Synthesis antimicrobial and antioxidant studies of new oximes of steroidal chalcones

Lone, Imtiyaz H.; Khan, Khaliquz Zaman; Fozdar, Bharat Inder; Hussain, Fida

doi:10.1016/j.steroids.2013.05.015

Cited by 63 publications

(36 citation statements)

References 22 publications

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“…[17][ 19] Table 6 shows the strongest activity observed for each compound on the L5178 and L5178 MDR cell lines; further details and results at other compound:doxorubicin ratios are available in supporting information Table S1. All tested derivatives showed strong synergism (0.1< CI avg <0.3) [25] with doxorubicin on the P-gp expressing L5178 MDR cells, similarly to their parental compound (1). As it was previously M A N U S C R I P T…”

Section: Accepted Manuscriptsupporting

confidence: 60%

“…Synthetic modification of steroidal compounds remains a promising strategy in the hunt for novel drug candidates since even minor changes in the substitution pattern of their chemical backbone may significantly modify specific bioactivities. Certain steroidal oximes and oxime ethers were shown to have antioxidant, [1] antimicrobial, [1] antineoplastic [2] or neuromuscular blocking [3] activities.…”

Section: Introductionmentioning

confidence: 99%

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Nitrogen-containing ecdysteroid derivatives vs. multi-drug resistance in cancer: Preparation and antitumor activity of oximes, oxime ethers and a lactam

Vágvölgyi

Martins

Kulmány

et al. 2018

European Journal of Medicinal Chemistry

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Multidrug resistance is a widespread problem among various diseases and cancer is no exception. We had previously described the chemo-sensitizing activity of ecdysteroid derivatives with low polarity on drug susceptible and multi-drug resistant (MDR) cancer cells. We have also shown that these molecules have a marked selectivity towards the MDR cells. Recent studies on the oximation of various steroid derivatives indicated remarkable increase in their antitumor activity, but there is no related bioactivity data on ecdysteroid oximes. In our present study, 13 novel ecdysteroid derivatives (oximes, oxime ethers and a lactam) and one known compound were synthesized from 20-hydroxyecdysone 2,3;20,22-diacetonide and fully characterized by comprehensive NMR techniques revealing their complete H andC signal assignments. The compounds exerted moderate to strong in vitro antiproliferative activity on HeLa, SiHa, MCF-7 and MDA-MB-231 cell lines. Oxime and particularly oxime ether formation strongly increased their inhibitory activity on the efflux of rhodamine 123 by P-glycoprotein (P-gp), while the new ecdysteroid lactam did not interfere with the efflux function. All compounds exerted potent chemo-sensitizing activity towards doxorubicin on a mouse lymphoma cell line and on its MDR counterpart, and, on the latter, the lactam was found the most active. Because of its MDR-selective chemo-sensitizing activity with no functional effect on P-gp, this lactam is of high potential interest as a new lead for further antitumor studies.

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Section: Accepted Manuscriptsupporting

confidence: 60%

Section: Introductionmentioning

confidence: 99%

Nitrogen-containing ecdysteroid derivatives vs. multi-drug resistance in cancer: Preparation and antitumor activity of oximes, oxime ethers and a lactam

Vágvölgyi

Martins

Kulmány

et al. 2018

European Journal of Medicinal Chemistry

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“…A similar result was reported by Nazarbahjat, et al . and Lone et al ., in which the compounds with halogen substituents on the para ‐position had good DPPH IC 50 values …”

Section: Resultsmentioning

confidence: 99%

“…A similar result was reported by Nazarbahjat, et al and Lone et al, in which the compounds with halogen substituents on the para-position had good DPPH IC 50 values. 33,34 Prediction of Radical Scavenging Activity Using a Computational Method. One of the pathways in which antioxidants can play a radical scavenger role is H-atom transfer.…”

Section: Ohmentioning

confidence: 99%

Synthesis of the Hydrazones of 2‐((3,5‐Di‐tert‐butyl‐4‐hydroxybenzyl)thio) acetohydrazide and the Study of their Radical Scavenging Activity by the DPPH Assay and the Computational Method

Abdulwahab

Ariffin

Yehye

et al. 2015

Bulletin Korean Chem Soc

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The synthesis of antioxidant compounds bearing pharmacologically active groups has become a research interest in the last decade. A series of hydrazones containing a butylated hydroxyl group were synthesized from 2-((3,5-di-tert-butyl-4-hydroxybenzyl)thio)acetohydrazide and various benzaldehyde derivatives, and their radical scavenging activity was explored by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay and computational calculations. Based on the results, the effects of different substituents on the DPPH IC 50 values were discussed. The bond dissociation enthalpies (BDE) of O H and N H bonds and the spin density (SD) values of the compounds were calculated using the density functional theory (DFT) to determine the theoretical capability of the hydrazones as radical scavengers. Based on the results, the effects of the thioether group and the substituent groups next to the N H bond on the BDE values were also discussed.

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“…To search for potential anti-infective agents, a C. elegans -S. aureus screening platform was developed to screen synthetic compounds consisting of chalcone derivatives for their ability to extend the lifespan of infected animals. A wide range of pharmacological activities have been attributed to chalcone (C 15 H 12 O) derivatives including anti-oxidant [4], anti-microbial [4] and anti-inflammatory properties [5]. Chalcones with anti-infective properties are those screened to rescue the worms from ensuing death following S. aureus infection.…”

Section: Introductionmentioning

confidence: 99%

Identification of potential anti-infectives against Staphylococcus aureus using a Caenorhabditis elegans infection model

Kong¹,

Rahman²,

Nathan³

2014

AIP Conference Proceedings

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Abstract. The alarming increase of antibiotic-resistant Staphylococcus aureus and a delay in antibiotics development point to the need for novel therapeutic approaches to combat infection. To discover novel anti-infective agents, we screened a number of synthetic compounds comprising mainly of chalcone derivatives to explore their potential in promoting the survival of the nematode Caenorhabditis elegans upon infection by S. aureus. Screening of seven chalcone derivatives using both agar-and liquid-based assays revealed three positive hits that significantly prolonged the survival of S. aureus-infected nematodes. All the hits did not interfere with bacterial growth in vitro, proposing that the three compounds identified most probably act through mechanisms distinct from conventional antibiotics that target bacterial replication.

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Synthesis antimicrobial and antioxidant studies of new oximes of steroidal chalcones

Cited by 63 publications

References 22 publications

Nitrogen-containing ecdysteroid derivatives vs. multi-drug resistance in cancer: Preparation and antitumor activity of oximes, oxime ethers and a lactam

Nitrogen-containing ecdysteroid derivatives vs. multi-drug resistance in cancer: Preparation and antitumor activity of oximes, oxime ethers and a lactam

Synthesis of the Hydrazones of 2‐((3,5‐Di‐tert‐butyl‐4‐hydroxybenzyl)thio) acetohydrazide and the Study of their Radical Scavenging Activity by the DPPH Assay and the Computational Method

Identification of potential anti-infectives against Staphylococcus aureus using a Caenorhabditis elegans infection model

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