Imidazo[2,1-b]thiazole derivatives as new inhibitors of 15-lipoxygenase

Tehrani, Maliheh Barazandeh; Emami, Saeed; Asadi, Mehdi; Saeedi, Mina; Mirzahekmati, Mohammadreza; Ebrahimi, Seyyed Mostafa; Mahdavi, Mohammad; Nadri, Hamid; Moradi, Alireza; Moghadam, Farshad Homayouni; Farzipour, Soghra; Vosooghi, Mohsen; Foroumadi, Alireza; Shafiee, Abbas

doi:10.1016/j.ejmech.2014.10.011

Cited by 35 publications

(13 citation statements)

References 32 publications

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“…As a continuation of their research on the development of 15-LOX inhibitors [ 75 ], a series of new 3,6-diphenylimidazo[2,1-b]thiazol-5-amine derivatives were designed, synthesized and evaluated as inhibitors of the above enzyme by Tehrani et al [ 76 ]. The study revealed that, among 14 synthesized and tested derivatives, 5a – 5d ( Figure 6 ) appeared to be the most potent with IC 50 values ranging between 11.5–35 μM.…”

Section: Thiazoles As Cox/lox Inhibitorsmentioning

confidence: 99%

Thiazoles and Thiazolidinones as COX/LOX Inhibitors

2018

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Inflammation is a natural process that is connected to various conditions and disorders such as arthritis, psoriasis, cancer, infections, asthma, etc. Based on the fact that cyclooxygenase isoenzymes (COX-1, COX-2) are responsible for the production of prostaglandins that play an important role in inflammation, traditional treatment approaches include administration of non-steroidal anti-inflammatory drugs (NSAIDs), which act as selective or non-selective COX inhibitors. Almost all of them present a number of unwanted, often serious, side effects as a consequence of interference with the arachidonic acid cascade. In search for new drugs to avoid side effects, while maintaining high potency over inflammation, scientists turned their interest to the synthesis of dual COX/LOX inhibitors, which could provide numerous therapeutic advantages in terms of anti-inflammatory activity, improved gastric protection and safer cardiovascular profile compared to conventional NSAIDs. Τhiazole and thiazolidinone moieties can be found in numerous biologically active compounds of natural origin, as well as synthetic molecules that possess a wide range of pharmacological activities. This review focuses on the biological activity of several thiazole and thiazolidinone derivatives as COX-1/COX-2 and LOX inhibitors.

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Section: Thiazoles As Cox/lox Inhibitorsmentioning

confidence: 99%

Thiazoles and Thiazolidinones as COX/LOX Inhibitors

2018

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“…RAMAMURTHY 1,* and E. JAYACHANDRAN Thiazolo imidazoles are the fused ring systems involving thiazole and imidazole with a common brige-head nitrogen at position-4. Substituted thiazolo imidazoles are also of great importance because of their remarkable biological activities including antimicrobial [16], anticancerous [17], antiproliferative [18], antitubercular [19], lipoxygenase inhibiting [20], anti-infective activity [16], etc. Still their antimicrobial activities have shown only handful of results so far.…”

Section: Synthesis and Antimicrobial Evaluation Of Some New Thiazolo mentioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of Some New Thiazolo Imidazole Analogs

Ramamurthy¹,

Jayachandran²

2017

Asian J. Chem.

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Thiazole and imidazole derivatives have attracted medicinal chemists owing to their extensive biological activities. Present paper describes the synthesis of some new thiazolo imidazole derivatives. 4-Substituted phenacyl bromides were prepared from substituted acetophenones. The products were condensed with thiourea to obtain 2-amino-4-(4-substituted phenyl)thiazoles which on further reaction with 4-substituted phenacyl bromides resulted in 3,6-di(substituted phenyl)imidazo[2,1-b] thiazoles (3a-3i). The formation of all the compounds was established by spectral techniques like IR, 1 H NMR and Mass spectral data. The title compounds were screened for their antimicrobial activity against Gram-positive bacteria S. aureus and B. subtilis, Gram-negative bacteria E. coli and K. pneumoniae and the fungal strains like A. niger, C. albicans and C. neoformans. The results indicated that the compounds coded 3a, 3c, 3g and 3i showed significant activity than the remaining compounds.

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“…Herein, we focused on 15-LOX inhibitors such as phthalimides bearing thiadiazoles, 16 2 H -chromen-2-ones, 4−6 imidazole-2(3H)-thiones, 17 pyrazoles, 18 imidazo[2,1-b]thiazoles, 19 and thioureas. 20 Recently, we studied the 15-LOX inhibitory activity of 3-aroyl-1-(4-sulfamoylphenyl)thiourea derivatives (A, Figure 1).…”

Section: −6mentioning

confidence: 99%

Synthesis of novel derivatives of chromenone bearing an $N$-carbamothioyl moiety as soybean 15-LOX inhibitors

Kaviani¹,

Saeedi²,

Mahdavi³

et al. 2017

Turk J Chem

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Novel derivatives of chromenone bearing an N -carbamothioyl moiety were synthesized and evaluated for their soybean 15-LOX inhibitory activity. Synthesis of the target compounds was started from 7-hydroxy-2 H -chromen-2-one.It was reacted with 1-fluoro-2(4)-nitrobenzene to obtain the corresponding nitrophenoxy-chromenone derivative. Reduction of the nitro group was achieved in the presence of Zn/NH 4 Cl and reaction of the latter compound with in situ prepared benzoyl isothiocyanate led to the formation of the title compounds. All compounds were characterized and tested against soybean 15-LOX. Among them, 4-methyl-N -((4-((2-oxo-2 H -chromen-7-yl)oxy)phenyl)carbamothioyl)benzamide (7l) showed the best activity as potent as the reference drug, quercetin.

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Imidazo[2,1-b]thiazole derivatives as new inhibitors of 15-lipoxygenase

Cited by 35 publications

References 32 publications

Thiazoles and Thiazolidinones as COX/LOX Inhibitors

Thiazoles and Thiazolidinones as COX/LOX Inhibitors

Synthesis and Antimicrobial Evaluation of Some New Thiazolo Imidazole Analogs

Synthesis of novel derivatives of chromenone bearing an $N$-carbamothioyl moiety as soybean 15-LOX inhibitors

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