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Odell, Luke R.
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Publications (10 of 72) 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, 2110-2113 p.Article 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, 6895-6898 p.Article 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
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, 4875-4881 p.Article 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, 349-361 p.Article 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, 4066-4069 p.Article 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
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, 2515-2522 p.Article 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
Roslin, S. & Odell, L. R. (2017). Visible-Light Photocatalysis as an Enabling Tool for the Functionalization of Unactivated C(sp(3))-Substrates. European Journal of Organic Chemistry, 2017(15), 1993-2007.
Open this publication in new window or tab >>Visible-Light Photocatalysis as an Enabling Tool for the Functionalization of Unactivated C(sp(3))-Substrates
2017 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2017, no 15, 1993-2007 p.Article, review/survey (Refereed) Published
Abstract [en]

Over the past decade, visible-light photocatalysis has emerged as one of the brightest and most dynamic fields in modern organic chemistry. By employing a transition-metal- or organic-dye-based photocatalyst in conjunction with a low-energy visible-light source, this synthetic manifold allows the facile generation of radical intermediates that can subsequently be directed through a wide range of transformations. Although initial studies focused largely on the functionalization of stabilized radical intermediates, over the past few years significant efforts have been directed towards the functionalization of challenging unactivated radical precursors. In this review we summarize the recent developments in the use of visible-light photocatalysis for the functionalization of unactivated C(sp(3))-substrates.

Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH, 2017
Keyword
Photocatalysis, Photochemistry, Alkyl radicals, Radical reactions, Visible light, Cross-coupling
National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-322303 (URN)10.1002/ejoc.201601479 (DOI)000399701800004 ()
Available from: 2017-05-19 Created: 2017-05-19 Last updated: 2017-10-26
Chow, S. Y., Odell, L. R. & Eriksson, J. (2016). Low-Pressure Radical C-11-Aminocarbonylation of Alkyl Iodides through Thermal Initiation. European Journal of Organic Chemistry (36), 5980-5989.
Open this publication in new window or tab >>Low-Pressure Radical C-11-Aminocarbonylation of Alkyl Iodides through Thermal Initiation
2016 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 36, 5980-5989 p.Article in journal (Refereed) Published
Abstract [en]

A radical C-11-aminocarbonylation protocol characterized by excellent substrate compatibility was developed to transform alkyl iodides into C-11-labelled amides, including the 11-HSD1 inhibitor [carbonyl-C-11]adamantan-1-yl(piperidin-1-yl)methanone. This protocol serves as a complementary extension of palladium-mediated C-11-aminocarbonylation, which is limited to the preparation of C-11-labelled compounds lacking beta-hydrogen atoms. The use of AIBN as a radical initiator and a low-pressure xenon-[C-11]CO delivery unit represents a simple and convenient alternative to previous radical C-11-carbonylation methodologies burdened with the need for a proprietary high pressure reactor connected to a light source.

Keyword
Radical reactions, Carbon isotopes, Carbon monoxide, Xenon, Radical initiator, Reductive dehalogenation, Radiochemistry, Carbonylation
National Category
Medicinal Chemistry
Identifiers
urn:nbn:se:uu:diva-316439 (URN)10.1002/ejoc.201601106 (DOI)000392534600010 ()
Funder
Carl Tryggers foundation , CTS13:333/14:356
Available from: 2017-03-01 Created: 2017-03-01 Last updated: 2018-01-13Bibliographically approved
Sawant, R. T., Stevens, M. Y., Sköld, C. & Odell, L. R. (2016). Microwave-Assisted Branching Cascades: A Route to Diverse 3,4-Dihydroquinazolinone-Embedded Polyheterocyclic Scaffolds. Organic Letters, 18(20), 5392-5395.
Open this publication in new window or tab >>Microwave-Assisted Branching Cascades: A Route to Diverse 3,4-Dihydroquinazolinone-Embedded Polyheterocyclic Scaffolds
2016 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 18, no 20, 5392-5395 p.Article in journal (Refereed) Published
Abstract [en]

A novel metal-free microwave-assisted branching cascades strategy for the efficient synthesis of 3,4-dihydro-quinazolinone-embedded polyheterocyclic scaffolds is reported. Starting from in situ generated key N-acyliminium ion precursors, 12 distinct and skeletally diverse polycyclic frameworks were accessed in a single step/pot via adjustment of the nucleophile(s) and reaction conditions. Postcascade functionalization of these compounds was also demonstrated, proving the utility of this method in accessing structurally diverse chemical entities.

National Category
Medicinal Chemistry
Identifiers
urn:nbn:se:uu:diva-308641 (URN)10.1021/acs.orglett.6b02774 (DOI)000386187300052 ()27726402 (PubMedID)
Available from: 2016-11-30 Created: 2016-11-29 Last updated: 2018-01-13Bibliographically approved
(2016). Mild and Low-Pressure fac-Ir(ppy)3-Mediated Radical Aminocarbonylation of Unactivated Alkyl Iodides through Visible-Light Photoredox Catalysis. Chemistry - A European Journal, 22(27), 9037-9037.
Open this publication in new window or tab >>Mild and Low-Pressure fac-Ir(ppy)3-Mediated Radical Aminocarbonylation of Unactivated Alkyl Iodides through Visible-Light Photoredox Catalysis
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2016 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 22, no 27, 9037-9037 p.Article in journal, Editorial material (Other academic) Published
Abstract [en]

Invited for the cover of this issue is the group of L. R. Odell at Uppsala University (Sweden). The image depicts iridium at the center of a vortex of electrons that are transferred to and from the surrounding reaction components in aradical aminocarbonylation method. Read the full text of the article at 10.1002/chem.201601694.

National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-304063 (URN)10.1002/chem.201602605 (DOI)
Note

Cover profile / cover page

Available from: 2016-09-29 Created: 2016-09-29 Last updated: 2017-11-21Bibliographically approved
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