Assembly of Benzothiazine and Triazole in a Single Molecular Entity: Synthesis of -Oxicam Derived Novel Molecules as Potential Antibacterial/ Anti-cancer Agents

Abstract

Background: Benzothiazine derivatives, because of their various biological activities have attracted particular attention in Med Chem and drug discovery efforts. The synthetic modifications of 1,2-benzothiazine 1,1-dioxides have been undertaken in order to explore and identify novel compounds or new analogues possessing promising biological activities. In our effort we have designed -oxicam derived bezothiazine-1,2,3-triazole derivatives as potential antibacterial agents. Methods: These compounds were synthesized via a multi-step sequence involving the Cu catalyzed azide- alkyne cycloaddition (CuAAC) as a key step. The CuAAC proceeded at room temperature in DMF to afford 26 novel molecules in good (70-90%) yields. Results: All these compounds were tested for their antibacterial properties against four strains of bacterial microorganisms and subsequently cytotoxic properties against lung and colon cancer cell lines. The compound 4e showed activities against majority of the bacterial species used (nearly comparable to amoxicillin, ciprofloxacin and ofloxacin against P. vulgaris) whereas 4d and 4f showed cytotoxicities selective towards cancer cells. Conclusion: The present bezothiazine-1,2,3-triazole framework represents a new template for the identification of novel and potent antibacterial/anticancer agents.

One‐pot two‐step synthesis of fused thiazinofuranone linked geminal bis 1,2,3‐triazole hybrids and their in vitro cytotoxic screening

“…In recent years, molecular hybridization [29][30][31][32][33][34] is emerged as an important tool in medicinal chemistry to develop new molecular entities by combining two or more pharmacophores in such a way to improve their therapeutic potency and efficacy. A wide number of hybrid molecules containing 1,2,3-triazole pharmacophores [35][36][37] [Correction added on 22 March 2021, after first online publication: '5-Acetyl-4-Hydroxy-1,3-thiazine' was corrected in 'abstract', 'results and discussions' and section '4.1.1' in this version.] have been proved to be shown remarkable pharmacological activities.…”

Antibacterial and Cytotoxic Effects of Cyclodextrin-Triazole-Titanium Based Nanocomposite

“…The exploration of new agents with dual antibacterial and anticancer activities is necessary because of promising therapeutic potential due to their capability to decrease the threat of bacterial infections in the frequently immunocompromised cancer patient [30][31][32]. This class of compounds with dual antibacterial and anticancer effects not only controlling growth of cancer related bacterial infections but also protecting patients from the infection due to downplay of immune system [33].…”

Synthesis, Biological Evaluation and In silico Studies of Compounds Based on Tryptophan‐Naproxen‐Triazole Hybrids

“…[5][6][7][8][9][10][11][12] On the other hand compounds containing the 1,2,3-triazole framework (a bioisostere of peptide) displayed various pharmacological activities. [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29] The indole nucleus, an important heterocyclic moiety is prevalent in many natural and unnatural bioactive molecules. It is also present in proteins in the form of amino acid i. e. tryptophan.…”

“…The derivatives of naproxen (a well‐known NSAID) are known to possess a broad array of biological properties including antimicrobial, antifungal, antibacterial, antimalarial, antiviral and antitumor activities [5–12] . On the other hand compounds containing the 1,2,3‐triazole framework (a bioisostere of peptide) displayed various pharmacological activities [13–29] . The indole nucleus, an important heterocyclic moiety is prevalent in many natural and unnatural bioactive molecules.…”