Synthesis and microbiological activity of some N-(2-hydroxy-4-substitutedphenyl)benzamides, phenylacetamides and furamides as the possible metabolites of antimicrobial active benzoxazoles

Aki-Sener, Esin; Bingöl, Kamuran K.; Temiz-Arpacı, Özlem; Yalçın, İsmail; Altanlar, Nurten

doi:10.1016/s0014-827x(02)01226-0

Cited by 38 publications

(8 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…13 The compounds possess 3 different fused ring systems such as benzoxazole, benzimidazole, benzoxazin and an amide derivative (X12), which is the hydrolyzed form of the corresponding benzoxazole structure consisting of a cleavage of the oxazolo ring at the (CÀ ÀO) linkage that revealed at the phase I possible metabolites of benzoxazoles in the rabbit by mild hydrolysis. 34,35 In this study, we investigated the potential efficacy of these compounds in various human cancer cell lines that were derived from different tumor entities. Moreover, different multidrug-resistant variants of these cells with decreased Topo II expression were analyzed.…”

Section: Discussionmentioning

confidence: 99%

High antineoplastic activity of new heterocyclic compounds in cancer cells with resistance against classical DNA topoisomerase II‐targeting drugs

Lage

Aki-Sener

Yalçın

2006

Intl Journal of Cancer

View full text Add to dashboard Cite

Twenty previously synthesized fused heterocyclic DNA-topoisomerase II (Topo II)-inhibiting compounds were investigated for their potential efficacy in various human cancer cell lines that were derived from different tumor entities. Moreover, different multidrug-resistant variants of these cancer cell lines with decreased Topo II expression were investigated. In parental, drugsensitive cells merely the compounds BD3 and G35 showed efficacies, in terms of lM, which were similar to that of the classical Topo II inhibitor etoposide. On the other hand, most of the tested heterocyclic compounds were found more effective in drug-resistant cells than in the parental, drug-sensitive ones, and some of the compounds showed high antineoplastic efficacy in several drug-resistant cell models. Compounds BD13, BD14 and BD16 exhibited high antineoplastic activities against the drug-resistant sublines EPG85-257RNOV and EPG85-257RDB derived from gastric carcinoma, EPP85-181RNOV and EPP85-181RDB derived from pancreatic carcinoma, MCF-7/Adr derived from breast cancer, D79/ 86RNOV derived from fibrosarcoma, and MeWoETO1 derived from melanoma. Furthermore, compound D23 was found highly efficient in the multidrug-resistant variants HT-29RNOV and HT-29RDB derived from colon carcinoma, and compound D24 exhibited the highest antineoplastic activity among the tested compounds in the drug-resistant subline MDA-MB-231ROV derived from breast cancer. Key words: benzoxazole; benzimidazole; benzoxazin; DNA topisomerase II inhibitors; multidrug resistance DNA topoisomerases (Topo) 1 are enzymes that isomerise the tertiary structure of DNA without changing its primary structure. The high degree of conservation of these enzymes among prokaryotes and eukaryotes indicates an essential role in cell biology. Because its structure is a double helix, DNA is under tortional stress that results in multiplex twisting of the molecule. To be processed for replication or gene expression, the supercoiled DNA must become accessible to nucleic acids polymerases or components of the transcription machinery. This change requires relaxation and untangling of the intertwined DNA strands, which are the typical tasks of Topo.In humans, 2 classes of Topo are well characterized, type I and type II. Topo type II (Topo II) are useful as drug target, since they have an indispensable function in cell biology and they lack biological redundancy. Inhibitors of these enzymes have become central parts of both primary and adjuvant chemotherapy regimens in neoplastic diseases, and they probably will remain so for the foreseeable future. 2 Two Topo II isoforms, the 170 kDa Topo IIa and the 180 kDa Topo IIb, exist as homodimers and their amino acid sequences show homology at regions believed to be functionally significant (72% identical amino acid residues), 3 suggesting a comparable mode of action. The expression of Topo IIa varies during the cell cycle. It is low in quiescent cells, but maximal in the G 2 -M phase, whereas the expression level of Topo IIb remains constant througho...

show abstract

Section: Discussionmentioning

confidence: 99%

High antineoplastic activity of new heterocyclic compounds in cancer cells with resistance against classical DNA topoisomerase II‐targeting drugs

Lage

Aki-Sener

Yalçın

2006

Intl Journal of Cancer

View full text Add to dashboard Cite

show abstract

“…reported the synthesis of N ‐(2‐hydroxy‐4 (or 5) nitro/aminophenyl) benzamides and phenylacetamide derivatives as potential antibacterial and antifungal agents. Further, Esin et al [22] . reported the synthesis of substituted phenylacetamides and benzamide derivatives as potential antimicrobials.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking and Biological Evaluation of 2‐Aryloxy‐N‐Phenylacetamide and N′‐(2‐Aryloxyoxyacetyl) Benzohydrazide Derivatives as Potential Antibacterial Agents

Yele

Azam

Wadhwani

2021

Chemistry & Biodiversity

View full text Add to dashboard Cite

A new class of 2‐aryloxy‐N‐phenylacetamide and N′‐(2‐aryloxyoxyacetyl) benzohydrazide derivatives with different active moieties were synthesized and screened for their antibacterial activity. Structural characterization of synthesized compounds was performed using HR‐MS, 1H‐NMR, and 13C‐NMR spectral data. Amongst the synthesized compounds, 4‐{2‐[2‐(2‐chloroacetamido)phenoxy]acetamido}‐3‐nitrobenzoic acid (3h) and 2‐chloro‐N‐(2‐{2‐[2‐(2‐chlorobenzoyl)hydrazinyl]‐2‐oxoethoxy}phenyl)acetamide (3o) have shown good antibacterial activity against a selected panel of bacteria. Besides, compounds also exhibited bactericidal activity against P. aeruginosa (3h, 0.69 μg/mL) and S. aureus (3o, 0.62 μg/mL) as evident by MBC and time‐kill kinetics studies. In silico molecular docking and ADMET properties of newly synthesized compounds revealed that compounds could be considered as promising antibacterial agents.

show abstract

“…Benzamide pharmacophores are essential bioactivities in drug discovery methods and have pharmacological and biological applications. Benzamide and its derivatives involved as antimicrobial, analgesic anticancer, carbonic anhydrase inhibitory and a cholinesterase inhibitor [ 1 , 2 , 3 ]. According to the National Institute of Aging, Alzheimer's disease (AD) is the most common cause of death in the United States of America [ 4 ].…”

Section: Introductionmentioning

confidence: 99%

Structural, vibrational, electronic properties, hirshfeld surface analysis topological and molecular docking studies of N-[2-(diethylamino)ethyl]-2-methoxy-5-methylsulfonylbenzamide

Janani

Hemamalini

Muthu³

et al. 2021

Heliyon

View full text Add to dashboard Cite

The theoretical (Freebase, Cationic species) and experimental investigations on the molecular structural, spectroscopic characterization, and electronic properties of N2M5MB are reported. The most stable structure of the N2M5MB was analysed by employing Density Functional Theory (DFT) at different functional such as B3LYP, PBEPBE, TPSSTPSS and IEF-PCM (Freebase) and Cationic (B3LYP, IEF-PCM)/ 6-311þþG (d,p) basis set level. The Potential Energy Scan (PES) analysis has been employed to investigate the conformational preference of the title molecule. The optimized molecular geometry, vibrational assignments (FT-IR, FT-Raman) of wavenumbers have been performed for freebase, cationic species (Gas, PCM) for the individual modes of vibration. The experimental UV-Vis absorption spectrum was obtained and compared with the simulated (Freebase, Cationic species) Time-Dependent (TD-DFT-M062X) method. The FMO's, electron-hole distributions, HOMA, FLU, Hirshfeld surface analysis, Electrostatic potential surface (ESP), Fukui functions, and topological parameters were discussed. Molecular docking studies were performed for the N2M5MB (ligand) into the active site of targeted proteins (1H22, 4DTL, 5OV9) which belong to AChE inhibitors with the minimum binding energy was detected.

show abstract

Synthesis and microbiological activity of some N-(2-hydroxy-4-substitutedphenyl)benzamides, phenylacetamides and furamides as the possible metabolites of antimicrobial active benzoxazoles

Cited by 38 publications

References 10 publications

High antineoplastic activity of new heterocyclic compounds in cancer cells with resistance against classical DNA topoisomerase II‐targeting drugs

High antineoplastic activity of new heterocyclic compounds in cancer cells with resistance against classical DNA topoisomerase II‐targeting drugs

Synthesis, Molecular Docking and Biological Evaluation of 2‐Aryloxy‐N‐Phenylacetamide and N′‐(2‐Aryloxyoxyacetyl) Benzohydrazide Derivatives as Potential Antibacterial Agents

Structural, vibrational, electronic properties, hirshfeld surface analysis topological and molecular docking studies of N-[2-(diethylamino)ethyl]-2-methoxy-5-methylsulfonylbenzamide

Contact Info

Product

Resources

About