Imidazo[2,1-b]thiazole derivatives. XI. Modulation of the CD2-receptor of human T trypsinized lymphocytes by several imidazo[2,1-b]thiazoles

Harraga, S.; Nicod, Laurence; Drouhin, J. P.; Xicluna, Alain; Panouse, J. J.; Seillès, Estelle; Robert, J. F.

doi:10.1016/0223-5234(94)90101-5

Cited by 19 publications

(4 citation statements)

References 15 publications

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“…33 The synthetic route of the compounds is outlined in Scheme 1. Condensation of 2 with appropriate aromatic aldehyde afforded the corresponding N 2 -arylidene-(6-(4-chlorophenyl)imidazo[2,1-b]thiazol-3-yl)acetic acid hydrazides (3a-j).…”

Section: Resultsmentioning

confidence: 99%

Antibacterial, Antitubercular and Antiviral Activity Evaluations of Some Arylidenehydrazide Derivatives Bearing Imidazo[2,1-<i>b</i>]thiazole Moiety

Güzeldemirci

Karaman

Küçükbasmacı

2017

tjps

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ÖZObjectives: The aim of this study was to determine the probable antibacterial, antitubercular, and antiviral activities of some N 2 -arylidene-(6-(4-chlorophenyl)imidazo[2,1-b]thiazol-3-yl) acetic acid hydrazides (3a-j). Further structural optimization of the identified lead structures can lead us to new more active potential antibacterial, antitubercular, and antiviral agents. Materials and Methods:Antibacterial activities of the title compounds against Staphylococcus aureus ATCC 29213, Pseudomonas aeruginosa ATCC 27853 and Escherichia coli ATCC 25922. These molecules were also evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv (ATCC 27294) using the BACTEC 460 radiometric system and BACTEC 12B medium. Moreover, all the compounds (3a-j) were also evaluated against some DNA and RNA viruses in Madin-Darby Canine Kidney, Crandell-Rees Feline Kidney (CRFK), Vero, human embryonic lung (HEL) and HeLa cells. Results:Among the tested compounds, 3i displayed the highest efficacy against S. aureus and E. coli. Compound 3j, 5-nitro-2-furfurylidene derivative showed the highest antituberculosis activity (IC 50 : 6.16 μg/mL and IC 90 : 14.390 μg/mL). Compound 3i showed the most potent antiviral activity against feline corona virus in CRFK cell cultures (antiviral EC 50 : 7.5 μM and SI>13). Furthermore, compounds 3c and 3g displayed activity against herpes simplex virus-1 and vaccinia virus in HEL cell cultures (antiviral EC 50 values of 9; 16 and 20; 14 μM, respectively). Conclusion:On the basis of aforementioned results, it can be conluded that imidazo[2,1-b]thiazole derivatives bearing hydrazone moieties serve as promising chemical probes to design therapeutic agents with antibacterial, antitubercular, and antiviral properties.

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Section: Resultsmentioning

confidence: 99%

Antibacterial, Antitubercular and Antiviral Activity Evaluations of Some Arylidenehydrazide Derivatives Bearing Imidazo[2,1-<i>b</i>]thiazole Moiety

Güzeldemirci

Karaman

Küçükbasmacı

2017

tjps

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“…After standing for 3 days, 2amino-3-[(4-bromobenzoyl)methyl]-4-(ethoxycarbonylmethyl)thiazolium bromide (1) was obtained [29]. By heating the compound 2 and hydrazine hydrate in ethanol, 2-[6-(4-bromophenyl)imidazo[2,1-b]thiazole-3-yl]acetohydrazide (3) was obtained [30]. By heating the compound 2 and hydrazine hydrate in ethanol, 2-[6-(4-bromophenyl)imidazo[2,1-b]thiazole-3-yl]acetohydrazide (3) was obtained [30].…”

Section: Chemistrymentioning

confidence: 99%

Design and synthesis of novel Imidazo[2,1-b]thiazole derivatives as potent antiviral and antimycobacterial agents

Gürsoy

Dincel

Naesens

et al. 2020

Bioorganic Chemistry

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A B S T R A C TA series of novel acyl-hydrazone (4a-d) and spirothiazolidinone (5a-d, 6a-d) derivatives of imidazo[2,1-b] thiazole were synthesized and evaluated for their antiviral and antimycobacterial activity. The antituberculosis activity was evaluated by using the Microplate Alamar Blue Assay and the antiviral activity was evaluated against diverse viruses in mammalian cell cultures. According to the biological activity studies of the compounds, 5a-c displayed hope promising antitubercular activity, 6d was found as potent for Coxsackie B4 virus, 5d was found as effective against Feline corona and Feline herpes viruses. Consequently, the obtained results displayed that, 5a-d and 6d present a leading structure for future drug development due to its straightforward synthesis and relevant bioactivity.

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“…Recently much interest has been focused on the chemistry and the biological activity of imidazothiazoles and their derivatives [1−3]. Therefore, fusion of imidazole and thiazole moieties into a single drug gave a potent immunomodulating drug called levamisole, which is 2,3,5,6-tetrahydro-6-phenylimidazo [2,1-b]thiazole [4]. Recently we reported on the antimicrobial activity of imidazo [2,1-b]thiazole derivatives [5−7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antituberculosis Activity of Cycloalkylidenehydrazide and 4-Aza-1-thiaspiro [4.5] decan-3-one Derivatives of Imidazo [2][1-b]thiazole

Ulusoy

2011

Arzneimittelforschung

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New N2-cycloalkylidene-(6-phenyl/4-chlorophenylimidazo[2,1-b]thiazol-3-yl) acetic acid hydrazides (2a-h and 3a-b) were synthesized by reacting (6-phenyl/4-chlorophenylimidazo[2,1-b]thiazol-3-yl)acetic acid hydrazides with cyclohexanones or cyclopentanone. Furthermore, 2a-h were refluxed with thioglycolic or thiolactic acid to give 4-[[(6-phenyl/4-chlorophenylimidazo[2,1-b]thiazol-3-yl) acetyl]amino]-4-aza-1-thiaspiro[4.5]decan-3-ones (4a-h and 5a-h). The structures of the title compounds were established by spectral data (IR, 1H-NMR, 13C-NMR and EIMS (Electron Impact Mass Spectrometry)) and elemental analysis. The synthesized compounds were evaluated for antituberculosis activity against Mycobacterium tuberculosis H37Rv (ATCC 27294). The compounds exhibited varying degrees of inhibition in the in vitro primary screening that was conducted at a concentration of 6.25 micrograms/ml against M. tuberculosis H37Rv (ATCC 27294) in Bactec 12B medium using the Bactec 460 radiometric system or a broth microdilution assay, the Microplate Alamar Blue Assay (MABA). Compounds 2f, 2h, 3b, 4a, 4c, 4d, 5a-e and 5h demonstrating at 1-east 90% inhibition in the primary screen were re-tested at lower concentrations against M. tuberculosis H37Rv (ATCC 27294) to determine the actual minimum inhibitory concentration (MIC) using MABA. The most active compounds were found to be 4d and 5c. The structure-activity relationships of the derivatives were investigated.

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Imidazo[2,1-b]thiazole derivatives. XI. Modulation of the CD2-receptor of human T trypsinized lymphocytes by several imidazo[2,1-b]thiazoles

Cited by 19 publications

References 15 publications

Antibacterial, Antitubercular and Antiviral Activity Evaluations of Some Arylidenehydrazide Derivatives Bearing Imidazo[2,1-<i>b</i>]thiazole Moiety

Antibacterial, Antitubercular and Antiviral Activity Evaluations of Some Arylidenehydrazide Derivatives Bearing Imidazo[2,1-<i>b</i>]thiazole Moiety

Design and synthesis of novel Imidazo[2,1-b]thiazole derivatives as potent antiviral and antimycobacterial agents

Synthesis and Antituberculosis Activity of Cycloalkylidenehydrazide and 4-Aza-1-thiaspiro [4.5] decan-3-one Derivatives of Imidazo [2][1-b]thiazole

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