Synthesis of benzo[d]thiazole-hydrazone analogues: molecular docking and SAR studies of potential H+/K+ ATPase inhibitors and anti-inflammatory agents12. Issue 6 (26th April 2017)

• Record Type: Journal Article
• Authors: Wang, Shi-Meng; Zha, Gao-Feng; Rakesh, K. P.; Darshini, N.; Shubhavathi, T.; Vivek, H. K.; Mallesha, N.; Qin, Hua-Li
• Is Part Of: MedChemComm. Volume 8:Issue 6(2017)
• Page Start: 1173
• Page End: 1189
• Publication Date: 2017-04-26
• Subjects: Pharmaceutical chemistry -- Periodicals; 615.19
• DOI: 10.1039/c7md00111h
• Languages: English
• ISSNs: 2040-2503

Abstract

Abstract : A series of new benzo[ d ]thiazole-hydrazones were synthesized and characterized by analytical and spectroscopic techniques. Abstract : A series of new benzo[ d ]thiazole-hydrazones were synthesized and characterized by analytical and spectroscopic techniques. All the compounds were screened for their in vitro inhibition of H + /K + ATPase and anti-inflammatory effects. The results revealed that compounds6–8, 13–15, 18–20, 22, 23 and27–30 displayed excellent inhibitory activity against H + /K + ATPase, and their IC50 values were lower than those of the standard compound omeprazole. Compounds2–5, 9–12, 28 and30 exhibited better anti-inflammatory activity in comparison to the standard compound indomethacin. Studies of the structure–activity relationship (SAR) showed that electron-donating groups (OH and OCH3 ) favored inhibitory activity against H + /K + ATPase, whereas electron-withdrawing groups (F, Cl, Br and NO2 ) favored anti-inflammatory activity, and derivatives with both electron-donating (OH and OCH3 ) and electron-withdrawing (Br) groups (16–18 ) displayed reasonable activity, whereas aliphatic analogues (24–26 ) exhibited less activity and heterocyclic analogues (27–30 ) displayed moderate activity in both biological studies. Molecular docking studies were performed for all the synthesized compounds, among which compounds19 and20 exhibited the highest docking scores for inhibitory activity against H + /K + ATPase, whereas compounds10 and12 displayed the highest docking scores for anti-inflammatory activity.