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Design, Synthesis, and Molecular Docking Studies of a Conjugated-Thiadiazole Thiourea Scaffold as Antituberculosis Agents

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dc.contributor.authorTATAR, ESRA
dc.contributor.authorsTatar, Esra; Karakus, Sevgi; Kucukguzel, Sukriye Guniz; Okullu, Sinem Oktem; Unubol, Nihan; Kocagoz, Tanil; De Clercq, Erik; Andrei, Graciela; Snoeck, Robert; Pannecouque, Christophe; Kalayci, Sadik; Sahin, Fikrettin; Sriram, Dharmarajan; Yogeeswari, Perumal; Kucukguzel, Ilkay
dc.date.accessioned2022-03-14T08:14:58Z
dc.date.available2022-03-14T08:14:58Z
dc.date.issued2016
dc.description.abstractIn view of the emergence and frequency of multidrug-resistant and extensively drug-resistant tuberculosis and consequences of acquired resistance to clinically used drugs, we undertook the design and synthesis of novel prototypes that possess the advantage of the two pharmacophores of thiourea and 1,3,4-thiadiazole in a single molecular backbone. Three compounds from our series were distinguished from the others by their promising activity profiles against Mycobacterium tuberculosis strain H(37)Rv. Compounds 11 and 19 were the most active representatives with minimum inhibitory concentration (MIC) values of 10.96 and 11.48 mu m, respectively. Compound 15 was shown to inhibit M. tuberculosis strain H(37)Rv with an MIC value of 17.81 mu m. Cytotoxicity results in the Vero cell line showed that these three derivatives had selectivity indices between 1.8 and 8.7. In order to rationalize the biological results of our compounds, molecular docking studies with the enoyl acyl carrier protein reductase (InhA) of M. tuberculosis were performed and compounds 11, 15, and 19 were found to have good docking scores in the range of -7.12 to -7.83 kcal/mol.
dc.identifier.doi10.1248/bpb.b15-00698
dc.identifier.issn0918-6158
dc.identifier.pubmed27040623
dc.identifier.urihttps://hdl.handle.net/11424/241290
dc.identifier.wosWOS:000373246100006
dc.language.isoeng
dc.publisherPHARMACEUTICAL SOC JAPAN
dc.relation.ispartofBIOLOGICAL & PHARMACEUTICAL BULLETIN
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subject1,3,4-thiadiazole
dc.subjectthiourea
dc.subjectantituberculosis activity
dc.subjectcytotoxicity
dc.subjectmolecular docking
dc.subjectDRUG-RESISTANT TUBERCULOSIS
dc.subjectANTIMYCOBACTERIAL ACTIVITY
dc.subjectBIOLOGICAL EVALUATION
dc.subjectMULTIDRUG-RESISTANT
dc.subjectMYCOBACTERIUM-TUBERCULOSIS
dc.subjectNONNUCLEOSIDE INHIBITORS
dc.subjectMANNICH-BASES
dc.subjectDISCOVERY
dc.subjectDERIVATIVES
dc.subjectACTIVATION
dc.titleDesign, Synthesis, and Molecular Docking Studies of a Conjugated-Thiadiazole Thiourea Scaffold as Antituberculosis Agents
dc.typearticle
dspace.entity.typePublication
local.avesis.id72152714-03f6-4574-a392-dafce3a61c18
local.import.packageSS16
local.indexed.atWOS
local.indexed.atSCOPUS
local.indexed.atPUBMED
local.journal.numberofpages14
local.journal.quartileQ3
oaire.citation.endPage515
oaire.citation.issue4
oaire.citation.startPage502
oaire.citation.titleBIOLOGICAL & PHARMACEUTICAL BULLETIN
oaire.citation.volume39
relation.isAuthorOfPublicatione2c939bf-1387-4174-802c-e714419b20af
relation.isAuthorOfPublication.latestForDiscoverye2c939bf-1387-4174-802c-e714419b20af

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