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Synthesis, X-ray, H...
Synthesis, X-ray, Hirshfeld surface analysis, exploration of DNA binding, urease enzyme inhibition and anticancer activities of novel adamantane-naphthyl thiourea conjugate
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- Arshad, Nasima (författare)
- Allama Iqbal Open Univ, Dept Chem, Islamabad 44000, Pakistan.
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- Saeed, Aamer (författare)
- Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan.
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- Perveen, Fouzia (författare)
- Natl Univ Sci & Technol NUST, Res Ctr Modeling & Simulat, Islamabad, Pakistan.
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- Ujan, Rabail (författare)
- Univ Sindh, MA Kazi Inst Chem, Jamshoro 76080, Pakistan.
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- Farooqi, Shahid, I (författare)
- Allama Iqbal Open Univ, Dept Chem, Islamabad 44000, Pakistan.
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- Channar, Pervaiz Ali (författare)
- Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan.
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- Shabir, Ghulam (författare)
- Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan.
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- El-Seedi, Hesham (författare)
- Uppsala universitet,Farmakognosi
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- Javed, Aneela (författare)
- Natl Univ Sci & Technol NUST, Atta Ur Rehman Sch Appl Biosci, Healthcare Biotechnol, Islamabad, Pakistan.
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- Yamin, Maham (författare)
- Natl Univ Sci & Technol NUST, Atta Ur Rehman Sch Appl Biosci, Healthcare Biotechnol, Islamabad, Pakistan.
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- Bolte, Michael (författare)
- Goethe Univ Frankfurt, Inst Anorgan Chem, Max von Laue Str 7, D-60438 Frankfurt, Germany.
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- Hökelek, Tuncer (författare)
- Hacettepe Univ, Dept Phys, TR-06800 Beytepe, Turkey.
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Allama Iqbal Open Univ, Dept Chem, Islamabad 44000, Pakistan Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan. (creator_code:org_t)
- Elsevier, 2021
- 2021
- Engelska.
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Ingår i: Bioorganic chemistry (Print). - : Elsevier. - 0045-2068. ; 109
- Relaterad länk:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- 1-(adamantane-1-carbonyl-3-(1-naphthyl)) thiourea (C22H24N2OS (4), was synthesized by the reaction of freshly prepared adamantane-1-carbonyl chloride from corresponding acid (3) with ammonium thiocyanate in 1:1 M ratio in dry acetone to afford the adamantane-1-carbonyl isothiocyanate (2) in situ followed by treatment with 1-naphthyl amine (3). The structure was established by elemental analyses, FTIR, H-1, C-13 NMR and mass spectroscopy. The molecular and crystal structure were determined by single crystal X-ray analysis. It belongs to triclinic system P - 1 space group with a = 6.7832(5) angstrom, b = 11.1810(8) angstrom, c = 13.6660(10) angstrom, alpha = 105.941(6)degrees, beta = 103.730(6)degrees, gamma = 104.562(6)degrees, Z = 2, V = 910.82(11) angstrom(3). The naphthyl group is almost planar. In the crystal structure, intermolecular C-H center dot center dot center dot O hydrogen bonds link the molecules into centrosymmetric dimers, enclosing R-2(2)(14) ring motifs, while the intramolecular N-H center dot center dot center dot O hydrogen bonds enclose S(6) ring motifs, in which they may be effective in the stabilization of the structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H center dot center dot center dot H (59.3%), H center dot center dot center dot C/C center dot center dot center dot H (19.8%) and H center dot center dot center dot S/S center dot center dot center dot H (10.1%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. DFT, molecular docking and urease inhibition studies revealed stability and electron withdrawing nature of 4 as compared to DNA base pairs and residues of urease. The DNA binding results from docking, UV-visible spectroscopy, and viscosity studies indicated significant binding of 4 with the DNA via intercalation and groove binding. Further investigation of the compound was done on hepatocellular carcinoma; Huh-7 cell line as well as normal human embryonic kidney; Hek-293 cell line. The compound showed significant cytotoxic activity against Huh-7 cells in comparison to normal Hek-293 cells indicating selective cytotoxicity towards cancer cells.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Nyckelord
- Adamantanyl thiourea
- X-ray
- Hirshfeld surface analysis
- DNA binding
- Urease inhibition
- Anticancer potential
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Arshad, Nasima
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Saeed, Aamer
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Perveen, Fouzia
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Ujan, Rabail
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Farooqi, Shahid, ...
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Channar, Pervaiz ...
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visa fler...
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Shabir, Ghulam
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El-Seedi, Hesham
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Javed, Aneela
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Yamin, Maham
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Bolte, Michael
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Hökelek, Tuncer
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- Om ämnet
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- NATURVETENSKAP
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NATURVETENSKAP
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och Kemi
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och Organisk kemi
- Artiklar i publikationen
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Bioorganic chemi ...
- Av lärosätet
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Uppsala universitet