Tandem synthesis and antibacterial screening of novel thieno[2,3-<i>b</i>]thiophene-linked <i>bis</i>(thiazole) hybrids

Sanad, Sherif M. H.; Mekky, Ahmed E. M.; Elreedy, Ahmed

doi:10.1080/00397911.2021.1918170

Cited by 6 publications

(1 citation statement)

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“…With the goal of synthesizing new chromene and thiazole‐based compounds with promising bioactivity, particularly antibacterial activity, [46–50] we aimed to study the impact of arylazo units on the antibacterial activity of new chromene‐thiazole hybrids. Using a three‐component protocol, we prepared hybrid 1 and new hybrids 2 – 4 with arylazo units attached to chromene‐C6 and/or thiazole‐C5 (see Figure 2).…”

Section: Introductionmentioning

confidence: 99%

New Arylazo‐Based (Chromene‐Thiazole) Hybrids as Potential MRSA Inhibitors

Abdallah

Sanad

Mekky

et al. 2023

Chemistry & Biodiversity

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A three-component protocol was established to efficiently synthesize (chromene-thiazole) and related arylazo analogs in good to excellent yields. The desired products were prepared by reacting the appropriate salicylaldehydes, 2-cyanothioacetamide, and chloroacetone or hydrazonyl chlorides. Using piperidine as a mediator in ethanol at 80 °C for 4 -6 h, the three-component protocol produce the target hybrids in 87 -96 % yields. The newly synthesized products showed a broad range of antibacterial activity. The addition of an arylazo unit at the chromene-C6 position significantly improved the antibacterial activity, while the impact of adding an arylazo group at the thiazole-C5 position varied based on the electronic characteristics of the para-substituted arene unit. Generally, series that is linked to two arylazo units, one at chromene-C6 and the other at thiazole-C5, showed the best activity. Some new hybrids showed effective antibacterial activity than ciprofloxacin with MIC/ MBC values up to 1.9/3.9 μM against S. aureus and E. coli. Additionally, they demonstrated better effectiveness against MRSA ATCC:33591 and ATCC:43300 compared to linezolid, with MIC/MBC values up to 4.0/16.1 and 3.9/ 15.6 μM, respectively. The data predicted for the physicochemical properties, lipophilicity, pharmacokinetics, and drug-likeness of new arylazo-based chromene-thiazole hybrids evaluated by SwissADME. As a result of the above, products that are linked to two arylazo units can be considered drug-like scaffolds.

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Section: Introductionmentioning

confidence: 99%