Crystal Structure of 4-Hydroxy-3-methoxybenzaldehyde-4-methylthiosemicarbazone

Oliveira, Adriano Bof de; Beck, Johannes; Daniels, Jörg; Feitosa, Bárbara Regina Santos

doi:10.2116/xraystruct.31.5

Cited by 2 publications

(4 citation statements)

References 4 publications

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“…The peak at 1343 cm −1 corresponds to v(N=O). The obtained peaks are consistent with previous reports with minor changes [43,66,67]. The peaks between 1451-1454 cm −1 are due to the aromatic C=C stretching.…”

Section: Synthesis and Characterization Of 3-mbtsc And 4-nbtsc Compoundssupporting

confidence: 92%

Synthesis, In Silico Study, and Anti-Cancer Activity of Thiosemicarbazone Derivatives

et al. 2021

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Thiosemicarbazones are known for their biological and pharmacological activities. In this study, we have synthesized and characterized 3-Methoxybenzaldehyde thiosemicarbazone (3-MBTSc) and 4-Nitrobenzaldehyde thiosemicarbazone (4-NBTSc) using IR, 1HNMR and 13C NMR. The compound’s in vitro anticancer activities against different cell lines were evaluated. Molecular docking, Insilco ADMET, and drug-likeness prediction were also done. The test compounds showed a comparative IC50 and growth inhibition with the standard drug Doxorubicin. The IC50 ranges from 2.82 µg/mL to 14.25 µg/mL in 3-MBTSc and 2.80 µg/mL to 7.59 µg/mL in 4-NBTSc treated cells. The MTT assay result revealed, 3-MBTSc inhibits 50.42 and 50.31 percent of cell growth in B16-F0 and EAC cell lines, respectively. The gene expression showed that tumor suppressor genes such as PTEN and BRCA1 are significantly upregulated in 7.42 and 5.33 folds, and oncogenes, PKC, and RAS are downregulated −7.96 and −7.64 folds, respectively in treated cells. The molecular docking performed on the four targeted proteins (PARP, VEGFR-1, TGF-β1, and BRAFV600E) indicated that both 4-NBTSc and 3-MBTSc potentially bind to TGF-β1 with the best binding energy of −42.34 Kcal/mol and −32.13 Kcal/mol, respectively. In addition, the test compound possesses desirable ADMET and drug-likeness properties. Overall, both 3-MBTSc and 4-NBTSc have the potential to be multitargeting drug candidates for further study. Moreover, 3-MBTSc showed better activity than 4-NBTSc.

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Section: Synthesis and Characterization Of 3-mbtsc And 4-nbtsc Compoundssupporting

confidence: 92%

Synthesis, In Silico Study, and Anti-Cancer Activity of Thiosemicarbazone Derivatives

et al. 2021

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“…The second selected molecule is the vanilline 4-methylthiosemicarbazone derivative (Oliveira, Beck et al, 2015) in which the thiosemicarbazone entities are connected by N-H� � �S interactions, with graph-set motif R 2 2 (8), into centrosymmetric dimers. The dimers are further linked through N-H� � �S and O-H� � �S interactions and can be considered subunits of a hydrogen-bonded tape-like supramolecular arrangement.…”

Section: Compound Atom Chain Torsion Angle Atom Chain Torsion Anglementioning

confidence: 99%

“…The starting materials are commercially available and were used without further purification. The synthesis of the cisjasmone 4-methylthiosemicarbazone derivative was adapted from previously reported procedures (Oliveira, Beck et al, 2015;Orsoni et al, 2020). A mixture of ethanolic solutions of cis-jasmone (8 mmol in 50 ml) and 4-methylthiosemicarbazide (8 mmol in 50 ml) was catalysed with HCl and refluxed for 8 h. After cooling, the precipitated product was filtered off and washed with cold ethanol.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

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N-Methyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide

Oliveira,

Bresolin,

Beck

et al. 2024

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The equimolar and hydrochloric acid-catalysed reaction between cis-jasmone and 4-methylthiosemicarbazide in ethanolic solution yields the title compound, C13H21N3S (common name: cis-jasmone 4-methylthiosemicarbazone). Two molecules with all atoms in general positions are present in the asymmetric unit. In one of them, the carbon chain is disordered [site occupancy ratio = 0.821 (3):0.179 (3)]. The thiosemicarbazone entities [N—N—C(=S)—N] are approximately planar, with the maximum deviation from the mean plane through the selected atoms being −0.0115 (16) Å (r.m.s.d. = 0.0078 Å) for the non-disordered molecule and 0.0052 (14) Å (r.m.s.d. = 0.0031 Å) for the disordered one. The molecules are not planar, since the jasmone groups have a chain with sp 3-hybridized carbon atoms and, in addition, the thiosemicarbazone fragments are attached to the respective carbon five-membered rings and the dihedral angles between them for each molecule amount to 8.9 (1) and 6.3 (1)°. In the crystal, the molecules are connected through pairs of N—H...S and C—H...S interactions into crystallographically independent centrosymmetric dimers, in which rings of graph-set motifs R 2 2(8) and R 2 1(7) are observed. A Hirshfeld surface analysis indicates that the major contributions for the crystal cohesion are from H...H (70.6%), H...S/S...H (16.7%), H...C/C...H (7.5%) and H...N/N...H (4.9%) interactions [considering the two crystallographically independent molecules and only the disordered atoms with the highest s.o.f. for the evaluation].

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Crystal Structure of 4-Hydroxy-3-methoxybenzaldehyde-4-methylthiosemicarbazone

Cited by 2 publications

References 4 publications

Synthesis, In Silico Study, and Anti-Cancer Activity of Thiosemicarbazone Derivatives

Synthesis, In Silico Study, and Anti-Cancer Activity of Thiosemicarbazone Derivatives

N-Methyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide

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