## 1 Introduction  
Anthracenes are known scaffold due to their versatile applications, including pharmaceutical drugs [1; 2; 3; 4; 5; 6; 7; 8; 9] and molecular sensors [10]. Anthracenes, as a core structure, are explored in many transformations, due to more electrons, with the largest coefficients at C9/C10 [11; 12; 13; 14]. Building an ethano-bridge on the central ring of anthracenes is an attractive approach, and ethanoanthracenes are of significant interest in the context of drug discovery of anticancer [5; 6], antimalarial [15; 16], and antidepressant agents, as well as in overcoming drug resistance in multi-drug resistant cancers [17; 18; 19].  
Diels-Alder (DA) reaction [20], for which German chemists [PERSON] and [PERSON] were awarded the Nobel Prize in chemistry in 1950, is one of the most useful synthetic approaches for building ethanoanthracenes [21; 22; 23]. For example, maprotiline is a selective norepinephrine reuptakeinhibitor (sNRI), and was conventionally synthesized by [PERSON] et al., where the key step was the DA reaction of ethylene as dienophile to 9-substitutedanthracene precursor under high pressure (50 bar) and high temperature (150 \({}^{\circ}\)C) [24]. Later, many DA reactions have been developed using ethylene-equivalent dienophiles, such as phenyl vinyl sulfone [25; 26; 27; 28; 29], acrolein [18; 30], nitroethylene [31; 32], vinyldihaloborane [33], and vinyl phenyl sulfoxide [34]. The steric effect was found to play a major role on the regioselectivity of the DA reaction of 10-allyl-1,8-dichloroanthracene with 2-chloroacrylonitrile, 1-cyanovinyl acetate, and phenyl vinyl sulfone [25].  
The cheminformatic tools, including the Prediction of Activity Spectra for Substances (PASS), Lipinski's rule of five, predictions of absorption, distribution, metabolism, excretion, and toxicity (ADMET) are useful applications for the optimization and well-targeting of chemical synthesis, biological testing, and drug discovery [35; 36; 37]. Molecular docking is another cheminformatics technique that is based on the energy scoring function in order to identify the most energetically favorable ligand conformation when bound with the active site of the target [38]. The general hypothesis is that lower energy scores represent better protein-ligand bindings compared to higher energy values [38; 39]. The amine transporters regulate the neurotransmitter concentrations and play a role in mood and behavior disorders. These transporters are well known as targets for a broad range of antidepressant drugs, which are selective as norepinephrine reuptake inhibitors (sNRIs). Although the crystal structure of the human norepinephrine transporter (hNET) has not been reported yet, to understand the mechanism of action of norepinephrine reuptake inhibitors (NRIs), several attempts have been conducted by employing the homolog crystalized structures of the bacterial and invertebrate [40; 41; 42]. To design and discover new compounds could be work, as antidepressant-like agents are a challenge. Recently, we reported the DA reaction of 1,8-dichloroanthracene **2** and 2-chloroacrylonitrile under xylene reflux, affording two regioisomers [43]. To an extent, based on our research and the finding mention above, the microwave-assisted synthesis of new DA adduct ethanoanthracenes are reported, and the dienophile substituent effects on DA regioselectivity are described. In addition, the physiochemical properties, pharmacokinetics parameters, and biological activities of these adducts are theoretically investigated, in-depth. The docking of the compounds and marotiline to the target models Drosophila model 4 xnx [44], Bacterial Model 2 QJU [45], and Bacterial Model 3 GWU [46] were run, and the binding affinity was recorded as MolDock score function.