Design, synthesis, antitubercular and antiviral properties of new spirocyclic indole derivatives
A series of indole-based spirothiazolidinones have been designed, synthesized and evaluated, in vitro, for their antitubercular, antiviral, antibacterial, and antifungal activities. The structures of the new compounds were established by IR, 1 H NMR, 13 C NMR (proton decoupled, APT, and DEPT), elect...
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| Veröffentlicht in: | Monatshefte für Chemie 2019-01, Vol.150 (8), p.1533-1544 |
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| creator | Cihan-Üstündağ, Gökçe Naesens, Lieve Şatana, Dilek Erköse-Genç, Gonca Mataracı-Kara, Emel Çapan, Gültaze |
| description | A series of indole-based spirothiazolidinones have been designed, synthesized and evaluated, in vitro, for their antitubercular, antiviral, antibacterial, and antifungal activities. The structures of the new compounds were established by IR,
1
H NMR,
13
C NMR (proton decoupled, APT, and DEPT), electrospray ionization mass spectrometry, and microanalysis. Compounds bearing a phenyl substituent at position 8 of the spiro ring, exhibited significant antitubercular activity against
Mycobacterium tuberculosis
H37Rv ATCC 27294 at concentrations of 3.9 and 7.8 µM. Still, some of the tested compounds displayed activity on mycobacteria with MIC values of 16 and 31 µM. Four of the indole-spirothiazolidinone derivatives were found to be moderately active against Punta Toro virus, yellow fever virus or Sindbis virus in Vero cells. The antiviral EC
50
values were in the range of 1.9–12 µM and the selectivity index (ratio of cytotoxic to antivirally effective concentration) was above 10 in some cases. The most potent effect was seen with the compound that is methylated at positions 2 and 8 of the spirothiazolidinone system.
Graphic abstract |
| doi_str_mv | 10.1007/s00706-019-02457-9 |
| format | Article |
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1
H NMR,
13
C NMR (proton decoupled, APT, and DEPT), electrospray ionization mass spectrometry, and microanalysis. Compounds bearing a phenyl substituent at position 8 of the spiro ring, exhibited significant antitubercular activity against
Mycobacterium tuberculosis
H37Rv ATCC 27294 at concentrations of 3.9 and 7.8 µM. Still, some of the tested compounds displayed activity on mycobacteria with MIC values of 16 and 31 µM. Four of the indole-spirothiazolidinone derivatives were found to be moderately active against Punta Toro virus, yellow fever virus or Sindbis virus in Vero cells. The antiviral EC
50
values were in the range of 1.9–12 µM and the selectivity index (ratio of cytotoxic to antivirally effective concentration) was above 10 in some cases. The most potent effect was seen with the compound that is methylated at positions 2 and 8 of the spirothiazolidinone system.
Graphic abstract</description><identifier>ISSN: 0026-9247</identifier><identifier>EISSN: 1434-4475</identifier><identifier>DOI: 10.1007/s00706-019-02457-9</identifier><identifier>PMID: 32214484</identifier><language>eng</language><publisher>Vienna: Springer Vienna</publisher><subject>Analytical Chemistry ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Derivatives ; Fungicides ; Inorganic Chemistry ; Ions ; Mass spectrometry ; NMR ; Nuclear magnetic resonance ; Organic Chemistry ; Original Paper ; Physical Chemistry ; Selectivity ; Theoretical and Computational Chemistry ; Tuberculosis ; Viruses</subject><ispartof>Monatshefte für Chemie, 2019-01, Vol.150 (8), p.1533-1544</ispartof><rights>Springer-Verlag GmbH Austria, part of Springer Nature 2019</rights><rights>Springer-Verlag GmbH Austria, part of Springer Nature 2019.</rights><rights>2019© Springer-Verlag GmbH Austria, part of Springer Nature 2019</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c511t-dd8d1264e75196bc8d73057899b7ba69324b560d83534296402bfa326173bcb33</citedby><cites>FETCH-LOGICAL-c511t-dd8d1264e75196bc8d73057899b7ba69324b560d83534296402bfa326173bcb33</cites><orcidid>0000-0003-0516-6010</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00706-019-02457-9$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00706-019-02457-9$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>230,314,776,780,881,27901,27902,41464,42533,51294</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32214484$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Cihan-Üstündağ, Gökçe</creatorcontrib><creatorcontrib>Naesens, Lieve</creatorcontrib><creatorcontrib>Şatana, Dilek</creatorcontrib><creatorcontrib>Erköse-Genç, Gonca</creatorcontrib><creatorcontrib>Mataracı-Kara, Emel</creatorcontrib><creatorcontrib>Çapan, Gültaze</creatorcontrib><title>Design, synthesis, antitubercular and antiviral properties of new spirocyclic indole derivatives</title><title>Monatshefte für Chemie</title><addtitle>Monatsh Chem</addtitle><addtitle>Monatsh Chem</addtitle><description>A series of indole-based spirothiazolidinones have been designed, synthesized and evaluated, in vitro, for their antitubercular, antiviral, antibacterial, and antifungal activities. The structures of the new compounds were established by IR,
1
H NMR,
13
C NMR (proton decoupled, APT, and DEPT), electrospray ionization mass spectrometry, and microanalysis. Compounds bearing a phenyl substituent at position 8 of the spiro ring, exhibited significant antitubercular activity against
Mycobacterium tuberculosis
H37Rv ATCC 27294 at concentrations of 3.9 and 7.8 µM. Still, some of the tested compounds displayed activity on mycobacteria with MIC values of 16 and 31 µM. Four of the indole-spirothiazolidinone derivatives were found to be moderately active against Punta Toro virus, yellow fever virus or Sindbis virus in Vero cells. The antiviral EC
50
values were in the range of 1.9–12 µM and the selectivity index (ratio of cytotoxic to antivirally effective concentration) was above 10 in some cases. The most potent effect was seen with the compound that is methylated at positions 2 and 8 of the spirothiazolidinone system.
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1
H NMR,
13
C NMR (proton decoupled, APT, and DEPT), electrospray ionization mass spectrometry, and microanalysis. Compounds bearing a phenyl substituent at position 8 of the spiro ring, exhibited significant antitubercular activity against
Mycobacterium tuberculosis
H37Rv ATCC 27294 at concentrations of 3.9 and 7.8 µM. Still, some of the tested compounds displayed activity on mycobacteria with MIC values of 16 and 31 µM. Four of the indole-spirothiazolidinone derivatives were found to be moderately active against Punta Toro virus, yellow fever virus or Sindbis virus in Vero cells. The antiviral EC
50
values were in the range of 1.9–12 µM and the selectivity index (ratio of cytotoxic to antivirally effective concentration) was above 10 in some cases. The most potent effect was seen with the compound that is methylated at positions 2 and 8 of the spirothiazolidinone system.
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| subjects | Analytical Chemistry Chemistry Chemistry and Materials Science Chemistry/Food Science Derivatives Fungicides Inorganic Chemistry Ions Mass spectrometry NMR Nuclear magnetic resonance Organic Chemistry Original Paper Physical Chemistry Selectivity Theoretical and Computational Chemistry Tuberculosis Viruses |
| title | Design, synthesis, antitubercular and antiviral properties of new spirocyclic indole derivatives |
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