Synthesis, crystal structures and antimicrobial activities of 3-methyl and 3-bromo substituted benzo[b]thiophene based thiosemicarbazones

IF 2.1 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Sulfur Chemistry Pub Date : 2024-01-01 DOI:10.1080/17415993.2023.2260916

Emine Öztürk , Elif Subaşı , Ece Su Çakmakçı , Aslı Şahiner , Betül Şen Yüksel

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Abstract

A series of thiosemicarbazones (TSCs) (L^1–5) containing benzothiophen moiety were prepared via the reaction of 3-methyl/3-bromobenzo[b]thiophene-2-carboxaldehyde with appropriate thiosemicarbazides. The compounds were confirmed by elemental analysis, FT-IR, ¹H NMR, MALDI-TOF and single crystal X-Ray diffraction techniques. The compounds exist in the E conformation with respect to the azomethine C = N double bond as confirmed by their C8/C9/N1/N2 torsion angles being 178.4(2)° (L¹), – 175.2(5)/177.4(5)° (L²), 177.5(2)° (L³), 179.7(3)° (L⁴), and – 177.4(7)° (L⁵). These compounds were researched for their antibacterial activity against Gram-positive bacteria (E. faecalis and S. aureus), Gram-negative bacteria (E. coli, P. aeruginosa and S. marcescens) and antifungal activity against a yeast species C. albicans. The ligands possessed varying degrees of antimicrobial activity. Generally, the compounds demonstrated higher efficacy against gram-positive bacteria than gram-negative ones. The antifungal activity of the compounds against C. albicans was found to be lower in comparison to their activity against bacteria.

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3-甲基和 3-溴取代的苯并[b]噻吩基硫代氨基甲酸盐的合成、晶体结构和抗菌活性

通过 3-甲基/3-溴苯并[b]噻吩-2-甲醛与适当的硫代氨基脲反应，制备了一系列含有苯并噻吩分子的硫代氨基脲（TSCs）（L1-5）。这些化合物通过元素分析、傅立叶变换红外光谱、1H NMR、MALDI-TOF 和单晶 X 射线衍射技术得到了证实。这些化合物的 C8/C9/N1/N2 扭转角分别为 178.4(2)° (L1)、- 175.2(5)/177.4(5)° (L2)、177.5(2)° (L3)、179.7(3)° (L4) 和 - 177.4(7)° (L5)，证实了偶氮甲基 C = N 双键的 E 构象。研究了这些化合物对革兰氏阳性菌（粪大肠杆菌和金黄色葡萄球菌）、革兰氏阴性菌（大肠杆菌、绿脓杆菌和马氏酵母菌）的抗菌活性，以及对酵母菌白僵菌的抗真菌活性。配体具有不同程度的抗菌活性。一般来说，这些化合物对革兰氏阳性菌的效力高于对革兰氏阴性菌的效力。与对细菌的活性相比，这些化合物对白癣菌的抗真菌活性较低。

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来源期刊

Journal of Sulfur Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

4.10

自引率

9.10%

发文量

审稿时长

6-12 weeks

期刊介绍： The Journal of Sulfur Chemistry is an international journal for the dissemination of scientific results in the rapidly expanding realm of sulfur chemistry. The journal publishes high quality reviews, full papers and communications in the following areas: organic and inorganic chemistry, industrial chemistry, materials and polymer chemistry, biological chemistry and interdisciplinary studies directly related to sulfur science. Papers outlining theoretical, physical, mechanistic or synthetic studies pertaining to sulfur chemistry are welcome. Hence the target audience is made up of academic and industrial chemists with peripheral or focused interests in sulfur chemistry. Manuscripts that truly define the aims of the journal include, but are not limited to, those that offer: a) innovative use of sulfur reagents; b) new synthetic approaches to sulfur-containing biomolecules, materials or organic and organometallic compounds; c) theoretical and physical studies that facilitate the understanding of sulfur structure, bonding or reactivity; d) catalytic, selective, synthetically useful or noteworthy transformations of sulfur containing molecules; e) industrial applications of sulfur chemistry; f) unique sulfur atom or molecule involvement in interfacial phenomena; g) descriptions of solid phase or combinatorial methods involving sulfur containing substrates. Submissions pertaining to related atoms such as selenium and tellurium are also welcome. Articles offering routine heterocycle formation through established reactions of sulfur containing substrates are outside the scope of the journal.