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Record W2018894316 · doi:10.1002/ejoc.200701077

Chemical Synthesis of (<i>S</i>)‐Spiro(estradiol‐17,2′‐[1,4]oxazinan)‐6′‐one Derivatives Bearing Two Levels of Molecular Diversity

2008· article· en· W2018894316 on OpenAlexfundno aff
François Rouillard, Jenny Roy, Donald Poirier

Bibliographic record

VenueEuropean Journal of Organic Chemistry · 2008
Typearticle
Languageen
FieldChemistry
TopicSynthesis and Biological Evaluation
Canadian institutionsnot available
FundersCanadian Institutes of Health ResearchMcGill University
KeywordsChemistryMoietyRegioselectivityKetoneAlkylationNitrogen atomEstroneStereochemistryStereoselectivityLactoneCarbonyl groupRing (chemistry)Combinatorial chemistryOrganic chemistryCatalysisBiochemistryHormone

Abstract

fetched live from OpenAlex

Abstract The present study shows the development of a strategy that can afford different estradiol derivatives bearing a 17‐spiro‐δ‐lactone moiety with a nitrogen atom inserted in the lactone ring. Such [1,4]oxazinan‐6′‐one derivatives contain two levels of molecular diversity introduced to modulate biological activity. The strategy employed to prepare these compounds includes the stereoselective formation of a 17β‐oxirane from the carbonyl group of estrone, the regioselective opening of the resulting oxirane with various hydrophobic amino acids (giving the first level of diversity), the spirolactonization, the alkylation of nitrogen by different functional groups (producing the second level of diversity), and final deprotection, when necessary. A series of ( S )‐spiro(estradiol‐17,2′‐[1,4]oxazinan)‐6′‐one derivatives was generated to illustrate the usefulness of this diversification strategy, which could easily be extended to other steroidal and nonsteroidal ketone scaffolds for interacting with additional biological targets. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2008)

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesInsufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.010
Threshold uncertainty score0.998

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0030.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.048
GPT teacher head0.231
Teacher spread0.183 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one teacher head, not a consensus.

Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations11
Published2008
Admission routes1
Has abstractyes

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