Benzyl 6-oxo-3,6-dihydro-1(2H)-pyridinecarboxylate
CAS Number:
725746-35-0
Molecular Formula:
C13H13NO3
Isofagomine lactams, synthesis and enzyme inhibition
Literature Information
Publication Date
2002-12-19
DOI
10.1039/B208784G
Impact Factor
3.876
Authors
Vinni H. Lillelund, Huizhen Liu, Xifu Liang, Helmer Søhoel, Mikael Bols
View Original
Abstract
The synthesis of isofagomine lactams (2-oxoisofagomines) corresponding to the biologically important hexoses is presented. The D-glucose/D-mannose analogue (3S,4R,5R)-3,4-dihydroxy-5-hydroxymethylpiperidin-2-one (9) was synthesised in 9 steps from D-arabinose, the D-galactose analogue (3S,4S,5R)-3,4-dihydroxy-5-hydroxymethylpiperidin-2-one (10) was synthesised in 11 steps from D-arabinose and the L-fucose analogue (3R,4R,5R)-3,4-dihydroxy-5-methylpiperidin-2-one (11) was synthesised in 12 steps from L-arabinose. The three lactams 9–11 were found to be glycosidase inhibitors with micro- to nanomolar inhibition constants. The lactam 10 showed slow onset inhibition of β-galactosidase from A. Oryzae. The rate constants for this process were determined to be kon = 2.55 × 104 M−1 s−1 and koff = 1.7 × 10−3 s−1. The activation energies and standard thermodynamic functions were also determined.
Related Literature
Fluorescence microscopy coupled to electrochemistry: a powerful tool for the controlled electrochemical switch of fluorescent molecules
Fabien Miomandre, Rachel Meallet-Renault, Jean-Jacques Vachon, Robert Bernard Pansu, Pierre Audebert
2008-02-19
Communication
DOI: 10.1039/B718899D
Chemoenzymatic synthesis of prodigiosin analogues—exploring the substrate specificity of PigC
Suresh R. Chawrai, Neil R. Williamson, George P. C. Salmond, Finian J. Leeper
2008-02-05
Communication
DOI: 10.1039/B719353J
Controlled regio- and chemoselective addition of isothiocyanate to the dione moiety of a cage-opened fullerene-mixed peroxide derivative
Zheming Wang
2008-02-25
Communication
DOI: 10.1039/B800722E
Single molecule conformational analysis of the biologically relevant DNA G-quadruplex in the promoter of the proto-oncogene c-MYC
Pravin S. Shirude, Liming Ying, Shankar Balasubramanian
2008-03-20
Communication
DOI: 10.1039/B801465E
Synthesis of iron oxide nanoparticles in a microfluidic device: preliminary results in a coaxial flow millichannel
Ali Abou Hassan, Olivier Sandre, Valérie Cabuil, Patrick Tabeling
2008-02-18
Communication
DOI: 10.1039/B719550H
Size matters—strong binding of the terephthalate dianion by thiourea functionalised fused [n]polynorbornane hosts
Adam J. Lowe, Frederick M. Pfeffer
2008-03-18
Communication
DOI: 10.1039/B801798K
Mutual induced coordination in halogen-bonded anionic assemblies with (6,3) cation-templated topologies
Pierangelo Metrangolo, Frank Meyer, Tullio Pilati, Giancarlo Terraneo
2008-01-14
Communication
DOI: 10.1039/B716879A
One-step solid-state thermolysis of a metal–organic framework: a simple and facile route to large-scale of multiwalled carbon nanotubes
Linyun Chen, Junfeng Bai, Chunzhao Wang, Yi Pan, Manfred Scheer, Xiaozeng You
2008-01-31
Communication
DOI: 10.1039/B718476J
You might also like
Compound Q&A
What is the market or research trend for N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0)?
N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0) is increasingly being used ...
52818-63-0N-(4-Methoxybenzyl)-...
Compound Q&A
What precautions should be taken when handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate (CAS: 1050507-06-6)?
When handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate, appropriate p...
1050507-06-6Ethyl 4-(2-chlorophe...
Compound Q&A
What regulatory guidelines apply to diethyldiselane (CAS: 628-39-7)?
Diethyldiselane (CAS: 628-39-7) is classified under the Globally Harmonized Syst...
628-39-7Diethyldiselane
Compound Q&A
What is the market or research trend for oxocopper (CAS: 12053-18-8)?
The market for oxocopper (CAS: 12053-18-8) is primarily driven by its use in cat...
12053-18-8oxocopper; oxo-(oxoc...
Compound Q&A
What is the market or research trend for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-carboxylic acid?
The market for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-c...
1268519-54-55-{[(2-Methyl-2-prop...
Compound Q&A
What is 2-(1-Pyrrolidinyl)-4-pyridinamine (CAS: 35981-63-6)?
2-(1-Pyrrolidinyl)-4-pyridinamine is a chemical compound with the CAS number 359...
35981-63-62-(1-Pyrrolidinyl)-4...
Compound Q&A
What are the physical and chemical properties of 2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1)?
2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1) is a crystalline sol...
91556-75-12-(3-Pyridinyl)-1-az...
Compound Q&A
How is (S)-Alpha-allyl-proline hydrochloride (CAS: 129704-91-2) typically synthesized?
(S)-Alpha-allyl-proline hydrochloride is usually synthesized via a Wittig reacti...
129704-91-2(S)-Alpha-allyl-prol...
Compound Q&A
What is 3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5)?
3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5) is an organic compound w...
4857-42-53-Methyl-1,2-oxazole...
Compound Q&A
How is Lys-SMCC-DM1 (CAS: 1281816-04-3) typically synthesized?
Lys-SMCC-DM1 is synthesized via a multi-step process involving the coupling of S...
1281816-04-3Lys-SMCC-DM1
Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
![1,10-bis(3,5-dimethylphenyl)-12-hydroxy-4,5,6,7-tetrahydroiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocine 12-oxide structure](https://static.chemtradehub.com/structs/141/1412439-82-7-b9a9.webp "1,10-bis(3,5-dimethylphenyl)-12-hydroxy-4,5,6,7-tetrahydroiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocine 12-oxide structure")
1,10-bis(3,5-dimethylphenyl)-12-hydroxy-4,5,6,7-tetrahydroiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocine 12-oxide
CAS Number:
1412439-82-7
Molecular Formula:
C33H31O4P
Recommended Suppliers
Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.