New triazinoindole bearing thiazole/oxazole analogues: Synthesis, α-amylase inhibitory potential and molecular docking study

Tariq, Sundas; Taha, Muhammad; Ullah, Hayat; Zaman, Khalid; Uddin, Imad; Wadood, Abdul; Khan, Aftab Ahmad; Rehman, Ashfaq Ur; Uddin, Nizam; Zafar, Saima

doi:10.1016/j.bioorg.2019.103284

Cited by 46 publications

(17 citation statements)

References 32 publications

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“…Thiazole- and tetrazole-derived synthetic antibacterial drugs exhibited broad-spectrum antimicrobial efficacy. , Therefore, the biological isosteres thiazole and tetrazole fragments were introduced to replace 1,3,4-oxadiazole-2-thiol at the C-4 position of the carbazole scaffold to investigate the effect of different five-membered aromatic heterocycles. Triazinoindole with an electron-rich system in comparison to carbazole ring has been considered to be a versatile fragment in medicinal chemistry. , Consequently, triazinoindole fragment was combined with 1,3,4-oxadiazole-2-thiol structure to study whether the increase of electronegativity contributed to antibacterial activities. Finally, in this work, antibacterial activities of novel carbazole-oxadiazole derivatives and their SARs were adequately explored, including cytotoxic activity, resistant development, and so on.…”

Section: Introductionmentioning

confidence: 99%

Unique Carbazole-Oxadiazole Derivatives as New Potential Antibiotics for Combating Gram-Positive and -Negative Bacteria

et al. 2022

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Novel carbazole-oxadiazoles were developed as new potential antibacterial agents to combat dreadful resistance. Some target compounds displayed predominant inhibitory effects on the tested Gram-positive and -negative bacteria, and carbazole-oxadiazoles 5g, 5i–k, 16a–c, and tetrazole analogues 23b–c were found to be efficient in impeding the growth of MRSA and Pseudomonas aeruginosa ATCC 27853 (MICs = 0.25–4 μg/mL). Furthermore, compounds 5g and 23b–c not only possessed rapid bactericidal ability and low tendency to develop resistance but also exhibited low cytotoxic effects toward Hek 293T, HeLa, and red blood cells (RBCs), especially molecule 5g also showed low toxicity in vivo, which showed the therapeutic potential of these compounds. Further exploration indicated that compounds 5g, 5i, and 23b–c could disintegrate the integrity of bacterial cell membranes to leak the cytoplasmic contents, thus exerting excellent antibacterial effects. These facts mean that carbazole-based antibacterial agents might have bright prospects in confronting bacterial infections.

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Section: Introductionmentioning

confidence: 99%

Unique Carbazole-Oxadiazole Derivatives as New Potential Antibiotics for Combating Gram-Positive and -Negative Bacteria

et al. 2022

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“…As shown in scheme 23 isatin 69 gave compound 70 by reacting with thiosemicarbazide in presence of K 2 CO 3 in distilled H 2 O. [71] Then phenacyl group was attached to 70 by reaction with phenacyl bromide in ethanol using K 2 CO 3 . Compound 72 was obtained by reacting semi carbazide or thiosemicarbazide with 71 in ethanol using acetic acid which gave final product 73 on treating with phenacyl bromides in ethanolic trimethylamine.…”

Section: Five or Six Membered Unsaturated Ring Containing Three Nitro...mentioning

confidence: 99%

“…Rahim et al ( 2019 ) introduced triazin indole motifs with more aromaticity by including thiazole/oxazole groups. As shown in scheme 23 isatin 69 gave compound 70 by reacting with thiosemicarbazide in presence of K 2 CO 3 in distilled H 2 O [71] . Then phenacyl group was attached to 70 by reaction with phenacyl bromide in ethanol using K 2 CO 3 .…”

Section: Synthetic Developments On N‐heterocyclic Compoundsmentioning

confidence: 99%

Recent Developments in the Synthesis of N‐Heterocyclic Compounds as α‐Amylase Inhibitors via In‐Vitro and In‐Silico Analysis: Future Drugs for Treating Diabetes

et al. 2022

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In nature, N‐heterocyclic compounds and their derivatives are abundant. They serve as the building blocks of many biological entities, such as enzymes, alkaloids, hormones, antibiotics, and vitamins. The treatment of diabetes is one of the major applications of heterocyclic compounds. Natural as well as synthetic, both types of heterocyclic compounds show anti‐diabetic activity. There is a plethora of literature on the hyper/hypoglycaemic activity of natural compounds. This review discusses the synthesis methods, yields of the reactions and Inhibitory concentration (IC50) values of all the synthesized derivatives via different assays such as 3,5‐dinitrosalicylic acid (DNS) or starch assays. IC50 values of all the derivatives have been compared with those of standard acarbose. Structure activity relationship of most potential compounds with α‐amylase enzyme is established to show the type of interactions between them. Molecular docking studies show the type of interaction between compounds and enzyme.

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“…Then, 500 µL of 1% starch solution in 0.02 M sodium phosphate buffer (pH 6.9 with 0.006 M sodium chloride) was added to each tube [9]. The reaction mixture was incubated at 25°C for 10 min and stopped with 1.0 mL of dinitrosalicylic acid colour reagent.…”

Section: Enzyme Methodsmentioning

confidence: 99%

Introducing a novel chemotherapeutic drug formulated with anthraflavic acid for treating human breast carcinoma and type 2 diabetes mellitus

et al. 2021

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IntroductionMolecular docking as a versatile theoretical method was used to investigate the biological activities of anthraflavic acid in the presence of alpha amylase. The outcomes revealed that anthraflavic acid has a considerable binding affinity to the enzyme with a docking score of -7.913 kcal/mol.Material and methodsThese outcomes were further evaluated with free binding energy calculations, and it was concluded that anthraflavic acid could be a potential inhibitor for alpha amylase. The as Anthraflavic acid was explored in the anti-human breast carcinoma tests. The in vitro cytotoxic and anti-breast carcinoma effects of biologically synthesized Anthraflavic acid against MCF-7, CAMA-1, SK-BR-3, MDA-MB-231, AU565 [AU-565], and Hs 281.T cancer cell lines were assessed.ResultsThe anti-breast carcinoma properties of the Anthraflavic acid could significantly remove MCF-7, CAMA-1, SK-BR-3, MDA-MB-231, AU565 [AU-565], and Hs 281.T cancer cell lines in a time and concentration-dependent manner by MTT assay.ConclusionsThe IC50 of the Anthraflavic acid were 159, 193, 253, 156, 241, and 218 µg/mL against MCF-7, CAMA-1, SK-BR-3, MDA-MB-231, AU565 [AU-565], and Hs 281.T cancer cell lines. It seems that the anti-human breast carcinoma effect of recent nanoparticles is due to their antioxidant effects.After clinical study, Anthraflavic acid can be utilized as an efficient drug in the treatment of breast carcinoma in humans.

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New triazinoindole bearing thiazole/oxazole analogues: Synthesis, α-amylase inhibitory potential and molecular docking study

Cited by 46 publications

References 32 publications

Unique Carbazole-Oxadiazole Derivatives as New Potential Antibiotics for Combating Gram-Positive and -Negative Bacteria

Unique Carbazole-Oxadiazole Derivatives as New Potential Antibiotics for Combating Gram-Positive and -Negative Bacteria

Recent Developments in the Synthesis of N‐Heterocyclic Compounds as α‐Amylase Inhibitors via In‐Vitro and In‐Silico Analysis: Future Drugs for Treating Diabetes

Introducing a novel chemotherapeutic drug formulated with anthraflavic acid for treating human breast carcinoma and type 2 diabetes mellitus

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