Experimental and computational structural studies of 5-substituted-3-(1-arylmethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indoles
Bibliographic record
Abstract
Four compounds ( 1–4 ) reported in our previous work as potential antipsychotics with affinity for dopamine D 2 and serotonin 5-HT 1A and 5-HT 2A receptors, were now subjected to detailed structural characterization. The X-ray analysis conducted for studied compounds proved that interatomic distances and bond angles in their crystal structures lie within normal values. The indole group in all compounds is planar, whereas tetrahydropyridine moiety exhibits almost ideal or close to half-chair conformation and is slightly or significantly rotated in relation to the indole group plane by 9.49(1)°, 30.24(11)°, 7.43(6)° and 15.98(18)° in compounds 1–4, respectively. The R 1 substituents of tetrahydropyridine group in all cases form a dihedral angle with the indole moiety with value ranging from 66.57(14)° ( 2 ) to 86.73(17)° ( 4 ). The crystal structure of 1 is stabilized by N–H···N hydrogen bonds and C–H···π interactions. The intermolecular C(12)−H(12B)··· Cg (2) interactions form a supramolecular two-dimensional network. The molecules in the crystal of 2 are linked by N–H···N. The formed chains are additionally stabilized with C–H···S hydrogen bonds. In case of compound 3 , molecule chains are formed by N–H···N hydrogen bonds and are further linked via C–H···O hydrogen bonds into layer. The crystal structure is also stabilized by intermolecular C–H···π interactions. The molecules of compound 4 are linked by N–H···N hydrogen bonds and further stabilized by intermolecular C–H···π interactions. Crystallographic analysis was complemented with computational studies, such as Frontier Molecular Orbital analysis, which indicated that all four compounds display similar chemical reactivity, regardless of different R 1 and R 2 substituents. In addition, the most reactive parts of the compounds appear to be the indole and double bond located in tetrahydropyridine moiety. Lastly, the calculations of electrostatic potential and non-covalent interactions have been performed.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.001 | 0.001 |
| Meta-epidemiology (narrow) | 0.001 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.001 |
| Bibliometrics | 0.001 | 0.001 |
| Science and technology studies | 0.001 | 0.001 |
| Scholarly communication | 0.001 | 0.001 |
| Open science | 0.002 | 0.000 |
| Research integrity | 0.001 | 0.001 |
| Insufficient payload (model declined to judge) | 0.009 | 0.001 |
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 source (direct Gemma or distilled Codex), 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".