ChemInform Abstract: Synthesis and Cytotoxic Evaluation of Some Carbohydrazones and Thiocarbohydrazones of Various Unsaturated Ketones and Related Mannich Bases.

Dimmock, Jonathan R.; Kumar, P.; Allen, Theresa M.; Kao, G. Y.; Halleran, S.; Balzarini, Jan; Clercq, E. De

doi:10.1002/chin.199727084

Cited by 8 publications

(9 citation statements)

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“…On the other hand, the compounds in series 45 (R = N-piperidylmethyl) were more potent cytotoxic agents than their corresponding precursors 44. Some compounds displayed activity comparable with or exceeding that of melphalan 146 .…”

Section: Reaction With Hydroxybenzaldehydementioning

confidence: 97%

Thiocarbohydrazides: Synthesis and Reactions

Metwally¹,

Khalifa²,

Koketsu³

2012

CHEMISTRY

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Thiocarbohydrazides are an important class of compounds which possess applications in many fields. The chemistry of thiocarbohydrazides has gained increased interest in both synthetic organic chemistry and biological fields and has considerable value in many useful applications such as the assessment process of the three-dimensional ultrastructure examination techniques of interphase nuclei and tissues, besides their therapeutic importance. They are also described for use as fogging agents and are considered as safe, storable, and cool-burning pyrotechnic compounds for dissemination of smoke, chemical warfare agents. On the other hand, thiocarbohydrazides are used in performing a highly selective heavy metal ion adsorbent and as complexing agents for the solvent extraction separation methods. The present review covers the literature up to date for the synthesis, reactions and applications of such compounds.

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Section: Reaction With Hydroxybenzaldehydementioning

confidence: 97%

Thiocarbohydrazides: Synthesis and Reactions

Metwally¹,

Khalifa²,

Koketsu³

2012

CHEMISTRY

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“…The α,β‐unsaturated ketones have alkylation ability, especially toward thiols. [ 16,17 ] They have no reactivity or far less reactivities for amino and hydroxyl groups of available nucleic acids, [ 16,18,19 ] whereas classical alkylating agents alkylate hydroxyl and amino groups of nucleic acids, and lead to mutagenicity and carcinogenicity. [ 20 ] The level of glutathione (a thiol compound) increases before the cell division.…”

Section: Introductionmentioning

confidence: 99%

New halogenated chalcones with cytotoxic and carbonic anhydrase inhibitory properties: 6‐(3‐Halogenated phenyl‐2‐propen‐1‐oyl)‐2(3H)‐benzoxazolones

Bilginer

Gül

Erdal

et al. 2020

Archiv der Pharmazie

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In this study, novel halogenated chalcones, 6-(3-halogenated phenyl-2-propen-1-one)-2(3H)-benzoxazolones (2a-n), were synthesized for the first time (except 2a), and their chemical structures were characterized by 1 H nuclear magnetic resonance (NMR), 13 C NMR, and high-resolution mass spectrometry spectra. Cytotoxic activities and carbonic anhydrase (CA) inhibitory effects of the compounds were studied to identify new possible drug candidate molecules. Cytotoxicity results pointed out that compound 2m, 6-[3-(3-bromophenyl)-2-propenoyl]-2(3H)-benzoxazolone, had the highest cytotoxicity (CC 50 ) and potency selectivity expression (PSE) values. Thus, compound 2m can be considered as a lead compound of the series in terms of cytotoxicity. When the CA inhibition results of the compounds were evaluated, it was found that the K i values of the compounds ranged from 30.5 ± 11.3 to 65.5 ± 25.6 µM toward hCA I, and they ranged from 7.3 ± 1.8 to 58.8 ± 12.3 µM toward hCA II. However, the K i values of the reference drug, acetazolamide (AZA), were 30.2 ± 7.8 and 4.4 ± 0.6 μM toward hCA I and hCA II, respectively. According to the results obtained, compounds 2a-n had lower K i values than AZA, whereas compounds 2a, 2b, 2e-g, 2l, and 2n had similar K i values, compared with AZA. So, the compounds 2a, 2b, 2e-g, 2l, and 2n can be considered as lead molecules of this series for further considerations.

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“…Thiocarbohydrazones (TCHs) are higher homologues of thiosemicarbazones, which are known for various biological activities such as antituberculous, antimicrobial, anti‐inflammatory, anticonvulsant, antihypertensive, local anesthetic, antimycobacterial and antiviral activity, cytotoxic as well as antioxidative activity . TCHs, made of various unsaturated aldehydes, ketones and related Mannich bases, were evaluated for their cytotoxic properties . Recently a series of 2‐acetylpyridine thiocarbonohydrazones were synthesized and tested as inactivators of iron‐dependant enzyme herpes simplex virus (HSV‐1) ribonucleotide reductase with better results than the analogous 2‐acetylpyridine thiosemicarbazone derivatives.…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial Activity of Thiocarbohydrazones: Experimental Studies and Alignment‐Independent 3D QSAR Models

Božić

Bjelogrlić²,

Novaković

et al. 2018

ChemistrySelect

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Due to the rise of microbial strains resistant to conventional therapies, there is an urgent need for finding the new antimicrobial chemotypes. Heterocyclic compounds such as thiocarbohydrazones (TCHs) are able to interact with many metalloenzymes essential for microbes, while sulfur atom increases lipophilicity which is generally positively correlated with potency. In this paper, we report antibacterial and antifungal activity of twenty-two TCHs toward eight bacterial and three fungal strains. Furthermore, three alignment independent 3D QSAR models based on descriptors derived from molecular interaction fields (MIFs) are developed in order to rationalize structure-activity relationships for activities of TCHs toward S. aureus, P. aeruginosa and C. albicans. Several structural fragments important for biological activity are recognized in each model, and structural modifications which could lead to increased potency are suggested. Designed structures will be synthesized accordingly and tested toward the same microbial strains in order to obtain more potent derivatives.

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ChemInform Abstract: Synthesis and Cytotoxic Evaluation of Some Carbohydrazones and Thiocarbohydrazones of Various Unsaturated Ketones and Related Mannich Bases.

Cited by 8 publications

References 0 publications

Thiocarbohydrazides: Synthesis and Reactions

Thiocarbohydrazides: Synthesis and Reactions

New halogenated chalcones with cytotoxic and carbonic anhydrase inhibitory properties: 6‐(3‐Halogenated phenyl‐2‐propen‐1‐oyl)‐2(3H)‐benzoxazolones

Antimicrobial Activity of Thiocarbohydrazones: Experimental Studies and Alignment‐Independent 3D QSAR Models

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