Isonicotinoyl-butanoic acid hydrazone derivatives as anti-tubercular agents: In-silico studies, synthesis, spectral characterization and biological evaluation

Lone, Mehak Saba; Mubarak, Mohamad Mosa; Nabi, Syed Ayaz; Wani, Farhat Ramzan; Amin, Shaista; Nabi, Sayima; Kantroo, Hadiya Amin; Samim, Mohammed; Shafi, Syed; Ahmad, Shamim; Ahmad, Zahoor; Rizvi, Syed Ovais; Javed, Kalim

doi:10.1007/s00044-023-03039-5

Cited by 8 publications

(4 citation statements)

References 41 publications

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“…[16] This discovery has had a substantial impact on medical chemistry. These compounds' acetylcholinesterases, [17] anticancer, [18] α-glucosidase, [19] antitubercular, [20] anti-mitotic, [21] antimicrobial, [22] and antifungal [23] properties are also of great interest.…”

Section: Introductionmentioning

confidence: 99%

Imidazole‐hydrazone derivatives: Synthesis, characterization, X‐ray structures and evaluation of anticancer and carbonic anhydrase I–II inhibition properties

et al. 2023

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The nine new imidazole-hydrazone derivatives of Schiff base were synthesized from the condensation reactions of 1-methyl-1H-imidazole-2-carbaldehyde with various substitutedhydrazide derivatives. Structures of the final compounds (1 a-1 i) were characterized by using 1 H NMR, 13 C NMR spectroscopic techniques, elemental analysis, and crystal X-ray diffraction. The in vitro carbonic anhydrase I and II potentials of these synthesized were evaluated. The result suggests that compound 1 a, a 4-methoxy substituted analog with an IC 50 of 0.949 μM, was found to have the most potent hCA I inhibitory activity. Compounds 1 c, 1 d, and 1 h were the most potent compounds on hCA II with IC 50 values of 3.330, 4.454, and 5.66 μM, respectively. All compounds were examined for their cytotoxicity towards human colorectal adenocarcinoma cell (HT29) and rat glioma cell line (C6) compared to mouse fibroblast normal cell line (L929) using the MTT assay method. The compounds 1 a, 1 d, and 1 i exhibited significant antiproliferative activity with less toxicity to a health cell line. Consequently, compound 1 a could be the potential lead for emerging selective cytotoxic compounds directing hCA I. Compound 1 d could be the potential lead for emerging selective cytotoxic compounds directing hCA II.

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Section: Introductionmentioning

confidence: 99%

Imidazole‐hydrazone derivatives: Synthesis, characterization, X‐ray structures and evaluation of anticancer and carbonic anhydrase I–II inhibition properties

et al. 2023

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“…Isoniazid contains an isonicotinyl group, which is a pyridine derivative 21 . This group is responsible for this molecule's activity against tuberculosis 22,23 . Isoniazid is metabolized by the enzyme catalase peroxidase in tuberclosis bacillus producing toxic radicals which are responssible for toxic effects against this bacillus.…”

Section: Discussionmentioning

confidence: 99%

“…tuberculosis. 22,23 Isoniazid is metabolized by the enzyme catalase peroxidase in tuberclosis bacillus producing toxic radicals which are responssible for toxic effects against this bacillus. Peroxidases are a family of enzymes that play a key role in synthesizing and regulating melanin.…”

Section: Ta B L E 4 Mean Modified Melasmamentioning

confidence: 99%

Topical isoniazid as a novel treatment for melasma: A randomized, double‐blind, vehicle‐controlled clinical trial

Ahramiyanpour,

Mahmoudi,

Nezhad

et al. 2024

J of Cosmetic Dermatology

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IntroductionMelasma is a chronic hyperpigmentation disorder, and its treatment poses a challenge to dermatologists due to its chronicity and resistance to conventional therapies. Oral isoniazid is used for the treatment of tuberculosis. One of us had previously showed that topical isoniazid exerts a strong depigmenting action in animal models. In this clinical trial, we assessed the therapeutic effect of topical isoniazid on melasma.MethodsTwenty female patients suffering from epidermal melasma were enrolled and divided equally into two groups. The treatment group received topical isoniazid 10%, and the control group received the cold cream vehicle as the placebo. All participants were advised to avoid sunlight and used SPF 50 sunscreen. Patients applied topical agents once daily at night for 3 months. The melanin and erythema indices were measured by colorimetric evaluations at baseline and after 4, 8, and 12 weeks of treatment. At these time points, the (mMASI) score was also determined, as was the subjective evaluation through Melasma Quality of Life Scale (MELASQOL) scores. Blood tests were performed to evaluate CBC and the liver enzymes.ResultsAll patients completed the 12‐week study. In the treatment group, a significant decrease in melanin index from 63.77 ± 6.27 at baseline to 55.92 ± 5.79 was recorded (p = 0.001). Very minimal clinical changes were also seen in the control group and melanin index was decreased from 62.65 ± 2.23 to 61.25 ± 2.34 (p = 0.004). Clinically significant differences were observed in the rate of changes between both groups. These findings indicate that topical isoniazid has significant depigmenting effects compared to the placebo (p = 0.001). The erythema index remained unchanged in both groups. In the treatment group, the mMASI score was 5.63 ± 3.28 at baseline and 2.13 ± 1.71 at the last follow‐up, significantly reduced compared to the control group (p = 0.002). The MELASQOL score indicated a significant improvement in the quality of life in the treatment group.ConclusionThis clinical trial shows for the first time that topical isoniazid is effective in treating melasma. Further clinical trials are necessary to confirm the efficacy and tolerability of topical isoniazid in comparison with other skin‐depigmenting compounds.

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“…61,62 Lone et al (2023),examined hydrazones of butanoic acid (97) for their anti-Mtb activity. Compound (97) was found to be active against H37Ra and H37Rv strains with MIC value of 0.0042 μM each 63.…”

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confidence: 99%

Hydrazide–Hydrazones as Potential Antitubercular Agents: An Overview of the Literature (1999–2023)

Mali,

Pandey,

Shah

et al. 2024

SynOpen

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Hydrazide-hydrazone derivatives are prevalent in numerous bioactive compounds, showcasing a diverse array of biological effects including antibacterial, antitubercular, antifungal, anticancer, anti-inflammatory, anticonvulsant, antiviral, and antiprotozoal properties. Consequently, numerous medicinal chemists undertake the synthesis of various hydrazide-hydrazones, subjecting them to evaluation for their biological activities. Among these, antituberculosis activity stands out as a recurring focus in scientific literature. This paper provides a comprehensive overview of research spanning the last twenty-four years (1999-2023), concentrating on the antituberculosis properties of hydrazide-hydrazone derivatives. The insights presented herein could serve as a valuable roadmap for the development of novel hydrazide-hydrazones with potential antimicrobial efficacy.

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Isonicotinoyl-butanoic acid hydrazone derivatives as anti-tubercular agents: In-silico studies, synthesis, spectral characterization and biological evaluation

Cited by 8 publications

References 41 publications

Imidazole‐hydrazone derivatives: Synthesis, characterization, X‐ray structures and evaluation of anticancer and carbonic anhydrase I–II inhibition properties

Imidazole‐hydrazone derivatives: Synthesis, characterization, X‐ray structures and evaluation of anticancer and carbonic anhydrase I–II inhibition properties

Topical isoniazid as a novel treatment for melasma: A randomized, double‐blind, vehicle‐controlled clinical trial

Hydrazide–Hydrazones as Potential Antitubercular Agents: An Overview of the Literature (1999–2023)

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