An efficient synthesis of imidazo[2,1-<i>b</i>][1,3,4]thiadiazol-7-ium hydroxides by a one-pot, three-component reaction in water

Khalafy, Jabbar; Etivand, Nasser; Khalillou, Neda

doi:10.1515/hc-2018-0117

Cited by 10 publications

(2 citation statements)

References 47 publications

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“…In recent years, a diverse set of 1,3,4-thiadiazole analogs have been developed, exhibiting a broad spectrum of biological activities, such as antiparasitic ( 13 ), anticancer ( 14 ), antibacterial ( 15 ), antiviral ( 16 ), and antitubercular ( 17 - 19 ) activities. Furthermore, several studies on molecules with antiplatelet activity have revealed that analogs containing N -acylhydrazone and its isosteres exhibit remarkable antiplatelet activity ( 3 , 20 - 23 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Novel Thiadiazole Derivatives as Antiplatelet Agents

Khakpash,

Esfahanizadeh,

Mahboubi-Rabbani

et al. 2024

Iran J Pharm Res

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: A novel series of thiadiazole compounds was synthesized through the reaction of thiosemicarbazone intermediates with 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone (DDQ). The antiplatelet activity of the synthesized compounds was evaluated using an aggregation test with adenosine diphosphate (ADP) and arachidonic acid (AA) as platelet aggregation inducers. Among the synthesized analogs, compound 3b exhibited the most potent inhibition of platelet aggregation induced by ADP (half maximal inhibitory concentration [IC50] = 39 ± 11 µM). Molecular docking studies of 3b revealed hydrogen bonds between the nitrogen of the thiadiazole ring and Lys280. The tolyl ring exhibited hydrophobic interactions with Tyr105, similar to the antagonist co-crystallized with P2Y12 (PDB ID: 4NTJ). These compounds have the potential to serve as lead molecules for designing P2Y12 inhibitors.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Novel Thiadiazole Derivatives as Antiplatelet Agents

Khakpash,

Esfahanizadeh,

Mahboubi-Rabbani

et al. 2024

Iran J Pharm Res

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“…The imidazo[2,1-b] [1,3,4]thiadiazole bicycle system has imidazole and 1,3,4-thiadiazole moieties. [12] Many imidazoles have been used since more than 70 years ago as Carbonic anhydrase inhibitor(CAI). Based on imidazo[2,1b] [1,3,4]thiadiazole ring [13] medications have been used in therapeutics, including acetazolamide, methazolamide, ethoxzolamide, and dorzolamide.…”

Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Synthesis and Characterization of Some Aldehyde Derivatives of Imidazo[2,1‐b][1,3,4]thiadiazole: Crystal Structure Insights, In‐Silico and Biological Studies

Sagar,

Kumara,

et al. 2023

ChemistrySelect

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The microwave‐assisted synthesis, crystallographic studies, in‐silico docking and the evaluation of in‐vitro biological activities of 2‐(3,4‐dimethoxy)‐6‐(substituted phenyl)‐ imidazo[2,1‐b][1,3,4]thiadiazole‐5‐carbaldehydes is represented here. Single‐crystal X‐ray diffraction experiments were used to identify the crystal structure of the 6‐(4‐chlorophenyl)‐2‐(3,4‐dimethoxybenzyl)imidazo[2,1‐b][1,3,4]thiadiazole‐5‐carbaldehyde. Using fingerprint plots, Hirshfeld surface analysis was used to confirm the contributions of distinct intermolecular interactions in the development of the crystal packing. Further, density functional theory calculations were employed to calculate the molecule's electronic properties. The chemically active regions on the molecule are identified by analysing the molecular electrostatic potential map. in‐silico studies revealed that the molecules can be effectively used as antibacterial agents by taking the 3q82 receptor with chloramphenicol as a standard. As compared to the chloramphenicol standard, in‐vitro tests showed that molecules 4 a, 4 b, 4 c, and 4 f had a zone of inhibition that ranged from 9 to 11 mm against both Gram‐positive (Bacillus subtilis) and Gram‐negative (Escherichia coli) bacteria. The minimum inhibitory concentration was between 40 to 70 μg/ml. These compounds′ Hydroxyl free radical scavenging activity was between 40 to 85 %. Whereas, DPPH radical scavenging activity was between 40 and 70 %. Percentage hemolysis or cell protective activity of the compounds was ineffective at 20–40 %.

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Synthesis of 4‐Hydroxy‐3‐(2‐arylimidazo[1,2‐a]pyridin‐3‐yl)quinolin‐2(1H)‐ones in the Presence of DABCO as an Efficient Organocatalyst

Khalafy

Marjani

Khalillou

2019

Journal of Heterocyclic Chem

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The one‐pot, three‐component, synthesis of a new series of 4‐hydroxy‐3‐(2‐arylimidazo[1,2‐a]pyridin‐3‐yl)quinolin‐2(1H)‐ones in the presence of DABCO as a catalyst has been achieved using aryl glyoxal monohydrates, quinoline‐2,4(1H,3H)‐dione, and 2‐aminopyridine in H2O/EtOH under reflux conditions. The cheapness of organocatalyst, simple workup, operational simplicity, regioselectivity, and high yields are some advantages of this protocol.

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An efficient synthesis of imidazo[2,1-b][1,3,4]thiadiazol-7-ium hydroxides by a one-pot, three-component reaction in water

Cited by 10 publications

References 47 publications

Synthesis and Biological Evaluation of Novel Thiadiazole Derivatives as Antiplatelet Agents

Synthesis and Biological Evaluation of Novel Thiadiazole Derivatives as Antiplatelet Agents

Microwave‐Assisted Synthesis and Characterization of Some Aldehyde Derivatives of Imidazo[2,1‐b][1,3,4]thiadiazole: Crystal Structure Insights, In‐Silico and Biological Studies

Synthesis of 4‐Hydroxy‐3‐(2‐arylimidazo[1,2‐a]pyridin‐3‐yl)quinolin‐2(1H)‐ones in the Presence of DABCO as an Efficient Organocatalyst

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