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Find video protocols related to scientific articles indexed in Pubmed.
Short and efficient synthesis of fluorinated ?-lactams.
Org. Biomol. Chem.
PUBLISHED: 09-24-2014
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The diastereoselective synthesis of fluorinated ?-lactams has been achieved through an efficient five step process. The route can tolerate a range of functionalities, and provides a quick route for the generation of new fluorinated medicinal building blocks.
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Healthy aging diets other than the Mediterranean: a focus on the Okinawan diet.
Mech. Ageing Dev.
PUBLISHED: 01-04-2014
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The traditional diet in Okinawa is anchored by root vegetables (principally sweet potatoes), green and yellow vegetables, soybean-based foods, and medicinal plants. Marine foods, lean meats, fruit, medicinal garnishes and spices, tea, alcohol are also moderately consumed. Many characteristics of the traditional Okinawan diet are shared with other healthy dietary patterns, including the traditional Mediterranean diet, DASH diet, and Portfolio diet. All these dietary patterns are associated with reduced risk for cardiovascular disease, among other age-associated diseases. Overall, the important shared features of these healthy dietary patterns include: high intake of unrefined carbohydrates, moderate protein intake with emphasis on vegetables/legumes, fish, and lean meats as sources, and a healthy fat profile (higher in mono/polyunsaturated fats, lower in saturated fat; rich in omega-3). The healthy fat intake is likely one mechanism for reducing inflammation, optimizing cholesterol, and other risk factors. Additionally, the lower caloric density of plant-rich diets results in lower caloric intake with concomitant high intake of phytonutrients and antioxidants. Other shared features include low glycemic load, less inflammation and oxidative stress, and potential modulation of aging-related biological pathways. This may reduce risk for chronic age-associated diseases and promote healthy aging and longevity.
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Aziridine-based concise synthesis of (±)-alstonerine.
Chem. Commun. (Camb.)
PUBLISHED: 09-04-2013
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A concise synthesis of the macroline-related alkaloid (±)-alstonerine is reported. Key steps are regioselective and stereospecific aziridine ring-opening using a sulfone-stabilised carbanion, Me3Al-mediated O ? N-transacylation-elimination, intramolecular Michael reaction, and one-pot reduction-dehydration-Pictet-Spengler cyclisation.
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Transannular Claisen rearrangement reactions for the synthesis of vinylcyclobutanes: formal synthesis of (±)-grandisol.
Org. Biomol. Chem.
PUBLISHED: 10-20-2011
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Unsaturated eight-membered lactones undergo decarboxylative and non-decarboxylative transannular Ireland-Claisen rearrangement reactions, to give substituted vinylcyclobutanes. A formal synthesis of (±)-grandisol is described.
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Decarboxylative Claisen rearrangement reactions: synthesis and reactivity of alkylidene-substituted indolines.
Org. Biomol. Chem.
PUBLISHED: 10-04-2011
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Microwave-assisted decarboxylative Claisen rearrangement (dCr) reactions of substituted acetate derivatives of 3-(hydroxyalkyl)indoles give de-aromatised products. The reactivity of the resultant compounds was evaluated.
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Claisen rearrangements of equilibrating allylic azides.
Org. Biomol. Chem.
PUBLISHED: 08-30-2011
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Equilibrating mixtures of allylic azide-containing allylic alcohols or allylic 2-tolylsulfonylacetic esters undergo Johnson-Claisen or Ireland-Claisen rearrangement reactions to give unsaturated ?-azidoesters and -acids, respectively. Decarboxylation of the acids under basic conditions gives azidosulfones, with moderate to high diastereoselectivity.
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Design of a potent, soluble glucokinase activator with increased pharmacokinetic half-life.
Bioorg. Med. Chem. Lett.
PUBLISHED: 03-03-2011
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The continued optimization of a series of glucokinase activators is described, including attempts to understand the interplay between molecular structure and the composite parameter of unbound clearance. These studies resulted in the discovery of a new scaffold for glucokinase activators and further exploration of this scaffold led to the identification of GKA60. GKA60 maintains an excellent balance of potency and physical properties whilst possessing a significantly different, but complimentary, pre-clinical pharmacokinetic profile compared with the previously disclosed compound GKA50.
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Are men aging as oaks and women as reeds? A behavioral hypothesis to explain the gender paradox of French centenarians.
J Aging Res
PUBLISHED: 02-27-2011
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Since the 1990s, several studies involving French centenarians have shown a gender paradox in old age. Even if women are more numerous in old age and live longer than men, men are in better physical and cognitive health, are higher functioning, and have superior vision. If better health should lead to a longer life, why are men not living longer than women? This paper proposes a hypothesis based on the differences in the generational habitus between men and women who were born at the beginning of the 20th century. The concept of generational habitus combines the generation theory of Mannheim with the habitus concept of Bourdieu based on the observation that there exists a way of being, thinking, and doing for each generation. We hypothesized that this habitus still influences many gender-linked behaviours in old age. Men, as "oaks," seem able to delay the afflictions of old age until a breaking point, while women, as "reeds," seem able to survive despite an accumulation of health deficits.
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Isolation of a sultone as an unusual acetolysis product.
Carbohydr. Res.
PUBLISHED: 01-23-2011
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Acetolysis of methyl 5,6-di-O-acetyl-2,3-O-isopropylidene-?-L-gulofuranoside has yielded a sultone, 4-(1,2,5,6-tetra-O-acetyl-?-L-gulofuranos-3-yl)-6-methyl-1,2-oxathiin 2,2-dioxide (2) whose structure was determined by X-ray diffraction. (1)H and (13)C NMR spectral properties of 2 are presented together with a rationale for its formation. Preparation and properties of the related ?-d-mannofuranos-3-yl compound 4 are described.
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Exopericyclic stereocontrol in Johnson-Claisen rearrangements of allylic sulfides.
Chem. Commun. (Camb.)
PUBLISHED: 08-23-2010
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A study of the effects of exopericyclic stereocentres on the stereoselectivity of Johnson-Claisen rearrangements of thioether-containing allylic alcohols shows that selectivity is highly dependent upon allylic substitution patterns.
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Transannular, decarboxylative Claisen rearrangement reactions for the synthesis of sulfur-substituted vinylcyclopropanes.
Chem. Commun. (Camb.)
PUBLISHED: 06-01-2010
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Unsaturated epsilon-lactones bearing an alpha-arylsulfonyl or alpha-arylsulfoximinyl substituent undergo stereoselective transannular, decarboxylative Claisen rearrangement to give substituted vinylcyclopropanes.
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Magneto-structural correlations of a three-dimensional Mn based metal-organic framework.
Dalton Trans
PUBLISHED: 03-29-2010
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A 3D metal-organic framework, [Na{Mn(3)(Hbtc)(2)(btc)}.5H(2)O](n) () (H(3)btc = 1,3,5-benzene tricarboxylic acid), was synthesized under hydrothermal conditions. The structure of was established by single crystal X-ray diffraction analysis; crystallizes in the monoclinic space group P2/c, a = 9.753(3) A, b = 12.751(2) A, c = 14.174(4) A, beta = 109.41(1) degrees . The complex is isostructural to previously reported MIL-45 and consists of one dimensional wave like chains of carboxylate bridged hexa-coordinated Mn(ii) ions. Variable temperature magnetic susceptibility measurements revealed dominant antiferromagnetic exchange interactions and the intra-chain exchange constants J(1) = -2.4 cm(-1) and J(2) = -0.6 cm(-1) compare well with literature values for similar materials. Inter-chain interactions are expected to be very small in this compound and there is no indication of magnetic ordering phenomena in the temperature range from 300-2 K.
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7?,15?-Dibromo-8,16-diphenyl-6,7,14,15-tetra-hydro-6?,14?-epithio-cyclo-octa-[1,2-b:5,6-b]diquinoline deuterochloro-form solvate.
Acta Crystallogr Sect E Struct Rep Online
PUBLISHED: 08-07-2009
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In the racemic title compound, C(34)H(22)Br(2)N(2)S·CDCl(3), pairs of diquinoline host mol-ecules form centrosymmetric brick-like dimers utilizing three different aryl edge-to-face inter-actions (EF(1-3)). The dimeric (EF)(6) (i.e. 2 × EF(1-3)) building blocks pack with the deuterochloro-form guest mol-ecules positioned near each of their corners. The Cl atoms of the latter are disordered over two sets of sites in a 0.53?(2):0.47?(2) ratio.
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Fluxionality in a paramagnetic seven-coordinate iron(II) complex: a variable-temperature, two-dimensional NMR and DFT study.
Inorg Chem
PUBLISHED: 04-30-2009
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The preparation and detailed characterizations of the high-spin seven-coordinate complexes [M(kappa(7)N-L)](ClO(4))(2) (M = Mn(II), Fe(II); L = N,N,N,N-tetrakis(2-pyridylmethyl)-2,6-bis(aminomethyl)pyridine) are described. The X-ray crystal structures reveal seven-coordinate metal complex ions. Consideration of continuous shape measures reveals that the coordination environments about the metal ions are better described as having (C(s)) face-capped trigonal prismatic symmetry than (C(2)) pentagonal bipyramidal symmetry. The (S = (5)/(2)) Mn(II) species shows complicated X-band electron paramagnetic resonance (EPR) spectra and broad, unrevealing (1)H NMR spectra. In contrast, the (S = 2) Fe(II) complex is EPR-silent and shows completely interpretable (1)H NMR spectra containing the requisite number of paramagnetically shifted peaks in the range delta +150 to -60. The (13)C NMR spectra are likewise informative. Variable-temperature (1)H NMR spectra show coalescences and decoalescences indicative of an intramolecular process that pairwise-exchanges the nonequivalent pyridylmethyl "arms" of the two bis(pyridylmethyl)amine (bpa) domains. A suite of NMR techniques, including T(1) relaxation measurements and variable-temperature (1)H-(1)H correlation spectroscopy, (1)H-(1)H total correlation spectroscopy, (1)H-(1)H nuclear Overhauser effect spectroscopy/exchange spectroscopy, and (1)H-(13)C heteronuclear multiple-quantum coherence experiments, has been used to assign the NMR spectra and characterize the exchange process. Analysis of the data from these experiments yields the following thermodynamic parameters for the exchange: DeltaH++ = 53.6 +/- 2.8 kJ mol(-1), DeltaS++ = -10.0 +/- 9.8 J K(-1) mol(-1), and DeltaG++ (298 K) = 50.6 kJ mol(-1). Density functional theory (B3LYP) calculations have been used to explore the energetics of possible mechanistic pathways for the underlying fluxional process. The most plausible mechanism found involves dissociation of a pyridylmethyl arm to afford a strained six-coordinate species followed by rebinding of the arm in a different position to afford a new seven-coordinate transition state in which the pyridylmethyl arms within each bpa domain are essentially equivalent; the calculated energy barrier for this process is 53.5 kJ mol(-1), in good agreement with the observations.
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2,8-Dimethyl-tricyclo-[5.3.1.1]dodecane-syn-2,syn-8-diol-propanoic acid (1/1).
Acta Crystallogr Sect E Struct Rep Online
PUBLISHED: 04-24-2009
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The racemic title compound, C(14)H(24)O(2)·C(3)H(6)O(2), crystallizes in the monoclinic space group P2(1)/c as a 1:1 diol/carboxylic acid cocrystal, A-B. The lattice incorporates infinite chains of the alcohol-carboxylic acid-alcohol supra-molecular synthon, (?O-H?O=C(R)-O-H?O-H?), in which the hydrogen-bonded mol-ecules (A-B-A)(n) surround a pseudo-threefold screw axis. The carboxylic acid group functions like an extended alcohol hydr-oxy group. Each diol, A, takes part in two such threefold screw arrangements, leading to a hydrogen-bonded layer structure, with adjacent layers containing diol mol-ecules of opposite handedness. The central C atom of the propano bridge is disordered over two sites of occupancies 0.75?(1) and 0.25?(1). The methyl group of the propanoic acid molecule is disordered over two sites of occupancies 0.68?(1) and 0.32?(1).
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Making medicinal chemistry more effective--application of Lean Sigma to improve processes, speed and quality.
Drug Discov. Today
PUBLISHED: 03-03-2009
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The pharmaceutical industry, particularly the small molecule domain, faces unprecedented challenges of escalating costs, high attrition as well as increasing competitive pressure from other companies and from new treatment modes such as biological products. In other industries, process improvement approaches, such as Lean Sigma, have delivered benefits in speed, quality and cost of delivery. Examining the medicinal chemistry contributions to the iterative improvement process of design-make-test-analyse from a Lean Sigma perspective revealed that major improvements could be made. Thus, the cycle times of synthesis, as well as compound analysis and purification, were reduced dramatically. Improvements focused on team, rather than individual, performance. These new ways of working have consequences for staff engagement, goals, rewards and motivation, which are also discussed.
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2,3-Dichloro-benzene-1,4-diol.
Acta Crystallogr Sect E Struct Rep Online
PUBLISHED: 03-03-2009
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The achiral title compound, C(6)H(4)Cl(2)O(2), crystallizes with O-H?O hydrogen bonding linking mol-ecules into layers. Between layers there are chains of Cl?Cl?Cl inter-actions with alternating distances of 3.274?(2) and 3.742?(2)?Å. Augmenting this arrangement there are also C-H?Cl (2.97 and 3.17?Å) and Cl?? (shortest distances 3.40 and 3.54?Å) inter-actions.
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(1R*,2R*,4S*,5R*,6R*,8S*)-4,8-Dimethyl-2,6-diphenyl-bicyclo-[3.3.1]nonane-2,6-diol.
Acta Crystallogr Sect E Struct Rep Online
PUBLISHED: 02-23-2009
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The racemic title compound, C(23)H(28)O(2), crystallizes in the space group C2/c as a layered structure in which a centrosymmetric three hydrogen bond sequence links four molecules. Both hydroxy groups are involved in this arrangement, but they differ in that one participates in two hydrogen bonds while the other takes part in only one. Between layers, the aromatic rings take part in edge-face interactions [shortest C-H?C distances 3.04, 3.10 and 3.12?Å and angle between normal to planes 86.7(2)°], forming a centrosymmetric dimer. The lattice is further stabilized by C-H?? interactions involving both methyl (shortest C?C 3.82 and 3.97?Å) and methylene (shortest C?C 3.60?Å) groups.
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1,4-Dichloro-naphthalene-2,3-diol.
Acta Crystallogr Sect E Struct Rep Online
PUBLISHED: 02-02-2009
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The achiral planar (maximum deviation 0.014?Å) title compound, C(10)H(6)Cl(2)O(2), crystallizes in the chiral space group P2(1)2(1)2(1) in an arrangement incorporating conventional O-H?O hydrogen bonding leading to a supra-molecular chain.
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Highly regioselective ring-opening of trisubstituted aziridines by sulfur-stabilised carbanions.
Chem. Commun. (Camb.)
PUBLISHED: 01-12-2009
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The highly regioselective, stereospecific ring-opening of trisubstituted N-tosylaziridines possessing vinyl and hydroxymethyl groups by sulfone- and sulfide-stablised carbanions is reported.
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Free-Wilson and structural approaches to co-optimizing human and rodent isoform potency for 11?-hydroxysteroid dehydrogenase type 1 (11?-HSD1) inhibitors.
J. Med. Chem.
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11?-Hydroxysteroid dehydrogenase 1 (11?-HSD1) has been a target of intensive research efforts across the pharmaceutical industry, due to its potential for the treatment of type II diabetes and other elements of the metabolic syndrome. To demonstrate the value of 11?-HSD1 in preclinical models, we required inhibitors with good potency against both human and rodent isoforms. Herein, we describe our efforts to understand how to co-optimize human and murine potency within the (5-hydroxy-2-adamantyl)-pyrimidine-5-carboxamide series. Two approaches are described-a data-driven (Free-Wilson) analysis and a structure-based design approach. The conclusions from these approaches were used to inform an efficient campaign to design compounds with consistently good human/murine potency within a logD(7.4) range of 1-3. Compounds 20 and 26 demonstrated good rodent PK, which allowed us to demonstrate a PK/PD relationship in rat and mouse. We then evaluated 26 against glycemic and body weight end points in murine disease models, where it demonstrated glucose and body weight efficacy at 300 mg/kg/day but only body weight efficacy at 50 mg/kg/day, despite providing >90% target engagement in the liver.
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Identification, optimisation and in vivo evaluation of oxadiazole DGAT-1 inhibitors for the treatment of obesity and diabetes.
Bioorg. Med. Chem. Lett.
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A novel series of DGAT-1 inhibitors was discovered from an oxadiazole amide high throughput screening (HTS) hit. Optimisation of potency and ligand lipophilicity efficiency (LLE) resulted in a carboxylic acid containing clinical candidate 53 (AZD3988), which demonstrated excellent DGAT-1 potency (0.6 nM), good pharmacokinetics and pre-clinical in vivo efficacy that could be rationalised through a PK/PD relationship.
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Preparation of ?- and ?-D-glucoseptanose pentaacetates.
Carbohydr. Res.
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The ?- and ?-D-glucoseptanose pentaacetates have been prepared by treatment of ethyl 1-thio-?-D-glucoseptanoside tetraacetate with mercury(II) acetate in acetic acid. The solid state structure of the ?-isomer has been determined by X-ray diffraction.
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(3R,4S,5S,8S,10R,13R)-3-Hy-droxy-kaura-9(11),16-dien-18-oic acid.
Acta Crystallogr Sect E Struct Rep Online
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The title compound, C(20)H(28)O(3), was isolated during our investigation into the chemical composition and pharmacological activity of Centipeda cunninghamii (DC.) A. Braun & Asch. (Asteraceae). The enanti-opure compound, a diterpene with a carbon skeleton, is composed of three six- and one five-membered rings in chair, twist-boat, half-chair and envelope conformations, respectively. Each mol-ecule makes one intra- and one inter-molecular O-H?O hydrogen bond in the crystal lattice, forming hydrogen-bonded chains along [010]. The absolute configuration of the compound was assigned on the basis of optical rotation measurements.
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JoVE Visualize is a tool created to match the last 5 years of PubMed publications to methods in JoVE's video library.

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