Novel synthesis of steroidal oximes and lactams and their biological evaluation as antiproliferative agents

Martínez-Pascual, Roxana; Meza‐Reyes, Socorro; Vega-Báez, José Luis; Merino-Montiel, Penélope; Padrón, José M.; Mendoza, Ángel; Montiel‐Smith, Sara

doi:10.1016/j.steroids.2017.03.008

Cited by 24 publications

(20 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the plant kingdom, oximes play a vital role in metabolism (Sørensen et al, 2018). Aldoximes, RCH NOH, are found in many biologically active compounds (Abele et al, 2008;Nikitjuka & Jirgensons, 2014), having a diverse range of uses including as anti-tumour agents (Martínez-Pascual et al, 2017;Qin et al, 2017;Canario et al, 2018;Huang et al, 2018), acaricidal and insecticidal agents (Dai et al, 2017), thymidine phosphorylase inhibitors (Zhao et al, 2018), anti-microbial agents (Yadav et al, 2017), bacteriocides (Kozlowska et al, 2017), anti-inflammatory agents (Mohassab et al 2017), and in the treatment of nerve-gas poisoning (Lorke et al, 2008;Voicu et al, 2010;Katalinić et al, 2017;Radić et al, 2013).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structures and Hirshfeld surfaces of four methoxybenzaldehyde oxime derivatives, 2-MeO-XC₆H₃C=NOH (X= H and 2-, 3- and 4-MeO): different conformations and hydrogen-bonding patterns

Gomes¹,

Souza²,

Costa³

et al. 2018

Acta Cryst E

View full text Add to dashboard Cite

The crystal structures of four (E) -methoxybenzaldehyde oxime derivatives, namely (2-methoxybenzaldehyde oxime, 1, 2,3-dimethoxybenzaldehyde oxime, 2, 4-dimethoxybenzaldehyde oxime, 3, and 2,5-dimethoxybenzaldehyde oxime, 4, are discussed. The arrangements of the 2-methoxy group and the H atom of the oxime unit are s-cis in compounds 1–3, but in both independent molecules of compound 4, the arrangements are s-trans. The primary intermolecular O—H(oxime)⋯O(hydroxy) hydrogen bonds generate C(3) chains in 1 and 2. In contrast, in compound 3, the O—H(oxime)⋯O(hydroxy) hydrogen bonds generate symmetric (6) dimers. A more complex dimer is generated in 4 from the O—H(oxime)⋯O(hydroxy) and C—H(2-methoxy)⋯O(hydroxy) hydrogen bonds.

show abstract

Section: Chemical Contextmentioning

confidence: 99%

Crystal structures and Hirshfeld surfaces of four methoxybenzaldehyde oxime derivatives, 2-MeO-XC₆H₃C=NOH (X= H and 2-, 3- and 4-MeO): different conformations and hydrogen-bonding patterns

Gomes¹,

Souza²,

Costa³

et al. 2018

Acta Cryst E

View full text Add to dashboard Cite

show abstract

“…The oxime group, R 1 R 2 C=NOH, is found in many biologically active compounds [1,2], with a wide range of uses including as antitumor agents [3][4][5][6], acaricides and insecticides [7], thymidine phosphorylase inhibitors [8], anti-microbial agents [9], bactericides [10] and antiinflammatory agents [11], as well as in the treatment of nerve-gas poisoning [12][13][14][15]. In the plant kingdom, oximes play vital metabolic roles [16].…”

Section: Introductionmentioning

confidence: 99%

Different substituent effects on the supramolecular arrays in some (E)-halo- and nitro-benzaldehyde oximes: confirmation of attractive π(C=N)···π(phenyl) interactions

Gomes

Low

Mourik

et al. 2019

Zeitschrift Für Naturforschung B

View full text Add to dashboard Cite

The crystal structures and Hirshfeld surface analyses are reported for four aldoximes, (E)-X–C6H4CH=N–OH [X = 3-Cl (1), 4-F (2), 2-O2N (3) and 4-O2N (4)]. The strong classical O–H · · · N hydrogen bonds involving the oxime group generate C(3) chains in compound 1, in contrast to the R22(6) dimers formed in compounds 2–4; such arrangements have been shown to be the most frequently found for oximes other than salicylaldoximes (2-hydroxybenzaldehyde oximes). In general, weaker intermolecular interactions involving the X substituents, as well as C–H · · · O and π · · · π interactions have significant effects on the supramolecular arrays generated in the aggegation. A further important interaction in compound 1, and to a lesser extent in compound 4, is a π(C=N) · · · π(phenyl) molecular stacking. A data base search has indicated that short Cg(C=N) · · · Cg(phenyl) distances, <3.3 Å (Cg = centre of gravity), have been found in various compounds, including other oximes. A theoretical study was carried out starting from the crystal structure data of compound 1, with optimisation at the BLYP-D3/def2-DZVP level, as well as at the higher PBE0/ma-def2-TZVP level. Breakdown of the interaction energy into separate contributions was achieved using SAPT (using the jun-cc-pvdz basis set). Overall, the calculations indicate that the π(C=N) ·· · π(phenyl) interaction is attractive, with a magnitude of 14–18 kJ mol−1.

show abstract

“…The oxime group, R1R2C=NOH, is found in many biologically active compounds [1,2], with a wide range of uses including as antitumor agents [3][4][5][6], acaricidal and insecticidal agents [7], thymidine phosphorylase inhibitors [8], antimicrobial agents [9], bactericides [10], anti-inflammatory agents [11] and in the treatment of nerve-gas poisoning [12][13][14][15]. In the plant kingdom, oximes play a vital role in metabolisms [16].…”

Section: Introductionmentioning

confidence: 99%

Structural study of three heteroaryl oximes, heteroaryl-N=OH: Compounds forming strong C3 molecular chains

et al. 2018

View full text Add to dashboard Cite

In order to further investigate the structural chemistry of oximes and to further establish the main structural arrangements adopted, we have determined the crystal structure of and carried out Hirshfeld surface calculations on three heteroaryl oximes, namely (Z)-thiophene-2-carbaldehyde oxime (1), (Z)-1H-pyrrole-2 carbaldehyde oxime (2) and (Z)-5-nitrofuran-2-carbaldehyde oxime (3). As confirmed by both techniques, the major intermolecular interactions in each compound are classical N—H···O hydrogen bonds, which link the molecules into C3 chains. Such an arrangement has been previous reported as an important aggregation mode for oximes. Secondary interactions, C—H···π and C—H···O interactions, in compounds 1 and 2, and interactions involving the nitro group oxygen atoms in compound 3 link the chains into three dimensional arrays.

show abstract

Novel synthesis of steroidal oximes and lactams and their biological evaluation as antiproliferative agents

Cited by 24 publications

References 36 publications

Crystal structures and Hirshfeld surfaces of four methoxybenzaldehyde oxime derivatives, 2-MeO-XC₆H₃C=NOH (X= H and 2-, 3- and 4-MeO): different conformations and hydrogen-bonding patterns

Crystal structures and Hirshfeld surfaces of four methoxybenzaldehyde oxime derivatives, 2-MeO-XC₆H₃C=NOH (X= H and 2-, 3- and 4-MeO): different conformations and hydrogen-bonding patterns

Different substituent effects on the supramolecular arrays in some (E)-halo- and nitro-benzaldehyde oximes: confirmation of attractive π(C=N)···π(phenyl) interactions

Structural study of three heteroaryl oximes, heteroaryl-N=OH: Compounds forming strong C3 molecular chains

Contact Info

Product

Resources

About

Novel synthesis of steroidal oximes and lactams and their biological evaluation as antiproliferative agents

Cited by 24 publications

References 36 publications

Crystal structures and Hirshfeld surfaces of four methoxybenzaldehyde oxime derivatives, 2-MeO-XC6H3C=NOH (X= H and 2-, 3- and 4-MeO): different conformations and hydrogen-bonding patterns

Crystal structures and Hirshfeld surfaces of four methoxybenzaldehyde oxime derivatives, 2-MeO-XC6H3C=NOH (X= H and 2-, 3- and 4-MeO): different conformations and hydrogen-bonding patterns

Different substituent effects on the supramolecular arrays in some (E)-halo- and nitro-benzaldehyde oximes: confirmation of attractive π(C=N)···π(phenyl) interactions

Structural study of three heteroaryl oximes, heteroaryl-N=OH: Compounds forming strong C3 molecular chains

Contact Info

Product

Resources

About

Crystal structures and Hirshfeld surfaces of four methoxybenzaldehyde oxime derivatives, 2-MeO-XC₆H₃C=NOH (X= H and 2-, 3- and 4-MeO): different conformations and hydrogen-bonding patterns

Crystal structures and Hirshfeld surfaces of four methoxybenzaldehyde oxime derivatives, 2-MeO-XC₆H₃C=NOH (X= H and 2-, 3- and 4-MeO): different conformations and hydrogen-bonding patterns