Abstract
Three hexahydroquinoline derivatives were synthesized and crystallized in an effort to study the structure–activity relationships of these calcium-channel antagonists. The derivatives are ethyl 4-(2-methoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C22H27NO4, (I), ethyl 4-(4-methoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C22H27NO4, (II), and ethyl 4-(3,4-dihydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C21H24NO5, (III). In these hexahydroquinoline derivatives, common structural features such as a flat-boat conformation of the 1,4-dihydropyridine (1,4-DHP) ring, an envelope conformation of the fused cyclohexanone ring, and a substituted phenyl group at the pseudo-axial position are retained. Hydrogen bonds are the main contributors to the packing of the molecules in these crystals.
| Original language | English |
|---|---|
| Pages (from-to) | 1089-1096 |
| Number of pages | 8 |
| Journal | Acta Crystallographica Section E: Crystallographic Communications |
| Volume | 78 |
| Issue number | 11 |
| DOIs | |
| State | Published - Nov 1 2022 |
Funding
The authors thank the University of Montana for grant 325490. CL thanks all the faculty in the ACA Summer Course 2016, from whom CL has learned a lot in refining disordered and twinned structures. The authors also thank Eric Schultz for mass spectra, supported by the National Institute of General Medical Sciences of the National Institutes of Health under Award No. P30GM140963. Funding for this research was provided by: University of Montana (grant No. 325490 to Nicholas R. Natale); National Institutes of Health, National Institute of General Medical Sciences (grant No. P30GM140963 to Nicholas R. Natale).
| Funder number |
|---|
| P30GM140963 |
| 325490 |
Keywords
- 1,4-dihydro-pyridine (1,4-DHP)
- calcium-channel antagonist
- crystal structure; hydrogen bonding; hexahydroquinoline (HHQ)
- multi-drug resistance (MDR)