Synthesis, characterization and evaluation of novel benzothiazole clubbed chromene derivatives for their anti-inflammatory potential

Gandhi, Divyani; Agarwal, Dinesh K.; Kalal, Priyanka; Bhargava, Amit; Jangid, Dinesh Kumar; Agarwal, Shikha

doi:10.1080/10426507.2018.1514502

Cited by 12 publications

(5 citation statements)

References 38 publications

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“…Another interesting structural core is the chromen ring. Chromen derivatives were also reported to display a wide range of biological activities such as antioxidant [ 36 , 37 ], anti-inflammatory [ 38 , 39 ], antimicrobial [ 40 , 41 , 42 , 43 , 44 , 45 ], anti-HIV [ 46 , 47 ] and others [ 48 , 49 ].…”

Section: Introductionmentioning

confidence: 99%

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

et al. 2021

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Herein we report the synthesis of some new 1H-1,2,4-triazole functionalized chromenols (3a–3n) via tandem reactions of 1-(alkyl/aryl)-2-(1H-1,2,4-triazole-1-yl) with salicylic aldehydes and the evaluation of their antifungal activity. In silico prediction of biological activity spectra with computer program PASS indicate that the compounds have a high novelty compared to the known antifungal agents. We did not find any close analog among the over 580,000 pharmaceutical agents in the Cortellis Drug Discovery Intelligence database at the similarity cutoff of 70%. The evaluation of antifungal activity in vitro revealed that the highest activity was exhibited by compound 3k, followed by 3n. Their MIC values for different fungi were 22.1–184.2 and 71.3–199.8 µM, respectively. Twelve from fourteen tested compounds were more active than the reference drugs ketoconazole and bifonazole. The most sensitive fungus appeared to be Trichoderma viride, while Aspergillus fumigatus was the most resistant one. It was found that the presence of the 2-(tert-butyl)-2H-chromen-2-ol substituent on the 4th position of the triazole ring is very beneficial for antifungal activity. Molecular docking studies on C. albicans sterol 14α-demethylase (CYP51) and DNA topoisomerase IV were used to predict the mechanism of antifungal activities. According to the docking results, the inhibition of CYP51 is a putative mechanism of antifungal activity of the novel chromenol derivatives. We also showed that most active compounds have a low cytotoxicity, which allows us to consider them promising antifungal agents for the subsequent testing activity in in vivo assays.

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Section: Introductionmentioning

confidence: 99%

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

et al. 2021

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“…25 Furthermore, synthesized derivatives tend to have significant anti-inflammatory activity and shall prove as structural templates in the design and development of new anti-inflammatory drugs. 31 Moreover, benzofuran can exert regulatory effects on various cellular activities, potentially by modifying signaling pathways such as MAPK and PPAR-ɣ. 32 As well, Park et al studied MAPKs pathways by evaluating the phosphorylation of JNK, p38, and ERK.…”

Section: Anti-inflammatory Properties Of Natural Benzofuransmentioning

confidence: 99%

<p>Recent Updates on Anti-Inflammatory and Antimicrobial Effects of Furan Natural Derivatives</p>

Alizadeh¹,

Moludi²,

Khodaei³

et al. 2020

JIR

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The furan nucleus is found in a large number of biologically active materials. In recent years, many natural furan derivatives were isolated and their biological effects were investigated. In this review, we focused on the anti-inflammatory and antimicrobial effects of some natural furans and discussed their effects on the immune system. Our investigation revealed that furan natural derivatives have effective antioxidant activities and exert regulatory effects on various cellular activities by modifying some signaling pathways such as MAPK (mitogen-activated Protein Kinase) and PPAR-ɣ (peroxisome proliferator-activated receptor gamma). The antimicrobial activity of these natural compounds was performed through selective inhibition of microbial growth and modification of enzymes. Further studies are needed for isolation and detection of different furan derivatives from natural compounds and investigation of their precise mechanisms for revealing health beneficial effects of these compounds.

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“…Medicinal chemists have been continuous embarking on the synthesis of novel compounds of this chemotype due to the broad spectrum of medicinal uses associated with the benzothiazole scaffold [3]. The modified analogues of benzothiazole revealed a significant number of pharmacological properties such as antifungal [4], cyclooxygenase inhibitors [5], antimicrobial [6], anticonvulsant [7], mosquitocidal [8], anticancer [9], antioxidant [10], anti-inflammatory [11], bacterial type II topoisomerase inhibitors [12], photosensitizers [13], selective PI3Kβ inhibitors [14], topoisomerase I inhibitors [15], cytotoxic agents [16], falcipain inhibitors [17], tubulin polymerization inhibitors [18], p53 inhibitors [19], neuroprotective [20], antiacetylcholinesterase [21], vasorelaxants [22], inhibitors of the insulin releasing process [22], antiproliferative agents [23], anti-influenza [24], hemostatic agents [25], antitubercular agents [26], chemokine receptor 2 (CXCR2) inhibitors [27], EGFR inhibitors [28], cyclin-dependent kinase 2 inhibitors [29], β-amyloid imaging agents [30], α-glucosidase inhibitor [31], antidepressant [32], monoamine oxidase A/B inhibitors [33], non-carboxylic PTP1B inhibitors [34], histone deacetylase inhibitors [35], β-glucuronidase activity [36], antiviral [37], tyrosine kinase inhibitors [38], antibacterial…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, in vitro Biological Evaluation of a Series of Benzothiazole Amides as Antibacterial Agents

Alazmaa,

Avupati,

Santiago

2024

ajc

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A series of benzothiazole amides (VH01-06) were synthesized by using modified Schotten-Baumann reaction conditions, all the resultant compounds were obtained in good yields and purity. The molecular structure of the compounds was characterized using physical and spectral methods. The structures of the compounds were consistent with the analytical data obtained for FT-IR, 1H NMR, 13C NMR and HRMS ESI-Mass spectroscopic techniques. Further, compounds were subjected to the in vitro antibacterial activity screening against various strains that includes Gram-positive bacteria (methicillin-resistant Staphylococcus aureus (MRSA) ATCC 3359 and methicillin-sensitive Staphylococcus aureus (MSSA) ATCC 2592) and Gram-negative bacteria (Escherichia coli J53 R1, Escherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 10031 and Klebsiella pneumonia BAA-1075). Based on the biological screening results, compounds VH01-06 were found to possesses limited antibacterial properties against selected strains, since the recorded activity was found at 100 µM concentration. While compound VH05 displayed specific activity against E. coli ATCC 25923 at 200 µg/mL.

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Synthesis, characterization and evaluation of novel benzothiazole clubbed chromene derivatives for their anti-inflammatory potential

Cited by 12 publications

References 38 publications

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

<p>Recent Updates on Anti-Inflammatory and Antimicrobial Effects of Furan Natural Derivatives</p>

Synthesis, Characterization, in vitro Biological Evaluation of a Series of Benzothiazole Amides as Antibacterial Agents

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