Antidiabetic potential and enzyme kinetics of benzothiazole derivatives and their non-bonded interactions with α-glucosidase and α-amylase

Puranik, Ninad V.; Puntambekar, Hemalata M.; Srivastava, Pratibha

doi:10.1007/s00044-016-1520-3

Cited by 27 publications

(12 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Benzothiazole compounds display a broad-spectrum biological activity [5,6,8,11,14,17,[20][21][22][23][24]. Thus, they usually act as an important guide frame and parent skeleton, which plays very important roles in medicinal chemistry and agrochemicals.…”

Section: Discussionmentioning

confidence: 99%

“…The benzothiazole nucleus, with a variety of modifications, has demonstrated a wide range of pharmacological properties including antimicrobial [5], anti-HIV [6], anthelmintic [7], antidiabetic [8], anticonvulsant [9], larvicidal [10], antimalarial [11], and anticancer activities [12]. In addition, the potential antimicrobial activity of benzothiazole derivatives was previously illustrated [13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Screening and Molecular Docking of Novel Benzothiazole Derivatives as Potential Antimicrobial Agents

et al. 2020

View full text Add to dashboard Cite

The burden of antibiotic resistance necessitates a continued search for new antimicrobials. We evaluated the antimicrobial activities of novel benzothiazoles synthesized by our group. Antibacterial activity was evaluated in vitro in Staphylococcus aureus, Bacillus subtilis, and Escherichia coli, while the antifungal activity was tested in Candida albicans and Aspergillus niger, and expressed as the minimum inhibitory concentration (MIC; µg/mL). MIC values of benzothiazole compounds ranged from 25 to 200 µg/mL. Compounds 3 and 4 gave high antibacterial and moderate antifungal activities, while 10 and 12 showed moderate activity against all tested organisms. In addition, some benzothiazole compounds significantly suppressed the activity of Escherichia coli dihydroorotase and inhibited the dimorphic transition of Candida albicans. Moreover, the active benzothiazole compounds induced DNA and protein leakage in Aspergillus niger spores. Molecular interactions of benzothiazole derivatives with dihydroorotase revealed the formation of hydrogen bonds with the active site residues LEU222 or ASN44. Strong hydrophobic interactions of the bulky thiazole and naphthalene rings at the entrance to the active site might interfere with the access of substrates to their binding sites, which results in dihydroorotase inhibition. Thus, inhibition of dihydroorotase might contribute to the observed antimicrobial actions of these compounds.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Screening and Molecular Docking of Novel Benzothiazole Derivatives as Potential Antimicrobial Agents

et al. 2020

View full text Add to dashboard Cite

show abstract

“…247～249 ℃ [19] , compound 8: m.p. 34 ℃ [20] . [d]thiazol-2-yl-methyl)thio)-6-(trifluoromethyl)pyrimidin-4-ol (9) Compound 6 (5.00 g, 25.49 mmol) was dissolved in KOH aqueous solution (33.14 mmol, 30 mL), and a solution of compound 8 (4.68 g, 25.49 mmol) in dioxane (18 mL) was added dropwise at room temperature.…”

Section: Preparation Of Compounds 6 Andmentioning

confidence: 99%

Synthesis and Antitumor Evaluation of 2,4,6-Trisubstituted Pyrimidine Derivatives Containing Benzothiazole Moiety

Li¹,

Meng²,

Zhang³

et al. 2020

Chin. J. Org. Chem.

View full text Add to dashboard Cite

a 郑州大学药学院郑州 450001) (b 新药创制与药物安全性评价河南省协同创新中心郑州 450001) (c 河南省药物质量评价重点实验室郑州 450001) (d 教育部药物制备关键技术重点实验室郑州 450001) 摘要为了寻找高效的抗肿瘤药物, 设计并合成了一系列含苯并噻唑砌块的 2,4,6-三取代嘧啶衍生物. 采用噻唑蓝 (MTT)法对目标化合物在人类四种癌细胞[EC-109(人食管癌细胞)、MGC-803(人胃癌细胞)、PC-3(人前列腺癌细胞)、 HepG-2(人肝癌细胞)]、GES-1(人正常胃黏膜上皮细胞)和 HEEC(人正常食管细胞)中进行抗肿瘤活性评价, 结果显示部分化合物对 MGC-803 和 PC-3 细胞表现出中度至强效的抗肿瘤活性. 其中 2-(((4-(4-(吡啶-2-基)哌嗪-1-基)-6-(三氟甲基) 嘧啶-2-基)硫基)甲基)苯并[d]噻唑(13h)和 2-(((4-(4-(嘧啶-2-基)哌嗪-1-基)-6-(三-氟甲基)嘧啶-2-基)硫代)甲基)苯并[d]噻唑(13i)对 PC-3 表现出比较好的抗肿瘤活性, IC 50 值分别 3.82 和 2.29 μmol/L, 且化合物 13h 和 13i 对 GES-1 的细胞增值毒性明显小于阳性对照 5-氟尿嘧啶.

show abstract

“…Benzothiazole is an important scaffold in bioorganic and medicinal chemistry, and has broad applications in drug discovery and development [ 8 ]. Benzothiazole-based compounds exhibit numerous biological activities such as anticonvulsant [ 9 ], anti-inflammatory [ 10 ], antimicrobial [ 11 ], anticancer [ 12 ] and anti-diabetic activities [ 13 ]. Some of benzothiazole-containing drugs, such as riluzole (anticonvulsant), ethoxzolamide (glaucoma, ulcers and as a diuretic), and zopolrestat (diabetic nephropathy and diabetes), have been used clinically for many years ( Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, In Vitro α-Glucosidase Inhibitory Activity and Molecular Docking Studies of Novel Benzothiazole-Triazole Derivatives

et al. 2017

View full text Add to dashboard Cite

Benzothiazole-triazole derivatives 6a–6s have been synthesized and characterized by 1H-NMR and 13C-NMR. All synthetic compounds were screened for their in vitro α-glucosidase inhibitory activity by using Baker’s yeast α-glucosidase enzyme. The majority of compounds exhibited a varying degree of α-glucosidase inhibitory activity with IC50 values between 20.7 and 61.1 μM when compared with standard acarbose (IC50 = 817.38 μM). Among the series, compound 6s (IC50 = 20.7 μM) bearing a chlorine group at the 5-position of the benzothiazole ring and a tert-butyl group at the para position of the phenyl ring, was found to be the most active compound. Preliminary structure-activity relationships were established. Molecular docking studies were performed to predict the binding interaction of the compounds in the binding pocket of the enzyme.

show abstract

Antidiabetic potential and enzyme kinetics of benzothiazole derivatives and their non-bonded interactions with α-glucosidase and α-amylase

Cited by 27 publications

References 33 publications

Screening and Molecular Docking of Novel Benzothiazole Derivatives as Potential Antimicrobial Agents

Screening and Molecular Docking of Novel Benzothiazole Derivatives as Potential Antimicrobial Agents

Synthesis and Antitumor Evaluation of 2,4,6-Trisubstituted Pyrimidine Derivatives Containing Benzothiazole Moiety

Synthesis, In Vitro α-Glucosidase Inhibitory Activity and Molecular Docking Studies of Novel Benzothiazole-Triazole Derivatives

Contact Info

Product

Resources

About