Stereochemical Control in the Still-Wittig Rearrangement Synthesis of Cyclohexyl (Z)-Alkene Inhibitors of Pin1
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{"title"=>"Stereochemical control in the still-wittig rearrangement synthesis of cyclohexyl (Z)- alkene inhibitors of Pin1", "type"=>"journal", "authors"=>[{"first_name"=>"Xingguo R.", "last_name"=>"Chen", "scopus_author_id"=>"56982158600"}, {"first_name"=>"Shuang A.", "last_name"=>"Fan", "scopus_author_id"=>"56912700500"}, {"first_name"=>"Rachel I.", "last_name"=>"Ware", "scopus_author_id"=>"56982533200"}, {"first_name"=>"Felicia A.", "last_name"=>"Etzkorn", "scopus_author_id"=>"6701488020"}], "year"=>2015, "source"=>"PLoS ONE", "identifiers"=>{"scopus"=>"2-s2.0-84948701708", "doi"=>"10.1371/journal.pone.0139543", "issn"=>"19326203", "pui"=>"607096766", "sgr"=>"84948701708", "isbn"=>"1932-6203 (Electronic)\\r1932-6203 (Linking)", "pmid"=>"26445009"}, "id"=>"c0f010ad-5b4f-3bc4-ad9c-79334110a765", "abstract"=>"Three stereoisomeric inhibitors of Pin1: (2R,5S)-, (2S,5R)- and (2S,5S)-Ac-pSer- ψ [(Z) CH = C] -pipecolyl(Pip) -2-(2-naphthyl)ethylamines (I), (II) and (III), that mimic L-pSer-D-Pro, D-pSer-L-Pro, and D-pSer-D-Pro amides resp., were synthesized by a 13-step route. The newly formed stereogenic centers in the pipecolyl ring were introduced by Luche redn., followed by stereospecific -Still-Wittig rearrangement. The (Z)- to (E)-alkene ratio in the rearrangements were consistently 5.5 to 1. The stereochem. at the original Ser α-carbon controlled the stereochem. of the Luche redn., but it did not affect the stereochem. outcome of the rearrangement, which consistently gave the (Z)-alkene. The IC50 values for I, II and III Pin1 inhibition were: 52, 85, and 140 μM, resp. [on SciFinder(R)]", "link"=>"http://www.mendeley.com/research/stereochemical-control-stillwittig-rearrangement-synthesis-cyclohexyl-z-alkene-inhibitors-pin1", "reader_count"=>5, "reader_count_by_academic_status"=>{"Student > Ph. D. Student"=>1, "Student > Master"=>1, "Student > Bachelor"=>2, "Professor"=>1}, "reader_count_by_user_role"=>{"Student > Ph. D. Student"=>1, "Student > Master"=>1, "Student > Bachelor"=>2, "Professor"=>1}, "reader_count_by_subject_area"=>{"Biochemistry, Genetics and Molecular Biology"=>1, "Chemistry"=>4}, "reader_count_by_subdiscipline"=>{"Chemistry"=>{"Chemistry"=>4}, "Biochemistry, Genetics and Molecular Biology"=>{"Biochemistry, Genetics and Molecular Biology"=>1}}, "group_count"=>0}

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Figshare

  • {"files"=>["https://ndownloader.figshare.com/files/2349487", "https://ndownloader.figshare.com/files/2349488"], "description"=>"<div><p>Three stereoisomeric inhibitors of Pin1: (2<i>R</i>,5<i>S</i>)-, (2<i>S</i>,5<i>R</i>)- and (2<i>S</i>,5<i>S</i>)-Ac–pSer–Ψ[(<i>Z</i>)CH = C]–pipecolyl(Pip)–2-(2-naphthyl)ethylamine <b>1</b>, that mimic L-pSer–D-Pro, D-pSer–L-Pro, and D-pSer–D-Pro amides respectively, were synthesized by a 13-step route. The newly formed stereogenic centers in the pipecolyl ring were introduced by Luche reduction, followed by stereospecific [<a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0139543#pone.0139543.ref002\" target=\"_blank\">2</a>,<a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0139543#pone.0139543.ref003\" target=\"_blank\">3</a>]-Still-Wittig rearrangement. The (<i>Z</i>)- to (<i>E</i>)-alkene ratio in the rearrangements were consistently 5.5 to 1. The stereochemistry at the original Ser α-carbon controlled the stereochemistry of the Luche reduction, but it did not affect the stereochemical outcome of the rearrangement, which consistently gave the (<i>Z</i>)-alkene. The epimerized by-product, <b>(2<i>S</i>,5<i>S</i>)-10</b>, resulting from the work-up after Na/NH<sub>3</sub> debenzylation of <b>(2<i>S</i>,5<i>R</i>)-9</b>, was carried on to the <b>(2<i>S</i>,5<i>S</i>)-1</b> isomer. Compound <b>(2<i>S</i>,5<i>S</i>)-10</b> was resynthesized from the Luche reduction by-product, <b>(2<i>R</i>,3<i>R</i>)-3</b>, and the stereochemistry was confirmed by comparison of the optical rotations. The IC<sub>50</sub> values for <b>(2<i>R</i>,5<i>S</i>)-1</b>, <b>(2<i>S</i>,5<i>R</i>)-1</b> and <b>(2<i>S</i>,5<i>S</i>)-1</b> Pin1 inhibition were: 52, 85, and 140 μM, respectively.</p></div>", "links"=>[], "tags"=>["rearrangement", "IC 50 values", "Luche reduction", "140 μ M", "stereochemistry"], "article_id"=>1567924, "categories"=>["Uncategorised"], "users"=>["Xingguo R. Chen", "Shuang A. Fan", "Rachel I. Ware", "Felicia A. Etzkorn"], "doi"=>["https://dx.doi.org/10.1371/journal.pone.0139543.s001", "https://dx.doi.org/10.1371/journal.pone.0139543.s002"], "stats"=>{"downloads"=>2, "page_views"=>5, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/Stereochemical_Control_in_the_Still_Wittig_Rearrangement_Synthesis_of_Cyclohexyl_Z_Alkene_Inhibitors_of_Pin1/1567924", "title"=>"Stereochemical Control in the Still-Wittig Rearrangement Synthesis of Cyclohexyl (<i>Z</i>)-Alkene Inhibitors of Pin1", "pos_in_sequence"=>0, "defined_type"=>4, "published_date"=>"2015-10-07 04:04:36"}
  • {"files"=>["https://ndownloader.figshare.com/files/2349447"], "description"=>"<p>Designed enantiomeric inhibitors synthesized.</p>", "links"=>[], "tags"=>["rearrangement", "IC 50 values", "Luche reduction", "140 μ M", "stereochemistry"], "article_id"=>1567894, "categories"=>["Uncategorised"], "users"=>["Xingguo R. Chen", "Shuang A. Fan", "Rachel I. Ware", "Felicia A. Etzkorn"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0139543.g001", "stats"=>{"downloads"=>3, "page_views"=>11, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Designed_enantiomeric_inhibitors_synthesized_/1567894", "title"=>"Designed enantiomeric inhibitors synthesized.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2015-10-07 04:04:36"}
  • {"files"=>["https://ndownloader.figshare.com/files/2349448"], "description"=>"<p>Synthesis of the Ac–L-pSer–Ψ[(<i>Z</i>)CH = C]-D-Pip–NEA inhibitor (2<i>R</i>,5<i>S</i>)-1.</p>", "links"=>[], "tags"=>["rearrangement", "IC 50 values", "Luche reduction", "140 μ M", "stereochemistry"], "article_id"=>1567895, "categories"=>["Uncategorised"], "users"=>["Xingguo R. Chen", "Shuang A. Fan", "Rachel I. Ware", "Felicia A. Etzkorn"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0139543.g002", "stats"=>{"downloads"=>0, "page_views"=>6, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Synthesis_of_the_Ac_L_pSer_Z_CH_C_D_Pip_NEA_inhibitor_2_R_5_S_1_/1567895", "title"=>"Synthesis of the Ac–L-pSer–Ψ[(<i>Z</i>)CH = C]-D-Pip–NEA inhibitor (2<i>R</i>,5<i>S</i>)-1.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2015-10-07 04:04:36"}
  • {"files"=>["https://ndownloader.figshare.com/files/2349449"], "description"=>"<p>Cyclic compounds <b>13</b> were synthesized. <sup>1</sup>H NMR coupling constants (<i>J</i>) were used to determine the relative stereochemistry at the carbons to which H<sub>a</sub> and H<sub>b</sub> are attached.</p>", "links"=>[], "tags"=>["rearrangement", "IC 50 values", "Luche reduction", "140 μ M", "stereochemistry"], "article_id"=>1567896, "categories"=>["Uncategorised"], "users"=>["Xingguo R. Chen", "Shuang A. Fan", "Rachel I. Ware", "Felicia A. Etzkorn"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0139543.g003", "stats"=>{"downloads"=>1, "page_views"=>1, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Synthesis_and_determination_of_the_stereochemistry_of_derivative_2_S_3_R_13_/1567896", "title"=>"Synthesis and determination of the stereochemistry of derivative (2<i>S</i>,3<i>R</i>)-13.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2015-10-07 04:04:36"}
  • {"files"=>["https://ndownloader.figshare.com/files/2349451"], "description"=>"<p>The 1D nOe <sup>1</sup>H NMR. Irradiation of <sup>1</sup>H<sub>f</sub> shows an nOe at <sup>1</sup>H<sub>m</sub> and not at <sup>1</sup>H<sub>h</sub>.</p>", "links"=>[], "tags"=>["rearrangement", "IC 50 values", "Luche reduction", "140 μ M", "stereochemistry"], "article_id"=>1567898, "categories"=>["Uncategorised"], "users"=>["Xingguo R. Chen", "Shuang A. Fan", "Rachel I. Ware", "Felicia A. Etzkorn"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0139543.g004", "stats"=>{"downloads"=>1, "page_views"=>9, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Determination_of_the_Z_alkene_stereochemistry_of_intermediate_2_R_5_S_6_/1567898", "title"=>"Determination of the (<i>Z</i>)-alkene stereochemistry of intermediate (2<i>R</i>,5<i>S</i>)-6.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2015-10-07 04:04:36"}
  • {"files"=>["https://ndownloader.figshare.com/files/2349452"], "description"=>"<p>(A) Compound <b>(2<i>S</i>,5<i>R</i>)-14</b> was synthesized to rigidify intermediate <b>(2<i>R</i>,5<i>S</i>)-6</b> for nOe determination. (B) Structure of <b>(2<i>S</i>,5<i>R</i>)-14</b> with lettering of the protons, structure of the major conformation showing nOe interactions, the <sup>1</sup>H NMR and 1D nOe spectra in CDCl<sub>3</sub> (400 MHz) are shown. Irradiation of H<sub>i</sub> shows an nOe at H<sub>h</sub>. Irradiation of H<sub>g</sub> shows an nOe at H<sub>i’</sub>. (C) The stereochemistry of enantiomer <b>(2<i>R</i>,5<i>S</i>)-14</b> was determined. Structure with lettering of the protons, structure of the major conformation showing nOe interactions, and a 1D nOe spectrum in CDCl<sub>3</sub> (400 MHz) are shown. Irradiation of H<sub>g</sub> shows an nOe at H<sub>i’</sub>.</p>", "links"=>[], "tags"=>["rearrangement", "IC 50 values", "Luche reduction", "140 μ M", "stereochemistry"], "article_id"=>1567899, "categories"=>["Uncategorised"], "users"=>["Xingguo R. Chen", "Shuang A. Fan", "Rachel I. Ware", "Felicia A. Etzkorn"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0139543.g005", "stats"=>{"downloads"=>1, "page_views"=>16, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Determination_of_the_stereochemistry_of_Still_Wittig_intermediates_6_/1567899", "title"=>"Determination of the stereochemistry of Still-Wittig intermediates 6.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2015-10-07 04:04:36"}
  • {"files"=>["https://ndownloader.figshare.com/files/2349454"], "description"=>"<p>The 2D NOESY spectrum is shown with lettering of the major conformation showing key nOe interactions. Crosspeaks between H<sub>i</sub> and H<sub>h</sub>, and between H<sub>e</sub> and H<sub>i’</sub> show the stereochemistry given.</p>", "links"=>[], "tags"=>["rearrangement", "IC 50 values", "Luche reduction", "140 μ M", "stereochemistry"], "article_id"=>1567901, "categories"=>["Uncategorised"], "users"=>["Xingguo R. Chen", "Shuang A. Fan", "Rachel I. Ware", "Felicia A. Etzkorn"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0139543.g006", "stats"=>{"downloads"=>0, "page_views"=>2, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Determination_of_the_stereochemistry_of_of_2_S_5_S_14_/1567901", "title"=>"Determination of the stereochemistry of of (2<i>S</i>,5<i>S</i>)-14.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2015-10-07 04:04:36"}

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Relative Metric

{"start_date"=>"2015-01-01T00:00:00Z", "end_date"=>"2015-12-31T00:00:00Z", "subject_areas"=>[]}
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