# Novel Adamantane Derivatives: Synthesis, Cytotoxicity and Antimicrobial Properties
## 4 Discussion  
### Chemistry  
The chemical syntheses described in the current research enabled us to obtain seventeen novel adamantane derivatives not described in the scientific literature so far, i.e., two derivatives of 3-aminotricyclo[3.3.1.1\({}^{37}\)]decan-1-ol (**2**,3**), seven derivatives of tricyclo [3.3.1.1\({}^{37}\)]decan-1-amine (**5**-**11**), five derivatives of 1-tricyclo[3.3.1.1\({}^{37}\)]dec-1-yl)methananamine (**13**-**17**) and four adamantancarboxylic acid derivatives with a hydrazide-hydrazzone moi  
\begin{table}
\begin{tabular}{c c c c c c c c c c c c c} \hline \hline  & \multicolumn{4}{c}{**7**} & \multicolumn{4}{c}{**10**} & \multicolumn{4}{c}{**21**} \\ \cline{2-13}
**Compound No/Concentration** & \multicolumn{4}{c}{**Repeat**} & \multicolumn{4}{c}{**Repeat**} & \multicolumn{4}{c}{**Repeat**} \\ \cline{2-13}
**(\(\mu\)M)** & **No** & **No** & **No** & **No** & **No** & **No** & **No** & **No** & **No** & **No** & **No** & **No** \\  & **1** & **2** & **3** & **4** & **1** & **2** & **3** & **4** & **1** & **2** & **3** & **4** \\ \hline
**control** & 78 & 108 & 102 & 78 & 96 & 93 & 87 & 100 & 98 & 83 & 104 & 101 \\ \hline
**5** & 98 & 91 & 98 & 84 & 87 & 100 & 109 & 87 & 89 & 94 & 88 & 102 \\ \hline
**10** & 102 & 102 & 95 & 98 & 93 & 94 & 98 & 81 & 86 & 94 & 83 & 100 \\ \hline
**25** & 73 & 84 & 94 & 86 & 88 & 106 & 87 & 85 & 51 & 59 & 89 & 77 \\ \hline
**50** & 67 & 79 & 89 & 88 & 91 & 101 & 89 & 107 & 87 & 92 & 68 & 63 \\ \hline
**100** & 87 & 73 & 43 & 81 & 112 & 104 & 78 & 99 & 89 & 102 & 87 & 83 \\ \hline
**150** & 68 & 71 & 75 & 68 & 102 & 97 & 75 & 88 & 73 & 69 & 71 & 84 \\ \hline
**200** & 74 & 78 & 76 & 85 & 94 & 92 & 84 & 72 & 75 & 81 & 86 & 94 \\ \hline \hline \end{tabular}
\end{table}
Table 7: The cell proliferation in % after 48 h exposition on studied compounds in T47D cell line.  
\begin{table}
\begin{tabular}{c c c c c c c c c c c c c} \hline \hline  & \multicolumn{4}{c}{**7**} & \multicolumn{4}{c}{**10**} & \multicolumn{4}{c}{**21**} \\ \cline{2-13}
**Compound No/Concentration** & \multicolumn{4}{c}{**Repeat**} & \multicolumn{4}{c}{**Repeat**} & \multicolumn{4}{c}{**Repeat**} \\ \cline{2-13}
**(\(\mu\)M)** & **No** & **No** & **No** & **No** & **No** & **No** & **No** & **No** & **No** & **No** & **No** & **No** \\  & **1** & **2** & **3** & **4** & **1** & **2** & **3** & **4** & **1** & **2** & **3** & **4** \\ \hline
**control** & 89 & 107  
ety (**20-23**). Compounds **2**, **3**, **5**-**11**, **13**-**17** and **20**-**23** were synthesized based on a typical condensation reaction between the amine group of one compound and the carbonyl group of another substance. For the synthesis of the above-mentioned derivatives, we used the following starting materials: 1.2 mmol of 3-aminotricyclo[3.3.1.137]decan-1-ol (**1**) or 1.3 mmol of 1-adamantanylamine (**4**) or 1.2 mmol of 1-adamantanemethylamine (**12**) or 1.0 mmol of hydrazide of 1-adamantanecarboxylic acid (**19**) and an appropriate amount of aldehydes or ketones.  
The yields of the condensation reaction were different for each of the obtained derivatives, and they varied significantly. The yields of the synthesis depended on the aldehydes or ketones used for the synthesis. The lack of a catalyst used in our research may also have contributed to the low efficiency of the reactions performed. A review of the literature shows that the addition of a few drops of glacial acetic acid is usually used to obtain substances based on condensation reactions [36].  
The yields of the performed reactions were within the scope of 4-96%. The highest yield of 96% was found in the synthesis of 3-[(2,4-dimethoxybenzylidene)amino]tricyclo[3.3.1.137]decan-1-ol (**3**), whereas the lowest yield of 4% was found for 1-(3-nitrophenyl)-\(N\)-(tricyclo[3.3.1.137]decan-1-ylmethyl)methanimine (**14**) and \(N\)-(5-hydroxytricyclo[3.3.1.137]decan-2-ylidene)tricyclo[3.3.1.137]decan-1-carbohydrazide (**23**).