Solid-phase synthesis of 1,3-diamino ketones

Subramanyam, Chakrapani; Chang, Shang-Poa

doi:10.1016/s0040-4039(00)01262-4

Cited by 6 publications

(6 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Finally, without separation, 2 was oxidized to the corresponding ketone 4. This Dess-Martin Periodinane (DMP, 1,1,1-triacetoxy-1,1-dihydro-1,2benziodoxol-3-(1H)-one) oxidation was worked-up using Dowex1-X4 in its thiosulfate form 12 to yield ketone 4 13 (85%) with no need for further purification (Scheme 3).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 6,6-Difluorohomopiperazines via Microwave-Assisted Detosylation

Wellner¹,

Sandin²,

Pääkkönen³

2003

Synthesis

View full text Add to dashboard Cite

show abstract

Section: Methodsmentioning

confidence: 99%

Synthesis of 6,6-Difluorohomopiperazines via Microwave-Assisted Detosylation

Wellner¹,

Sandin²,

Pääkkönen³

2003

Synthesis

View full text Add to dashboard Cite

show abstract

“…The parallel synthesis strategy geared towards synthesis of these ketone-based target compounds, Researchers at Pfizer have disclosed the design and synthesis of a novel class of cysteine protease inhibitors based on a 1,3-diamino ketone motif [229]. By immobilizing the orthogonally-protected diaminopropanol on solid support via a THP linker, both ends of the scaffold were modified, enabling a diverse library to be produced based on the structure of (172).…”

Section: Cysteine Proteasesmentioning

confidence: 99%

Design and Synthesis of Protein Superfamily-Targeted Chemical Libraries for Lead Identification and Optimization

Shuttleworth¹,

Connors²,

Fu³

et al. 2005

CMC

View full text Add to dashboard Cite

This review chronicles original literature dating back to 1992 outlining the applications of parallel synthesis and combinatorial chemistry to the synthesis of compound libraries focused towards specific superfamilies of molecular targets. Target families that have received significant literature coverage include kinases, proteases, nuclear hormone receptors and cell surface receptors, notably GPCRs.

show abstract

“…An alternate, general, solid‐phase route to amidomethyl ketones has also recently been reported. This strategy allows the display of a diverse set of functionality about the amidomethyl ketone core, although the method is limited in that P 1 side‐chain diversity cannot be incorporated into the synthesis scheme 64. The diamino propanol core, which is orthogonally protected with two different amine protecting groups, is linked to a tetrahydropyran (THP) linker in excellent yield (Scheme ).…”

Section: Protease Inhibitor Designmentioning

confidence: 99%

Combinatorial Strategies for Targeting Protein Families: Application to the Proteases

2002

View full text Add to dashboard Cite

Tens of thousands of proteins have been identified as a result of recent large scale genomic and proteomic efforts. With this large influx of new proteins, the formidable task of elucidating their function begins. However, this task becomes more manageable if proteins are divided into families based upon sequence homology, thereby allowing tools for their systematic study to be developed based upon their common structural and mechanistic characteristics. Combinatorial chemistry is ideally suited for the systematic study of protein families because a large amount of diversity can be readily displayed about a common scaffold designed to target a given protein family. Targeted combinatorial libraries have been particularly effective for the study of a ubiquitous family of proteins, the proteases. Substrate-specificity profiles of many proteases have been determined by using combinatorial libraries of appropriately labeled peptides. This specificity information been utilized to identify the physiological protein substrates of these enzymes and has facilitated inhibitor design efforts. Furthermore, combinatorial libraries of small molecules prepared with mechanism-based scaffolds have resulted in the identification of potent, small-molecule inhibitors of numerous proteases. Cell-permeable small-molecule inhibitors identified by these methods have served as powerful chemical tools to study protease function in vitro and in vivo and have served as leads for the development of therapeutic agents.

show abstract

Solid-phase synthesis of 1,3-diamino ketones

Cited by 6 publications

References 6 publications

Synthesis of 6,6-Difluorohomopiperazines via Microwave-Assisted Detosylation

Synthesis of 6,6-Difluorohomopiperazines via Microwave-Assisted Detosylation

Design and Synthesis of Protein Superfamily-Targeted Chemical Libraries for Lead Identification and Optimization

Combinatorial Strategies for Targeting Protein Families: Application to the Proteases

Contact Info

Product

Resources

About

Solid-phase synthesis of 1,3-diamino ketones

Cited by 6 publications

References 6 publications

Synthesis of 6,6-Difluorohomopiperazines via Microwave-Assisted Detosylation­

Synthesis of 6,6-Difluorohomopiperazines via Microwave-Assisted Detosylation­

Design and Synthesis of Protein Superfamily-Targeted Chemical Libraries for Lead Identification and Optimization

Combinatorial Strategies for Targeting Protein Families: Application to the Proteases

Contact Info

Product

Resources

About

Synthesis of 6,6-Difluorohomopiperazines via Microwave-Assisted Detosylation

Synthesis of 6,6-Difluorohomopiperazines via Microwave-Assisted Detosylation