William T. A. Harrison

University of Aberdeen, Aberdeen, Scotland, United Kingdom

Are you William T. A. Harrison?

Claim your profile

Publications (753)1076.86 Total impact

  • [Show abstract] [Hide abstract]
    ABSTRACT: Oxazolidin-2-ones are widely used as protective groups for 1,2-amino alcohols and chiral derivatives are employed as chiral auxiliaries. The crystal structures of four differently substituted oxazolidinecarbohydrazides, namely N'-[(E)-benzylidene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazide, C12H12N3O3, (I), N'-[(E)-2-chlorobenzylidene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazide, C12H12ClN3O3, (II), (4S)-N'-[(E)-4-chlorobenzylidene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazide, C12H12ClN3O3, (III), and (4S)-N'-[(E)-2,6-dichlorobenzylidene]-N,3-dimethyl-2-oxo-1,3-oxazolidine-4-carbohydrazide, C13H13Cl2N3O3, (IV), show that an unexpected mild-condition racemization from the chiral starting materials has occurred in (I) and (II). In the extended structures, the centrosymmetric phases, which each crystallize with two molecules (A and B) in the asymmetric unit, form A+B dimers linked by pairs of N-H...O hydrogen bonds, albeit with different O-atom acceptors. One dimer is composed of one molecule with an S configuration for its stereogenic centre and the other with an R configuration, and possesses approximate local inversion symmetry. The other dimer consists of either R,R or S,S pairs and possesses approximate local twofold symmetry. In the chiral structure, N-H...O hydrogen bonds link the molecules into C(5) chains, with adjacent molecules related by a 21 screw axis. A wide variety of weak interactions, including C-H...O, C-H...Cl, C-H...π and π-π stacking interactions, occur in these structures, but there is little conformity between them.
    08/2015; 71(Pt 8):647-52. DOI:10.1107/S2053229615012450
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: The crystal structures of three methyl­ated hydrazine carbamate derivatives prepared by multi-step syntheses from L-serine are presented, namely benzyl N-{(E)-1-[2-(4-cyanobenzylidene)-1-methylhydrazinyl]-3-hydroxy-1-oxopro­pan-2-yl}carbamate, C20H20N4O4, tert-butyl N-{(E)-1-[2-(4-cyanobenzylidene)-1-methylhydrazinyl]-3-hydroxy-1-oxopropan-2-yl}carbamate, C17H22N4O4, and tert-butyl N-[(E)-1-(2-benzylidene-1-methylhydrazinyl)-3-hydroxy-1-oxopro­pan-2-yl]carbamate, C16H23N3O4. One of them shows that an unexpected racemization has occurred during the mild-condition methyl­ation reaction. In each crystal structure, the mol­ecules are linked into chains by O-HO hydrogen bonds, but with significant differences between them.
    07/2015; 71(7):752-756. DOI:10.1107/S2056989015010440
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: A series of thiazole, pyridine and benzylidene derivatives derived from thiophene scaffold have been synthesized. The antitumor evaluation of the newly synthesized products against four cancer cell lines, namely breast carcinoma (MCF-7), liver carcinoma (HepG2), colon carcinoma (HCT-116) and prostate carcinoma (PC3), indicated that the thiazole derivative 11b showed remarkable activity against all cell lines with LC50 values of 18.3, 2.5, 7.5 and 7.6 µM, respectively. Cytotoxicity toward normal cell lines was also investigated and indicated that compound 21c displayed remarkable potency against PC3 with LC50 values of 7.1 µM and showed weak inhibition of normal cell lines at (GI %) of 41.2 % and thus could be considered as an important lead compound for potential application in anticancer chemotherapy. Brine shrimp lethality assay of the most active compounds was carried out to detect possible cytotoxicity effects and indicated that highly active compound, 21c, is not harmful. The X-ray crystallographic analysis of compounds 3 and 11b was obtained thus establishing with certainty the proposed structures in this work. The synthesized compounds were also screened for their free radical scavenging activity. Hydrazino–thiazole derivatives 15 and 16 showed remarkable antioxidant activity with IC50 values of 60.9 and 61.9 μg ml−1, respectively.
    Medicinal Chemistry Research 07/2015; 24(7):3021-3036. DOI:10.1007/s00044-015-1353-5 · 1.61 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: The crystal structures of four indole derivatives with various substituents at the 2-, 3- and 5-positions of the ring system are described, namely, ethyl 3-(5-chloro-2-phenyl-1H-indol-3-yl)-3-phenyl­propano­ate, C25H22ClNO2, (I), 2-bromo-3-(2-nitro-1-phenyl­eth­yl)-1H-indole, C16H13BrN2O2, (II), 5-meth­oxy-3-(2-nitro-1-phenyl­eth­yl)-2-phenyl-1H-indole, C23H20N2O3, (III), and 5-chloro-3-(2-nitro-1-phenyl­eth­yl)-2-phenyl-1H-indole, C22H17ClN2O2, (IV). The dominant inter­molecular inter­action in each case is an N-HO hydrogen bond, which generates either chains or inversion dimers. Weak C-HO, C-H and - inter­actions occur in these structures but there is no consistent pattern amongst them. Two of these compounds act as modest enhancers of CB1 cannabanoid signalling and two are inactive.
    06/2015; 71(6):654-659. DOI:10.1107/S2056989015008476
  • M. John Plater · William T. A. Harrison
    [Show abstract] [Hide abstract]
    ABSTRACT: The synthesis of mellite from mellitic acid, KOH and Al2(SO4)3•18H2O is demonstrated and discussed as a potential geomimetic process for the formation of the mineral mellite in brown coal. The single crystal structures and IR spectra of the mineral mellite and of synthetic mellite are identical.
    Journal of Chemical Research 05/2015; 39(5). DOI:10.3184/174751915X14303279945021 · 0.70 Impact Factor
  • M. John Plater · Ben M. De Silva · Mark R. St J. Foreman · William T.A. Harrison
    [Show abstract] [Hide abstract]
    ABSTRACT: The syntheses and structures of the coordination polymers [Cd(ppeb)2(H2O)2]n·(NO3)2n (1), [Cd(ppeb)2(ClO4)2]n (2), [Cd(opeb)2(NO3)2]n (3) and [Cd(opeb)2(H2O)2]n·(ClO4)2n (4), where ppeb and opeb represent the 1,4- and 1,2-isomers of bis[2-(3-pyridyl)ethyl]-benzene, C20H20N2, respectively, are described. Each structure contains trans-CdO2N4 octahedra. In 1 and 2, they are bridged by pairs of ligands to generate looped chains, whereas in 3 and 4 the ligands link the metal nodes into squashed 44 polymeric sheets. In 1 and 4, O-H…O hydrogen bonds from the coordinated water molecules to the uncoordinated anions help to consolidate the structures.
    Journal of Coordination Chemistry 03/2015; 68(10):1-27. DOI:10.1080/00958972.2015.1028381 · 2.22 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: Novel palladium(II) and platinum(II) complexes of 5,5-diethylbarbiturate (barb) with 2-phenylpyridine (Hppy), 2,2’-bipyridine (bpy) and 2,2’-dipyridylamine (dpya) have been prepared and characterized by elemental analysis, IR, UV-Vis, NMR and ESI-MS. Single-crystal diffraction measurements show that complex 1 consists of binuclear [Pd2(μ-barb-κN,O)2(ppy-κN,C)2] moieties, while complexes 3–5 are mononuclear, [M(barb-κN)2(L-κN,N’)] (L = bpy or dpya). 6 has a composition of [Pt(dpya- κN,N’)2][Ag(barb-κN)2]2·4H2O and 2 was assumed to have a structure of [Pt(barb)(Hppy-κN)(ppy- κN,C)]·3H2O. The complexes were found to exhibit significant DNA binding affinity by a non-covalent binding mode, in accordance with molecular docking studies. In addition, complexes 1 and 2 displayed strong binding with supercoiled pUC19 plasmid DNA. Cellular uptake studies were performed to assess the subcellular localization of the selected complexes. A moderate radical scavenging activity of 1 and 2 was confirmed by DPPH and ABTS tests. Complexes 1, 2, and 5 showed selectivity against HT-29 (colon) cell line.
    Dalton Transactions 03/2015; 44:6880 - 6895. DOI:10.1039/C5DT00728C · 4.20 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: Novel palladium(II) and platinum(II) complexes of 5,5-diethylbarbiturate (barb) with 2-phenylpyridine (Hppy), 2,2’-bipyridine (bpy) and 2,2’-dipyridylamine (dpya) have been prepared and characterized by elemental analysis, IR, UV-Vis, NMR and ESI-MS. Single-crystal diffraction measurements show that complex 1 consists of binuclear [Pd2(μ-barb-κN,O)2(ppy-κN,C)2] moieties, while complexes 3–5 are mononuclear, [M(barb-κN)2(L-κN,N’)] (L = bpy or dpya). 6 has a composition of [Pt(dpya- κN,N’)2][Ag(barb-κN)2]2·4H2O and 2 was assumed to have a structure of [Pt(barb)(Hppy-κN)(ppy- κN,C)]·3H2O. The complexes were found to exhibit significant DNA binding affinity by a non-covalent binding mode, in accordance with molecular docking studies. In addition, complexes 1 and 2 displayed strong binding with supercoiled pUC19 plasmid DNA. Cellular uptake studies were performed to assess the subcellular localization of the selected complexes. A moderate radical scavenging activity of 1 and 2 was confirmed by DPPH and ABTS tests. Complexes 1, 2, and 5 showed selectivity against HT-29 (colon) cell line.
    Dalton Transactions 03/2015; · 4.20 Impact Factor
  • Source
    M. John Plater · William T.A. Harrison
    [Show abstract] [Hide abstract]
    ABSTRACT: 2,4-Difluoronitrobenzene is reacted with either one or two amines selected from aniline, ammonia, butylamine and benzylamine. All products are characterised spectroscopically and by single-crystal structure determinations. When formed as a minor component alongside 4-dimethylamino-2-(phenylamino)nitrobenzene, 2,4-bis(phenylamino)nitrobenzene crystallises as a hydrogen-bonded hexamer, or paddle-wheel motif, encompassing one-dimensional channels, but as a dense framework when pure. 2,4-Bis(butylamino)nitrobenzene crystallises with the same hexamer motif but with offset sheets.
    Journal of Chemical Research 02/2015; 39(2). DOI:10.3184/174751915X14223549608222 · 0.70 Impact Factor
  • S. Hussain · I. U. Khan · William T. A. Harrison · M. N. Tahir · S. Ahmad
    Journal of Structural Chemistry 01/2015; 56(1):126-133. DOI:10.1134/S0022476615010187 · 0.50 Impact Factor
  • M. John Plater · William T.A. Harrison
    [Show abstract] [Hide abstract]
    ABSTRACT: Heating p-toluidine hydrochloride in tert-butanol gave a crystalline precipitate of N-tert-butyl-p-toluidine hydrochloride. This compound, now readily available by this simple procedure, was used to make mauveine, which was found by TLC analysis to be identical to authentic mauveine.
    Journal of Chemical Research 11/2014; 38(11). DOI:10.3184/174751914X14136446204529 · 0.70 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: Three heteroleptic divalent-metal alkyl-carbazate-thiocyanate complexes, [M(NCS)2(NH2NHCOOR)2] [M = Co and R = CH2CH3 (1); M = Co and R = CH3 (2); M = Zn and R = CH3 (3)], have been prepared and characterized, and their crystal structures determined. In 1, Co(II) adopts a fairly regular centrosymmetric trans-CoO2N4 octahedral geometry arising from its coordination by two N,O-bidentate ethylcarbazate ligands and two trans N-bonded thiocyanates. In isostructural 2 and 3, the metals adopt distorted cis-MO2N4 octahedral geometries arising from two N,O-bidentate methylcarbazate ligands with cis N-bonded thiocyanates. The crystal structures feature N–H…O and N–H…S interactions. Thermal analysis data show that these compounds begin to decompose at temperatures between 130 and 160 °C. Crystal data: 1, CoC8H16N6O4S2, M r = 383.32, P2 1 /n (No. 14), a = 5.2599(3) Å, b = 7.4209(4) Å, c = 20.1948(12) Å, β = 94.070(1)°, V = 786.28(8) Å3, Z = 2, R(F) = 0.028, wR(F 2) = 0.073; 2, CoC6H12N6O4S2, M r = 355.27, P2 1 /n (No. 14), a = 7.8663(3) Å, b = 10.5804(3) Å, c = 17.6313(5) Å, β = 102.019(10)°, V = 1435.26(8) Å3, Z = 4, R(F) = 0.036, wR(F 2) = 0.097; 3, ZnC6H12N6O4S2, M r = 361.71, P2 1 /n (No. 14), a = 7.8883(2) Å, b = 10.5756(3) Å, c = 17.5827(5) Å, β = 101.676(1)°, V = 1436.46(7) Å3, Z = 4, R(F) = 0.031, wR(F 2) = 0.084.
    Journal of Coordination Chemistry 10/2014; 67(20). DOI:10.1080/00958972.2014.965697 · 2.22 Impact Factor
  • Chiara - Zanato · Sonia - Watson · Guy S. Bewick · Matteo Zanda · William T. A. Harrison
    [Show abstract] [Hide abstract]
    ABSTRACT: (−)-Kainic acid potently increases stretch-induced afferent firing in muscle spindles, probably acting through a hitherto uncloned phospholipase D (PLD)-coupled mGlu receptor. Structural modification of (−)-kainic acid was undertaken to explore the C-4 substituent effect on the pharmacology related to muscle spindle firing. Three analogues 1a-c were synthesised by highly stereoselective additions of a CF3, a hydride and an alkynyl group to the Re face of the key pyrrolidin-4-one intermediate 5a followed by further structural modifications. Only the 4-(1,2,3-triazolyl)-kainate derivative 1c retained the kainate-like agonism, increasing firing in a dose-dependent manner. Further modification of 1c by introduction of a PEG-biotin chain on the 1,2,3-triazole fragment afforded compound 14 which retained robust agonism at 1 μM and appears to be suitable for future use in pull-down assays and far western blotting for PLD-mGluR isolation.
    Organic & Biomolecular Chemistry 10/2014; 12(47). DOI:10.1039/C4OB02002B · 3.49 Impact Factor
  • William T. A. Harrison · Magnus G. Johnston
    [Show abstract] [Hide abstract]
    ABSTRACT: (NH4)(VIVO2)(VVO2) (TeO3) is obtained by solvothermal processing of a mixture of V2O5, TeO2, NH3, and H2O (pH 8.5, autoclave, 438 K, 3 d).
    ChemInform 09/2014; 45(38). DOI:10.1002/chin.201438014
  • Source
    William T A Harrison
    [Show abstract] [Hide abstract]
    ABSTRACT: The complete polyoxidometallate anion in the title compound, (CH6N3)4[H6V4As6O30]·4H2O, is generated by crystallographic inversion symmetry. The polyhedral building units are distorted VO6 octa-hedra and AsO3OH tetra-hedra. The VO6 units feature a short formal V=O double bond and are linked by a common edge. Two such V2O6 double octahedral units are linked by four isolated AsO3OH tetra-hedra to complete the anion, which features two inter-nal O-H⋯O hydrogen bonds. In the crystal, O-H⋯O hydrogen bonds between the polyoxidometallate anions generate (01-1) sheets. The sheets are connected by cation-to-cluster N-H⋯O hydrogen bonds, and cation-to-water N-H⋯O links also occur. The O atom of one of the water mol-ecules is disordered over two sites in a 0.703 (17):0.297 (17) ratio.
    Acta Crystallographica Section E Structure Reports Online 09/2014; 70(Pt 9):m305-6. DOI:10.1107/S1600536814011349 · 0.35 Impact Factor
  • Source
    William T A Harrison · Ola K Al-Sakka · Daisy H Fleita · Amina Saleh · Sara Salem
    [Show abstract] [Hide abstract]
    ABSTRACT: In the title compound, C9H13N3O, the cyclo­hexyl­idene ring adopts a chair conformation and the bond-angle sum at the C atom linked to the N atom is 359.6°. The cyano­acetohydrazide grouping is close to planar (r.m.s. deviation for the non-H atoms = 0.031 Å) and subtends a dihedral angle of 64.08 (4)° with the four C atoms forming the seat of the chair. The C=O and N—H groups are in a syn conformation (O—C—N—H = −5°). In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R 2 2(8) loops; this dimer linkage is reinforced by a pair of C—H⋯O inter­actions, which generate R 2 2(14) loops. The dimers are linked by C—H⋯Nc (c = cyanide) inter­actions into [100] ladders, which feature C(4) chains and R 4 4(20) loops.
    Acta Crystallographica Section E Structure Reports Online 09/2014; 70(Pt 9):o886. DOI:10.1107/S1600536814009350 · 0.35 Impact Factor
  • Source
    William T A Harrison · John Nicolson Low · James L Wardell
    [Show abstract] [Hide abstract]
    ABSTRACT: In the title benzohydrazide hydrate, C14H12N2O3·H2O, the dihedral angle between the aromatic rings is 58.11 (6)° and the C=O and N—H groups adopt an anti orientation. The main twist in the mol­ecule occurs about the C(=O)—Car (ar = aromatic) bond, with an N—C(=O)—Car—Car torsion angle of −43.5 (2)°. In the crystal, the components are linked by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds. These inter­actions generate [10-1] chains, with adjacent organic mol­ecules linked by inversion symmetry generating either pairs of N—H⋯O links [R 2 2(16) loops] or pairs of O—H⋯O links [R 2 2(20) loops]. Pairs of water mol­ecules are located in the R 2 2(20) loops and form their own O—H⋯O and O—H⋯N hydrogen bonds to adjacent organic mol­ecules in the chain. Finally, an inter­chain O—H⋯O hydrogen-bond link from the 4-hy­droxy group generates (010) sheets.
    Acta Crystallographica Section E Structure Reports Online 09/2014; 70(Pt 9):o891-2. DOI:10.1107/S1600536814011908 · 0.35 Impact Factor
  • Source
    William T A Harrison · Lutfun Nahar · Alan B Turner
    [Show abstract] [Hide abstract]
    ABSTRACT: In the title compound, C40H50O6, a symmetrical steroid oxalate diester, the dihedral angle between the CO2 planes of the oxalate linker is 61.5 (5)° and the C-C bond length is 1.513 (6) Å. The steroid B, C and D rings adopt half-chair, chair and envelope conformations, respectively, in both halves of the mol-ecule, which adopts an overall shallow V-shaped conformation. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions, forming a three-dimensional network.
    Acta Crystallographica Section E Structure Reports Online 08/2014; 70(Pt 8):62-4. DOI:10.1107/S1600536814009349 · 0.35 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: The title compound, poly[[di­aqua­bis­[1,5-bis­(pyridin-4-yl)pentane-κ2 N:N′]cadmium] bis­(perchlorate) 1,5-bis­(pyridin-4-yl)pentane ethanol mono­solvate], [Cd(C15H18N2)2(H2O)2](ClO4)2·C15H18N2·C2H6O, is a layered coordination polymer built up from highly squashed 44 nets in which the octa­hedral trans-CdO2N4 nodes (Cd site symmetry -1) are linked by the bifunctional ligands, forming infinite (110) sheets. The cationic sheets are charge-balanced by inter­layer perchlorate ions. A free 1,5-bis­(pyridin-4-yl)pentane mol­ecule and an ethanol mol­ecule of crystallization are also found in the inter­sheet region. A number of O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds help to consolidate the layered structure.
    Acta Crystallographica Section E Structure Reports Online 08/2014; 70(Pt 8):80-3. DOI:10.1107/S1600536814014779 · 0.35 Impact Factor
  • Source
    William T A Harrison · James L Wardell
    [Show abstract] [Hide abstract]
    ABSTRACT: The title compounds, K+·C7H7BF3O−, (I), and K+·C6H4BF4 −, (II), are mol­ecular salts containing para-substituted phenyl­tri­fluorido­borate anions. In each compound, the B atom adopts a distorted tetra­hedral BCF3 geometry. Despite their different compositions and space groups, the irregular KF8 coordination polyhedra of the potassium cations in the structures are almost identical. These polyhedra share faces and edges, generating infinite (010) layers in (I) and infinite (001) layers in (II). In (I), adjacent layers are stacked in an AAA… fashion, whereas in (II), they are stacked in an ABAB… sequence.
    Acta Crystallographica Section E Structure Reports Online 08/2014; 70(Pt 8):68-71. DOI:10.1107/S1600536814009684 · 0.35 Impact Factor

Publication Stats

6k Citations
1,076.86 Total Impact Points

Institutions

  • 1999–2014
    • University of Aberdeen
      • Department of Chemistry
      Aberdeen, Scotland, United Kingdom
  • 1993–2010
    • University of Houston
      • Department of Chemistry
      Houston, Texas, United States
  • 1988–2010
    • University of California, Santa Barbara
      • • Department of Chemistry and Biochemistry
      • • Materials Research Laboratory
      Santa Barbara, California, United States
    • University of Oxford
      • Inorganic Chemistry Laboratory
      Oxford, England, United Kingdom
  • 1997–2005
    • University of Western Australia
      • School of Chemistry and Biochemistry
      Perth, Western Australia, Australia
  • 2004
    • University of the West of Scotland
      Пейсли, Scotland, United Kingdom
    • Ondokuz Mayıs Üniversitesi
      • Faculty of Arts and Sciences
      Djanik, Samsun, Turkey
  • 1995
    • AT&T Labs
      Austin, Texas, United States
  • 1989
    • University of Leeds
      Leeds, England, United Kingdom
    • Osaka University
      • Department of Multimedia Engineering
      Suika, Ōsaka, Japan