35511-15-0Relevant articles and documents
A facile one-pot synthesis of 4-hydroxy-3-methoxycarbonyl-2-methyl-2H-1,2-benzothiazine 1,1-dioxide, a key intermediate in the synthesis of oxicam anti-inflammatory agents
Manjarrez, Norberto,Perez, Herminia I.,Solis, Aida,Luna, Hector
, p. 585 - 591 (1996)
4-Hydroxy-3-methoxycarbonyl-2-methyl-2H-1,2-benzothiazine 1,1-dioxide (8) was synthesized by a one-pot procedure, starting from the readily available saccharine. The synthesis involves 4 transformations with an overall yield equivalent to that from the stepwise process.
Synthesis, monoamine oxidase inhibition activity and molecular docking studies of novel 4-hydroxy-N′-[benzylidene or 1-phenylethylidene]-2-H/methyl/benzyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides
Saddique, Furqan Ahmad,Zaib, Sumera,Jalil, Saquib,Aslam, Sana,Ahmad, Matloob,Sultan, Sadia,Naz, Humera,Iqbal, Mazhar,Iqbal, Jamshed
, p. 1373 - 1386 (2017/11/13)
Three series of 4-hydroxy-N′-[benzylidene/1-phenylethylidene]-2-H/methyl/benzyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides (9–11)a-l were synthesized and unraveled to be highly potent dual inhibitors of monoamine oxidases (MAO-A and MAO-B). All the examined compounds demonstrated IC50 values in lower micro-molar range for both MAO-A as well as MAO-B. The most active MAO-A inhibitor was 4-hydroxy-N′-(1-phenylethylidene)-2H-benzo[e][1,2]thiazine-3-carbohydrazide 1,1-dioxide (9i) with an IC50 value of 0.11 ± 0.005 μM, whereas, methyl 4-hydroxy-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide (3) was the most active MAO-B inhibitor with an IC50 value of 0.21 ± 0.01 μM. Enzyme kinetics studies revealed that the most potent compounds inhibited both MAO enzymes (A & B) in a competitive fashion. Molecular docking studies were also performed to obtain an intuitive picture of inhibition potential for potent inhibitors. The high potency of these compounds is optimally combined with highly favorable ADME profile with predicted good oral bioavailability.
Microwave assisted synthesis and structure-activity relationship of 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl-1,2-benzothiazine-3- carbohydrazide 1,1-dioxides as anti-microbial agents
Ahmad, Naveed,Zia-Ur-Rehman, Muhammad,Siddiqui, Hamid Latif,Ullah, Muhammad Fasih,Parvez, Masood
experimental part, p. 2368 - 2377 (2011/06/21)
A series of 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl, 1,2-benzothiazine-3-carbohydrazide 1,1-dioxides was synthesized from commercially available sodium saccharin. Base catalyzed ring expansion of methyl (1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)acetate followed by ultrasound mediated hydrazinolysis and subsequent reaction with 1-phenylethanones under the influence of microwaves yielded the title compounds. Besides, microwave assisted synthesis of 1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide and 4-methyl-1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide is also discussed. Most of the synthesized compounds were found to possess moderate to significant anti-microbial (anti-bacterial and anti-fungal) activities. It is found that compounds with greater lipophilicity (N-methyl analogues) possessed higher anti-bacterial activities.
Process for the preparation of crystalline form-1 of 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide
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Page/Page column 1 - 3, (2010/02/15)
The present invention is related to an improved process for preparing crystalline Form I of meloxicam, which produces the Form I in high yield.