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Benzydamine
Published in Anton C. de Groot, Monographs in Contact Allergy, 2021
Benzydamine is an indazole non-steroidal anti-inflammatory drug with analgesic, antipyretic, and anti-edema properties. Available as a liquid mouthwash, spray for mouth and throat, topical cream, and vaginal irrigation (formerly also available in tablets, suppositories and intramuscular injections), benzydamine is most frequently employed for the relief of painful inflammatory conditions of the mouth and the musculoskeletal system, respectively. It is also said to promote healing. In pharmaceutical products, benzydamine is employed as benzydamine hydrochloride (CAS number 132-69-4, EC number 205-076-0, molecular formula C19H24ClN3O) (1).
The Renewal of Interest in Nitroaromatic Drugs
Published in Venkatesan Jayaprakash, Daniele Castagnolo, Yusuf Özkay, Medicinal Chemistry of Neglected and Tropical Diseases, 2019
Nicolas Primas, Caroline Ducros, Patrice Vanelle, Pierre Verhaeghe
Other nitroheterocycles investigated for their antichagasic activity include indazole-based derivatives. A series of 3-alkoxy-1-alkyl-5-nitro-1H-indazoles were evaluated against the CL-Brener clone of T. cruzi epimastigotes, affording moderately active derivatives (51) (Figure 12) (Rodríguez et al. 2009a, b). Closely related analogs in 5-nitroindazolin-3-one series showed interesting sub-micromolar activity for the compound (52) (Vega et al. 2012, Fonseca-Berzal et al. 2016a). Varying the 1-alkyl chain led to a marked improvement in the anti-Trypanosoma cruzi activity, which became as potent as the reference drug benznidazole (9). SAR analysis suggests that electron-donating groups at position 1 of the indazolinone ring are associated with improved antichagasic activity. Compound (53), although only moderately active on the epimastigote form, was very efficacious against amastigotes from CL-Brener as well as Tulahuen and Y strains of T. cruzi (IC50 = 0.22, 0.81 and 0.60 μM, respectively), and showed low cytotoxicity against fibroblasts and cardiac cells (Fonseca-Berzal et al. 2016b). The SAR analysis suggests that electron-donating groups at position 1 of the indazolinone ring are associated with improved antichagasic activity. When the water-soluble amino group was introduced (54), there was a great improvement of the activity on the epimastigote form of the parasite and the activity on the amastigote form was also very potent (IC = 0.25 μM). In addition, (54) was active against other T. cruzi strains without cytotoxicity on fibroblastic or cardiac cells (Aran et al. 2018). Structure of compounds (51–53) is shown in Figure 12. Structures and in vitro activities of 5-nitroindazole derivatives against epimastigote T. cruzi.
Lactoperoxidase, an antimicrobial enzyme, is inhibited by some indazoles
Published in Drug and Chemical Toxicology, 2020
In present study we aimed to investigate the inhibitory effects of some indazole derivatives [1H-indazole (1a), 4-Bromo-1H-indazole (2a), 6-Bromo-1H-indazole (3a), 7-Bromo-1H-indazole (4a), 4-chloro-1H-indazole (5a), 6-chloro-1H-indazole (6a), 7-chloro-1H-indazole (7a), 4-fluoro-1H-indazole (8a), 6-fluoro-1H-indazole (9a), 7-fluoro-1H-indazole (10a)] on bovine milk LPO enzyme activity and assess their potential to be used as inhibitors. For this aim, LPO enzyme was purified from bovine milk then Ki constants and inhibition types were firstly determined for these indazole molecules. No previous study in the literature so far investigated the inhibitory effects of these molecules on bovine milk LPO. Indazoles are an important class of heterocyclic compounds with a wide range of application as biologic and pharmaceutic agents. They have been extensively studied due to their interesting chemical and biological characteristics. Indazole belongs to the azoles family, which includes carbon, hydrogen and a nitrogen atom. Indazole has a heterocyclic structure made up of benzene and pyrazole rings. Indazole derivatives have a wide range of biological activities. For instance, indazole derivatives show vasorelaxant and anti-aggregator activities by stimulating NO release and increasing cGMP levels. Recent medical research and development studies resulted in the production of indazole derivatives for the treatment of osteoporosis, inflammatory diseases and neurodegenerative disorders (Gaikwad et al.2015).
Some indazoles reduced the activity of human serum paraoxonase 1, an antioxidant enzyme: in vitro inhibition and molecular modeling studies
Published in Archives of Physiology and Biochemistry, 2019
Zuhal Alım, Deryanur Kılıç, Yeliz Demir
In view of the pharmacological aspect of PON1, we examined the in vitro inhibition effects of some indazoles on human serum PON1 (hPON1) activity in this study. Indazole is an important class of heterocyclic compounds formed by the fusion of benzene and pyrazole rings (Gaikwad et al.2015). Indazole derivatives display a wide range of biological activities such as anti-inflammatory (Cheekavolu and Muniappan 2016), anti-tumor (Abbasi et al.2014), anti-HIV (Kim et al.2013), antimicrobial, antiparasitic, antiplatelet (Cerecetto et al.2005), and serotonin 5-HT3 receptor antagonist activities (Bermudez et al.1990). For this reason, indazole derivatives have a very important role in pharmacological applications for the synthesis of new drugs. There are three tautomers, 1H-indazole, 2H-indazole, and 3H-indazole, according to position of the heteroatoms in the ring of the indazole molecule (Shrivastava et al.2016). Among these, 1H-indazole exhibits a wide range of biological and pharmaceutical activities (Markina et al.2012).
Novel 3-chloro-6-nitro-1H-indazole derivatives as promising antileishmanial candidates: synthesis, biological activity, and molecular modelling studies
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2022
Mohamed Mokhtar Mohamed Abdelahi, Youness El Bakri, Chin-Hung Lai, Karthikeyan Subramani, El Hassane Anouar, Sajjad Ahmad, Mohammed Benchidmi, Joel T. Mague, Jelena Popović-Djordjević, Souraya Goumri-Said
In the present work, synthesis of new heterocyclic systems originated from 3-chloro-6-nitro-1H-indazole was carried out in satisfactory yields by cycloaddition reactions under thermal and catalytic conditions (CuI). The results showed a periselectivity and regioselectivity as a function of the dipole (azides F, G, and H) employed. Additionally, it was shown that indazole derivatives have biological potency against three species of Leishmania and can be utilised as an excellent inhibitor for the parasite of leishmania. Moreover, in comparison of the findings of all the derivatives with the Glucantime as a reference standard, it was observed that indazole could be exploited as a useful source in the discovery of new antileishmania drugs. The inhibitory efficacy of indazole derivatives was changed significantly when the rings associated with indazole were changed. Thus compounds containing triazole, proved more efficient in inhibition than compounds containing oxazoline while those containing oxazole had the lowest effectiveness. This may be due to the interactions between the core, 3-chloro-6-nitro-1H-indazole, and the side chain of the triazolic derivatives. The molecular docking, molecular dynamics, and MM/GBSA binding free energy results were in good agreement with the experimental studies. Triazoles are reported as a potent inhibitor of cytochrome P450 particularly CYP3A4, which often leads to toxic effects and drug interactions when used in combination with drugs that are dependent for metabolism on cytochrome P450 enzymes. Therefore care should be taken while using it in combination with other drugs to avoid this phenomenon.