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Odell, Luke R.
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Publications (10 of 76) Show all publications
Sawant, R. T., Stevens, M. Y. & Odell, L. R. (2017). Acetic acid-promoted cascade N-acyliminium ion/aza-Prins cyclization: stereoselective synthesis of functionalized fused tricyclic piperidines. Chemical Communications, 53(13), 2110-2113
Open this publication in new window or tab >>Acetic acid-promoted cascade N-acyliminium ion/aza-Prins cyclization: stereoselective synthesis of functionalized fused tricyclic piperidines
2017 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 53, no 13, p. 2110-2113Article in journal (Refereed) Published
Abstract [en]

A novel acetic acid-promoted metal-free cascade N-acyliminium ion/aza-Prins cyclization of o-formyl carbamates and homoallylamines is reported. This one-pot protocol provides efficient and rapid access to masked cis-hydroxyhexahydropyrido[1,2-c] quinazolin-6-ones with concomitant generation of two stereogenic centers, four C-C/C-O/C-N bonds and two new rings in good yield and excellent diastereoselectivity.

Place, publisher, year, edition, pages
ROYAL SOC CHEMISTRY, 2017
National Category
Medicinal Chemistry
Identifiers
urn:nbn:se:uu:diva-319679 (URN)10.1039/c6cc09805c (DOI)000395625700006 ()28133651 (PubMedID)
Available from: 2017-04-07 Created: 2017-04-07 Last updated: 2018-01-13Bibliographically approved
Roslin, S. & Odell, L. R. (2017). Palladium and Visible-Light Mediated Carbonylative Suzuki-Miyaura Coupling of Unactivated Alkyl Halides and Aryl Boronic Acids. Chemical Communications, 53, 6895-6898
Open this publication in new window or tab >>Palladium and Visible-Light Mediated Carbonylative Suzuki-Miyaura Coupling of Unactivated Alkyl Halides and Aryl Boronic Acids
2017 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 53, p. 6895-6898Article in journal (Refereed) Published
Abstract [en]

Herein, a simple and efficient method for the palladium-catalyzed carbonylation of aryl boronic acids with unactivated alkyl iodides and bromides under visible-light irradiation, ambient temperature and low CO-pressure is presented. Notably, the procedure uses readily available equipment and an inexpensive palladium catalyst to generate the key alkyl radical intermediate. These mild conditions enabled the synthesis of a range of functionalized aryl alkyl ketones including the antipsychotic drug, melperone.

Place, publisher, year, edition, pages
ROYAL SOC CHEMISTRY, 2017
National Category
Chemical Sciences
Identifiers
urn:nbn:se:uu:diva-329634 (URN)10.1039/c7cc02763j (DOI)000404282900021 ()
Available from: 2017-09-26 Created: 2017-09-26 Last updated: 2017-10-26
Åkerbladh, L., Schembri, L. S., Larhed, M. & Odell, L. R. (2017). Palladium(0)-Catalyzed Carbonylative One-Pot Synthesis of N-Acylguanidines. Journal of Organic Chemistry, 82(23), 12520-12529
Open this publication in new window or tab >>Palladium(0)-Catalyzed Carbonylative One-Pot Synthesis of N-Acylguanidines
2017 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 82, no 23, p. 12520-12529Article in journal (Refereed) Published
Abstract [en]

A convenient synthetic strategy toward N-acylguanidines via a sequential one-pot multicomponent carbonylation/amination reaction has been developed. The compounds were readily obtained via an N-cyanobenzamide intermediate formed from the Pd(0)-catalyzed carbonylative coupling of cyanamide and aryl iodides or bromides. Subsequent amination with a large variety of amines provided the final N-acylguanidines, with the overall formation of one C-C and two C-N bonds, in moderate to excellent yields. The substrate scope was found to be wide and the methodology was used to produce over 50 compounds, including 29 novel molecules. Furthermore, three separate nitrogen-containing heterocycles were prepared from the N-acylguanidines synthesized using the developed multicomponent, carbonylative method.

National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-343509 (URN)10.1021/acs.joc.7b02294 (DOI)000417342300056 ()29027801 (PubMedID)
Available from: 2018-02-27 Created: 2018-02-27 Last updated: 2018-03-08Bibliographically approved
Nordeman, P., Chow, S. Y., Odell, A. F., Antoni, G. & Odell, L. R. (2017). Palladium-mediated C-11-carbonylations using aryl halides and cyanamide. Organic and biomolecular chemistry, 15(22), 4875-4881
Open this publication in new window or tab >>Palladium-mediated C-11-carbonylations using aryl halides and cyanamide
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2017 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 15, no 22, p. 4875-4881Article in journal (Refereed) Published
Abstract [en]

A robust and high-yielding radiochemical synthesis of C-11-N-cyanobenzamides using a palladium-mediated aminocarbonylation with C-11-CO, aryl halides and cyanamide is described. The bidentate ligand 1,1'-bis(diphenylphosphino)ferrocene provided C-11-N-cyanobenzamides from aryl-iodides, bromides, triflates and even chlorides in 28-79% radiochemical yield after semi-preparative HPLC. To further highlight the utility of this method, novel C-11-N-cyanobenzamide analogs of flufenamic acid, meflanamic acid, dazoxiben and tamibarotene were synthesized in 34-71% radiochemical yields.

National Category
Medicinal Chemistry
Identifiers
urn:nbn:se:uu:diva-327370 (URN)10.1039/c7ob01064h (DOI)000403005500018 ()28537303 (PubMedID)
Available from: 2017-08-11 Created: 2017-08-11 Last updated: 2018-01-13Bibliographically approved
Odell, L. R., Abdel-Hamid, M. K., Hill, T. A., Chau, N., Young, K. A., Deane, F. M., . . . McCluskey, A. (2017). Pyrimidine-Based Inhibitors of Dynamin I GTPase Activity: Competitive Inhibition at the Pleckstrin Homology Domain. Journal of Medicinal Chemistry, 60(1), 349-361
Open this publication in new window or tab >>Pyrimidine-Based Inhibitors of Dynamin I GTPase Activity: Competitive Inhibition at the Pleckstrin Homology Domain
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2017 (English)In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 60, no 1, p. 349-361Article in journal (Refereed) Published
Abstract [en]

The large GTPase dynamin mediates membrane fission during clathrin-mediated endocytosis (CME). The aminopyrimidine compounds, were reported to disrupt clynamin localization to the plasina membrane via the PH domain and,iniplicate this mechanism in the inhibition of CME. We have used a computational approach of binding site identification, docking, and interaction energy calculations to design and synthesize a new library of aminopyrimidine analogues targeting site-2 of the pleckstrin homology (PH) domain. The optimized analogues showed low micromolar inhibition against both dynamin I (IC50 = 10.6 +/- 1.3 to 1.6 +/- 0.3 mu M) and CME (IC50(CME) = 65.9 +/- 7.7 to 17 +/- 1.1 mM), which makes this. series among The more potent inhibitors of dynamin.and CME yet reported. In:CME and growth inhibition cell-based assays, the data obtained Was consistent with dynamin inhibition. CEREP ExpresS profiling identified off-.target effects at the cholecystokinin, dopamine D-2, histamine H-1 and H-2, melanocortin, rnelatonin, muscarir* M-1 and M-3 neurokinin, opioid KOP and serotonin receptors.

National Category
Medicinal Chemistry
Identifiers
urn:nbn:se:uu:diva-316033 (URN)10.1021/acs.jmedchem.6b01422 (DOI)000392035100023 ()27997171 (PubMedID)
Funder
Australian Research Council
Available from: 2017-02-24 Created: 2017-02-24 Last updated: 2018-01-13Bibliographically approved
Rydfjord, J., Skillinghaug, B., Brandt, P., Odell, L. R. & Larhed, M. (2017). Route to 3-Amidino Indoles via Pd(II)-Catalyzed C-H Bond Activation. Organic Letters, 19(15), 4066-4069
Open this publication in new window or tab >>Route to 3-Amidino Indoles via Pd(II)-Catalyzed C-H Bond Activation
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2017 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 19, no 15, p. 4066-4069Article in journal (Refereed) Published
Abstract [en]

We report a facile synthesis of 3-amidino indoles from indoles and cyanamides. The reaction is Pd(II)-catalyzed and proceeds via C-H bond activation of the indole in its 3-position followed by a 1,2-addition of the resulting indole-palladium σ-complex to a cyanamide, which provides the corresponding amidine. The preference for 4,5-diazafluoren-9-one (DAF) as the ligand is investigated using DFT calculations, and a plausible reaction pathway is presented.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2017
National Category
Pharmaceutical Sciences
Research subject
Pharmaceutical Science
Identifiers
urn:nbn:se:uu:diva-326815 (URN)10.1021/acs.orglett.7b01836 (DOI)000407307900031 ()28741950 (PubMedID)
Available from: 2017-07-31 Created: 2017-07-31 Last updated: 2018-01-13Bibliographically approved
Roslin, S., De Rosa, M., Deuther-Conrad, W., Eriksson, J., Odell, L. R., Antoni, G., . . . Larhed, M. (2017). Synthesis and In Vitro Evaluation of 5-Substituted Benzovesamicol Analogs containing N-Substituted Amides as Potential Positron Emission Tomography Tracers for the Vesicular Acetylcholine Transporter. Bioorganic & Medicinal Chemistry, 25(19), 5095-5106
Open this publication in new window or tab >>Synthesis and In Vitro Evaluation of 5-Substituted Benzovesamicol Analogs containing N-Substituted Amides as Potential Positron Emission Tomography Tracers for the Vesicular Acetylcholine Transporter
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2017 (English)In: Bioorganic & Medicinal Chemistry, ISSN 0968-0896, E-ISSN 1464-3391, Vol. 25, no 19, p. 5095-5106Article in journal (Refereed) Published
Abstract [en]

Herein, new ligands for the vesicular acetylcholine transporter (VAChT), based on a benzovesamicol scaffold, are presented. VAChT is acknowledged as a marker for cholinergic neurons and a positron emission tomography tracer for VAChT could serve as a tool for quantitative analysis of cholinergic neuronal density. With an easily accessible triflate precursor, aminocarbonylations were utilized to evaluate the chemical space around the C5 position on the tetrahydronaphthol ring. Synthesized ligands were evaluated for their affinity and selectivity for VAChT. Small, preferably aromatic, N-substituents proved to be more potent than larger substituents. Of the fifteen compounds synthesized, benzyl derivatives (+/-)-7i and (+/-)-7l had the highest affinities for VAChT. Compound (+/-)-7i was chosen to investigate the importance of stereochemistry for binding to VAChT and selectivity toward the sigma(1) and sigma(2) receptors. Enantiomeric resolution gave (+/-)-7i and (-)-7i, and the eutomer showed seven times better affinity. Although racemate (+/-)-7i was initially promising, the affinity of (-)-7i for VAChT was not better than 56.7 nM which precludes further preclinical evaluation. However, the nanomolar binding together with the ready synthesis of [C-11]-(+/-)-7i shows that (-)-7i can serve as a scaffold for future optimizations to provide improved C-11-labelled VAChT PET tracers.

National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-332288 (URN)10.1016/j.bmc.2017.01.041 (DOI)000413401200010 ()28185725 (PubMedID)
Funder
Swedish Society for Medical Research (SSMF)
Available from: 2017-10-26 Created: 2017-10-26 Last updated: 2018-09-14Bibliographically approved
Bergman, S., Brandt, P., Nordeman, P., Larhed, M., Odell, L. R. & Eriksson, J. (2017). Synthesis of 11C-Labelled Ureas by Palladium(II)-Mediated Oxidative Carbonylation. Molecules, 22(10), Article ID 1688.
Open this publication in new window or tab >>Synthesis of 11C-Labelled Ureas by Palladium(II)-Mediated Oxidative Carbonylation
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2017 (English)In: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 22, no 10, article id 1688Article in journal (Refereed) Published
Abstract [en]

Positron emission tomography is an imaging technique with applications in clinical settings as well as in basic research for the study of biological processes. A PET tracer, a biologically active molecule where a positron-emitting radioisotope such as carbon-11 has been incorporated, is used for the studies. Development of robust methods for incorporation of the radioisotope is therefore of the utmost importance. The urea functional group is present in many biologically active compounds and is thus an attractive target for incorporation of carbon-11 in the form of [C-11] carbon monoxide. Starting with amines and [C-11] carbon monoxide, both symmetrical and unsymmetrical C-11-labelled ureas were synthesised via a palladium(II)-mediated oxidative carbonylation and obtained in decay-corrected radiochemical yields up to 65%. The added advantage of using [C-11] carbon monoxide was shown by the molar activity obtained for an inhibitor of soluble epoxide hydrolase (247 GBq/mu mol-319 GBq/mu mol). DFT calculations were found to support a reaction mechanism proceeding through an C-11-labelled isocyanate intermediate.

National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-332289 (URN)10.3390/molecules22101688 (DOI)000414670600115 ()
Available from: 2017-10-26 Created: 2017-10-26 Last updated: 2018-03-12Bibliographically approved
Åkerbladh, L., Chow, S. Y., Odell, L. R. & Larhed, M. (2017). Synthesis of 4H-Benzo[e][1,3]oxazin-4-ones by a Carbonylation-Cyclization Domino Reaction of ortho-Halophenols and Cyanamide. ChemistryOpen, 6(5), 620-628
Open this publication in new window or tab >>Synthesis of 4H-Benzo[e][1,3]oxazin-4-ones by a Carbonylation-Cyclization Domino Reaction of ortho-Halophenols and Cyanamide
2017 (English)In: ChemistryOpen, ISSN 2191-1363, Vol. 6, no 5, p. 620-628Article in journal (Refereed) Published
Abstract [en]

A mild and convenient one-step preparation of 4H-1,3-benzoxazin-4-ones by a domino carbonylation-cyclization process is developed. Readily available ortho-iodophenols are subjected to palladium-catalyzed carbonylative coupling with Mo(CO)(6) and cyanamide, followed by a spontaneous, intramolecular cyclization to afford 4H-1,3-benzaxazin-4-ones in moderate to excellent yields. Furthermore, the scope of the reaction is ex tended to include challenging orthobromophenols. Finally, to highlight the versatility of the developed method, Mo(CO), is successfully replaced with a wide array of CO-releasing reagents, such as oxalyl chloride, phenyl formate, 9-methylfluorene-9-carbonyl chloride, and formic acid, making this an appealing strategy for the synthesis of 4H-benzo[e][1,3]oxazin-4-ones.

National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-329967 (URN)10.1002/open.201700130 (DOI)000413038400003 ()29046856 (PubMedID)
Available from: 2017-09-24 Created: 2017-09-24 Last updated: 2018-02-05Bibliographically approved
Chow, S. Y. & Odell, L. R. (2017). Synthesis of N-Sulfonyl Amidines and Acyl Sulfonyl Ureas from Sulfonyl Azides, Carbon Monoxide, and Amides. Journal of Organic Chemistry, 82(5), 2515-2522
Open this publication in new window or tab >>Synthesis of N-Sulfonyl Amidines and Acyl Sulfonyl Ureas from Sulfonyl Azides, Carbon Monoxide, and Amides
2017 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 82, no 5, p. 2515-2522Article in journal (Refereed) Published
Abstract [en]

A Pd-catalyzed and ligand-free carbonylation/cycloaddition/decarboxylation cascade synthesis of sulfonyl amidines from sulfonyl azides and substituted amides at low CO pressure is reported. The reaction proceeds via an initial Pd-catalyzed carbonylative generation of sulfonyl isocyanates from sulfonyl azides, followed by a [2 + 2] cycloaddition with amides and subsequent decarboxylation, which liberates the desired sulfonyl amidines, generating N-2 and CO2 as the only reaction byproducts. Using this simple protocol, a diverse range of sulfonyl amidines was obtained in moderate to excellent yields. In addition, the reaction can also be directed through a more conventional amidocarbonylation pathway by employing N-monosubstituted amide nucleophiles to afford acyl sulfonyl ureas in good yields.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC, 2017
National Category
Medicinal Chemistry
Identifiers
urn:nbn:se:uu:diva-320261 (URN)10.1021/acs.joc.6b02894 (DOI)000395726000020 ()28150496 (PubMedID)
Funder
Carl Tryggers foundation , CTS13:333 CTS14:356
Available from: 2017-04-18 Created: 2017-04-18 Last updated: 2018-01-13Bibliographically approved
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