Automated Synthesis of a 184-Member Library of Thiadiazepan-1,1-dioxide-4-ones

Fenster, Erik; Long, Toby R.; Zang, Qin; Hill, David R.; Neuenswander, Benjamin; Lushington, Gerald H.; Zhou, Aihua; Santini, Conrad; Hanson, Paul R.

doi:10.1021/co100060x

Cited by 18 publications

(10 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…17 In addition, domino HaM protocols have been developed in our laboratory for the synthesis of a library of functionalized 1,1-dioxido-1,2-benzisothiazolines. 18 Along these lines, we envisioned the construction of a tricyclic sultam library via integration of a HaM protocol with vinylsulfonamides, as outlined in Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of a Unique Isoindoline/Tetrahydroisoquinoline-based Tricyclic Sultam Library Utilizing a Heck-aza-Michael Strategy

et al. 2012

Self Cite

View full text Add to dashboard Cite

The synthesis of a unique isoindoline- and tetrahydroisoquinoline (THIQ)-containing tricyclic sultam library, utilizing a Heck-aza-Michael (HaM) strategy is reported. Both isoindoline and THIQ rings are installed through a Heck reaction on a vinylsulfonamide, followed by one-pot deprotection and intramolecular aza-Michael reaction. Subsequent cyclization with either paraformaldehyde condensation or 1,1'-carbonyldiimidazole coupling generates a variety of tricyclic sultams. Overall, a 160-member library of these sultams, together with their isoindolines/THIQ and secondary sulfonamides precursors, were constructed using this strategy.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of a Unique Isoindoline/Tetrahydroisoquinoline-based Tricyclic Sultam Library Utilizing a Heck-aza-Michael Strategy

et al. 2012

Self Cite

View full text Add to dashboard Cite

show abstract

“…9 Recently, a number of enabling synthetic methodologies have been developed give rapid access to diverse sultam libraries for HTS. 10 Building on these reports, it was envisioned that a variety of core sultam scaffolds prepared via MACOS could be quickly diversified in a facile, purification-free process utilizing a suite of ROMP-derived reagents. 11,12 Towards this goal, a suite of soluble, high-load ROMP-derived benzyl- and triazole- phosphates have been developed for the facile, purification-free diversification of nucleophilic small molecules.…”

Section: Resultsmentioning

confidence: 99%

Facile (Triazolyl)methylation of MACOS-derived Benzofused Sultams Utilizing ROMP-derived OTP Reagents

et al. 2012

Self Cite

View full text Add to dashboard Cite

A combination of MACOS scale-out and ROMP-derived oligomeric triazole phosphates (OTPn) have been successfully utilized for the preparation of a 106-member library of triazole containing benzothiaoxazepine-1,1-dioxides. This report demonstrates the utilization of a suite of soluble OTPn reagents for facile (triazolyl)methylation of 10 MACOS-derived sultam scaffolds in purification-free process for parallel synthesis of small molecule collections for HTS.

show abstract

“…63 Systems for carrying out reactions in parallel under different conditions have been implemented by Chemspeed, Hel Ltd., and other vendors. [64][65][66][67][68][69][70][71][72][73][74][75][76][77][78][79][80][81] Specifically, high-and medium-throughput facilities have been implemented in the pharmaceutical industry, where large numbers of compounds and reactions should be screened. Some examples are represented by high-capacity storage facilities handled by moving robots and/or robotic arms and miniaturized prototypes for synthesis and testing.…”

Section: Robotic Platformsmentioning

confidence: 99%

Automated robotic platforms in design and development of formulations

2021

View full text Add to dashboard Cite

Product design for formulations is an active and challenging area of research. The new challenges of a fast-paced market, products of increasing complexity, and practical translation of sustainability paradigms require to reexamine the existing theoretical frameworks to include the advantages deriving from the new reality of digitalization of business and research. In this work, we review the existing approaches, clearly stating the role of automation and machine-learning-guided optimization in the broader framework. Moving from this, we review the state of the art of automated hardware and software for formulated product design, and identify the open challenges for future research. Perspectives are given on the emerging fields of automated discovery, scale-up, and multistage optimization, and a unitary picture of the existing connections is provided, in the general context of a completely digital R&D workflow.

show abstract

Automated Synthesis of a 184-Member Library of Thiadiazepan-1,1-dioxide-4-ones

Cited by 18 publications

References 49 publications

Synthesis of a Unique Isoindoline/Tetrahydroisoquinoline-based Tricyclic Sultam Library Utilizing a Heck-aza-Michael Strategy

Synthesis of a Unique Isoindoline/Tetrahydroisoquinoline-based Tricyclic Sultam Library Utilizing a Heck-aza-Michael Strategy

Facile (Triazolyl)methylation of MACOS-derived Benzofused Sultams Utilizing ROMP-derived OTP Reagents

Automated robotic platforms in design and development of formulations

Contact Info

Product

Resources

About