Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities

Krstić, Natalija M.; Bjelaković, Mira S.; Žižak, Željko; Pavlović, Mirjana; Juranić, Zorica D.; Pavlović, Vera P.

doi:10.1016/j.steroids.2007.02.005

Cited by 60 publications

(25 citation statements)

References 25 publications

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“…This indicates that the copper(II) complexes have tetragonally distorted octahedral geometries [46,47]. The spectrum of the Mn(II) complex (6) had three bands at 575, 475 and 410 nm, assignable to 6 A 1g −→ 4 T 1g , 6 A 1g −→ 4 E and 6 A 1g −→ 4 T 1g transitions, indicating tetrahedral geometry [46,48]. The spectrum of Co(II) complex (8) had three bands at 640, 520 and 450 nm, which can be assigned to the 4 T lg (F) −→ 4 T 2g (F) (ν t ), 4 T lg (F) −→ 4 A 2g (F) (ν 2 ) and 4 T lg (F)−→ 4 T 2g (P) (ν 3 ) transitions respectively.…”

Section: Electronic Spectramentioning

confidence: 99%

“…Great interest is currently being paid to metal complexes for their interesting anticancer activities [2,3]. Recently, considerable attention has been given to oximes and their coordination compounds due to their utility as fungicides [4], bactericides [5], analgesics and anti-inflammatory agents [6], antioxidants [7], antitumor agents [2,3], insecticides (against Aphis Craccivora [8]) and catalytic properties [9]. Metal(II) complexes of benzidine diacetyloxime have been prepared and spectrally characterized [10].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, spectroscopic characterization and antitumor activity of new metal complexes of isonicotinoylhydrazide oxime

El‐Tabl

El-Waheed

Shakdofa

et al. 2013

Main Group Chemistry

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A new series of manganese(II), cobalt(II), nickel(II), copper(II), zinc(II) cadmium(II) and mercury(II) complexes of N -(3-(hydroxyimino)-4-oxopentan-2-ylidene) isonicotinoylhydrazide (H 2 L) have been prepared and characterized by elemental and thermal (DTA and TGA) analyses, IR, UV-VIS, 1 H-NMR, ESR, mass spectroscopy, magnetic susceptibility, and conductivity. Molar conductance in DMF solution indicated that the complexes are nonelectrolytes. IR spectral data showed that the ligand is either neutral bidentate, (4), neutral tridentate, (3) and (12) or monobasic tridentate (2), (5)-(11). The ESR spectra of solid copper(II) complexes (2), (4), (11) and (12) showed g > g ⊥ > g e , indicating a distorted octahedral structure and the presence of the unpaired electron in a d (x2-y2) orbital. However, copper(II), manganese(II) and cobalt(II) complexes (3), (6) and (8), respectively, had isotropic spectra. Complexes (2), (3), (4), (5), (7), (11) and (12) demonstrated potential antiproliferative activity against the growth of human breast cancer tumor cell line MCF-7. A.S. El-Tabl et al. / Antitumor activity of isonicotinoylhydrazide oxime ligand and its metal complexesHydrazones and their coordination compounds are well known to be biologically important and have antibacterial, antitumor and antitubercular activity [11,12]. Also, these compounds have been used as an analytical reagent [13], polymer-coating, ink pigment [14] and fluorescent material [15]. Metal complexes of a bis-hydrazone derived from isatin monohydrazone and 2-hydroxy-l-naphthaldhyde possess interesting biological properties [16,17]. Oximes and hydrazones are important classes of compounds owing to their wide applications in industry, medicine, and detection of various metal ions [18,19]. Oxime hydrazones can react with metal(II) salts to produce either mono-or bi-nuclear complexes. The keto hydrazone moiety may coordinate to metals in the keto hydrazone or deprotonated enolimine form. Such compounds containing both oxime and hydrazone groups are typically act as tridentate, mono-or biprotic ligands coordinating through the amide oxygen, imine and oxime nitrogen atom depending on the reaction conditions [20]. Metal complexes are now routinely studied as potential chemotherapeutic and diagnostic agents because they offer structural, electronic and optical versatility, which cannot be attained by organic molecules. Coordination compounds have been investigated as potential antiproliferative agents only in the last few decades. Copper is an essential cofactor in a number of enzymes and physiological processes and may be less toxic than non-essential metals. Up to now, a great variety of copper complexes have been tested as cytotoxic agents and found to have antitumor activity in several in vitro tests and a few in vivo experiments [21,22]. It should be of interest to design, synthesize, and use a new type of coordination compounds containing oxime and hydrazine functional groups. This paper describes the synthesis, spectral characterization and antitumor...

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Section: Electronic Spectramentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, spectroscopic characterization and antitumor activity of new metal complexes of isonicotinoylhydrazide oxime

El‐Tabl

El-Waheed

Shakdofa

et al. 2013

Main Group Chemistry

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“…Steroids are an important group of natural compounds playing a crucial role in many physiological and reproductive functions in the human body. Also, different types of steroids have been developed as drugs and anticancer agents [1]. The ability of hydrophobic steroid core to interact with cell membrane can enable transport of various functional groups or heterocyclic structures through them.…”

Section: Introductionmentioning

confidence: 99%

Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro

Živković

Matić

Rodić

et al. 2017

The Journal of Steroid Biochemistry and Molecular Biology

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The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (E)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC values from 8.5μM to 14.9μM), eight on HeLa cells (IC values ranging from 8.9μM to 15.1μM) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC values from 12.7μM to 25.6μM) than cisplatin (21.5μM) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.

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“…The synthesis of some aza-homosteroid compounds with unusual and interesting structures had been reported recently [9,10,11,12,13,14]. These compounds exhibited cytotoxic, antibacterial, antileukemic, and antiandrogenic activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Some New Aza-B-homocholestane Derivatives as Anticancer Agents

et al. 2014

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Using analogues of some marine steroidal oximes as precursors, a series of aza-B-homocholestane derivatives possessing different substituted groups at the 3-position of the steroidal nucleus were synthesized. Their biological activity against cancer cell proliferation was determined with multiple cancer cell lines. Aza-B-homocholestane derivatives possessing 3-hydroxyl, 3-hydroximino and 3-thiosemicarbazone groups displayed remarkable cytotoxicity to cancer cells via apoptosis inducing mechanism. Compounds 5, 10, 12, 15 and 18 exhibited better potency to inhibit cancer cell proliferation. In addition, compound 15 was further evaluated with three dimensional (3D) multicellular spheroids assay to determine its potency against spheroid growth. The structure-activity relationship (SAR) generated in the studies is valuable for the design of novel chemotherapeutic agents.

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Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities

Cited by 60 publications

References 25 publications

Synthesis, spectroscopic characterization and antitumor activity of new metal complexes of isonicotinoylhydrazide oxime

Synthesis, spectroscopic characterization and antitumor activity of new metal complexes of isonicotinoylhydrazide oxime

Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro

Synthesis and Evaluation of Some New Aza-B-homocholestane Derivatives as Anticancer Agents

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