Design, synthesis and DNA-binding study of some novel morpholine linked thiazolidinone derivatives

War, Javeed Ahmad; Srivastava, Santosh K.; Srivastava, S. K.

doi:10.1016/j.saa.2016.07.054

Cited by 44 publications

(21 citation statements)

References 61 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…An attempt by War et al towards the design of potent broad‐spectrum antimicrobial agents led to the combination of thiazolidinone (known for its antimicrobial and antifungal properties) with the morpholine moiety (known for its contribution to both pharmacophore and pharmacokinetic properties). The activity of the most potent compound against P. aeruginosa , 66 (Figure ), with a MIC value 6.25 μg/mL, is comparable with that of standard drugs such as Streptomycin and Ciprofloxacin with MIC values around 3.1 μg/mL.…”

Section: Pharmacological Activity Of Morpholine Derivatives On Varioumentioning

confidence: 99%

Morpholine as a privileged structure: A review on the medicinal chemistry and pharmacological activity of morpholine containing bioactive molecules

Kourounakis

Xanthopoulos

Tzara

2019

Medicinal Research Reviews

147

103

View full text Add to dashboard Cite

Morpholine is a heterocycle featured in numerous approved and experimental drugs as well as bioactive molecules. It is often employed in the field of medicinal chemistry for its advantageous physicochemical, biological, and metabolic properties, as well as its facile synthetic routes. The morpholine ring is a versatile and readily accessible synthetic building block, it is easily introduced as an amine reagent or can be built according to a variety of available synthetic methodologies. This versatile scaffold, appropriately substituted, possesses a wide range of biological activities. There are many examples of molecular targets of morpholine bioactive in which the significant contribution of the morpholine moiety has been demonstrated; it is an integral component of the pharmacophore for certain enzyme active‐site inhibitors whereas it bestows selective affinity for a wide range of receptors. A large body of in vivo studies has demonstrated morpholine's potential to not only increase potency but also provide compounds with desirable drug‐like properties and improved pharamacokinetics. In this review we describe the medicinal chemistry/pharmacological activity of morpholine derivatives on various therapeutically related molecular targets, attempting to highlight the importance of the morpholine ring in drug design and development as well as to justify its classification as a privileged structure.

show abstract

Section: Pharmacological Activity Of Morpholine Derivatives On Varioumentioning

confidence: 99%

Morpholine as a privileged structure: A review on the medicinal chemistry and pharmacological activity of morpholine containing bioactive molecules

Kourounakis

Xanthopoulos

Tzara

2019

Medicinal Research Reviews

147

103

View full text Add to dashboard Cite

show abstract

“…Molecular docking is a type of computer simulation technology developed in recent years . Docking of small molecules into target DNA was carried out using SYBYL software with spatial conformation matching, energy matching, and microenvironment matching.…”

Section: Resultsmentioning

confidence: 99%

“…Molecular docking was conducted using Sybyl‐2.1.1 software (Tripos, USA). The 3D crystal structure of DNA (PDB number: 1D64) was obtained from the RSCB protein database . Cephalosporin was optimized structurally via a Tripos force field, and a Gasteiger–Huckel charge was added.…”

Section: Methodsmentioning

confidence: 99%

Comparative study of two cephalosporin antibiotics binding to calf thymus DNA by multispectroscopy, electrochemistry, and molecular docking

et al. 2019

View full text Add to dashboard Cite

The over-use of antibiotics has caused a number of problems such as contamination of antibiotic residues and virus resistance, and therefore has attracted global attention. In this study, spectroscopic techniques and molecular docking were employed to predict conformational changes and binding interaction between two cephalosporins (cefaclor and cefixime) and calf thymus DNA (ctDNA). Fluorescence and UV-vis spectra suggested that static quenching was predominant and cephalosporin bound to the groove region of ctDNA. Binding parameters calculated by the Stern-Volmer and Scatchard equations showed that cephalosporin bound to ctDNA with a binding affinity in the order of 10 3 L mol −1 . Thermodynamic parameters further indicated that the reaction was a spontaneous process driven by enthalpy and entropy, and that the main binding force was an electrostatic force. The effects of iodide, denaturant, thermal denaturation and pH on a cephalosporin-Hoechst-DNA complex were also studied, and the results confirmed that cephalosporin bound to the groove area of DNA.Finally, these results were further confirmed by molecular docking and electrochemical studies.

show abstract

“…The incorporation of morpholine as a substituent leads to either Gram‐positive or broad spectrum antimicrobial molecules. These effects are related to morpholine‐containing derivatives’ interaction with topoisomerases, peptidyl transferase, ribonucleotide reductase, even to the ability to act as intercalating agents …”

Section: Introductionmentioning

confidence: 99%

Morpholine As a Scaffold in Medicinal Chemistry: An Update on Synthetic Strategies

2020

View full text Add to dashboard Cite

Morpholine is a frequently used heterocycle in medicinal chemistry and a privileged structural component of bioactive molecules. This is mainly due to its contribution to a plethora of biological activities as well as to an improved pharmacokinetic profile of such bioactive molecules. The synthesis of morpholines is a subject of much study due to their biological and pharmacological importance, with the last such review being published in 2013. Here, an overview of the main approaches toward morpholine synthesis or functionalization is presented, emphasizing on novel work which has not been reviewed so far. This review is an update on synthetic strategies leading to easily accessible libraries of bioactives which are of interest for drug discovery projects.

show abstract

Design, synthesis and DNA-binding study of some novel morpholine linked thiazolidinone derivatives

Cited by 44 publications

References 61 publications

Morpholine as a privileged structure: A review on the medicinal chemistry and pharmacological activity of morpholine containing bioactive molecules

Morpholine as a privileged structure: A review on the medicinal chemistry and pharmacological activity of morpholine containing bioactive molecules

Comparative study of two cephalosporin antibiotics binding to calf thymus DNA by multispectroscopy, electrochemistry, and molecular docking

Morpholine As a Scaffold in Medicinal Chemistry: An Update on Synthetic Strategies

Contact Info

Product

Resources

About