3,5‐Bis(arylidene)piperid‐4‐ones Containing 1,3,2‐Oxazaphosphorinane Moieties: Synthesis and Antitumor Activity

Шипов, А. Г.; Makarov, Mikhail V.; Petrovskii, P. V.; Rybalkina, Ekaterina Yu.; Nelyubina, Yulia V.; Odinets, Irina L.

doi:10.1002/hc.21082

Cited by 7 publications

(1 citation statement)

References 25 publications

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“…For example, in [52,53], the crystal adducts of various phosphine oxides (Ph 2 (Me)P=O, Ph 3 PO) with strong halogen donors such as pentafluoroiodoebenzene C 6 F 5 I and 1,4-diaryl-5-iodotriazole are described. Finally, for a series of crystals containing molecules with P=O groups, the presence of short X···O contacts (X = Cl, Br, I), which can be interpreted as halogen bonds, has been established with the help of X-ray analysis and quantum-chemical calculations [54][55][56][57][58][59][60][61]. Many other examples of XBs with phosphine oxides and related compounds can be found in CCDC data, which allowed us to perform an extensive database search and analyze the distributions of geometric parameters, as described in Section 4.…”

Section: Introductionmentioning

confidence: 99%

Phosphine Oxides as Spectroscopic Halogen Bond Descriptors: IR and NMR Correlations with Interatomic Distances and Complexation Energy

et al. 2020

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An extensive series of 128 halogen-bonded complexes formed by trimethylphosphine oxide and various F-, Cl-, Br-, I- and At-containing molecules, ranging in energy from 0 to 124 kJ/mol, is studied by DFT calculations in vacuum. The results reveal correlations between R–X⋅⋅⋅O=PMe3 halogen bond energy ΔE, X⋅⋅⋅O distance r, halogen’s σ-hole size, QTAIM parameters at halogen bond critical point and changes of spectroscopic parameters of phosphine oxide upon complexation, such as 31P NMR chemical shift, ΔδP, and P=O stretching frequency, Δν. Some of the correlations are halogen-specific, i.e., different for F, Cl, Br, I and At, such as ΔE(r), while others are general, i.e., fulfilled for the whole set of complexes at once, such as ΔE(ΔδP). The proposed correlations could be used to estimate the halogen bond properties in disordered media (liquids, solutions, polymers, glasses) from the corresponding NMR and IR spectra.

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Section: Introductionmentioning

confidence: 99%

Phosphine Oxides as Spectroscopic Halogen Bond Descriptors: IR and NMR Correlations with Interatomic Distances and Complexation Energy

et al. 2020

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ChemInform Abstract: 3,5‐Bis(arylidene)piperid‐4‐ones Containing 1,3,2‐Oxazaphosphorinane Moieties: Synthesis and Antitumor Activity.

et al. 2013

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3,5-Bis(arylidene)piperid-4-ones Containing 1,3,2-Oxazaphosphorinane Moieties: Synthesis and Antitumor Activity. -Introduction of oxaphosphorinane moieties into the backbone of the title piperidones results in compounds possessing high antitumor properties toward human carcinoma cell lines. Thioureas (V) are found to be more active than the corresponding diamidophosphates (III). -(SHIPOV, A. E.; MAKAROV*, M. V.; PETROVSKII, P. V.; RYBALKINA, E. Y.; NELYUBINA, Y. V.; ODINETS, I. L.; Heteroat. Chem. 24 (2013) 3, 191-199, http://dx.

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Organocatalytic Enantioselective Synthesis of P‐Stereogenic Chiral Oxazaphospholidines

Wang

et al. 2016

Eur J Org Chem

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The enantioselective synthesis of P‐stereogenic chiral organophosphines under organocatalysis is a challenging research field, and reports that use this approach are rare. Herein, we have developed the enantioselective synthesis of P‐stereogenic chiral oxazaphospholidines by using a bicyclic thiazole as the organocatalyst in the P–N and P–O bond‐forming reaction. The P‐chiral products were prepared in high yields with moderate enantioselectivities. The base that was used in this process had a significant influence on the enantioselectivity of the reaction and in some cases led to the opposite configuration of the P‐chiral center.

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3,5‐Bis(arylidene)piperid‐4‐ones Containing 1,3,2‐Oxazaphosphorinane Moieties: Synthesis and Antitumor Activity

Cited by 7 publications

References 25 publications

Phosphine Oxides as Spectroscopic Halogen Bond Descriptors: IR and NMR Correlations with Interatomic Distances and Complexation Energy

Phosphine Oxides as Spectroscopic Halogen Bond Descriptors: IR and NMR Correlations with Interatomic Distances and Complexation Energy

ChemInform Abstract: 3,5‐Bis(arylidene)piperid‐4‐ones Containing 1,3,2‐Oxazaphosphorinane Moieties: Synthesis and Antitumor Activity.

Organocatalytic Enantioselective Synthesis of P‐Stereogenic Chiral Oxazaphospholidines

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