No regioselectivity for the steroid α-face in cocrystallization of exemestane with aromatic cocrystal formers based on phenanthrene and pyrene
Bibliographic record
Abstract
The anti-cancer steroidal drug exemestane presents significantly different behavior in cocrystallization with arenes compared with the previously explored steroid progesterone. Mechanochemical and solution-based cocrystallization of exemestane with hydroxy derivatives of phenanthrene and pyrene leads to the formation of cocrystals exhibiting clear O–H···O type arene-steroid hydrogen bonds. So far, exemestane and 1-hydroxypyrene have been observed to form only one type of cocrystal, with the 1:1 stoichiometric ratio of the two components. However, there are two stoichiometric variations of the cocrystal of 9-hydroxyphenanthrene and exemestane, with the arene:steroid stoichiometric ratio of either 1:1 or 1:2. Importantly, although cocrystallization of progesterone with the same arene cocrystal formers was previously reported to take place regioselectively through α···π contacts between the α-face of the steroid and the π-electron surface of the arene, the herein explored cocrystals of exemestane reveal α···π and β···π contacts, as well as sidewise interactions involving the arene π-system and different edges of the steroid molecule. The loss of regioselectivity for the steroid α-face in cocrystallization with the two monohydroxylated arenes is tentatively explained by the highly positive electrostatic surface potential of the steroid β-face and a diminished number of C–H groups on the α-face of exemestane compared with progesterone.
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How this classification was reachedexpand
Full frame distilled prediction
Teacher imitationNot 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.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
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.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one teacher head, not a consensus.
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".