Mechanism-based approaches of 1,3,4 thiadiazole scaffolds as potent enzyme inhibitors for cytotoxicity and antiviral activity

Kumar, Davinder; Kumar, Harsh; Kumar, Virender; Deep, Aakash; Sharma, Aastha; Marwaha, Minakshi Gupta; Marwaha, Rakesh Kumar

doi:10.1016/j.medidd.2022.100150

Cited by 22 publications

(17 citation statements)

References 114 publications

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“…Melting points were determined via an open capillary method using a STUART SMP3 (BIBBY STERILIN, UK). The 1 H and 13 C NMR spectra were recorded using an Avance AV500 Spectrometer (Bruker, Germany) at 500 MHz and 150 MHz, respectively, using DMSO-d 6 as the solvent and TMS as an internal standard. ESI-mass spectra were recorded using an LC-MS LTQ Orbitrap XL, ESI/HR-mass spectra were recorded using Thermo Scientific Exactive Plus Orbitrap spectrometers (ThermoScientific, USA) in methanol using the ESI method.…”

Section: Methodsmentioning

confidence: 99%

“…This isothiocyanate derivative was prepared from p-toluene sulfonyl chloride by reaction with ammonium thiocyanate in dried acetonitrile in the presence of pyridine as a base (Scheme 1). The synthesized sulfonyl thiourea compounds were characterized using 1 H NMR, 13 C NMR, and mass spectroscopic methods (see ESI †). All these obtained thioureas were soluble in a mixture of ethanol and/ or toluene (1 : 1 by volume), and could not be dissolved in water.…”

Section: Chemistrymentioning

confidence: 99%

“…4,12 Currently, numerous drugs containing a 1,3,4-thiadiazole ring are in clinical trials. 13 For example, sulfamethizole, a thiadiazole derivative, has been used as an antimicrobial agent. 14 Acetazolamide is used in the treatment of glaucoma, drug-induced edema, heart-failure-induced edema, epilepsy and reducing intraocular pressure after surgery.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, biological and molecular modelling for 1,3,4-thiadiazole sulfonyl thioureas: bacterial and fungal activity

Dinh Thanh,

Ngoc Toan,

Thi Kim Giang

et al. 2023

RSC Med. Chem.

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Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, biological and molecular modelling for 1,3,4-thiadiazole sulfonyl thioureas: bacterial and fungal activity

Dinh Thanh,

Ngoc Toan,

Thi Kim Giang

et al. 2023

RSC Med. Chem.

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“…The 1,3,4‐thiadiazoles are known to exhibit a wide range of biological actions such as antifungal, anticancer, antibacterial, anti‐leishmanial, antitubercular, antioxidative, and antidiabetic agents. [ 43–48 ] Additionally, they serve as the initial building blocks for the production of many different kinds of chemical compounds, including sulfa medicines, fungicides, dyes, and catalysts for chemical reactions. Megazol (antiparasitic), acetazolamide (carbonic anhydrase inhibitor), methazolamide (diuretic), sulfamethizole (antibacterial sulfonamide), and Cefazolin (first‐generation cephalosporin) are some of the most well‐known thiadiazole‐containing medications in the market (Figure 2).…”

Section: Introductionmentioning

confidence: 99%

“…The 1,3,4-thiadiazoles are known to exhibit a wide range of biological actions such as antifungal, anticancer, antibacterial, anti-leishmanial, antitubercular, antioxidative, and antidiabetic agents. [43][44][45][46][47][48] Additionally, they serve as the initial building blocks for the production of many different kinds of chemical compounds, including sulfa medicines, F I G U R E 1 Some drugs containing 1,3,4-thiadiazole and 1,2,3-triazole scaffolds. fungicides, dyes, and catalysts for chemical reactions.…”

mentioning

confidence: 99%

Synthesis of 1,2,3‐triazole‐1,3,4‐thiadiazole hybrids as novel α‐glucosidase inhibitors by in situ azidation/click assembly

Kumar

Dhameja

Kurella

et al. 2023

Archiv der Pharmazie

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α-Glucosidase inhibition is widely used in the oral management of diabetes mellitus (DM), a disease characterized by high blood sugar levels (hyperglycemia) and abnormal carbohydrate metabolism. In this respect, a series of 1,2,3-triazole-1,3,4thiadiazole hybrids 7a-j were synthesized, inspired by a copper-catalyzed one-pot azidation/click assembly approach. All the synthesized hybrids were screened for inhibition of the α-glucosidase enzyme, displaying IC 50 values ranging from 63.35 ± 0.72 to 613.57 ± 1.98 μM, as compared to acarbose (reference) with IC 50 of 844.81 ± 0.53 μM. The hybrids 7h and 7e with 3-nitro and 4-methoxy substituents at the phenyl ring of the thiadiazole moiety were the best active hybrids of this series with IC 50 values of 63.35 ± 0.72 μM, and 67.61 ± 0.64 μM, respectively. Enzyme kinetics analysis of these compounds revealed a mixed mode of inhibition. Moreover, molecular docking studies were also performed to gain insights into the structure-activity-relationships of the potent compounds and their corresponding analogs.

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Comprehensive Assessment of Antioxidant, Antimicrobial, and Cytotoxic Activities of Schiff Bases Synthesized from Phenyl Glyoxal: Insights from Molecular Docking and ADMET Analysis

Tomer,

Bansal,

Vats

et al. 2024

ChemistrySelect

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In this study, novel Schiff base, PTIEO and PABHP were synthesized using Phenyl Glyoxal as a major constituent and their structures were elucidated through modern spectroscopic techniques. Antioxidant assays were performed using DPPH and ABTS assays. Further, PTIEO and PABHP were subjected to in vitro biological evaluations against ESKAP pathogens. This investigation revealed significant antibacterial activity of both compounds, with MIC below 64 μg mL−1 against Staphylococcus aureus and 64 μg mL−1 against Acinetobacter baummanii. In molecular docking studies, PTIEO shows enhanced binding energy with Acinetobacter baumannii bacterial protein Diaminopimelate epimerase at −7.45 Kcal mol−1, while PABHP exhibited −8.32 Kcal mol−1 binding energy with NADH‐dependent enoyl‐ACP reductase. Additionally, PTIEO and PABHP demonstrated good binding energy with Sortase‐A of Staphylococcus aureus at −7.59 Kcal mol−1 and −8.75 Kcal mol−1, respectively. Moreover, antifungal capabilities of these compounds were evaluated against pathogenic fungi Candida Albicans, Candida Parapsilosis, and Candida tropicalis, highlighting their broad‐spectrum antimicrobial properties. Moreover, PABHP displayed cytotoxicity with an IC50 value of 23.50 μg mL−1, suggesting its safer administration. ADMET calculations were also performed to demonstrate their effectiveness. Overall, these experiments attribute to the significant therapeutic behavior of Schiff bases as comprehensive biomedical agents.

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Mechanism-based approaches of 1,3,4 thiadiazole scaffolds as potent enzyme inhibitors for cytotoxicity and antiviral activity

Cited by 22 publications

References 114 publications

Synthesis, biological and molecular modelling for 1,3,4-thiadiazole sulfonyl thioureas: bacterial and fungal activity

Synthesis, biological and molecular modelling for 1,3,4-thiadiazole sulfonyl thioureas: bacterial and fungal activity

Synthesis of 1,2,3‐triazole‐1,3,4‐thiadiazole hybrids as novel α‐glucosidase inhibitors by in situ azidation/click assembly

Comprehensive Assessment of Antioxidant, Antimicrobial, and Cytotoxic Activities of Schiff Bases Synthesized from Phenyl Glyoxal: Insights from Molecular Docking and ADMET Analysis

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