Synthesis and antitrichinellosis activity of some 2-substituted-[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-ones

Mavrova, Anelia Ts.; Anichina, Kameliya; Vuchev, Dimitar; Tsenov, Jordan A.; Kondeva, Magdalena S.; Micheva, Mitka K.

doi:10.1016/j.bmc.2005.06.046

Cited by 71 publications

(32 citation statements)

References 11 publications

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“…In this context, it is pertinent to mention that while the prevailing solution-phase protocol [30–32] uses an acid scavenger, such as sodium hydroxide, triethylamine, pyridine or sodium acetate, the solvent-free methodology involved in the present investigation does not require any acid scavenger.…”

Section: Resultsmentioning

confidence: 99%

A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions

Sathishkumar¹,

Nagarajan²,

Shanmugavelan³

et al. 2013

Beilstein J. Org. Chem.

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SummaryA rapid and efficient one pot solvent/scavenger-free protocol for the synthesis of 2-iminothiazolidin-4-ones has been developed. Interestingly, the regio/stereoselective synthesis affords the regioisomeric (Z)-3-alkyl/aryl-2-(2-phenylcyclohex-2-enylimino)thiazolidin-4-one as the sole product in good yield. The selectivities observed have been rationalized based on the relative magnitude of the allylic strains developed during the course of the reaction. This is the first report wherein the impact of allylic strains in directing the regiocyclization has been noted.

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Section: Resultsmentioning

confidence: 99%

A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions

Sathishkumar¹,

Nagarajan²,

Shanmugavelan³

et al. 2013

Beilstein J. Org. Chem.

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“…Within the small molecule compounds, the benzimidazole scaffold is a common therapeutic pharmacophore found in several bioactive compounds(7). Its pharmacological activities including anti-viral(40), anti-microbial(41, 42), anti-parasitic(43), anti-inflammatory(44) and anti-hypertensive(45). Therefore, we chose the benzimidazole as the pharmacophore scaffold and utilized combinatorial chemistry to generate benzimidazole-based compounds.…”

Section: Discussionmentioning

confidence: 99%

A Novel Galectin-1 Inhibitor Discovered through One-Bead Two-Compound Library Potentiates the Antitumor Effects of Paclitaxel in vivo

Shih

Liu

Fung

et al. 2017

Molecular Cancer Therapeutics

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Through the one-bead two-compound (OB2C) ultra-high throughput screening method, we discovered a new small molecule compound LLS2 that can kill a variety of cancer cells. Pull-down assay and LC MS/MS indicated that galectin-1 is the target protein of LLS2. Galectin-1 is known to be involved in the regulation of proliferation, apoptosis, cell cycle, and angiogenesis. Binding of LLS2 to galectin-1 decreased membrane-associated H-Ras and K-Ras, and contributed to the suppression of pErk pathway. Importantly, combination of LLS2 with paclitaxel (a very important clinical chemotherapeutic agent) was found to exhibit synergistic activity against several human cancer cell lines (ovarian cancer, pancreatic cancer, and breast cancer cells) in vitro. Furthermore, in vivo therapeutic study indicated that combination treatment with paclitaxel and LLS2 significantly inhibits the growth of ovarian cancer xenografts in athymic mice. Our results presented here indicate that the OB2C combinatorial technology is a highly efficient drug-screening platform and LLS2 discovered through this method can be further optimized for anti-cancer drug development.

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“…Finding good initial lead compounds and progressing compounds into the clinic has proven difficult owing to bottlenecks in the discovery pipeline [4]. Benzimidazolone derivatives have been found to exhibit anti-HIV [5], antitrichinellosis [6], antinociceptive [7], antitumor activities [8], and other pharmacological activities [9–12]. For instance, it has been reported in recent literature that benzimidazolone bearing a sugar or piperidine residue on the aromatic nitrogen effectively inhibits the growth of bacteria [13,14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Activities of 1-Alkyl-3-methacryloyl (Acryloyl) of Benzimidazolone (Thione) Derivatives

Sang¹,

Wu²,

Ji³

2012

IJMS

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A series of (28) 1-alkyl-3-methacryloyl (acryloyl)-benzimidazolone (thione) deriv-atives were synthesized. The structures of the new derivatives were confirmed by 1H-NMR, 13C-NMR and ESI-MS spectral analysis. The antibacterial activities of these compounds against several strains of bacteria, such as Bacillus cereus, Bacillus subtilis, Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa, were evaluated by methods of paper disc-diffusion and broth mciro-dilution. Methacryloyl derivatives displayed higher antibacterial activities against tested bacterial strains than those of acryloyl derivatives in in vitro tests. A structure-activity relationship (SAR) study revealed that the presences of the methacryloyl moieties is essential to the antibacterial activities of the compounds.

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Synthesis and antitrichinellosis activity of some 2-substituted-[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-ones

Cited by 71 publications

References 11 publications

A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions

A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions

A Novel Galectin-1 Inhibitor Discovered through One-Bead Two-Compound Library Potentiates the Antitumor Effects of Paclitaxel in vivo

Synthesis and Antibacterial Activities of 1-Alkyl-3-methacryloyl (Acryloyl) of Benzimidazolone (Thione) Derivatives

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