Synthesis, characterization and pharmacological evaluation of 2-aminothiazole incorporated azo dyes

Ravi, B. N.; Keshavayya, J.; Mallikarjuna, N.M.; Kumar, Vinod; Kandgal, Shivanand

doi:10.1016/j.molstruc.2019.127493

Cited by 40 publications

(21 citation statements)

References 40 publications

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“…an azo derivative from 4-aminoantipyrine and found effective in DNA cleaving activity by using pUC18 [ 60 ], the DNA binding activities of tetrahydro-1,3-benzothiazole incorporated azo dyes was found to have effective intercalation properties with circulating tumor DNA (CT-DNA) [ 61 ]. Another considerable DNA cleavage efficiency of 2-aminothiazole incorporated azo dyes against supercoiled pBR322 DNA is also reported in literature [ 62 ]. All efficient DNA cleaving azo derivatives are mentioned in ( Figure 7 ).…”

Section: Therapeutic Potential Of Azo Moietymentioning

confidence: 83%

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: 83%

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

et al. 2021

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“…ampicillin and moxifloxacin (MIC 62.5 µg/200 µL). It was also observed that the detrimental effect of derivatives on bacterial strains was due to the electron-withdrawing groups on the phenyl rings 4 .…”

Section: Resultsmentioning

confidence: 99%

“…The combination of aromatic substituted amines with coupling agents could yield a variety of azo compounds having versatile biological properties [1][2][3] . The presence of heterocyclic ring and transition metals in conjugation to azo pharmacophore enhances the bio-potency of the azo dyes 4 . Ravi and colleagues studied the anti-mycobacterial and DNA cleaving efficiency of 2-aminothiazole incorporated azo derivatives 4 , the most active derivative found to be intervened with the active amino acids of Mycobacterium tuberculosis.…”

Section: Introductionmentioning

confidence: 99%

“…The presence of heterocyclic ring and transition metals in conjugation to azo pharmacophore enhances the bio-potency of the azo dyes 4 . Ravi and colleagues studied the anti-mycobacterial and DNA cleaving efficiency of 2-aminothiazole incorporated azo derivatives 4 , the most active derivative found to be intervened with the active amino acids of Mycobacterium tuberculosis . Debnath et al evaluated the antimicrobial efficacy of triorganotin(IV) azo-carboxylates 5 against the bacterium ( S. aureus ) and the fungus ( F. oxysporum ) with significant antimicrobial properties compared to the standard antibiotics.…”

Section: Introductionmentioning

confidence: 99%

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Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies

Tahir

Shahzad

Tabassum

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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In the present study, a series of azo derivatives (TR-1 to TR-9) have been synthesised via the diazo-coupling approach between substituted aromatic amines with phenol or naphthol derivatives. The compounds were evaluated for their therapeutic applications against alpha-glucosidase (anti-diabetic) and pathogenic bacterial strains E. coli (gram-negative), S. aureus (gram-positive), S. aureus (gram-positive) drug-resistant strain, P. aeruginosa (gram-negative), P. aeruginosa (gram-negative) drug-resistant strain and P. vulgaris (gram-negative). The IC 50 (mg/mL) of TR-1 was found to be most effective (15.70 ± 1.3 mg/mL) compared to the reference drug acarbose (21.59 ± 1.5 mg/mL), hence, it was further selected for the kinetic studies in order to illustrate the mechanism of inhibition. The enzyme inhibitory kinetics and mode of binding for the most active inhibitor (TR-1) was performed which showed that the compound is a noncompetitive inhibitor and effectively inhibits the target enzyme by binding to its binuclear active site reversibly.

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“…The IR spectra of compounds 7a-e showed a new stretching absorption band from 1560 cm -1 to 1570 cm -1 which was assigned to the presence of the (N=N) azo group [32]. In addition, carbonyl absorption bands were observed at 1735 cm -1 to 1758 cm -1 due to the ɑ-Pyrano carbonyl group and from 1666 cm -1 to 1676 cm -1 as a stretching vibration absorption signal attributed to the quinolinone carbonyl group.…”

Section: Chemistrymentioning

confidence: 94%

Anticancer activity of novel Schiff bases and azo dyes derived from 3-amino-4-hydroxy-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione

Saeed

AlNeyadi

Abdou

2020

Heterocyclic Communications

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New Schiff bases and azo dyes derivatives have been synthesized via appropriate conventional methods using pyranoquinolinone as a starting material. The compounds obtained were characterized by spectral analysis and evaluated for anticancer activity in several human tumor cell lines: MCF-7 breast cancer, HepG2 liver cancer and HCT-116 colon carcinoma. 5-fluorouracil was used as a reference drug. The in vitro cytotoxicity screening results revealed that all tested compounds showed promising activity against MCF-7 cells. In particular, compounds 6a, 6b, and 7b showed excellent activity against the three human tumor cell lines. Structure-activity relationship studies indicated that the azo derivative with a trifluoromethoxy group (compound 7b) was the most potent candidate against the three human tumor cell lines (IC50, 1.82-8.06 μg/mL). Our findings highlight pyranoquinolinone analogues as a promising class of compounds for new anticancer therapies.

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Synthesis, characterization and pharmacological evaluation of 2-aminothiazole incorporated azo dyes

Cited by 40 publications

References 40 publications

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

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

Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies

Anticancer activity of novel Schiff bases and azo dyes derived from 3-amino-4-hydroxy-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione

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