Crystal structure of 4-((cyclohexylsulfonyl)methyl)-1,2,3,4-tetrahydrobenzo [4,5]imidazo[1,2-a]pyridine, C18H24N2O2S
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Jiajie Li
,
Yuanyuan Wang
und
Liyan Zhang
Abstract
C18H24N2O2S, monoclinic, P21/c (no. 14), a = 27.3975(7) Å, b = 6.16564(14) Å, c = 9.9182(2) Å, β = 99.202(2)°, V = 1653.86(7) Å3, Z = 4, R gt (F) = 0.0586, wR ref (F2) = 0.1544, T = 100(1) K.
The molecular structure is shown in the figure Table 1 contains the crystallographic data and the list of the atoms including atomic coordinates and displacement parameters can be found in the cif-file attached to this article.
Data collection and handling.
| Crystal: | Clear light colourless block |
| Size: | 0.16 × 0.13 × 0.12 mm |
| Wavelength: | Cu Kα radiation (1.54184 Å) |
| μ: | 1.83 mm−1 |
| Diffractometer, scan mode: | Bruker Apex-II, φ and ω scans |
| θmax, completeness: | 74.6°, 99 % |
| N(hkl)measured, N(hkl)unique, Rint: | 12558, 3262, 0.032 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 3222 |
| N(param)refined: | 209 |
| Programs: | Olex2, 1 Bruker, 2 SHELX, 3 Diamond 4 |
1 Source of material
To an oven-dried Schlenk tube equipped with a magnetic stir bar were sequentially added 1-(pent-4-en-1-yl)-1H-benzo[d]imidazole (40.43 mg, 0.2 mmol), diethyl 4-cyclohexyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (160.00 mg, 0.4 mmol), DABSO (96.12 mg, 0.4 mmol), ammonium persulfate (45.64 mg, 0.2 mmol), Eosin Y (2 mol %) and DCM (2.0 mL). After being degassed and refilled with nitrogen three times, the tube was sealed, and the reaction mixture was stirred under 20 W blue LED irradiation at room temperature for 24 h. After that, the solvent was removed by vacuum evaporation, and the crude residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and hexanes (1:10 to 1:8) to give the desired product.
2 Experimental details
The carbon-bound hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.
3 Comment
Benzimidazoles and their derivatives exhibit significant biological activity, positioning them as potential anticancer agents. Benzimidazole is a bicyclic compound characterized by an imidazole ring containing two non-adjacent nitrogen atoms thickened with a benzene ring. The backbone structure possesses diverse pharmacological properties including antiviral, antifungal, antioxidant, anticancer and anthelmintic activities. Incorporation of the core structure of benzimidazoles into drug development continues to play a key role in contemporary therapeutic research, providing versatile and effective therapeutic avenues for a wide range of diseases. 5 , 6 , 7 , 8
The title compound contains a sulfonyl group. 9 , 10 According to the title structure, the bond lengths and angles obtained are within normal ranges. The sulfonyl groups were determined at the distance of 1.447 (2) Å (S1–O1), 1.447 (2) Å (S1–O1), 1.789 (3) Å (S1–C12), 1.800 (3) Å (S2–C13). Geometric parameters are all in the expected range.
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Conflict of interest: The authors declare no conflicts of interest regarding this article.
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Research funding: Guizhou Provincial Basic Research Program (Natural Science) QKHJC–ZK[2021] general 086.
References
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