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Molecules 2016, 21(2), 214; doi:10.3390/molecules21020214

Synthesis, Molecular Structure Optimization, and Cytotoxicity Assay of a Novel 2-Acetyl-3-amino-5-[(2-oxopropyl)sulfanyl]-4-cyanothiophene

1
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
2
King Abdulaziz City for Science and Technology, P.O. Box 6086, Riyadh 11442, Saudi Arabia
3
Department of Chemistry, Rabigh College of Science and Art, King Abdulaziz University, P. O. Box 344, Rabigh 21911, Saudi Arabia
4
Department of Chemistry, Faculty of Science, Alexandria University, P. O. Box 426, Ibrahimia, 21321 Alexandria, Egypt
5
H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan
6
Lab of Chemical Material, Faculty of Sciences, University Mohammed Premier, Oujda 60000, Morocco
7
Department of Chemistry, The University of Jordan, Amman 11942, Jordan
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 8 January 2016 / Revised: 4 February 2016 / Accepted: 4 February 2016 / Published: 15 February 2016
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1834 KB, uploaded 19 February 2016]   |  

Abstract

A novel thiophene-containing compound, 2-acetyl-3-amino-5-[(2-oxopropyl)sulfanyl]-4-cyanothiophene (4) was synthesized by reaction of malononitrile with CS2 in the presence of K2CO3 under reflux in DMF and the subsequent reaction with chloroacetone followed by cyclization. This compound has been characterized by means of FT-IR, 1H-NMR, 13C-NMR, and mass spectrometry as well as elemental analysis. In addition, the molecular structures of compound 4 was determined by X-ray crystallography. The geometry of the molecule is stabilized by an intramolecular interaction between N1–H1···O1 to form S6 graf set ring motif. In the crystal, molecules are linked via N1–H2···O1 and C7–H7A···N2 interactions to form a three-dimensional network. Molecular structure and other spectroscopic properties of compound 4 were calculated using DFT B3LYP/6-31G (d,p) method. Results revealed a good agreement between the optimized geometric parameters and the observed X-ray structure. Furthermore, and by employing the natural bond orbital (NBO) method, the intramolecular charge transfer (ICT) interactions along with natural atomic charges at different sites, were calculated; results indicated strong n→π* ICT from LP(1)N5→BD*(2)C15-C16 (63.23 kcal/mol). In addition, the stabilization energy E(2) of the LP(2)O3→ BD*(1)N5-H6 ICT (6.63 kcal/mol) indicated the presence of intramolecular N-H···OH bonding. Similarly, calculations of the electronic spectra of compound 4 using, TD-DFT revealed a good agreement with the experimental data. Finally, compound 4 was evaluated for its in vitro cytotoxic effect against PC-3 and HeLa cell lines, as an anticancer agent, and found to be nontoxic. View Full-Text
Keywords: 2-acetyl-3-amino-5-[(2-oxopropyl)sulfanyl]-4-cyanothiophene; X-ray diffraction; DFT; molecular structure; cytotoxicity 2-acetyl-3-amino-5-[(2-oxopropyl)sulfanyl]-4-cyanothiophene; X-ray diffraction; DFT; molecular structure; cytotoxicity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Mabkhot, Y.N.; Aldawsari, F.D.; Al-Showiman, S.S.; Barakat, A.; Soliman, S.M.; Choudhary, M.I.; Yousuf, S.; Ben Hadda, T.; Mubarak, M.S. Synthesis, Molecular Structure Optimization, and Cytotoxicity Assay of a Novel 2-Acetyl-3-amino-5-[(2-oxopropyl)sulfanyl]-4-cyanothiophene. Molecules 2016, 21, 214.

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