Synthesis, characterization and antibacterial activity of a new calcium complex using sodium 2-mercaptobenzothiazole and 1, 10-phenanthroline as ligands

Gulab, Hussain; Shah, Zarbad; Mahmood, Mazhar; Shah, Syed Raza; Ali, Sajid; Iqbal, Muhammad; Khan, Muhammad Naeem; Flörke, Ülrich; Khan, Shahid Ali

doi:10.1016/j.molstruc.2017.10.045

Cited by 11 publications

(5 citation statements)

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“…The outcomes revealed that metal complexes 175a and 175b exhibited excellent antibacterial efficacy (ZOI = 12-18 mm) as compared to standard drug streptomycin (ZOI = 8 mm) against L. monocytogenes [83]. Gulab et al (2018) assessed the antimicrobial activity of calcium complexes of 2-mercaptobenzothiazole and 1,10phenanthroline (Scheme 40). The study showed that complex 179 exhibited a better antibacterial effect (ZOI = 25 mm) as compared to the reference compound levofloxacin (ZOI = 22 mm) towards P. aeruginosa [84].…”

Section: Other Miscellaneous Benzothiazole Derivatives As Antibacteri...mentioning

confidence: 99%

“…Gulab et al (2018) assessed the antimicrobial activity of calcium complexes of 2-mercaptobenzothiazole and 1,10phenanthroline (Scheme 40). The study showed that complex 179 exhibited a better antibacterial effect (ZOI = 25 mm) as compared to the reference compound levofloxacin (ZOI = 22 mm) towards P. aeruginosa [84]. Structure activity relationship of above-mentioned active benzothiazole derivatives have been presented in Fig.…”

Section: Other Miscellaneous Benzothiazole Derivatives As Antibacteri...mentioning

confidence: 99%

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Recent insights into antibacterial potential of benzothiazole derivatives

et al. 2023

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Antimicrobial resistance (AMR) is a worldwide concern among infectious diseases due to increased mortality, morbidity and treatment cost. According to WHO 2019 report, among the 32 antibiotics in the clinical trials, only six were classified as innovative and containing novel moiety. The remaining antibiotics from this list contain previously known moiety (WHO AMR 2019). Therefore, the development of novel antibiotics to control resistance problems is crucial. Benzothiazole derivatives are of great interest due to their wide range of biological activities and medicinal applications. Reported data indicated that benzothiazole derivatives displayed antibacterial activity by inhibiting the dihydroorotase, DNA gyrase, uridine diphosphate-n-acetyl enol pyruvyl glucosamine reductase (MurB), peptide deformylase, aldose reductase, casdihydrofolate reductase, enoyl acyl carrier protein reductase, dialkylglycine decarboxylase, dehydrosqualene synthase, dihydropteroate synthase and tyrosine kinase. The present review analyzed the synthesis, structure-activity relationship (SAR) and mechanism of action studies of benzothiazole derivatives as antibacterial agents reported by various research groups in the last five years (2018–2022). Different patents on the antimicrobial activity of benzothiazole derivatives have also been summarized. The finding of the present review will be beneficial for the researchers in the development of novel antibacterial molecules based on benzothiazole moiety. Graphical Abstract

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Section: Other Miscellaneous Benzothiazole Derivatives As Antibacteri...mentioning

confidence: 99%

Section: Other Miscellaneous Benzothiazole Derivatives As Antibacteri...mentioning

confidence: 99%

Recent insights into antibacterial potential of benzothiazole derivatives

et al. 2023

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“…It is noteworthy that their derivatives are of huge interest in scientific research owing to their potential pharmacological properties [ 1 ]. The widespread use of these substances in the medical field, such as their application as anti-inflammatory [ 2 ], antibacterial [ 3 , 4 ], and antifungal agents [ 5 ], along with their efficacy in treating diseases such as cancer and cardiovascular illnesses [ 6 ], has garnered considerable attention. The interest in this group of compounds arises not only from their medicinal applications but also from their diverse uses in various industries: 2-mercaptobenzothiazole serves as a widely utilized organic corrosion inhibitor [ 7 ] for copper [ 8 , 9 ] and zinc [ 10 , 11 ], and as a component of self-healing and anticorrosion smart coatings [ 12 , 13 , 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

“…H NMR (400 MHz, CDCl 3 ) δ (ppm): 7.72 (d, 1H,3 J H,H = 8.28 Hz, Ar), 7.51 (s, 1H, Ar), 7.21 (m, 1H, Ar), 6.41 (d, 1H,3 J H,H = 17.32 Hz, CH=CH 2 ), 6.11 (q, 1H, CH=CH 2 ), 5.82 (d, 1H,3 J H,H = 10.48 Hz, CH=CH 2 ), 4.53 (t, 2H, CH 2 -O), 3.63 (t, 2H, S-CH 2 ), 2.39 (t, 3H, CH 3 ) 13. C NMR (100 MHz, CDCl 3 ) δ (ppm): 165.8, 164.1, 151.1, 135.5, 134.6, 131.2, 128.0, 127.6, 121.1, 120.9, 62.3, 31.9, 21.4.…”

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Design, Synthesis, and Spectral Properties of Novel 2-Mercaptobenzothiazole Derivatives

Skotnicka,

Kabatc-Borcz

2024

Materials

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This paper is focused on the optimalization of methods for the synthesis, isolation, and purification of 2-mercaptobenzothiazole-based acrylic and methacrylic monomers. The structures of the newly synthesized compounds were confirmed through infrared (IR) and nuclear magnetic resonance spectroscopy (NMR). Spectroscopic properties of the resulting 2-mercaptobenzothiazole derivatives were determined based on their absorption spectra and molar absorption coefficients in solvents with varying polarities. A correlation was established between the calculated density functional theory (DFT) energies and Frontier Molecular Orbitals and the experimental observations, confirming their consistency. The practical utility of the synthesized compounds, particularly in future polymerization processes, hinges on a thorough understanding of these properties.

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“…[36][37][38] The s-block complexes of phen with S-donor co-ligands are rare; a CSD search (2019) resulted in only five hits. [39][40][41][42][43] 1,3-Benzothiazole-2-thiol (BT-H; Figure 1) is a natural product and was first isolated from a fermentation culture of a Micrococcus sp. bacterial symbiont of the marine sponge Tedania ignis.…”

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confidence: 99%

New s‐block complexes of 1,10‐phenanthroline and 1,3‐benzothizole‐2‐thiolate inhibit ureasein silicoandin vitro

Shah

Khiat

et al. 2020

Applied Organom Chemis

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The coordination chemistry of 1,10‐phenanthroline (phen) and sodium 1,3‐benzothiazole‐2‐thiolate (SBT) with selected s‐block elements has been investigated. Four metal complexes were prepared and their structures were characterized using a variety of analytical techniques including infrared, UV–visible, 1H NMR and 13C NMR spectroscopies, elemental analysis, mass spectrometry and single‐crystal X‐ray diffraction. The reactions of phen and SBT with M(X)n (M = K(I), Cs(I), Mg(II), Sr(II); X = OH−, CO3−, Cl−; n = 1, 2) in MeOH–H2O yielded one‐dimensional chains of both potassium [K2(phen)2(BT)2(H2O)4]n (1) and caesium [Cs(phen)(BS)(H2O)]n (2) (where BT = 1,3‐benzthiazole‐2‐thiolate and BS = 1,3‐benzthiazole‐2‐sulfinothiolate) and mononuclear complexes of both magnesium {[Mg(phen)(H2O)4](BT)2·phen} (3) and strontium {[Sr(phen)2(H2O)4](BT)2} (4). In these complexes, phen binds via an N,N′ chelate pocket, while the monoanonic BT− ligands either coordinate in a bidentate fashion (in the case of 1) or remain uncoordinated (in the case of 3 and 4). In complex 2, SBT ligand was oxidized in situ into a new BS ligand. The sulfinothiolate oxygen atoms in BS coordinate with caesium in a tridentate fashion. Complexes 1–4 were evaluated against urease for enzyme inhibition. The complexes displayed significant inhibition with IC50 values in the range 10.8–45.8 μM. In order to examine the structure–activity relationship, the complexes were docked at the active site of urease. Docking results clearly demonstrate the binding of each complex within the active site of the enzyme.

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Synthesis, characterization and antibacterial activity of a new calcium complex using sodium 2-mercaptobenzothiazole and 1, 10-phenanthroline as ligands

Cited by 11 publications

References 14 publications

Recent insights into antibacterial potential of benzothiazole derivatives

Recent insights into antibacterial potential of benzothiazole derivatives

Design, Synthesis, and Spectral Properties of Novel 2-Mercaptobenzothiazole Derivatives

New s‐block complexes of 1,10‐phenanthroline and 1,3‐benzothizole‐2‐thiolate inhibit ureasein silicoandin vitro

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