# Novel Adamantane Derivatives: Synthesis, Cytotoxicity and Antimicrobial Properties
## 2 Materials and Methods
### Experimental  
2.1 General Method for the Synthesis of 3-Aminotricyclo[3.3.1.1\({}^{37}\)]decan-1-ol Derivatives (**2**, **3**), Tricyclo[3.3.1.1\({}^{37}\)]decan-1-amine Derivatives (**5**-**11**), 1-(Tricyclo[3.3.1.1\({}^{37}\)]dec-1-yl)methanamine Derivatives (**13**-**17**)  
A total of 0.2 g (1.2 mmol) of 3-aminotricylo[3.3.1.1\({}^{37}\)]decan-1-ol (**1**) or 0.2 g (1.3 mmol) of 1-adamantanylamine (**4**) or 0.2 g (1.2 mmol) of 1-adamantanemethylamine (**12**) was placed in a round-bottomed flask and dissolved in ethanol (5 mL, 96%) by heating under reflux. Then, appropriate amounts of various aldehydes or ketones (1.3 mmol) were added, and the mixture in the flask was heated under reflux for 3 h. After that, the solution was allowed to cool and was put into the refrigerator for 24 h. Subsequently, a precipitate appeared, and it was filtered off under reduced pressure, then dried and re-crystallized from ethanol (96%). 3-[(2,3-dimethoxyylidene)amino]tricylcol[3.3.1.1\({}^{37}\)]decan-1-ol (**2**)  
Cream solid; M.p. : 116 \({}^{\circ}\)C; Yield: 87%; \({}^{1}\)H NMR (300 MHz, DMSO-\(d_{6}\)) \(\delta\) (ppm): 1.53-1.55 (d, \(J\) = 6.0 Hz, 2H, CH\({}_{\text{2-adamantane}}\)), 1.58-1.61 (m, 8H, 4\(\times\)CH\({}_{\text{2-adamantane}}\)), 1.64-1.66 (d, \(J\) = 6.0 Hz, 2H, CH\({}_{\text{2-adamantane}}\)), 2.24-2.26 (t, 2H, \(2\times\)CH\({}_{\text{adamantane}}\)), 3.77 (s, 3H, CH\({}_{3}\)), 3.83 (s, 3H, OCH\({}_{3}\)), 4.56 (s, 1H, OH), 7.08-7.10 (t, \(J\) = 6.0, 1H, ArH), 7.12-7.13 (d, \(J\) = 3.0 Hz, 1H, ArH), 7.41-7.43 (d, \(J\) = 6.0 Hz, 1H, ArH), 8.54 (s, 1H, =CH); \({}^{13}\)C NMR (150 MHz, DMSO-\(d_{6}\)) \(\delta\) (ppm): 30.74 (2\(\times\)CH\({}_{\text{adamantane}}\)), 35.30 (CH\({}_{\text{2-adamantane}}\)), 42.33 (2\(\times\)CH\({}_{\text{2-adamantane}}\)), 44.73 (2\(\times\)CH\({}_{\text{2-adamantane}}\)), 50.99 (CH\({}_{\text{2-adamantane}}\)), 56.26 (C\({}_{\text{adamantane}}\)), 60.98 (OCH\({}_{\text{3}}\)), 61.66 (OCH\({}_{\text{3}}\)), 68.30 (C\({}_{\text{adamantane}}\)), 114.97, 118.21, 124.42, 130.40 (4\(\times\)Car), 149.26 (=CH), 150.45, 153.05 (2\(\times\)Car). 3-[(2,4-dimethoxybenzylidene)amino]tricylcol[3.3.1.1\({}^{37}\)]decan-1-ol (**3**)  
Yellow solid; M.p. : 86 \({}^{\circ}\)C; Yield: 96%; \({}^{1}\)H NMR (300 MHz, DMSO-\(d_{6}\)) \(\delta\) (ppm): 1.51-1.53 (m, 4H, 2\(\times\)CH\({}_{\text{2-adamantane}}\)), 1.57-1.58 (d, \(J\) = 3.0 Hz, 6H, 3\(\times\)CH\({}_{\text{2-adamantane}}\)), 1.60-1.62 (d, \(J\) = 6.0 Hz, 2H, CH\({}_{\text{2-adamantane}}\)), 2.22-2.24 (t, \(J\) = 3.0 Hz, 2H, 2\(\times\)CH\({}_{\text{adamantane}}\)), 3.80 (s, 3H, OCH\({}_{3}\)), 3.84 (s, 3H, OCH\({}_{3}\)), 4.53 (s, 1H, OH), 6.55-6.56 (d, \(J\) = 3.0 Hz, 1H, ArH), 6.60-6.61 (d, \(J\) = 3.0 Hz, 1H, ArH), 7.76-7.78 (d, \(J\) = 3.0 Hz, 1H, ArH), 8.51 (s, 1H, =CH); \({}^{13}\)C NMR (150 MHz, DMSO-\(d_{6}\)) \(\delta\) (ppm): 30.74 (2\(\times\)CH\({}_{\text{adamantane}}\)), 35.31 (CH\({}_{\text{2-adamantane}}\)), 42.57 (2\(\times\)CH\({}_{\text{2-adamantane}}\)), 44.73 (2\(\times\)CH\({}_{\text{2-adamantane}}\)), 51.22 (CH\({}_{\text{2-adamantane}}\)), 56.06 (C\({}_{\text{adamantane}}\)), 60.55 (OCH\({}_{\text{3}}\)), 61.66 (OCH\({}_{\text{3}}\)), 68.34 (C\({}_{\text{adamantane}}\)), 98.35, 106.37, 118.07, 127.75 (4\(\times\)Car), 149.53 (=CH), 160.17, 162.95 (2\(\times\)Car). 2-ethoxy-6-[(tricyclo[3.3.1.1\({}^{37}\)]dec-1-ylimine)methyl]phenol (**5**)  
Yellow solid; M.p.