6 results on '"Patterson, Alyssa E."'
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2. Synthesis, characterization and anticancer properties of (salicylaldiminato)platinum(II) complexes
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Patterson, Alyssa E., Miller, Jessica J., Miles, Brittany A., Stewart, Erin L., Melanson, Josée-Marie E.J., Vogels, Christopher M., Cockshutt, Amanda M., Decken, Andreas, Morin, Pier, Jr., and Westcott, Stephen A.
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- 2014
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3. Antimicrobial and antimycobacterial activities of aliphatic amines derived from vanillin
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Patterson, Alyssa E., Flewelling, Andrew J., Clark, Trevor N., Geier, Stephen J., Vogels, Christopher M., Masuda, Jason D., Gray, Christopher A., and Westcott, Stephen A.
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X-rays -- Diffraction ,Vanillin -- Physiological aspects -- Research ,Antibiotics -- Chemical properties -- Research ,Chemistry - Abstract
Ten lipophilic amines were prepared from the reductive amination of vanillin and the corresponding primary amines using sodium borohydride in methanol. All compounds have been obtained elementally pure and an X-ray diffraction study on the 4-n-butylaniline derivative has confirmed the molecular structure. Whilst the overall antibiotic activity of the derivatives was low, some of these compounds, particularly the boronate ester 2-methoxy-4-((2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamino)methyl)phenol (7), showed a promising degree of antimycobacterial activity against Mycobacterium tuberculosis H37Ra, where activity seemed to vary by the position of the boron substitution on the aniline ring. Key words: aliphatic amines, antimicrobial, antimycobacterial, boronate esters, lipophilic, tuberculosis. Nous avons prepare dix amines lipophiles par amination reductrice de la vanilline avec les amines primaires correspondantes a l'aide du borohydrate de sodium dans le methanol. La purete des composes obtenus a ete verifiee par analyse elementaire, et une etude par diffraction des rayons X du derive 4-n-butylaniline a permis de confirmer la structure moleculaire. Bien que l'activite antibiotique des derives ait ete faible, certains de ces composes, en particulier l'ester boronique 2-methoxy-4-([2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamino]methyl)phenol (7), a fait preuve, dans une mesure prometteuse, d'une activite antimycobacterienne contre Mycobacterium tuberculosis H37Ra, ou l'activite semblait varier selon la position du substituant de bore sur le noyau aniline. [Traduit par la Redaction] Mots-cles: amines aliphatiques, agent antimicrobien, agent antimycobacterien, esters boroniques, lipophile, tuberculose., Introduction Although organoboron compounds, particularly boronic acids [RB[(OH).sub.2]] and boronate esters [RB[(OR').sub.2]], are ubiquitous in organic synthesis, (1,2) recent research has also found that these same small molecules can display [...]
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- 2015
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4. Synthesis, characterization, and anticancer properties of organometallic schiff base platinum complexes
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Jean, Stephanie, Cormier, Kevin, Patterson, Alyssa E., Vogels, Christopher M., Decken, Andreas, Robichaud, Gilles A., Turcotte, Sandra, and Westcott, Stephen A.
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Platinum compounds -- Chemical properties -- Health aspects -- Production processes ,Chemical synthesis -- Methods ,Chemistry - Abstract
A small family of organometallic platinum complexes containing a chloride, ris-cyclooctene, and a Schiff base ligand have been prepared and characterized fully. Three aliphatic amines and four aromatic amines were chosen as representative examples. All complexes were stable in air except for 7, derived from the pinacol-protected 4-aminophenylboronate ester 4-[H.sub.2]N[C.sub.6][H.sub.4]Bpin (pin = 1, 2-[O.sub.2][C.sub.2][Me.sub.4]), which decomposed via B-C bond cleavage. Both complexes 4 (derived from aniline) and 7 were further characterized by single-crystal X-ray diffraction studies and confirmed the square planar nature of the platinum centre whereby the chloride ligand lies trans to the deprotonated hydroxyl group of the Schiff base ligand. The imine functionality is trans to the organic cyclooctene group. Complex 3, which contained the longest aliphatic chain studied (an octyl group), was the most promising for inducing apoptosis in the malignant MB231 breast cancer cell line. Conversely, complexes 4-6, which contained aromatic groups, were the most active against renal cell carcinoma (RCC) cell lines. Keywords: anticancer, cytotoxicity, platinum, organometallic, Schiff base. Nous avons prepare et entierement caracterise une petite serie de complexes organometalliques a base de platine contenant les ligands suivants: chlorure, ris-cyclo-octene et une base de Schiff. Nous avons selectionne trois amines aliphatiques et quatre amines aromatiques a titre d'exemples representatifs. Tous, sauf le complexe 7, etaient stables a l'air. Ce dernier, derive ester du 4-aminophenylboronate protege par un groupement pinacol, le 4-[H.sub.2]N[C.sub.6][H.sub.4]Bpin (pin = 1, 2-[O.sub.2][C.sub.2][Me.sub.4]), s'est decompose par rupture de la liaison B-C. Nous avons caracterise davantage les complexes 4 (derive de l'aniline) et 7 par des etudes de diffraction des rayons X sur cristal unique et avons confirme la nature planaire carree de l'atome central de platine, de part et d'autre duquel se font face le ligand chlorure et le groupement hydroxyle deprotone de la base Schiff, dans un arrangement trans. En outre, la fonctionnalite imine est trans par rapport au groupement organique cyclo-octene. Le complexe 3, qui comprenait la plus longue chaine aliphatique etudiee (un groupement octyle), s'est revele le plus prometteur pour provoquer l'apoptose des cellules de cancer du sein de la lignee MB231. Inversement, les complexes 4-6, qui contiennent des groupements aromatiques, ont ete les plus actifs contre les cellules d'hypernephrome (RCC). [Traduit par la Redaction] Mots-cles: anticancereux, cytotoxicite, platine, organometallique, base de Schiff., Introduction Cisplatin, or ris-diamminedichloridoplatinum(II) (Fig. 1), is a remarkable small molecule that has made a large impact in the world of medicinal inorganic chemistry. Indeed, cisplatin has been used in [...]
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- 2015
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5. Anti-mycobacterial activities of copper(II) salicylaldimine complexes derived from long-chain aliphatic amines
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Patterson, Alyssa E., Bowes, Eric G., Bos, Allyson, O'Neill, Taryn, Li, Haoxin, Flewelling, Andrew, Vogels, Christopher M., Decken, Andreas, Gray, Christopher A., and Westcott, Stephen A.
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Schiff bases -- Properties -- Health aspects ,Copper compounds -- Properties -- Health aspects ,Mycobacterial infections -- Care and treatment ,Chemistry - Abstract
Twelve copper(II) Schiff base complexes derived from lipophilic amines have been prepared using either salicylaldehyde or ortho-vanillin via a microwave-assisted reaction. All complexes have been obtained elementally pure and an X-ray diffraction of an isopentyl derivative has confirmed the structure of these compounds. All complexes showed a promising degree of anti-mycobacterial activity against Mycobacterium tuberculosis, where activity seemed to increase with an increase in the length of the aliphatic chain. Key words: aliphatic amines, anti-mycobacterial, copper, lipophilic, tuberculosis. On a prepare douze complexes cuivre(II) base de Schiff a partir d'amines lipophiles et d'aldehyde salicylique ou d'ortho-vanilline par une reaction sous micro-ondes. Tous les complexes ont ete obtenus a l'etat pur et leur structure a ete confirmee par diffraction de rayons X sur un derive isopentylique. Tous les complexes presentaient un degre prometteur d'activite antimycobacterienne contre Mycobacterium tuberculosis, cette activite semblant augmenter avec la longueur de la chame aliphatique. [Traduit par la Redaction] Mots-cles: amines aliphatiques, antimycobacterien, cuivre, lipophile, tuberculose., Introduction Over the years, there has been considerable research into the development of metal complexes for their potential biological activities. Of singular interest in this area is the effectiveness of [...]
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- 2013
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6. Synthesis, characterization, and bioactivities of platinum(II) complexes bearing pyridinecarboxaldimines containing aliphatic groups
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Stewart, Erin L., Patterson, Alyssa E., O'Neill, Taryn, Li, Haoxin, Flewelling, Andrew, Vogels, Christopher M., Decken, Andreas, Lloyd, Vett K., Gray, Christopher A., and Westcott, Stephen A.
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Pyridine -- Chemical properties ,Platinum compounds -- Chemical properties -- Composition -- Production processes -- Identification and classification ,Chemical synthesis -- Methods ,Chemistry - Abstract
Condensation of 2-pyridinecarboxaldehyde with six primary amines containing aliphatic groups gave the corresponding pyridinecarboxaldimines (N-N'R). Addition of these ligands to [Pt[Cl.sub.2](coe)]2 (coe = ris-cyclooctene) gave complexes of the type ris-Pt[Cl.sub.2](N-N'R) (1: R = propyl, 2: R = hexyl, 3: R = octyl, 4: R = nonyl, 5: R = hexadecyl, and 6: R = octadecyl) in moderate yields. The molecular structure of the hexyl derivative (2) has been confirmed by an X-ray diffraction study. Crystals of 2 were triclinic with a = 8.6858(19) Å, b = 8.7567(19) Å, α = 9.5080(19) Å, a = 76.546(3)°, β = 87.151(3)°, and γ = 78.586(3)° in the space group P1. All platinum complexes show considerable anti-bacterial and anti-mycobacterial properties. Key words: aliphatic amines, anti-microbial, anti-mycobacterial, pyridinecarboxaldimines, platinum. La condensation du pyridine-2-carboxaldehyde avec six amines primaires contenant des groupes aliphatiques conduit a la formation des pyridinecarboxaldimines correspondantes (N-N'-R). L'addition de ces ligands au [Pt([Cl.sub.2])(coe)]2 (coe = riscyclooctene) conduit a la formation de complexes de type cis-Pt[Cl.sub.2](N-N'R) (1: R = propyle, 2: R = hexyle, 3: R = octyle, 4: R = nonyle, 5: R = hexadecyle et 6: R = octadecyle), avec des rendements moyens. On a pu confirmer la structure moleculaire du derive hexyle (2) par des etudes de diffraction des rayons X. Les cristaux du compose 2 sont tricliniques, dans le groupe d'espace P1, avec a = 8,6858(19) Å, b = 8,7567(19) Å, c = 9,5080(19) Å, [??] = 76,546(3)°, [??] = 87,151(3)° et [??] = 78,586(3)°. Tous les complexes de platine presentent des proprietes antibacteriennes et antimycobacteriennes importantes. Mots-cles: amines aliphatiques, antimicrobien, antimicybacterien, pyridinecarboxaldimines, platine., Introduction Cisplatin, cis-[Pt[Cl.sub.2][(N[H.sub.3]).sub.2]], and related platinum-based complexes are currently used as anti-cancer agents against testicular and ovarian malignancies. (1) The primary mechanism of action in these platinum drugs is believed [...]
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- 2013
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