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Review
. 2021 Aug 11;26(16):4872.
doi: 10.3390/molecules26164872.

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

Tehreem Tahir  1 , Muhammad Ashfaq  2 , Muhammad Saleem  3 , Muhammad Rafiq  4 , Mirza Imran Shahzad  1 , Katarzyna Kotwica-Mojzych  5 , Mariusz Mojzych  6
Affiliations
Review

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

Tehreem Tahir et al. Molecules. .

Abstract

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.

Keywords: azo; heterocyclic; hydroxyl; phenol; pyridine; therapeutic.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Biologically active pyrrolopyridine hybrid molecules.
Figure 2
Figure 2
Most active imidazo, thiazo, thieno and amide–pyridine analogues.
Figure 3
Figure 3
Chemical structures of commercially available phenolic drugs.
Figure 4
Figure 4
Biologically active phenolic cinnamic acid, phenolic carbamate and sulfa drugs based hydroxytriazenes derivatives; R, R1 and R2 are alkyl, alcoholic, alkoxy and tert–butyl moieties.
Figure 5
Figure 5
Some of the most active phenyl acrylamide, sulfonyl phenol and azo–phenol derivatives; R1 represent alkyl, alkoxy and halo substituent.
Scheme 1
Scheme 1
Synthesis of azodyes (c). (i) (a) (0.2 mmol), (b) (0.2 mmol), Ionic liquids (0.2 mmol) [51], H2O (1 mmol), room temperature, 4 hours.
Scheme 2
Scheme 2
Synthesis of target molecule (c); (ii) (a) (0.2 mmol), (b) (0.4 mmol), PhSiH3 (2 eq), metal salts (20 mol %), additive (1 eq), methanol (2 ml), room temperature.
Scheme 3
Scheme 3
Synthesis of target molecule (d); (iii) Sodium nitrite, HCl (iv) Salicylaldehyde (v) Coupling with amine derivatives.
Scheme 4
Scheme 4
Synthesis of target molecule (b); (vi) (a) (1 eq under nitrogen atmosphere), NaOH (0.2 eq), Au@OC1R (0.5 mol % Au), 2-propanol (15 mL), 2 hours, 30 °C.
Scheme 5
Scheme 5
Synthesis of target molecule (c); (vii) NaNO2/HCl, 0-5 °C, Coupling of (a) with (b) at pH 5–6.
Figure 6
Figure 6
Biologically active parent compounds of phthalocyanine incorporated azo moiety.
Figure 7
Figure 7
Most effective azo derivatives with DNA binding properties.
Figure 8
Figure 8
Some of the reported heterocyclic azo derivatives.
Figure 9
Figure 9
Bioactive metal incorporated azo derivatives.
Figure 10
Figure 10
Some reported azo derived chemosensors for metal detection and bio-imaging studies.
Figure 11
Figure 11
Some reported azo–based chemosensors.
See this image and copyright information in PMC

References

    1. Acharya P.T., Bhavsar Z.A., Jethava D.J., Patel D.B., Patel H.D. A review on development of bio-active thiosemicarbazide derivatives: Recent advances. J. Mol. Struct. 2021;1226:129268. doi: 10.1016/j.molstruc.2020.129268. - DOI
    1. Arumugam N., Almansour A.I., Kumar R.S., Siva Krishna V., Sriram D., Dege N. Stereoselective synthesis and discovery of novel spirooxindolopyrrolidine engrafted indandione heterocyclic hybrids as antimycobacterial agents. Bioorg. Chem. 2021;110:104798. doi: 10.1016/j.bioorg.2021.104798. - DOI - PubMed
    1. Iqbal N., Yaqoob M., Javed M., Abbasi M., Iqbal J., Iqbal M.A. Synthesis in combination with Biological and Computational evaluations of selenium-N-Heterocyclic Carbene compounds. Comput. Theor. Chem. 2021;1197:113135. doi: 10.1016/j.comptc.2020.113135. - DOI
    1. Kamo M., Ito M., Toma T., Gotoh H., Shimozono R., Nakagawa R., Koga R., Monde K., Tateishi H., Misumi S., et al. Discovery of anti-cell migration activity of an anti-HIV heterocyclic compound by identification of its binding protein hnRNP M. Bioorg. Chem. 2021;107:104627. doi: 10.1016/j.bioorg.2021.104627. - DOI - PubMed
    1. Kaur R., Kumar K. Synthetic and medicinal perspective of quinolines as antiviral agents. Eur. J. Med. Chem. 2021;215:113220. doi: 10.1016/j.ejmech.2021.113220. - DOI - PMC - PubMed

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