Thienopyrimidinone bis-aminopyrrolidine ureas as potent melanin-concentrating hormone receptor-1 (MCH-R1) antagonists

Zhang, Mingzhu; Tamiya, Junko; Nguyen, Linh Thuy; Rowbottom, Martin W.; Dyck, Brian; Vickers, Troy; Grey, Jonathan; Schwarz, David; Heise, Christopher E.; Haelewyn, Jason; Mistry, Monica S.; Goodfellow, Val S.

doi:10.1016/j.bmcl.2007.02.012

Cited by 21 publications

(2 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Having synthesized the pyrido[2,3- d ]pyrimidin-4(3 H )-one analogue 8 , we turned our attention to 5–6 fused heterocyclic scaffolds. The thieno[2,3- d ]pyrimidin-4(3 H )-one core was of interest, since spatially isosteric replacements for the quinazolin-4(3 H )-one core have been reported in a number of medicinal chemistry lead optimization campaigns, possessing “drug-like” properties and biological activity. − …”

Section: Resultsmentioning

confidence: 99%

Novel Fused Arylpyrimidinone Based Allosteric Modulators of the M₁ Muscarinic Acetylcholine Receptor

Mistry

Lim

Jörg

et al. 2016

ACS Chem. Neurosci.

View full text Add to dashboard Cite

. (2016) Novel fused arylpyrimidinone based allosteric modulators of the M1 muscarinic acetylcholine receptor. ACS Chemical Neuroscience, 7 (5). pp. 647-661. ISSN 1948-7193 Access from the University of Nottingham repository: http://eprints.nottingham.ac.uk/31897/1/acschemneuro%252E6b00018.pdf Copyright and reuse:The Nottingham ePrints service makes this work by researchers of the University of Nottingham available open access under the following conditions. This article is made available under the Creative Commons Attribution Non-commercial licence and may be reused according to the conditions of the licence. For more details see: http://creativecommons.org/licenses/by-nc/2.5/ A note on versions:The version presented here may differ from the published version or from the version of record. If you wish to cite this item you are advised to consult the publisher's version. Please see the repository url above for details on accessing the published version and note that access may require a subscription.For more information, please contact eprints@nottingham.ac.uk Just Accepted "Just Accepted" manuscripts have been peer-reviewed and accepted for publication. They are posted online prior to technical editing, formatting for publication and author proofing. The American Chemical Society provides "Just Accepted" as a free service to the research community to expedite the dissemination of scientific material as soon as possible after acceptance. "Just Accepted" manuscripts appear in full in PDF format accompanied by an HTML abstract. "Just Accepted" manuscripts have been fully peer reviewed, but should not be considered the official version of record. They are accessible to all readers and citable by the Digital Object Identifier (DOI®). "Just Accepted" is an optional service offered to authors. Therefore, the "Just Accepted" Web site may not include all articles that will be published in the journal. After a manuscript is technically edited and formatted, it will be removed from the "Just Accepted" Web site and published as an ASAP article. Note that technical editing may introduce minor changes to the manuscript text and/or graphics which could affect content, and all legal disclaimers and ethical guidelines that apply to the journal pertain. ACS cannot be held responsible for errors or consequences arising from the use of information contained in these "Just Accepted" manuscripts. ABSTRACT: Benzoquinazolinone 1 is a positive allosteric modulator (PAM) of the M 1 muscarinic acetylcholine receptor (mAChR), which is significantly more potent than the prototypical PAM, 1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (BQCA). In this study, we explored the structural determinants that underlie the activity of 1 as a PAM of the M 1 mAChR.We paid particular attention to the importance of the tricyclic scaffold of compound 1, for the activity of the molecule. Complete deletion of the peripheral fused benzene ring caused a significant decrease in affinity and binding cooperativity with acetylcholine (ACh). ...

show abstract

Section: Resultsmentioning

confidence: 99%

Novel Fused Arylpyrimidinone Based Allosteric Modulators of the M₁ Muscarinic Acetylcholine Receptor

Mistry

Lim

Jörg

et al. 2016

ACS Chem. Neurosci.

View full text Add to dashboard Cite

show abstract

“…The thieno[3,2‐ b ]pyridin‐5(4 H )‐one compound 3a was selected as a prototypical example of a 7‐alkoxy‐2,4,6‐trisubstituted‐thieno[3,2‐ b ]pyridin‐5(4 H )‐one derivative and was synthesized as shown in Scheme . Methyl 3‐amino‐5‐bromothiophene‐2‐carboxylate ( 4 ) was obtained through a previously reported reaction sequence from methyl 3‐aminothiophene‐2‐carboxylate . The bromide ( 4 ) was subjected to a Suzuki coupling reaction with (4‐fluorophenyl)boronic acid ( 5a ), under typical conditions, to give 3‐amino‐5‐(4‐fluorophenyl)thiophene‐2‐carboxylate ( 6a ) in 95% yield .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Tetrasubstituted Thieno[3,2‐b]pyridin‐5(4H)‐one Derivatives as a Heterocyclic Scaffold for Multisite‐specific Fluorous Fluorescent Tagging and Fluorous Solid‐Phase Extraction

Jeon

Son

2016

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

Tetrasubstituted thieno[3,2‐b]pyridin‐5(4H)‐one derivatives were selected as a highly functionalized heterocyclic scaffold for a multisite‐specific tagging process utilizing a previously devised fluorous fluorescent tag system. A suitable synthetic method was established for the 7‐alkoxy‐2,4,6‐trisubstituted‐thieno[3,2‐b]pyridin‐5(4H)‐one derivatives, and incorporating t‐butoxycarbonyl‐functionalized building blocks into the reaction sequence produced precursors that could be used in the tagging process. Fluorous solid‐phase extraction facilitated the purification of the tagged target compounds after a series of reactions, including t‐Bu deprotection/N‐hydroxysuccinimidyl ester formation/amidation.

show abstract

Phosphorus Ligands in Hydroformylation and Hydrogenation: A Personal Account

Tewari

Kumar

Chandanshive

et al. 2021

The Chemical Record

View full text Add to dashboard Cite

Metal‐catalyzed hydroformylation and hydrogenation heavily rely on ligands, among which phosphorous ligands play a pivotal role. This personal account presents a selection of three distinct classes of phosphorous ligands, namely, monodentate meta‐substituted phosphinites, bis‐phosphites, and P‐chiral supramolecular phosphines, developed in our group. The synthesis of these ligands, isolation, characterization, and their performance in transition metal‐catalyzed hydroformylation, isomerizing hydroformylation, and asymmetric hydrogenation of olefins is summarized. The state of the art development in iron‐catalyzed hydroformylation of alkenes and our contributions to the field is discussed. Use of phosphines enabled iron‐catalyzed hydroformylation of alkenes under mild conditions. Thus, this account demonstrates the central role of phosphorus ligands in industrially relevant transformations such as hydrogenation and hydroformylation. The seemingly matured field of ligand discovery still holds significant potential and will steer the field of homogeneous catalysis.

show abstract

Thienopyrimidinone bis-aminopyrrolidine ureas as potent melanin-concentrating hormone receptor-1 (MCH-R1) antagonists

Cited by 21 publications

References 29 publications

Novel Fused Arylpyrimidinone Based Allosteric Modulators of the M₁ Muscarinic Acetylcholine Receptor

Novel Fused Arylpyrimidinone Based Allosteric Modulators of the M₁ Muscarinic Acetylcholine Receptor

Synthesis of Tetrasubstituted Thieno[3,2‐b]pyridin‐5(4H)‐one Derivatives as a Heterocyclic Scaffold for Multisite‐specific Fluorous Fluorescent Tagging and Fluorous Solid‐Phase Extraction

Phosphorus Ligands in Hydroformylation and Hydrogenation: A Personal Account

Contact Info

Product

Resources

About

Thienopyrimidinone bis-aminopyrrolidine ureas as potent melanin-concentrating hormone receptor-1 (MCH-R1) antagonists

Cited by 21 publications

References 29 publications

Novel Fused Arylpyrimidinone Based Allosteric Modulators of the M1 Muscarinic Acetylcholine Receptor

Novel Fused Arylpyrimidinone Based Allosteric Modulators of the M1 Muscarinic Acetylcholine Receptor

Synthesis of Tetrasubstituted Thieno[3,2‐b]pyridin‐5(4H)‐one Derivatives as a Heterocyclic Scaffold for Multisite‐specific Fluorous Fluorescent Tagging and Fluorous Solid‐Phase Extraction

Phosphorus Ligands in Hydroformylation and Hydrogenation: A Personal Account

Contact Info

Product

Resources

About

Novel Fused Arylpyrimidinone Based Allosteric Modulators of the M₁ Muscarinic Acetylcholine Receptor

Novel Fused Arylpyrimidinone Based Allosteric Modulators of the M₁ Muscarinic Acetylcholine Receptor