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Mammino, Liliana Ghio, Caterina Tshilande, Neani 2019 2019-11-28T07:05:37Z 2019-11-28T07:05:37Z 2019-09-20 Tshilande, Neani (2019) AB INITIO and DFT computational study of Myristinin A and A structurally- related molecule, University of Venda, South Africa.<http://hdl.handle.net/11602/1508>. http://hdl.handle.net/11602/1508 Tshilande N. AB INITIO and DFT computational study of Myristinin A and A structurally- related molecule. []. , 2019 [cited yyyy month dd]. Available from: http://hdl.handle.net/11602/1508 Tshilande, N. (2019). <i>AB INITIO and DFT computational study of Myristinin A and A structurally- related molecule</i>. (). . Retrieved from http://hdl.handle.net/11602/1508 Tshilande, Neani. <i>"AB INITIO and DFT computational study of Myristinin A and A structurally- related molecule."</i> ., , 2019. http://hdl.handle.net/11602/1508 TY - Dissertation AU - Tshilande, Neani AB - The computational study of biologically active molecules is particularly important for drug development because it provides crucial information about the properties of a molecule, which determine its biological activities. The current work considers the results of a computational study of myristinin A and a structurally-related molecule (2-(4-hydroxyphenyl)-4-[2,4,6-trihydroxy-3-(9tetradecenoyl)phenyl]-3,4-dihydro-2H-benzopyran-7-ol, here denoted as DBPO). The two compounds pertain to the class of acylphloroglucinols. They were firstly isolated from Horsfieldia amygdaline, and they exhibit a variety of biological activities, including potent anti-inflammatory activity, potent DNA-damaging activity and DNA-polymerase ß inhibition. Their molecular structures differ only by the acyl chain. Both molecules have a bulky substituent meta to the acyl group consisting of a ring system (2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-7-ol). The DBPO molecule can exist as cis and trans isomers in relation to the double bond present in the R chain, and both isomers are here investigated individually. The OHs ortho to the acyl group can form an intramolecular hydrogen bond (referred to as the first IHB) with the sp2 O atom of the acyl group. The phenol OHs neighbouring the substituent ring system can form O–Hπ interaction with the aromatic rings of the substituent, if suitable oriented. This study focuses on the identification of the stable conformers of these molecules (considering all the possible geometries obtainable by rotations about relevant single bonds), and of the factors stabilising the conformers. Full-optimisation calculations were performed in vacuo and also in three conveniently selected solvents. The results show that the dominant stabilising factors are the first IHB and the O–Hπ interactions. Other factors which have significant influence on conformational preferences are the orientation of the ring systems of the substituent, the orientation of the OHs on substituent, the mutual orientation of the OHs of the phloroglucinol moiety and also the orientation of the acyl chain. The results in solution are consistent with the findings of other acylphloroglucinols, for instance, the narrowing of the energy gaps and the increase of the dipole moment with the increase of solvent polarity. DA - 2019-09-20 DB - ResearchSpace DP - Univen KW - AB INITIO KW - DFT KW - Computational study KW - Myristinin A. LK - https://univendspace.univen.ac.za PY - 2019 T1 - AB INITIO and DFT computational study of Myristinin A and A structurally- related molecule TI - AB INITIO and DFT computational study of Myristinin A and A structurally- related molecule UR - http://hdl.handle.net/11602/1508 ER - MSc (Chemistry) Department of Chemistry The computational study of biologically active molecules is particularly important for drug development because it provides crucial information about the properties of a molecule, which determine its biological activities. The current work considers the results of a computational study of myristinin A and a structurally-related molecule (2-(4-hydroxyphenyl)-4-[2,4,6-trihydroxy-3-(9tetradecenoyl)phenyl]-3,4-dihydro-2H-benzopyran-7-ol, here denoted as DBPO). The two compounds pertain to the class of acylphloroglucinols. They were firstly isolated from Horsfieldia amygdaline, and they exhibit a variety of biological activities, including potent anti-inflammatory activity, potent DNA-damaging activity and DNA-polymerase ß inhibition. Their molecular structures differ only by the acyl chain. Both molecules have a bulky substituent meta to the acyl group consisting of a ring system (2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-7-ol). The DBPO molecule can exist as cis and trans isomers in relation to the double bond present in the R chain, and both isomers are here investigated individually. The OHs ortho to the acyl group can form an intramolecular hydrogen bond (referred to as the first IHB) with the sp2 O atom of the acyl group. The phenol OHs neighbouring the substituent ring system can form O–Hπ interaction with the aromatic rings of the substituent, if suitable oriented. This study focuses on the identification of the stable conformers of these molecules (considering all the possible geometries obtainable by rotations about relevant single bonds), and of the factors stabilising the conformers. Full-optimisation calculations were performed in vacuo and also in three conveniently selected solvents. The results show that the dominant stabilising factors are the first IHB and the O–Hπ interactions. Other factors which have significant influence on conformational preferences are the orientation of the ring systems of the substituent, the orientation of the OHs on substituent, the mutual orientation of the OHs of the phloroglucinol moiety and also the orientation of the acyl chain. The results in solution are consistent with the findings of other acylphloroglucinols, for instance, the narrowing of the energy gaps and the increase of the dipole moment with the increase of solvent polarity. NRF 1 online resource ( en University of Venda AB INITIO DFT Computational study Myristinin A. UCTD 541.22 Molecules Biomolecules Chemical templates AB INITIO and DFT computational study of Myristinin A and A structurally- related molecule Dissertation open.access