μ3-OCH(CF3)2)2YbIII(OCH(CF3)2)2(THF)(Et2O)} Complex

et al. 2021

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The electron density distributions obtained by the quantum-chemical (density functional theory) calculations and molecular invariom model in the trimeric ytterbium complex with the hexafluoroisopropoxide ligands {$${\text{Yb}}_{{\text{2}}}^{{{\text{II}}}}$$(μ2-OR)3(μ3-OR)2YbIII(OR)2(THF)(Et2O)} (I) (where R is CH(CF3)2, and THF is tetrahydrofuran) are compared. The main topological characteristics of the electron density at the critical points (3, –1) corresponding to the interactions of the ytterbium atoms in the coordination sphere obtained using two studied approaches demonstrate excellent agreement. The maximum divergence between the density functional calculations and molecular invariom model is observed for the intramolecular interactions involving the fluorine atoms (F···F, F···H, and F···O) in the structure of complex I. Geometry optimization leads to a higher number of these interactions in the complex. The energy corresponding to these interactions also increases. However, the main topological characteristics for the F···X interactions (X = F, H, O), which can be localized in the framework of both methods, remain within the transferability index range. An analysis of the deformation electron density shows that the Fδ–···Fδ– interactions are determined by the correspondence of the region of electron density concentration on one of the fluorine atoms to the region of electron density depletion on the second fluorine atom regardless of the method of measuring the electron density distribution.

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Section: Introductionmentioning

confidence: 99%

Application of the Molecular Invariom Model for the Study of Interactions Involving Fluorine Atoms in the {$${\text{Yb}}_{{\text{2}}}^{{{\text{II}}}}$$(μ2-OCH(CF3)2)3(μ3-OCH(CF3)2)2YbIII(OCH(CF3)2)2(THF)(Et2O)} Complex

et al. 2021

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“… Entry Catalyst Conditions Reaction time (min) Yields% Ref. 1 PEG H 2 O/reflux ∼ 180 ∼ 90 [39] 2 activated zinc metal and solid NH 4 C Solvent free /MW ∼ 50 ∼ 90 [40] 3 1-butyl-3-methylimidazoliumtetrafluoroborate (BMIF) solvent free/∼200 ˚C ∼ 60 ∼ 90 [41] 4 Fe nanoparticles loaded in zeolite X (Fe-X) Solvent-free, 90°C ∼ 40 ∼ 90 [42] 5 SO 3 H@Fe 3 O 4 magnetic nanocatalyst Solvent-free, 80 ˚C ∼ 20 ∼ 90 [43] 6 Zr(HSO 4 ) 4 Solvent-free, 110°C 35-60 72-95 This work …”

Section: Resultsmentioning

confidence: 99%

Zr(HSO4)4: Green, efficient and reusable catalyst for one-pot synthesis of 1,8-dioxooctahydroxanthene under solvent-free conditions

Pourshamsian

2022

MethodsX

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“…The ecofriendly and efficient method has an excellent yield of up to 90%. Then, the in vitro antitumor activity of all synthesized compounds against human lung cancer cell lines(A549) was determined, finding that 9-(3,4-dimethoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione showed a marked inhibitory effect on the tested cancer cell line A549 [ 31 ].…”

Section: Ionic Liquids In Pharmaceutical Applicationsmentioning

confidence: 99%

Ionic Liquids in Pharmaceutical and Biomedical Applications: A Review

Zhuo,

Cheng,

Zhao

et al. 2024

Pharmaceutics

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The unique properties of ionic liquids (ILs), such as structural tunability, good solubility, chemical/thermal stability, favorable biocompatibility, and simplicity of preparation, have led to a wide range of applications in the pharmaceutical and biomedical fields. ILs can not only speed up the chemical reaction process, improve the yield, and reduce environmental pollution but also improve many problems in the field of medicine, such as the poor drug solubility, product crystal instability, poor biological activity, and low drug delivery efficiency. This paper presents a systematic and concise analysis of the recent advancements and further applications of ILs in the pharmaceutical field from the aspects of drug synthesis, drug analysis, drug solubilization, and drug crystal engineering. Additionally, it explores the biomedical field, covering aspects such as drug carriers, stabilization of proteins, antimicrobials, and bioactive ionic liquids.

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Synthesis of 1,8-dioxooctahydroxanthene derivatives using ionic liquids, quantum chemical studies and anticancer activity

Cited by 7 publications

References 46 publications

Application of the Molecular Invariom Model for the Study of Interactions Involving Fluorine Atoms in the {$${\text{Yb}}_{{\text{2}}}^{{{\text{II}}}}$$(μ2-OCH(CF3)2)3(μ3-OCH(CF3)2)2YbIII(OCH(CF3)2)2(THF)(Et2O)} Complex

Application of the Molecular Invariom Model for the Study of Interactions Involving Fluorine Atoms in the {$${\text{Yb}}_{{\text{2}}}^{{{\text{II}}}}$$(μ2-OCH(CF3)2)3(μ3-OCH(CF3)2)2YbIII(OCH(CF3)2)2(THF)(Et2O)} Complex

Zr(HSO4)4: Green, efficient and reusable catalyst for one-pot synthesis of 1,8-dioxooctahydroxanthene under solvent-free conditions

Ionic Liquids in Pharmaceutical and Biomedical Applications: A Review

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