Novel Potent Imidazo[1,2-a]pyridine-N-Glycinyl-Hydrazone Inhibitors of TNF-α Production: In Vitro and In Vivo Studies
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{"title"=>"Novel potent imidazo[1,2-a]pyridine-N-glycinyl-hydrazone inhibitors of TNF-α production: In Vitro and in Vivo studies", "type"=>"journal", "authors"=>[{"first_name"=>"Renata B.", "last_name"=>"Lacerda", "scopus_author_id"=>"36881758100"}, {"first_name"=>"Natália M.", "last_name"=>"Sales", "scopus_author_id"=>"56113140300"}, {"first_name"=>"Leandro L.", "last_name"=>"Da Silva", "scopus_author_id"=>"25723122800"}, {"first_name"=>"Roberta", "last_name"=>"Tesch", "scopus_author_id"=>"55322404100"}, {"first_name"=>"Ana Luisa P", "last_name"=>"Miranda", "scopus_author_id"=>"35509700600"}, {"first_name"=>"Eliezer J.", "last_name"=>"Barreiro", "scopus_author_id"=>"7005260008"}, {"first_name"=>"Patricia D.", "last_name"=>"Fernandes", "scopus_author_id"=>"34975072900"}, {"first_name"=>"Carlos A M", "last_name"=>"Fraga", "scopus_author_id"=>"7005407792"}], "year"=>2014, "source"=>"PLoS ONE", "identifiers"=>{"issn"=>"19326203", "pui"=>"372817452", "pmid"=>"24632827", "doi"=>"10.1371/journal.pone.0091660", "sgr"=>"84898476997", "scopus"=>"2-s2.0-84898476997"}, "id"=>"064d0a28-b814-3f2b-9f47-81cb1388b858", "abstract"=>"In this work, we describe the design, synthesis and pharmacological evaluation of novel imidazo[1,2-a]pyridine-N-glycinyl-hydrazone derivatives (1a-k) intended for use as inhibitors of tumor necrosis factor alpha (TNF-α) production. The compounds were designed based on the orally active anti-inflammatory prototype LASSBio-1504 (2), which decreases the levels of the pro-inflammatory cytokine TNF-α in vitro and in vivo. The in vitro pharmacological evaluation of the imidazo[1,2-a]pyridine compounds (1) showed that substitution of the N-phenylpyrazole core present in prototype 2 by a bioisosteric imidazo[1,2-a]pyridine scaffold generated anti-TNF-α compounds that were more potent than the previously described N-phenylpyrazole derivative 2 and as potent as SB-203580, a p38 MAPK inhibitor. The most active derivative (E)-2-(2-tert-butylimidazo[1,2-a]pyridin-3-ylamino)-N'-(4-chlorobenzylidene) acetohydrazide, or LASSBio-1749 (1i) was orally active as an anti-inflammatory agent in a subcutaneous air pouch model, reducing expressively the levels in vivo of TNF-α and other pro-inflammatory cytokines at all of the tested doses.", "link"=>"http://www.mendeley.com/research/novel-potent-imidazo12apyridinenglycinylhydrazone-inhibitors-tnf%CE%B1-production-vitro-vivo-studies-1", "reader_count"=>15, "reader_count_by_academic_status"=>{"Professor > Associate Professor"=>1, "Student > Doctoral Student"=>2, "Researcher"=>2, "Student > Ph. D. Student"=>2, "Student > Postgraduate"=>1, "Other"=>3, "Student > Master"=>2, "Student > Bachelor"=>1, "Lecturer"=>1}, "reader_count_by_user_role"=>{"Professor > Associate Professor"=>1, "Student > Doctoral Student"=>2, "Researcher"=>2, "Student > Ph. D. Student"=>2, "Student > Postgraduate"=>1, "Other"=>3, "Student > Master"=>2, "Student > Bachelor"=>1, "Lecturer"=>1}, "reader_count_by_subject_area"=>{"Biochemistry, Genetics and Molecular Biology"=>3, "Agricultural and Biological Sciences"=>3, "Medicine and Dentistry"=>1, "Business, Management and Accounting"=>1, "Chemistry"=>7}, "reader_count_by_subdiscipline"=>{"Medicine and Dentistry"=>{"Medicine and Dentistry"=>1}, "Chemistry"=>{"Chemistry"=>7}, "Agricultural and Biological Sciences"=>{"Agricultural and Biological Sciences"=>3}, "Business, Management and Accounting"=>{"Business, Management and Accounting"=>1}, "Biochemistry, Genetics and Molecular Biology"=>{"Biochemistry, Genetics and Molecular Biology"=>3}}, "reader_count_by_country"=>{"Denmark"=>2}, "group_count"=>1}

Scopus | Further Information

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Figshare

  • {"files"=>["https://ndownloader.figshare.com/files/1420924"], "description"=>"<div><p>In this work, we describe the design, synthesis and pharmacological evaluation of novel imidazo[1,2-a]pyridine-N-glycinyl-hydrazone derivatives (1a–k) intended for use as inhibitors of tumor necrosis factor alpha (TNF-α) production. The compounds were designed based on the orally active anti-inflammatory prototype LASSBio-1504 (2), which decreases the levels of the pro-inflammatory cytokine TNF-α in vitro and in vivo. The in vitro pharmacological evaluation of the imidazo[1,2-a]pyridine compounds (1) showed that substitution of the N-phenylpyrazole core present in prototype 2 by a bioisosteric imidazo[1,2-a]pyridine scaffold generated anti-TNF-α compounds that were more potent than the previously described N-phenylpyrazole derivative 2 and as potent as SB-203580, a p38 MAPK inhibitor. The most active derivative (E)-2-(2-tert-butylimidazo[1,2-a]pyridin-3-ylamino)-N’-(4-chlorobenzylidene) acetohydrazide, or LASSBio-1749 (1i) was orally active as an anti-inflammatory agent in a subcutaneous air pouch model, reducing expressively the levels in vivo of TNF-α and other pro-inflammatory cytokines at all of the tested doses.</p></div>", "links"=>[], "tags"=>["medicinal chemistry", "Drugs and devices", "Drug research and development", "drug discovery", "potent", "inhibitors", "studies"], "article_id"=>962636, "categories"=>["Medicine", "Chemistry"], "users"=>["Renata B. Lacerda", "Natália M. Sales", "Leandro L. da Silva", "Roberta Tesch", "Ana Luisa P. Miranda", "Eliezer J. Barreiro", "Patricia D. Fernandes", "Carlos A. M. Fraga"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0091660", "stats"=>{"downloads"=>0, "page_views"=>9, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/Novel_Potent_Imidazo_1_2_a_pyridine_N_Glycinyl_Hydrazone_Inhibitors_of_TNF_Production_In_Vitro_and_In_Vivo_Studies/962636", "title"=>"Novel Potent Imidazo[1,2-<i>a</i>]pyridine-<i>N</i>-Glycinyl-Hydrazone Inhibitors of TNF-α Production: <i>In Vitro</i> and <i>In Vivo</i> Studies", "pos_in_sequence"=>0, "defined_type"=>3, "published_date"=>"2014-03-14 03:56:02"}
  • {"files"=>["https://ndownloader.figshare.com/files/1420921"], "description"=>"<p>The results are expressed as the <sup>a</sup>percent inhibition and <sup>b</sup>percent cell viability compared to the vehicle (DMSO); n = 3 independent experiments performed in duplicate;</p><p>*p = 0.05 using student’s t test; <sup>c</sup>IC<sub>50</sub> values were determined using at least five concentrations, the range concentration are showed in parentheses; <sup>d</sup> SI = cytotoxicity IC<sub>50</sub>/anti-TNF-α IC<sub>50</sub>;<sup> e</sup> values calculated using ACDLABS software.</p>", "links"=>[], "tags"=>["medicinal chemistry", "Drugs and devices", "Drug research and development", "drug discovery", "derivatives", "viability", "murine", "peritoneal"], "article_id"=>962633, "categories"=>["Medicine", "Chemistry"], "users"=>["Renata B. Lacerda", "Natália M. Sales", "Leandro L. da Silva", "Roberta Tesch", "Ana Luisa P. Miranda", "Eliezer J. Barreiro", "Patricia D. Fernandes", "Carlos A. M. Fraga"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0091660.t002", "stats"=>{"downloads"=>0, "page_views"=>8, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Effects_of_imidazo_1_2_a_pyridine_N_glycinyl_hydrazone_derivatives_1a_k_on_TNF_production_and_cell_viability_in_murine_peritoneal_macrophages_/962633", "title"=>"Effects of imidazo[1,2-<i>a</i>]pyridine-<i>N</i>-glycinyl-hydrazone derivatives 1a–k on TNF-α production and cell viability in murine peritoneal macrophages.", "pos_in_sequence"=>0, "defined_type"=>3, "published_date"=>"2014-03-14 03:56:02"}
  • {"files"=>["https://ndownloader.figshare.com/files/1420919"], "description"=>"<p>Twenty-four hours prior to carrageenan (1%) injection into the subcutaneous air pouch (SAP), animals were pretreated by oral administration with different doses of a solution of 1i. The results are presented as the mean ± S. D. (n = 6–10) of each cytokine (ng/mL). Statistical significance was calculated by ANOVA followed by Bonferroni’s test. * indicates p<0.005 for the comparison of 1i -treated mice with the vehicle-treated group; # indicates p<0.005 for the comparison of vehicle-treated mice with the PBS-treated group.</p>", "links"=>[], "tags"=>["medicinal chemistry", "Drugs and devices", "Drug research and development", "drug discovery", "1i"], "article_id"=>962631, "categories"=>["Medicine", "Chemistry"], "users"=>["Renata B. Lacerda", "Natália M. Sales", "Leandro L. da Silva", "Roberta Tesch", "Ana Luisa P. Miranda", "Eliezer J. Barreiro", "Patricia D. Fernandes", "Carlos A. M. Fraga"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0091660.g005", "stats"=>{"downloads"=>0, "page_views"=>6, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Effect_of_compound_1i_on_IL_1_946_and_IFN_947_production_/962631", "title"=>"Effect of compound 1i on IL-1β and IFN-γ production.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2014-03-14 03:56:02"}
  • {"files"=>["https://ndownloader.figshare.com/files/1420918"], "description"=>"<p>Twenty-four hours prior to carrageenan (1%) injection into the subcutaneous air pouch (SAP), animals were pretreated by oral administration with different doses of a solution of 1i. The results are presented as the mean ± S. D. (n = 6–10) of TNF-α (pg/mL). Statistical significance was calculated by ANOVA followed by Bonferroni’s test. * indicates p<0.005 for the comparison of 1i -treated mice with the vehicle-treated group; # indicates p<0.005 for the comparison of vehicle-treated mice with the PBS-treated group.</p>", "links"=>[], "tags"=>["medicinal chemistry", "Drugs and devices", "Drug research and development", "drug discovery", "1i"], "article_id"=>962630, "categories"=>["Medicine", "Chemistry"], "users"=>["Renata B. Lacerda", "Natália M. Sales", "Leandro L. da Silva", "Roberta Tesch", "Ana Luisa P. Miranda", "Eliezer J. Barreiro", "Patricia D. Fernandes", "Carlos A. M. Fraga"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0091660.g004", "stats"=>{"downloads"=>0, "page_views"=>7, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Effect_of_compound_1i_on_TNF_945_production_/962630", "title"=>"Effect of compound 1i on TNF-α production.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2014-03-14 03:56:02"}
  • {"files"=>["https://ndownloader.figshare.com/files/1420914"], "description"=>"<p>Synthesis of imidazo[1,2-<i>a</i>]-pyridine-<i>N</i>-glycinyl-hydrazone derivatives 1a–k.</p>", "links"=>[], "tags"=>["medicinal chemistry", "Drugs and devices", "Drug research and development", "drug discovery", "derivatives"], "article_id"=>962626, "categories"=>["Medicine", "Chemistry"], "users"=>["Renata B. Lacerda", "Natália M. Sales", "Leandro L. da Silva", "Roberta Tesch", "Ana Luisa P. Miranda", "Eliezer J. Barreiro", "Patricia D. Fernandes", "Carlos A. M. Fraga"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0091660.g002", "stats"=>{"downloads"=>0, "page_views"=>22, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Synthesis_of_imidazo_1_2_a_pyridine_N_glycinyl_hydrazone_derivatives_1a_k_/962626", "title"=>"Synthesis of imidazo[1,2-<i>a</i>]-pyridine-<i>N</i>-glycinyl-hydrazone derivatives 1a–k.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2014-03-14 03:56:02"}
  • {"files"=>["https://ndownloader.figshare.com/files/1420922"], "description"=>"a<p>The analytical results for C, H and N were within 0.4% of the calculated values for all <i>N</i>-acylhydrazone derivatives 1a–k. The purity of <i>N</i>-acylhydrazone derivatives 1a–k was also determined by reversed-phase HPLC.</p>b<p>The yields refer to the condensation step of hydrazides 8a–b with the corresponding aromatic aldehydes (see <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0091660#pone-0091660-g002\" target=\"_blank\">Figure 2</a>).</p>c<p>Obtained as a yellow oil (see Material and Methods).</p>", "links"=>[], "tags"=>["medicinal chemistry", "Drugs and devices", "Drug research and development", "drug discovery", "derivatives"], "article_id"=>962634, "categories"=>["Medicine", "Chemistry"], "users"=>["Renata B. Lacerda", "Natália M. Sales", "Leandro L. da Silva", "Roberta Tesch", "Ana Luisa P. Miranda", "Eliezer J. Barreiro", "Patricia D. Fernandes", "Carlos A. M. Fraga"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0091660.t001", "stats"=>{"downloads"=>4, "page_views"=>6, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Yields_and_physical_properties_of_imidazo_1_2_a_pyridine_N_glycinyl_hydrazone_derivatives_1a_k_/962634", "title"=>"Yields and physical properties of imidazo[1,2-<i>a</i>]pyridine-<i>N</i>-glycinyl-hydrazone derivatives 1a–k.", "pos_in_sequence"=>0, "defined_type"=>3, "published_date"=>"2014-03-14 03:56:02"}
  • {"files"=>["https://ndownloader.figshare.com/files/1420916"], "description"=>"<p>Tridimensional representation of antiperiplanar (magenta) and synperiplanar (blue) conformers of LASSBio-1626 (1 g) identified in the Monte Carlo conformational search.</p>", "links"=>[], "tags"=>["medicinal chemistry", "Drugs and devices", "Drug research and development", "drug discovery", "conformational", "isomers", "nah"], "article_id"=>962628, "categories"=>["Medicine", "Chemistry"], "users"=>["Renata B. Lacerda", "Natália M. Sales", "Leandro L. da Silva", "Roberta Tesch", "Ana Luisa P. Miranda", "Eliezer J. Barreiro", "Patricia D. Fernandes", "Carlos A. M. Fraga"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0091660.g003", "stats"=>{"downloads"=>0, "page_views"=>16, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Probable_conformational_isomers_of_the_NAH_derivatives_/962628", "title"=>"Probable conformational isomers of the NAH derivatives.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2014-03-14 03:56:02"}
  • {"files"=>["https://ndownloader.figshare.com/files/1420913"], "description"=>"<p>Design of the novel imidazo[1,2-<i>a</i>]pyridine-<i>N</i>-glycinyl-hydrazone derivatives 1a–k.</p>", "links"=>[], "tags"=>["medicinal chemistry", "Drugs and devices", "Drug research and development", "drug discovery", "derivatives"], "article_id"=>962625, "categories"=>["Medicine", "Chemistry"], "users"=>["Renata B. Lacerda", "Natália M. Sales", "Leandro L. da Silva", "Roberta Tesch", "Ana Luisa P. Miranda", "Eliezer J. Barreiro", "Patricia D. Fernandes", "Carlos A. M. Fraga"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0091660.g001", "stats"=>{"downloads"=>0, "page_views"=>32, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Design_of_the_novel_imidazo_1_2_a_pyridine_N_glycinyl_hydrazone_derivatives_1a_k_/962625", "title"=>"Design of the novel imidazo[1,2-<i>a</i>]pyridine-<i>N</i>-glycinyl-hydrazone derivatives 1a–k.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2014-03-14 03:56:02"}

PMC Usage Stats | Further Information

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Relative Metric

{"start_date"=>"2014-01-01T00:00:00Z", "end_date"=>"2014-12-31T00:00:00Z", "subject_areas"=>[{"subject_area"=>"/Engineering and technology/Industrial engineering", "average_usage"=>[262]}, {"subject_area"=>"/Engineering and technology/Technology development", "average_usage"=>[394, 576]}, {"subject_area"=>"/Medicine and health sciences/Immunology", "average_usage"=>[289]}]}
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