# Novel Adamantane Derivatives: Synthesis, Cytotoxicity and Antimicrobial Properties
## 2 Materials and Methods
### Experimental
: 266 \({}^{\circ}\)C; Yield: 95%; 1H NMR (300 MHz, DMSO-\(d_{6}\)) \(\delta\) (ppm): 1.50-1.52 (d, \(J\) = 6.0 Hz, 6H, 3\(\times\)CH\({}_{\rm 2-adamantane}\)), 1.55-1.61 (m, 4H, 2\(\times\)CH\({}_{\rm 2-adamantane}\)), 1.61-1.65 (m, 2H, CH\({}_{\rm 2-adamantane}\)), 1.65-1.74 (m, 10H, 5\(\times\)CH\({}_{\rm 2-adamantane}\)), 1.93-1.95 (m, 3H, 3\(\times\)CH\({}_{\rm 2}\)), 2.15-2.17 (m, 3H, 3\(\times\)CH\({}_{\rm adamantane}\)), 3.15 (s, 2H, CH\({}_{\rm 2}\)), 4.56 (s, 1H, OH); 1\({}^{\circ}\)C NMR (150 MHz, DMSO-\(d_{6}\)) \(\delta\) (ppm):the refrigerator for 24 h. The formed precipitate was filtered off under reduced pressure, dried and re-crystallized from ethanol (96%). tricylclo[3.3.1.137]decane-1-carbohydrazide (**19**)  
CAS Number: 81375-05-5; White powder; M.p. : 224 \({}^{\circ}\)C; Yield: 25%; \({}^{1}\)H NMR (300 MHz, DMSO-\(d_{\delta}\)) \(\delta\) (ppm): 1.63-1.69 (m, 6H, 3\(\times\)CH\({}_{\rm 2-adamantane}\)), 1.80-1.82 (d, \(J\) = 6.0 Hz, 6H, 3\(\times\)CH\({}_{\rm 2-adamantane}\)), 1.95-1.97 (m, 3H, 3\(\times\)CH\({}_{\rm 2-adamantane}\)), 4.04 (s, 2H, NH\({}_{2}\)), 9.13 (s, 1H, NH); \({}^{13}\)C NMR (150 MHz, DMSO-\(d_{\delta}\)) \(\delta\) (ppm): 27.84 (3\(\times\)CH\({}_{\rm adamantane}\)), 36.50 (3\(\times\)CH\({}_{\rm 2-adamantane}\)), 38.79 (3\(\times\)CH\({}_{\rm 2-adamantane}\)), 38.96 (Cadamantane), 178.85 (C=O). Synthesis of Hydrazide-Hydrazones of 1-Adamantancarbarboxylic Acid (**20-23**)  
A total of 1.0 mmol (0.19 g) of hydrazide of 1-adamantancarboxylic acid (**19**) was dissolved in a round-bottomed flask in ethanol (5 mL, 96%). Then 1.1 mmol of appropriate aldehyde or ketone was added, and the flask was heated under reflux for 3 h. The content of the flask was allowed to cool and was placed in the refrigerator for 24 h. The precipitate obtained was filtered off, dried and re-crystallized from ethanol (96%). N-[(4-hydroxy-3-ethoxyphenyl)methylidene]tricylclo[3.3.1.137]decane-1-carbohydrazide (**20**)  
Yellow solid; M.p. : 246 \({}^{\circ}\)C; Yield: 29%; \({}^{1}\)H NMR (300 MHz, DMSO-\(d_{\delta}\)) \(\delta\) (ppm): 1.36-1.38 (t, \(J\) = 3.0 Hz, 3H, CH\({}_{3}\)), 1.63-1.69 (m, 6H, 3\(\times\)CH\({}_{\rm 2-adamantane}\)), 1.81-1.82 (d, 6H, 3\(\times\)CH\({}_{\rm 2-adamantane}\)), 1.95-1.97 (t, 3H, 3 CH\({}_{\rm adamantane}\)), 4.06-4.09 (q, \(J\) = 3.0 Hz, 2H, CH\({}_{2}\)), 6.88-6.90 (d, \(J\) = 6.0 Hz, 1H, ArH), 7.23-7.25 (d, \(J\) = 9.0 Hz, 1H, ArH), 7.43 (s, 1H, ArH), 8.55 (s, 1H, =CH), 9.12 (s, 1H, OH), 9.66 (s, 1H, NH); \({}^{13}\)C NMR (150 MHz, DMSO-\(d_{\delta}\)) \(\delta\) (ppm): 15.19 (CH\({}_{3}\)), 28.03 (3\(\times\)CH\({}_{\rm 3-ethane}\)), 36.58 (3\(\times\)CH\({}_{\rm 2-adamantane}\)), 38.98 (3\(\times\)CH\({}_{\rm 2-adamantane}\)), 56.48 (Cadamantane), 64.29 (CH\({}_{2}\)), 111.90, 116.04, 123.75, 125.94 (4\(\times\)Car), 147.56 (=CH), 150.57, 161.05 (2\(\times\)Car), 176.38 (C=O). N-[(2-chloro-5-nitrophenyl)]methylidene]tricylclo[3.3.1.137]decane-1-carbohydrazide (**21**)  
Orange solid; M.p. : 196 \({}^{\circ}\)C; Yield: 5%; \({}^{1}\)H NMR (300 MHz, DMSO-\(d_{\delta}\)) \(\delta\) (ppm): 1.71-1.73 (m, 3H, CH\({}_{\rm 2-adamantane}\)), 1.75-1.77 (m, 4H, 2\(\times\)CH\({}_{\rm 2-adamantane}\)), 1.90-1.91 (d, \(J\) = 3.0 Hz, 6H, 3\(\times\)CH\({}_{\rm 2-adamantane}\)), 2.06-2.08 (t, \(J\) = 3.0 Hz, 3H, 3\(\times\)CH\({}_{\rm adamantane}\)), 7.60-7.61 (d, \(J\) = 3.0 Hz, 1H, ArH), 8.15-8.16 (d, \(J\) = 3.0 Hz, 1H, ArH), 8.33 (s, 1H, ArH), 8.54 (s, 1H, =CH), 10.34 (s, 1H, NH). N-(5-bromotricylclo[3.3.1.137]dec-2-ylidene)tricylclo[3.3.1.137]decane-1-carbohydrazide (**22**)  
Cream solid; M.p.