6639-62-9Relevant articles and documents
Synthesis, cytotoxic and antioxidant activities of azolyl benzothiazine carboxamides
Panga, Siva Sankar,Tamatam, Rekha,Adivireddy, Padmaja,Venkatapuram, Padmavathi,Narra, Siva Krishna,Paturu, Kondaiah
, p. 3053 - 3075 (2019/03/13)
Abstract: Azolyl benzothiazine carboxamides were prepared from benzothiazine carboxylate and azolyl amines in the presence of NaOMe under ultrasonication. 4-Bromothiophenylimidazolyl benzothiazine carboxamide (19b) and 4-bromopyrrolylimidazolyl benzothiazine carboxamide (22b) showed cytotoxic activity on HeLa cell lines (IC50 33.75, 47.52?μM) and MCF-7 cell lines (IC5031.75, 34.35?μM). Furthermore, methyl-substituted furanyloxazolyl benzothiazine carboxamide (14a), furanylimidazolyl benzothiazine carboxamide (16a), thiophenyloxazolyl benzothiazine carboxamide (17a) and pyrrolyloxazolyl benzothiazine carboxamide (20a) exhibited antioxidant activity greater than ascorbic acid. Graphical abstract: Azolyl benzothiazine carboxamides are prepared from benzothiazine carboxylate and azolyl amines. Optimization of reaction conditions is established using different molar concentrations of NaOMe. Compounds 19b and 22b showed cytotoxic activity on HeLa cell lines and MCF-7 cell lines. Compounds 14a, 16a, 17a and 20a exhibited prominent antioxidant activity.[Figure not available: see fulltext.].
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.
Hybrid compounds from chalcone and 1,2-benzothiazine pharmacophores as selective inhibitors of alkaline phosphatase isozymes
Ashraf, Adnan,Ejaz, Syeda Abida,Rahman, Shafiq Ur,Siddiqui, Waseeq Ahmad,Arshad, Muhammad Nadeem,Lecka, Joanna,Sévigny, Jean,Zayed, Mohie E. Moustafa,Asiri, Abdullah M.,Iqbal, Jamshed,Hartinger, Christian G.,Hanif, Muhammad
, p. 282 - 291 (2018/10/15)
Chalcones and 1,2-benzothiazines are two important classes of bioactive compounds, each scaffold endowed with diverse pharmacological activities. Combining both of these pharmacophores in a single molecule was aimed to yield multi-modal agents. Herein, we report a series of hybrid compounds 3a–3o derived from chalcones and 1,2-benzothiazine cores. They were synthesized from commercially available sodium saccharin, and the resulting 1,2-benzothiazine-derived ketone was then condensed with aromatic aldehydes in an aldol condensation to obtain the respective chalcones. The compounds were characterized using different analytical techniques including FT-IR, NMR spectroscopy, mass spectrometry and X-ray crystallography. Some synthesized chalcones revealed potent and/or selective inhibitory properties towards alkaline phosphatase isozymes transiently expressed in COS-7 cells. A detailed structure-activity and selectivity study was carried out with regard to the effect of different substituents at ortho-, meta- and para-positions of the phenyl residue. Compound 3c was the most effective human intestinal alkaline phosphatase (h-IAP) inhibitor (IC50 value of 1.04 μM), while it was not active against human tissue non-specific alkaline phosphatase (h-TNAP) isozyme. In contrast, 3i was a selective inhibitor of h-TNAP with IC50 values of 0.25 ± 0.01 μM. The possible binding interactions of the most effective inhibitors of h-TNAP and h-IAP were obtained from molecular docking studies.
Synthetic method of piroxicam
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Paragraph 0021; 0025; 0029, (2018/10/27)
The invention belongs to the field of chemical synthesis, and more specifically relates to a synthetic method of piroxicam. The synthetic method of piroxicam comprises following steps: 1, sodium saccharin and ethyl chloroacetate are taken as initial raw materials, and condensation reaction is carried out so as to obtain 3-oxo-1,2-benzoisothiazoline-2-methyl acetate-1,1-dioxide; 2, sodium methylateis added into the product in step 1, reaction is carried out under catalytic effect of potassium iodide, and 2-methyl-3,4- dioxo-4-oxo-2H-1,-2- benzothiazine-3-carboxylic acid methyl ester-1, 1-dioxide is obtained under the effect of DMSO; 3, the above product is reacted with 2-aminopyridine at 130 DEG C for 10h so as to obtain a high purity finished product. According to the synthetic method, potassium iodide is taken as a catalyst to increase the reaction conversion rate of step 2 obviously, impurity content is controlled effectively; and the total yield is increased to 69%.
Stereopure Functionalized Benzosultams via Ruthenium(II)-Catalyzed Dynamic Kinetic Resolution-Asymmetric Transfer Hydrogenation
Jeran, Marko,Cotman, Andrej Emanuel,Stephan, Michel,Mohar, Barbara
supporting information, p. 2042 - 2045 (2017/04/28)
A highly diastereo- and enantioselective Ru(II)-catalyzed dynamic kinetic resolution-asymmetric transfer hydrogenation (DKR-ATH) of α-(N-sulfonylimino) and α-(N-sulfonylamino) aryl ketones to 4-hydroxy-benzo-δ- and 3-(α-hydroxy-arylmethyl)-benzo-γ-sultams is presented. By employing enantiopure ansa-Ru[PipSO2DPEN(CH2)4Ph] cat. II with S/C = 10 000 in a HCO2H/Et3N binary mix, up to >99.9% ee and dr >99:1 are obtained with 100% conversion under mild conditions. Application to access the stereopure "structurally simplified TsDPEN" N,N-ligand syn-3-(α-aminobenzyl)-benzo-γ-sultam ("syn-ULTAM") and its structural isomer trans-4-amino-3-phenyl-benzo-δ-sultam (trans-4) is demonstrated.
Discovery of (2-benzoylethen-1-ol)-containing 1,2-benzothiazine derivatives as novel 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibiting-based herbicide lead compounds
Lei, Kang,Hua, Xue-Wen,Tao, Yuan-Yuan,Liu, Yang,Liu, Na,Ma, Yi,Li, Yong-Hong,Xu, Xiao-Hua,Kong, Chui-Hua
supporting information, p. 92 - 103 (2015/12/31)
A series of (2-benzoylethen-1-ol)-containing benzothiazine derivatives was synthesized, and their herbicidal activities were first evaluated. The bioassay results indicated that some of 3-benzoyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-1,1-dioxide derivatives displayed good herbicidal activity in greenhouse testing, especially, compound 4w had good pre-emergent herbicidal activities against Brassica campestris, Amaranthus retroflexus and Echinochloa crusgalli even at a dosage of 187.5 g ha-1. More importantly, compound 4w displayed significant inhibitory activity against Arabidopsis thaliana HPPD and was identified as the most potent candidate with IC50 value of 0.48 μM, which is better than the commercial herbicide sulctrione (IC50 = 0.53 μM) and comparable with the commercial herbicide mesotrione (IC50 = 0.25 μM). The structure-activity relationships was studied and provided some useful information for improving herbicidal activity. The present work indicated that (2-benzoylethen-1-ol)-containing 1,2-benzothiazine motif could be a potential lead structure for further development of novel HPPD inhibiting-based herbicides.
4-hydroxy-3-benzoyl-2-alkyl -1,2-benzothiazine -1,1-dioxide derivatives of the (by machine translation)
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Paragraph 0012; 0013, (2016/10/07)
The invention relates to a 4-hydroxy-3-benzoyl-2-alkyl -1,2-benzothiazine -1,1-dioxide derivatives, structural formula as (I). wherein: R 1 representative: C1-C5 alkyl; R 2 representative: 2-NO 2, 3-NO 2, 4-NO 2, 2-Br-4-Br, 2-Cl-3-Cl, 2-Cl-5-Cl, 2-Cl-4-F, 2-Cl-4-Br, 2-F-4-Cl, 2-Br-4-F, 2-Br-4-Cl, 2-Cl-4-NO 2, 2-Cl-4-CF 3, 4-SO 2 Me. To saccharines sodium salt as raw materials, by nucleophilic reaction, rearrangement Gabriel-Colman, decarboxylative, alkylation, condensation and Fries rearrangement reaction, the obtained 4-hydroxy-3-benzoyl-2-alkyl -1,2-benzothiazine -1,1-dioxide compound, and the herbicidal activity of the compound to the test, the results show that the compound has a good herbicidal activity, is a novel structure, application prospect of herbicides. (by machine translation)
1,2-Benzothiazine 1,1-dioxide carboxylate derivatives as novel potent inhibitors of aldose reductase
Chen, Xin,Zhang, Shuzhen,Yang, Yanchun,Hussain, Saghir,He, Minlan,Gui, Dequan,Ma, Bing,Jing, Chaojun,Qiao, Zhixin,Zhu, Changjin,Yu, Qun
experimental part, p. 7262 - 7269 (2012/01/03)
Due to the importance of aldose reductase (ALR2) as a potential drug target in the treatment of diabetic complications, there are increasing interests in design and synthesis of ALR2 inhibitors. Here, we prepared 1,2-benzothiazine 1,1-dioxide acetic acid derivatives and investigated their inhibition activity. Most of these derivatives were found to be active with IC50 values ranging from 0.11 μM to 10.42 μM, and compound 8d, 2-[2-(4-bromo-2- fluorobenzyl)-1,1-dioxido-2H-1,2-benzothiazin-4(3H)-ylidene]acetic acid, showed the most potent inhibition activity. Further, SAR and docking studies suggest that in comparison with the α,β-unsaturated derivatives, the saturated carboxylic acid derivatives had a greater binding affinity with the enzyme and thus an enhanced inhibition activity. Therefore, development of more powerful ARIs based on benzothiazine 1,1-dioxide by stereo-controlled synthesis could be expected.
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.
Antioxidant potential of new methyl-4-hydroxy-2h-1,2-benzothiazine-3- carboxylate-1,1-dioxide derivatives
Arshad, Muhammad Nadeem,Khan, Islam Ullah,Zia-Ur-Rehman, Muhammad,Shafiq, Muhammad
experimental part, p. 2801 - 2805 (2012/02/02)
An easy synthesis of a series of N-alkyl-1,2-benzothiazine-1,1-dioxide derivatives from commercially available saccharine is reported in order to explore their antioxidant potential. The newly synthesized compounds were characterized by spectroscopic techniques (FT-IR, NMR, MS) and single crystal X-ray diffraction analyses. All the synthesized compounds were screened for their DPPH and FRAP analyses to determine their antioxidant activity.
