Design, synthesis, and biological evaluation of amide derivatives of imidazo[2,1-<i>b</i>][1,3,4]thiadiazole as anticancer agents

Sridhar, Gattu; Palle, Sadanandam; Vantikommu, Jyothi; Gangarapu, Kiran

doi:10.1080/00397911.2020.1797814

Cited by 16 publications

(11 citation statements)

References 31 publications

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“…In the 1 This finding also shows parallelism with the data in the literature. [31,[41][42][43][44][45][46] When the 13 C-NMR spectra of compounds 7-15 are examined, the signals appearing in the range of 111.48 -108.98 ppm and 145.52 -145.28 ppm indicate that an imidazole-thiadiazole fused ring has formed.…”

Section: Chemistrysupporting

confidence: 90%

“…General Procedure for the Synthesis 2,5,6-Trisubstituted Imidazo [2,1-b] [1,3,4]-Thiadiazole Derivatives (16 -33) A mixture of secondary amine (morpholine/thiomorpholine/piperidine) (3.38 mmol), formaldehyde (0.35 mL), and glacial acetic acid (0.35 mL) was added to a 100 mL round-bottom flask. The mixture was dissolved in 20 mL of methanol.…”

Section: 14mentioning

confidence: 99%

“…Pharmaceutical chemistry is the best resource for the development of therapeutic drugs. [1] Cyclic structures containing atoms such as oxygen and nitrogen apart from the carbon and hydrogen atoms in their structures are called heterocyclic compounds. [2] Heterocyclic compounds are also an important branch of pharmaceutical chemistry.…”

Section: Introductionmentioning

confidence: 99%

“…ylmethyl group in the 5-position of imidazo[2,1-b][1,3,4]-thiadiazole increases the cytotoxic activity similarly to the morpholinomethyl group. Excluding one(33) of the six compounds, the IC 50 values of the others were found to be below 200 μM at 97.69, 47.31, 88.70, 102.70, and 109.80 μM for 28-32, respectively.…”

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confidence: 99%

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Novel Thioether‐Bridged 2,6‐Disubstituted and 2,5,6‐Trisubstituted Imidazothiadiazole Analogues: Synthesis, Antiproliferative Activity, ADME, and Molecular Docking Studies

Ozcan

Akkoç

Alıcı

et al. 2022

Chemistry & Biodiversity

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In this study, starting from 2‐amino‐1,3,4‐thiadiazole derivatives (3–5), a new series of 2,6‐disubstituted (compounds 7–15) and 2,5,6‐trisubstituted (compounds 16–33) imidazo[2,1‐b][1,3,4]‐thiadiazole derivatives were synthesized using cyclization and Mannich reaction mechanisms, respectively. All synthesized compounds were characterized by 1H‐NMR, 13C‐NMR, FT‐IR, elemental analysis, and mass spectroscopy techniques. Also, X‐ray diffraction analysis were used for compounds 4, 7, 11, 17, and 19. The cytotoxic effects of the new compounds on the viability of colon cancer cells (DLD‐1), lung cancer cells (A549), and liver cancer cells (HepG2) were investigated using the 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide (MTT) method in vitro. Compound 15 was found to be the most potent anticancer drug candidate in this series with an IC50 value of 3.63 μM against HepG2 for 48 h. Moreover, the absorption, distribution, metabolism, and excretion (ADME) parameters of the synthesized compounds were calculated and thus, their potential to be safe drugs was evaluated. Finally, to support the biological activity experiments, molecular docking studies of these compounds were carried out on three different target cancer protein structures (PDB IDs: 5ETY, 1M17, and 3GCW), and the amino acids that play key roles in the binding of the compounds to these proteins were determined.

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Section: Chemistrysupporting

confidence: 90%

Section: 14mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Novel Thioether‐Bridged 2,6‐Disubstituted and 2,5,6‐Trisubstituted Imidazothiadiazole Analogues: Synthesis, Antiproliferative Activity, ADME, and Molecular Docking Studies

Ozcan

Akkoç

Alıcı

et al. 2022

Chemistry & Biodiversity

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“…1,3,4-Thiadiazole derivatives have shown extensive biological activities, such as anti-inflammatory ( Maddila et al, 2016 ), anticancer ( Yang et al, 2012 ; Sridhar et al, 2020 ), antifungal ( Alwan et al, 2015 ; Bhinge et al, 2015 ; Chudzik et al, 2019 ), antibacterial ( Aggarwal et al, 2012 ; Taflan et al, 2019 ; Zhang et al, 2019 ), and plant growth regulator ( Knyazyan et al, 2012 ) activities. Since 1,3,4-thiadiazole compounds with antibacterial activity was synthesized by Masaki in the 1950s, 1,3,4-thiadiazole pesticides, such as Bismerthiazol and Thiodiazole-copper, have been developed and widely used in agriculture.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Bioactivities of Novel 1,3,4-Thiadiazole Derivatives of Glucosides

Chen

Zhang

et al. 2021

Front. Chem.

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A series of novel 1,3,4-thiadiazole derivatives of glucosides were synthesized by the starting materials d-glucose and 5-amino-1,3,4-thiadiazole-2-thiol in good yields with employing a convergent synthetic route. The results of bioactivities showed that some of the target compounds exhibited good antifungal activities. Especially, compounds 4i showed higher bioactivities against Phytophthora infestans (P. infestans), with the EC50 values of 3.43, than that of Dimethomorph (5.52 μg/ml). In addition, the target compounds exhibited moderate to poor antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas campestris pv. citri (Xcc).

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Design, Synthesis, Characterization, Antiproliferative Activity, and In Silico Studies of Novel Alkyl Ether Derivatives Containing 1H‐1,2,4‐Triazole Ring

et al. 2022

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In this study, starting from 1H-1,2,4-triazole, a new series of aliphatic ether derivatives containing phenyl and 1H-1,2,4triazole groups together were synthesized using reduction and Williamson ether synthesis mechanisms, respectively. The molecular structures of the synthesized compounds were characterized by fourier-transform infrared spectroscopy (FT-IR), 1 H and 13 C nuclear magnetic resonance ( 1 H NMR and 13 C NMR), mass spectroscopy, and elemental analysis techniques. All synthesized compounds were screened against three different human cancer cell lines, including colon, lung, and liver cancer cells. Some of the compounds showed exceptionally high antiproliferative effects against all three cancer cell lines, with IC 50 values much lower than the positive control drug bendamustine. In addition, molecular docking studies were performed to support the in vitro results and the interaction types and amino acids that play key roles in the binding of the compounds to enzymes were identified. Finally, the potential of these compounds to be drugs and their drug-likeness properties were evaluated by absorption, distribution, metabolism, and excretion-toxicity (ADMET) calculations and it was determined that the compounds could be drug candidates with the capacity to be effective and safe drugs for use in the treatment of different diseases.

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Design, synthesis, and biological evaluation of amide derivatives of imidazo[2,1-b][1,3,4]thiadiazole as anticancer agents

Cited by 16 publications

References 31 publications

Novel Thioether‐Bridged 2,6‐Disubstituted and 2,5,6‐Trisubstituted Imidazothiadiazole Analogues: Synthesis, Antiproliferative Activity, ADME, and Molecular Docking Studies

Novel Thioether‐Bridged 2,6‐Disubstituted and 2,5,6‐Trisubstituted Imidazothiadiazole Analogues: Synthesis, Antiproliferative Activity, ADME, and Molecular Docking Studies

Synthesis and Bioactivities of Novel 1,3,4-Thiadiazole Derivatives of Glucosides

Design, Synthesis, Characterization, Antiproliferative Activity, and In Silico Studies of Novel Alkyl Ether Derivatives Containing 1H‐1,2,4‐Triazole Ring

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