A new sulphur containing heterocycles having azo linkage: Synthesis, structural characterization and biological evaluation

Matada, Mallikarjuna Niluvanji; Keshavayya, J.; Rangappa, Maliyappa M.; Geoffry, Kiptoo; Kumar, Santosh; Nagarajappa, Ravi Berenkere; Zahara, Fiza Noor

doi:10.1016/j.jksus.2020.09.016

Cited by 23 publications

(7 citation statements)

References 33 publications

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“…In the similar interest, a new series of sulfur-containing heterocyclic azo compounds with appreciable antibacterial and antimycobacterial efficacy was designed. The most active derivative ( 8f ) was found to have significant interaction properties with the target receptor of mycobacterium RpsA (−5.5 kcal/mol) due to the number of heteroatoms in the phenyl ring [ 65 ] ( Figure 8 ).…”

Section: Therapeutic Potential Of Azo Moietymentioning

confidence: 99%

Pyridine Scaffolds, Phenols and Derivatives of Azo Moiety: Current Therapeutic Perspectives

et al. 2021

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Synthetic heterocyclic compounds have incredible potential against different diseases; pyridines, phenolic compounds and the derivatives of azo moiety have shown excellent antimicrobial, antiviral, antidiabetic, anti-melanogenic, anti-ulcer, anticancer, anti-mycobacterial, anti-inflammatory, DNA binding and chemosensing activities. In the present review, the above-mentioned activities of the nitrogen-containing heterocyclic compounds (pyridines), hydroxyl (phenols) and azo derivatives are discussed with reference to the minimum inhibitory concentration and structure–activity relationship, which clearly indicate that the presence of nitrogen in the phenyl ring; in addition, the hydroxyl substituent and the incorporation of a diazo group is crucial for the improved efficacies of the compounds in probing different diseases. The comparison was made with the reported drugs and new synthetic derivatives that showed recent therapeutic perspectives made in the last five years.

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Section: Therapeutic Potential Of Azo Moietymentioning

confidence: 99%

Pyridine Scaffolds, Phenols and Derivatives of Azo Moiety: Current Therapeutic Perspectives

et al. 2021

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“… 14 − 16 In these azo-biheterocyclic compounds, the presence of a −N=N–C=N- azo–imine, functional group between two N-heterocyclic substances promotes their activity. 17 , 18 Azo-benzimidazole compounds are of significant importance due to their use as potent antibacterial, antitubercular, antitumor, and antifungal substances. 19 , 20 Azo-benzimidazole also shows some particular physical properties, such as nonlinear optical and thermal properties.…”

Section: Introductionmentioning

confidence: 99%

“…N-Heterocyclic back bones are found in imidazole, pyridine, and benzimidazole derivatives, which are actively used in pharmaceutical fields. − N-Heterocyclic compound polarizability favors their solubility in many polar synthetic and natural solvents. , The majority of N-heterocyclic compounds having different physical properties are soluble in water. − Moderate solubility of benzimidazole in water allows its use in synthesis of useful drugs. Azo-heterocyclic compounds have been tremendously developed in the last few decades having valuable activity in biological fields. − But the amount of literature on mixed N-heterocyclic azo compounds is limited in literature. − In these azo-biheterocyclic compounds, the presence of a −NN–CN- azo–imine, functional group between two N-heterocyclic substances promotes their activity. , Azo-benzimidazole compounds are of significant importance due to their use as potent antibacterial, antitubercular, antitumor, and antifungal substances. , Azo-benzimidazole also shows some particular physical properties, such as nonlinear optical and thermal properties. , The presence of active N-hydrogen in the imidazole part of benzimidazole leads to a tendency to form H-bonds with several amino acids of different protein moieties. In contrast, one benzene ring fused within the imidazole (i.e., benzimidazole) decreases the solubility in hydrophilic solvent compare to the imidazole derivatives. − Essentially, one of these N-heterocyclic azo-imidazole compounds can exhibit many biological − and physical properties. , …”

Section: Introductionmentioning

confidence: 99%

Physicochemical Properties of a Bi-aromatic Heterocyclic-Azo/BSA Hybrid System at the Air–Water Interface

et al. 2022

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The interaction of a heterocyclic azo compound with itself and with bovine serum albumin (BSA) is realized by probing the structural modifications in Langmuir (L) monolayers and Langmuir–Blodgett (LB) films. It was found from the pressure–area/molecule isotherms that the elastic, thermodynamic, and hysteretic properties of the pure azo L monolayer were strongly altered due to the variation of temperature and pH of subphase water. In addition to that, the modification of such properties of the azo L monolayer due to mixing with BSA was also studied. The incorporation of BSA within the azo molecular assembly reduced the elasticity of that assembly. Such reduction of in-plane elasticity of the pure azo monolayer can also be achieved by reducing the temperature and pH of subphase water without adding BSA. A reduction in area per molecule of the azo assembly at the air–water interface associated with the conformational change from horizontal to vertical orientation facilitating π–π interaction was observed with increase in temperature and pH of the subphase. Such parameters also affected the interactions between azo and BSA molecules within the azo/BSA binary system. The structures of pure azo and binary films can be determined after they are transferred to hydrophilic and hydrophobic Si surfaces using the LB technique. Their out-of-plane and in-plane structures, as extracted from two complementary surface sensitive techniques, X-ray reflectivity and atomic force microscopy, were found to be strongly dependent on mixing with BSA, subphase pH, temperature, and substrate nature.

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“…Among the various heterocyclic scaffolds, compounds especially containing nitrogen, sulfur, and oxygen have recently gained the attention of researchers due to their countless biological applications. [ 18‐25 ] Thiazolidine is one such class of heterocyclic nuclei that has demonstrated profound pharmaceutical applications. [ 26‐29 ] Owing to the diverse range of biological activities like antidiabetic, anti‐inflammatory, anticancer, antifungal, antibacterial, antioxidant, and antihypertensive activities, etc., medicinal chemists have recently exploited this nucleus to design and develop potential novel compounds.…”

Section: Introductionmentioning

confidence: 99%

A comprehensive review on the antidiabetic attributes of thiazolidine‐4‐ones: Synthetic strategies and structure–activity relationships

Pradhan

Gupta

Kumar

et al. 2022

Archiv der Pharmazie

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The thiazolidine-4-one scaffold has recently emerged as a potential pharmacophore having clinical significance for medicinal chemists. This heterocyclic ring has been reported to possess a plethora of biological activities, including antidiabetic activity that has inspired researchers to integrate this core with different pharmacophoric fragments to design novel and effective antidiabetic leads. The antidiabetic activity has been observed due to the ability of the thiazolidine-4-one nucleus to interact with different biological targets, including peroxisome proliferator-activated receptor γ, protein tyrosine phosphatase 1B, aldose reductase, α-glucosidase, and α-amylase. The present review discusses the mode of action of thiazolidine-4-ones through these antidiabetic drug targets. This review attempts to summarize and analyze the recent developments with regard to the antidiabetic potential of thiazolidine-4-ones covering different synthetic strategies, structure-activity relationships, and docking studies reported in the literature. The significance of various structural modifications at C-2, N-3, and C-5 of the thiazolidine-4-one ring has also been discussed in this manuscript. This comprehensive compilation will provide an inevitable scope for the design and development of potential antidiabetic drug candidates having a thiazolidine-4-one core.

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A new sulphur containing heterocycles having azo linkage: Synthesis, structural characterization and biological evaluation

Cited by 23 publications

References 33 publications

Pyridine Scaffolds, Phenols and Derivatives of Azo Moiety: Current Therapeutic Perspectives

Pyridine Scaffolds, Phenols and Derivatives of Azo Moiety: Current Therapeutic Perspectives

Physicochemical Properties of a Bi-aromatic Heterocyclic-Azo/BSA Hybrid System at the Air–Water Interface

A comprehensive review on the antidiabetic attributes of thiazolidine‐4‐ones: Synthetic strategies and structure–activity relationships

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