Synthesis and Antiviral Activity of Several N-Containing 5α-STEROIDS
Identifieur interne : 000238 ( Pmc/Corpus ); précédent : 000237; suivant : 000239Synthesis and Antiviral Activity of Several N-Containing 5α-STEROIDS
Auteurs : N. Sh. Nadaraia ; E. O. Onashvili ; M. L. Kakhabrishvili ; N. N. Barbakadze ; B. Sylla ; A. PichetteSource :
- Chemistry of Natural Compounds [ 0009-3130 ] ; 2016.
Abstract
A study of the antiviral activity of several new hydrazones and amines and amides of 5α-steroids that were synthesized by us earlier found highly and moderately active compounds. The structures of the synthesized compounds were proven using IR, PMR, 13C NMR, and mass spectral data.
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DOI: 10.1007/s10600-016-1795-0
PubMed: NONE
PubMed Central: 7088190
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis and Antiviral Activity of Several <italic>N</italic>-Containing 5<italic>α</italic>-STEROIDS</title><author><name sortKey="Nadaraia, N Sh" sort="Nadaraia, N Sh" uniqKey="Nadaraia N" first="N. Sh." last="Nadaraia">N. Sh. Nadaraia</name><affiliation><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.412274.6</institution-id><institution-id institution-id-type="ISNI">0000000404288304</institution-id><institution>I. Kutateladze Institute of Pharmaceutical Chemistry,</institution><institution>Tbilisi State Medical University,</institution></institution-wrap>Tbilisi, 0159 Georgia</nlm:aff></affiliation></author><author><name sortKey="Onashvili, E O" sort="Onashvili, E O" uniqKey="Onashvili E" first="E. O." last="Onashvili">E. O. Onashvili</name><affiliation><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.412274.6</institution-id><institution-id institution-id-type="ISNI">0000000404288304</institution-id><institution>I. Kutateladze Institute of Pharmaceutical Chemistry,</institution><institution>Tbilisi State Medical University,</institution></institution-wrap>Tbilisi, 0159 Georgia</nlm:aff></affiliation></author><author><name sortKey="Kakhabrishvili, M L" sort="Kakhabrishvili, M L" uniqKey="Kakhabrishvili M" first="M. L." last="Kakhabrishvili">M. L. Kakhabrishvili</name><affiliation><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.412274.6</institution-id><institution-id institution-id-type="ISNI">0000000404288304</institution-id><institution>I. Kutateladze Institute of Pharmaceutical Chemistry,</institution><institution>Tbilisi State Medical University,</institution></institution-wrap>Tbilisi, 0159 Georgia</nlm:aff></affiliation></author><author><name sortKey="Barbakadze, N N" sort="Barbakadze, N N" uniqKey="Barbakadze N" first="N. N." last="Barbakadze">N. N. Barbakadze</name><affiliation><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.412274.6</institution-id><institution-id institution-id-type="ISNI">0000000404288304</institution-id><institution>I. Kutateladze Institute of Pharmaceutical Chemistry,</institution><institution>Tbilisi State Medical University,</institution></institution-wrap>Tbilisi, 0159 Georgia</nlm:aff></affiliation></author><author><name sortKey="Sylla, B" sort="Sylla, B" uniqKey="Sylla B" first="B." last="Sylla">B. Sylla</name><affiliation><nlm:aff id="Aff2"><institution-wrap><institution-id institution-id-type="GRID">grid.265695.b</institution-id><institution>LASEVE, Universite Quebec a Chicoutim,</institution></institution-wrap>Chicoutimi, QC Canada G7H 2BI</nlm:aff></affiliation></author><author><name sortKey="Pichette, A" sort="Pichette, A" uniqKey="Pichette A" first="A." last="Pichette">A. Pichette</name><affiliation><nlm:aff id="Aff2"><institution-wrap><institution-id institution-id-type="GRID">grid.265695.b</institution-id><institution>LASEVE, Universite Quebec a Chicoutim,</institution></institution-wrap>Chicoutimi, QC Canada G7H 2BI</nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmc">7088190</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7088190</idno><idno type="RBID">PMC:7088190</idno><idno type="doi">10.1007/s10600-016-1795-0</idno><idno type="pmid">NONE</idno><date when="2016">2016</date><idno type="wicri:Area/Pmc/Corpus">000238</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000238</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Synthesis and Antiviral Activity of Several <italic>N</italic>-Containing 5<italic>α</italic>-STEROIDS</title><author><name sortKey="Nadaraia, N Sh" sort="Nadaraia, N Sh" uniqKey="Nadaraia N" first="N. Sh." last="Nadaraia">N. Sh. Nadaraia</name><affiliation><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.412274.6</institution-id><institution-id institution-id-type="ISNI">0000000404288304</institution-id><institution>I. Kutateladze Institute of Pharmaceutical Chemistry,</institution><institution>Tbilisi State Medical University,</institution></institution-wrap>Tbilisi, 0159 Georgia</nlm:aff></affiliation></author><author><name sortKey="Onashvili, E O" sort="Onashvili, E O" uniqKey="Onashvili E" first="E. O." last="Onashvili">E. O. Onashvili</name><affiliation><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.412274.6</institution-id><institution-id institution-id-type="ISNI">0000000404288304</institution-id><institution>I. Kutateladze Institute of Pharmaceutical Chemistry,</institution><institution>Tbilisi State Medical University,</institution></institution-wrap>Tbilisi, 0159 Georgia</nlm:aff></affiliation></author><author><name sortKey="Kakhabrishvili, M L" sort="Kakhabrishvili, M L" uniqKey="Kakhabrishvili M" first="M. L." last="Kakhabrishvili">M. L. Kakhabrishvili</name><affiliation><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.412274.6</institution-id><institution-id institution-id-type="ISNI">0000000404288304</institution-id><institution>I. Kutateladze Institute of Pharmaceutical Chemistry,</institution><institution>Tbilisi State Medical University,</institution></institution-wrap>Tbilisi, 0159 Georgia</nlm:aff></affiliation></author><author><name sortKey="Barbakadze, N N" sort="Barbakadze, N N" uniqKey="Barbakadze N" first="N. N." last="Barbakadze">N. N. Barbakadze</name><affiliation><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.412274.6</institution-id><institution-id institution-id-type="ISNI">0000000404288304</institution-id><institution>I. Kutateladze Institute of Pharmaceutical Chemistry,</institution><institution>Tbilisi State Medical University,</institution></institution-wrap>Tbilisi, 0159 Georgia</nlm:aff></affiliation></author><author><name sortKey="Sylla, B" sort="Sylla, B" uniqKey="Sylla B" first="B." last="Sylla">B. Sylla</name><affiliation><nlm:aff id="Aff2"><institution-wrap><institution-id institution-id-type="GRID">grid.265695.b</institution-id><institution>LASEVE, Universite Quebec a Chicoutim,</institution></institution-wrap>Chicoutimi, QC Canada G7H 2BI</nlm:aff></affiliation></author><author><name sortKey="Pichette, A" sort="Pichette, A" uniqKey="Pichette A" first="A." last="Pichette">A. Pichette</name><affiliation><nlm:aff id="Aff2"><institution-wrap><institution-id institution-id-type="GRID">grid.265695.b</institution-id><institution>LASEVE, Universite Quebec a Chicoutim,</institution></institution-wrap>Chicoutimi, QC Canada G7H 2BI</nlm:aff></affiliation></author></analytic><series><title level="j">Chemistry of Natural Compounds</title><idno type="ISSN">0009-3130</idno><idno type="eISSN">1573-8388</idno><imprint><date when="2016">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p id="Par1">A study of the antiviral activity of several new hydrazones and amines and amides of 5α-steroids that were synthesized by us earlier found highly and moderately active compounds. 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<front><journal-meta><journal-id journal-id-type="nlm-ta">Chem Nat Compd</journal-id><journal-id journal-id-type="iso-abbrev">Chem Nat Compd</journal-id><journal-title-group><journal-title>Chemistry of Natural Compounds</journal-title></journal-title-group><issn pub-type="ppub">0009-3130</issn><issn pub-type="epub">1573-8388</issn><publisher><publisher-name>Springer US</publisher-name><publisher-loc>New York</publisher-loc></publisher></journal-meta><article-meta><article-id pub-id-type="pmc">7088190</article-id><article-id pub-id-type="publisher-id">1795</article-id><article-id pub-id-type="doi">10.1007/s10600-016-1795-0</article-id><article-categories><subj-group subj-group-type="heading"><subject>Article</subject></subj-group></article-categories><title-group><article-title>Synthesis and Antiviral Activity of Several <italic>N</italic>-Containing 5<italic>α</italic>-STEROIDS</article-title></title-group><contrib-group><contrib contrib-type="author" corresp="yes"><name><surname>Nadaraia</surname><given-names>N. Sh.</given-names></name><address><fax>(99532) 52 00 23</fax><email>nnadaraia@ymail.com</email></address><xref ref-type="aff" rid="Aff1">1</xref></contrib><contrib contrib-type="author"><name><surname>Onashvili</surname><given-names>E. O.</given-names></name><xref ref-type="aff" rid="Aff1">1</xref></contrib><contrib contrib-type="author"><name><surname>Kakhabrishvili</surname><given-names>M. L.</given-names></name><xref ref-type="aff" rid="Aff1">1</xref></contrib><contrib contrib-type="author"><name><surname>Barbakadze</surname><given-names>N. N.</given-names></name><xref ref-type="aff" rid="Aff1">1</xref></contrib><contrib contrib-type="author"><name><surname>Sylla</surname><given-names>B.</given-names></name><xref ref-type="aff" rid="Aff2">2</xref></contrib><contrib contrib-type="author"><name><surname>Pichette</surname><given-names>A.</given-names></name><address><fax>(1) 418 545 50 12</fax><email>andre_pichette@uqac.ca</email></address><xref ref-type="aff" rid="Aff2">2</xref></contrib><aff id="Aff1"><label>1</label><institution-wrap><institution-id institution-id-type="GRID">grid.412274.6</institution-id><institution-id institution-id-type="ISNI">0000000404288304</institution-id><institution>I. Kutateladze Institute of Pharmaceutical Chemistry,</institution><institution>Tbilisi State Medical University,</institution></institution-wrap>Tbilisi, 0159 Georgia</aff><aff id="Aff2"><label>2</label><institution-wrap><institution-id institution-id-type="GRID">grid.265695.b</institution-id><institution>LASEVE, Universite Quebec a Chicoutim,</institution></institution-wrap>Chicoutimi, QC Canada G7H 2BI</aff></contrib-group><pub-date pub-type="epub"><day>11</day><month>8</month><year>2016</year></pub-date><pub-date pub-type="ppub"><year>2016</year></pub-date><volume>52</volume><issue>5</issue><fpage>853</fpage><lpage>855</lpage><history><date date-type="received"><day>21</day><month>1</month><year>2016</year></date></history><permissions><copyright-statement>© Springer Science+Business Media New York 2016</copyright-statement><license><license-p>This article is made available via the PMC Open Access Subset for unrestricted research re-use and secondary analysis in any form or by any means with acknowledgement of the original source. These permissions are granted for the duration of the World Health Organization (WHO) declaration of COVID-19 as a global pandemic.</license-p></license></permissions><abstract id="Abs1"><p id="Par1">A study of the antiviral activity of several new hydrazones and amines and amides of 5α-steroids that were synthesized by us earlier found highly and moderately active compounds. The structures of the synthesized compounds were proven using IR, PMR, <sup>13</sup>C NMR, and mass spectral data.</p></abstract><kwd-group xml:lang="en"><title>Keywords</title><kwd>5<italic>α</italic>-steroids</kwd><kwd>synthesis</kwd><kwd>hydrazides</kwd><kwd>hydrazones</kwd><kwd>amines</kwd><kwd>amides</kwd><kwd>antiviral activity</kwd></kwd-group><custom-meta-group><custom-meta><meta-name>issue-copyright-statement</meta-name><meta-value>© Springer Science+Business Media New York 2016</meta-value></custom-meta></custom-meta-group></article-meta></front><body><p id="Par2">Broad spectra of biological activity make steroids and their derivatives promising for discovering new efficacious drugs [<xref ref-type="bibr" rid="CR1">1</xref>–<xref ref-type="bibr" rid="CR3">3</xref>]. The high antibacterial, antiviral, and antitumor activity of hydrazono-, amino-, and amido-derivatives of the androstane, estrane, and cholestane series [<xref ref-type="bibr" rid="CR4">4</xref>–<xref ref-type="bibr" rid="CR8">8</xref>] and the expanded scope of their synthetic analogs helped to find new biological properties of these compounds.</p><p id="Par3">In continuation of research on the synthesis of bioactive 5<italic>α</italic>-steroids from epiandrosterone <bold>1</bold> [<xref ref-type="bibr" rid="CR9">9</xref>, <xref ref-type="bibr" rid="CR10">10</xref>], a transformation product of tigogenin, hydrazones <bold>2–4</bold> were obtained.
<graphic position="anchor" xlink:href="10600_2016_1795_Figa_HTML" id="MO1"></graphic></p><p id="Par4">Herein we report results for the antiviral activity of synthesized <bold>2–4</bold> and <bold>7–12</bold> that were previously obtained from androst-2-en-17-one (<bold>5</bold>) and 17<italic>β</italic>-amino-5<italic>α</italic>-androst-2-ene (<bold>6</bold>) [<xref ref-type="bibr" rid="CR11">11</xref>–<xref ref-type="bibr" rid="CR13">13</xref>].</p><p id="Par5">Starting 5<italic>α</italic>-androstanolone (<bold>1</bold>) was synthesized by the literature method [<xref ref-type="bibr" rid="CR14">14</xref>]. Acid-catalyzed condensation of it with hydrazides of 2- and 4-benzyloxybenzoic and 2-furanoic acids produced hydrazones <bold>2–4</bold>. Epiandrosterone <bold>1</bold> was converted into ketone <bold>5</bold> and then into amine <bold>6</bold> or into 17<italic>β</italic>-(<italic>N</italic>,<italic>N</italic>-dimethylamino)-5<italic>α</italic>-androst-2-ene (<bold>7</bold>). Amides <bold>8–12</bold>, i.e., 17<italic>β</italic>-acetamido-5<italic>α</italic>-androst-2-ene (<bold>8</bold>), 17<italic>β</italic>-chloroacetylamino-5<italic>α</italic>-androst-2-ene (<bold>9</bold>), 17<italic>β</italic>-diethylaminoacetylamino-5<italic>α</italic>-androst-2-ene (<bold>10</bold>), 17<italic>β</italic>-morpholinoacetylamino-5<italic>α</italic>-androst-2-ene (<bold>11</bold>), and 17<italic>β</italic>-piperazinoacetylamino-5<italic>α</italic>-androst-2-ene (<bold>12</bold>), were synthesized from aminosteroid <bold>6</bold>.</p><p id="Par6">The structures of the synthesized compounds <bold>2</bold>, <bold>3</bold> were proven using IR, PMR, and mass spectra. IR spectra of hydrazones <bold>2</bold> and <bold>3</bold> contained characteristic absorption bands for NH and OH stretching vibrations at 3480–3310 and 3460–3305 cm<sup>–1</sup> and for amide carbonyl stretching vibrations at 1649 and 1647 cm<sup>–1</sup>. Characteristic frequencies of C=N bonds were observed at 1601 and 1608; aromatic C=C bonds, 1542 and 1501 cm<sup>–1</sup>. The C–O ether bond gave bands at 1227 and 1250 cm<sup>–1</sup>, respectively.</p><p id="Par7">PMR spectra (DMSO-d<sub>6</sub>) of <bold>2</bold> and <bold>3</bold> showed resonances for angular 18-CH<sub>3</sub> at δ 0.78 and 0.83 ppm; 19-CH<sub>3</sub>, 0.80 and 0.90 ppm as singlets; 3<italic>α</italic>-H, at 3.33 ppm as multiplets; 3<italic>β</italic> OH protons, at 3.91 and 3.90 ppm as doublets with J = 4.5 and 4.4 Hz, respectively. Benzyloxy methylene protons were found at 5.20 and 5.14 ppm as singlets; aromatic protons, at 6.96–8.10 ppm. Weak-field NH protons appeared at 9.94 and 9.77 ppm, respectively.</p><p id="Par8">The structure of <bold>4</bold> was confirmed by PMR, <sup>13</sup>C NMR (in CDCl<sub>3</sub>), and mass spectra. The PMR spectrum of <bold>4</bold> had angular 18-CH<sub>3</sub> and 19-CH<sub>3</sub> at 0.84 and 0.94 ppm as singlets; 3<italic>α</italic>-H, 3.60 as a multiplet; furan-ring proton, 7.63–6.52 ppm (br); and NH, 8.70 ppm. <sup>13</sup>C NMR spectra contained peaks for furan-ring C atoms at 146.5–112.2 ppm; amide C=O and hydrazone C=N, 166.2 and 165.5 ppm, respectively. The molecular ion <italic>m</italic>/<italic>z</italic> [M + H]<sup>+</sup> 399.2 corresponded to C<sub>24</sub>H<sub>35</sub>N<sub>2</sub>O<sub>3</sub>.</p><p id="Par9">Antiviral activity of <bold>2–4</bold> and <bold>7–12</bold> was studied at the National Institute of Allergy and Infectious Diseases (NIAID), University of Utah, USA. Studies on Vero 76 cell culture for poliovirus (strain Type 3, WM-3) showed that <bold>3</bold> had high antiviral activity; hydrazones <bold>2</bold> and <bold>4</bold>, moderate activity. The other steroids <bold>7–12</bold> were inactive. Steroids <bold>7</bold> and <bold>8</bold> exhibited moderate activity against Venezuelan equine encephalitis virus (strain TC-83); amide <bold>12</bold>, weak activity against Sars corona virus (strain Urbani). All other compounds were inactive. Only hydrazone <bold>3</bold> showed weak activity against Rift Valley fever virus (Vero 76 cell culture, strain MP-12); only <bold>4</bold>, against Respiratory syncytial virus (MA-104 cell culture, strain A-2). Compounds <bold>2–4</bold> and <bold>7–12</bold> were inactive against Influenza A virus H<sub>1</sub>N<sub>1</sub>, Takaribe virus, and Dengue virus (MDCK, Vero, Vero 76 cell cultures; strains California 07.2009, TRVL-11573, and Type-2, NewGuinea C, respectively).</p><sec id="Sec1"><title>Experimental</title><p id="Par10">PMR were recorded in DMSO-d<sub>6</sub> and CDCl<sub>3</sub> with SiMe4 internal standard on a Bruker Avance 400 spectrometer (400.13 MHz). IR spectra were taken from KBr pellets on a Varian 660 FT-IR spectrometer. Mass spectra were obtained on an Agilent 1100 series HPLC-APCIMS (positive mode) using an Inertsilprep-ODS column (6.0 × 250 mm) with elution by H<sub>2</sub>O–MeCN (20:80). Melting points were determined on a Nagema apparatus. The course of reactions and purity of synthesized compounds were monitored by TLC on Silufol UV254 plates (Kavalier, Czechoslovakia) using C<sub>6</sub>H<sub>6</sub>–Me<sub>2</sub>CO (4:1, 10:1). Chromatograms were detected by phosphomolybdic acid solution (10%) in EtOH followed by heating.</p><p id="Par11"><bold>General Method for Synthesizing 17-Hydrazono Derivatives of 5</bold><italic>α</italic><bold>-Androstan-3-ols 2–4.</bold> A mixture of <bold>1</bold> (0.1 g, 0.35 mmol) and the appropriate hydrazide (0.55 mmol) in EtOH (10 mL) with a catalytic amount of AcOH was refluxed for 6–10 h and cooled to room temperature. The resulting precipitate was filtered off, rinsed with H<sub>2</sub>O and Et<sub>2</sub>O, dried, and crystallized from EtOH.</p><p id="Par12"><bold>5</bold><bold><italic>α</italic></bold><bold>-Androstan-3</bold><bold><italic>β</italic></bold><bold>-ol-17-one 2-Benzyloxybenzoylhydrazone (2).</bold> Yield 70%, mp 232–233°C. IR spectrum (KBr, ν, cm<sup>–1</sup>): 3480–3310 (NH, OH), 1649 (NHC=O), 1601 (C=N), 1542 (C=CAr), 1227 (C–O eth.). <sup>1</sup>H NMR spectrum (DMSO-d<sub>6</sub>, δ, ppm, J/Hz): 0.78 (3H, s, 18-CH<sub>3</sub>), 0.80 (3H, s, 19-CH<sub>3</sub>), 3.33 (1H, m, H-3), 3.91 (1H, d, J = 4.5, OH), 5.20 (2H, s, OCH<sub>2</sub>), 7.09 (1H, t, J = 7.5, H-Ar), 7.23 (1H, d, J = 8.3, H-Ar), 7.34–7.56 (6H, m, H-Ar), 8.10 (1H, dd, J = 7.8, 1.8, H-Ar), 9.94 (1H, s, NH). LC-MS, <italic>m/z</italic> [M + H]<sup>+</sup> 515.3. C<sub>33</sub>H<sub>42</sub>N<sub>2</sub>O<sub>3</sub>, MM 514.3.</p><p id="Par13"><bold>5</bold><bold><italic>α</italic></bold><bold>-Androstan-3</bold><bold><italic>β</italic></bold><bold>-ol-17-one 4-Benzyloxybenzoylhydrazone (3).</bold> Yield 73%, mp 210–212°C. IR spectrum (KBr, ν, cm<sup>–1</sup>): 3460–3305 (NH, OH), 1647 (NHC=O), 1608 (C=N), 1501 (C=CAr), 1250 (C–O eth.). <sup>1</sup>H NMR spectrum (DMSO-d<sub>6</sub>, δ, ppm, J/Hz): 0.83 (3H, s, 18-CH<sub>3</sub>), 0.90 (3H, s, 19-CH<sub>3</sub>), 3.33 (1H, m, H-3), 3.90 (1H, d, J = 4.4, OH), 5.14 (2H, s, OCH<sub>2</sub>), 6.96 (2H, m, C<sub>6</sub>H<sub>4</sub>), 7.25–7.44 (5H, m, C<sub>6</sub>H<sub>5</sub>), 7.80 (2H, m, C<sub>6</sub>H<sub>4</sub>), 9.77 (1H, s, NH). LC-MS, <italic>m/z</italic> [M + H]<sup>+</sup> 515.3. C<sub>33</sub>H<sub>42</sub>N<sub>2</sub>O<sub>3</sub>, MM 514.3.</p><p id="Par14"><bold>5</bold><bold><italic>α</italic></bold><bold>-Androstan-3</bold><bold><italic>β</italic></bold><bold>-ol-17-one 2-Furanylhydrazone (4).</bold> Yield 62%, mp 240–242°C. <sup>1</sup>H NMR spectrum (CDCl<sub>3</sub>, δ, ppm, J/Hz): 0.84 (3H, s, 18-CH<sub>3</sub>), 0.94 (3H, s, 19-CH<sub>3</sub>), 3.60 (1H, m, H-3), 6.52 (1H, br.s, H-4′ fur.), 7.48 (1H, br.s, H-3′ fur.), 7.63 (1H, br.s, H-5′ fur.), 8.70 (1H, br.s, NH). <sup>13</sup>C NMR spectrum (CDCl<sub>3</sub>, δ, ppm): 12.2, 16.8, 20.6, 23.2, 25.9, 28.4, 31.4, 31.6, 33.8, 34.8, 35.0, 35.5, 36.8, 38.0, 44.7, 53.3, 54.4, 71.1 (C-3), 112.2 (C-4′ fur.), 116.8 (C-3′ fur.), 143.7 (C-5′ fur.), 146.5 (C-2′ fur.), 165.8 (C=N), 166.2 (C=O). LC-MS, <italic>m/z</italic> [M + H]<sup>+</sup> 399.2. 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