Synthesis and Anti‐inflammatory Activity of Some New 1,2,3‐Benzotriazine Derivatives Using 2‐(4‐Oxo‐6‐phenylbenzo[d][1,2,3]triazin‐3(4H)‐yl)acetohydrazide as a Starting Material

Abstract

In continuation to our search for new heterocyclic system‐based anti‐inflammatory activity, a series of novel 1,2,3‐benzotriazine derivatives were synthesized. The pharmacological screening showed that many of these compounds have good anti‐inflammatory activity. The structure assignments of the new synthesized compounds are based on spectroscopic data, and pharmacological properties are reported.

A Combined Experimental and Computational Study of Novel Benzotriazinone Carboxamides as Alpha-Glucosidase Inhibitors

“…13 the 1 HNMR spectrum, three proton signals were observed in the region of 2.55-4.69 ppm and eight protons appeared in the aryl region of 7.48-8.31 ppm. 13 the 1 HNMR spectrum, three proton signals were observed in the region of 2.55-4.69 ppm and eight protons appeared in the aryl region of 7.48-8.31 ppm. 13 the 1 HNMR spectrum, three proton signals were observed in the region of 2.55-4.69 ppm and eight protons appeared in the aryl region of 7.48-8.31 ppm.…”

“…Chemical structures of all compounds were characterized using FT-IR, 1 H-NMR, 13 C-NMR, and EIMS spectroscopic techniques. In FT-IR spectrum, isatoic anhydride 10 was confirmed by two carbonyl bands at 1765, 1722 cm −1 and these values were found to be consistent with the literature [29].…”

“…Heterocyclic compounds are widely used as pharmaceutical drugs and 1,2,3-benzotriazin-4(3 H )-one is one of the emerging nuclei for use as a bioactive scaffold. Previously, several analogues of benzotriazinone 1 have been reported as antibacterial 2 [ 11 ], anticonvulsant 3 [ 12 ], anti-inflammatory 4 [ 13 ], anticancer 5 [ 14 ], and anti-HIV 6 [ 15 ] ( Figure 1 ). Moreover, different benzotriazinone derivatives have been studied for their inhibition potency against hydrolase aminopeptidase [ 16 ], acetylcholinesterase [ 17 ], chorismate mutase [ 18 ], HepG2 [ 14 ], 4-hydroxyphenylpyruvate dioxygenase [ 19 ], and matrix metalloprotease [ 5 ].…”

Experimental and Computational Analysis of Newly Synthesized Benzotriazinone Sulfonamides as Alpha-Glucosidase Inhibitors

“…Coumarin sulfonamide 1 [ 21 ], chromone sulfonyl hydrazone 2 [ 21 ], indole sulfonyl hydrazide 3 [ 22 ] and indole sulfonamide 4 [ 23 ] have been reported to be strong alpha glucosidase inhibitors ( Figure 1 ). 1,2,3-Benzotriazin-4(3 H )-one is known for its biologically active nucleus, and its derivatives have been reported as anti-inflammatory [ 24 ], anti-depressant [ 25 ], anticancer [ 26 ], anti-diarrheal [ 27 ], HIV inhibitor [ 28 ] and as anesthetics [ 29 ]. Some of its derivatives had been studied as enzyme inhibitors of 4-hydroxyphenylpyruvate dioxygenase [ 30 ], matrix metalloprotease [ 31 ], alpha-glucosidase [ 15 ], chorismate mutase [ 32 ], HepG2 [ 33 ] and acetylcholinesterase [ 34 ].…”

Bifunctional Phosphine Ligand-Enabled Gold(I)-Catalyzed O-Nucleophilic Addition of N-Hydroxybenzo[1,2,3]-triazin-4(3H)-ones to Alkynes Followed by [3,3]-Rearrangement: Simultaneous Formation of C–O and C–N Bonds

“…Benzo­[1,2,3]­triazin-4-one derivatives represent an important class of nitrogen-containing heterocyclic compounds whose scaffold is often found in a broad spectrum of pharmaceutical, agrochemical, and biologically active molecules and may exhibit a range of pharmacological properties such as sedative, diuretic, anesthetic, antiarthritic, antitubercular, and antitumor activities . Besides, they are also widely used as synthetic intermediates due to their unique reactivities .…”