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

Tatar, Esra; Karakuş, Sevgi; Küçükgüzel, Ş. Güniz; Okullu, Sinem Öktem; Unubol, Nihan Aytekin; Kocagoz, Tanil; Clercq, Erik De; Andrei, Gracíela; Snoeck, Robert; Pannecouque, Christophe; Kalaycı, Sadık; Şahın, Fikrettin; Sriram, Dharmarajan; Yogeeswari, Perumal; Küçükgüzel, İlkay

doi:10.1248/bpb.b15-00698

Cited by 39 publications

(25 citation statements)

References 62 publications

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“…In the 1 H-NMR spectra of compound 2, resonances assigned to the N 1 -H and N 2 -H protons of thiourea were detected between 8.83-13.28 ppm as three broad singlets, which are supported by the literature (7,44,45). When we examined the IR spectra of compounds 3 and 4, we detected two C=S stretching bands at 1106-1170 cm -1 and 1216-1235 cm -1 , and N-H stretching bands at 3084-3188 cm -1 , whereas C=O stretching bands of the acylthioureas disappeared.…”

Section: Whensupporting

confidence: 83%

“…The IR spectra of compounds 1 and 2 have C=O, C=S and N-H stretching bands of acylthiourea group at 1674-1675 cm , and 3256-3274 cm -1 , respectively (7,43). In the 1 H-NMR spectra of compound 2, resonances assigned to the N 1 -H and N 2 -H protons of thiourea were detected between 8.83-13.28 ppm as three broad singlets, which are supported by the literature (7,44,45).…”

Section: Whensupporting

confidence: 77%

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Tiyoüreler, açiltiyoüreler ve 4-tiyazolidinonların sentezi, karakterizasyonu ve antikanser ve antiviral etkilerinin değerlendirilmesi

Kulabaş¹,

Özakpınar²,

Özsavcı³

et al. 2017

Marmara Pharmaceutical Journal

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In this study, thiourea derivatives [1][2][3][4] were synthesized by using 2-amino-4-substituted pyridine compounds and these compounds have been used as the starting materials for synthesis of 2-imino-1,3-thiazolidin-4-one ring [5,6]. Two different procedures for 4-thiazolidinone ring closure and synthesis method were optimized. The synthesized compounds were identified by the help of elemental analysis, IR, 1 H-NMR, 13 C-NMR and mass spectral data while the purities of them were proved with TLC. Synthesized compounds were evaluated for their antiviral and anticancer activity. Antiviral activity against Murine norovirus, Yellow fever, Enterovirus and Chikungunya strains of the test compounds were investigated and EC 50 values of these compounds were determined higher than 0,3 µM. Cytotoxicity of test compounds was examined on NIH3T3 cell line. When the anticancer activity of test compounds was examined against PC-3, A549, HeLa, HT-29, MCF-7, SJSA1 and K562 cell lines, the percent proliferation values of these compounds were observed over 61% for all cell lines.

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Section: Whensupporting

confidence: 83%

Section: Whensupporting

confidence: 77%

Tiyoüreler, açiltiyoüreler ve 4-tiyazolidinonların sentezi, karakterizasyonu ve antikanser ve antiviral etkilerinin değerlendirilmesi

Kulabaş¹,

Özakpınar²,

Özsavcı³

et al. 2017

Marmara Pharmaceutical Journal

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“…The structures of the obtained compounds were elucidated by spectral data. The IR spectra of 3a-f showed two separate bands resulting from the N-H and C=O streching bands of the amide function at about regions 3402-3277 and 1685-1653 cm -1 , respectively (19,20). In the spectra of 1 H-NMR of 3a-f the CH 2 and CONH of the acetylamino moiety were observed as a double singlets presumably due to the partial double bond character of the C-N bond and the bulk of the attached cyclohexyl structure which can disrupt free rotation about the cited bond (δ 3.73-3.35 and δ 10.41-10.16 ppm, respectively) (21).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and antiviral activity evaluation of some new cyclohexylidenehydrazide derivatives of 1,3-thiazole core

Ulusoy¹,

Pehlivan²,

Halamoğlu³

et al. 2016

Marmara Pharm J

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“…The binding affinity of b is slightly higher than a due to the electron donating inductive effect of the substituted methyl group, which provides better interactions network with the active site residues [36]. The absence of aromatic ring was accountable for lesser binding affinity resulting in less activity in a-b [37].…”

Section: Molecular Docking Design and Optimisationmentioning

confidence: 97%

One-Pot Multicomponent Synthesis of Thiourea Derivatives in Cyclotriphosphazenes Moieties

Ngaini

Zulkiplee

Halim

2017

Journal of Chemistry

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In this study, hexasubstituted thiourea was carried out via reaction of isothiocyanato cyclophosphazene intermediates with a series of aromatics amines and amino acids in a one-pot reaction system. The reaction was not as straightforward as typical thiourea synthesis. Six unexpected thiourea derivatives a-f were formed in the presence of cyclotriphosphazene moieties in good yields (53-82%). The structures of a-f were characterized by elemental analysis and FTIR, 1 H, 13 C, and 31 P NMR spectroscopies. The occurrence of reverse thioureas formation in a one-pot reaction system is discussed. The possible binding interaction of the synthesised thiourea a-b in comparison to the predicted phenyl thiourea a-b and the targeted a with enzyme enoyl ACP reductase (FabI) is also discussed. Molecular docking of the targeted hexasubstituted thiourea a is able to give higher binding affinity of −7.5 kcal/mol compared to a-b (−5.9 kcal/mol and −6.3 kcal/mol) and thiourea a-b (−4.5 kcal/mol and −4.7 Kcal/mol).

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

Cited by 39 publications

References 62 publications

Tiyoüreler, açiltiyoüreler ve 4-tiyazolidinonların sentezi, karakterizasyonu ve antikanser ve antiviral etkilerinin değerlendirilmesi

Tiyoüreler, açiltiyoüreler ve 4-tiyazolidinonların sentezi, karakterizasyonu ve antikanser ve antiviral etkilerinin değerlendirilmesi

Synthesis and antiviral activity evaluation of some new cyclohexylidenehydrazide derivatives of 1,3-thiazole core

One-Pot Multicomponent Synthesis of Thiourea Derivatives in Cyclotriphosphazenes Moieties

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