• Title/Summary/Keyword: 1,2-Benzothiazine derivatives

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Antiinflammatory Evaluation and Synthesis of Benzothiazine Derivatives as Cyclooxygenase-2 Inhibitor (Cyclooxygenase-2 저해제로서의 benzothiazine 유도체 합성과 항염작용 평가)

  • 신혜순;박명숙;권순경
    • YAKHAK HOEJI
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    • v.44 no.3
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    • pp.272-278
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    • 2000
  • The antiinflammatory mechanism of NSAIDs is attributed to the reduction of prostaglandin synthesis by the direct inhibition of cyclooxygenase. Inhibition of prostaglandin production in organs such as stomach and kidney can result in gastric lesions, nephrotoxicity and increased bleeding. In this study, newly designed COX-2 inhibitors, synthesized 1,2-benzothiazine derivatives, were screened in vitro for selectivity of COX-1 and COX-2 inhibition properties. Lead compounds in the structure-activity relationship were studied to synthesize new highly selective COX-2 inhibitors.13 determine inhibitory effect of COX-2, synthesized 1,2-benzothiazine derivatives were screened with accumulation of prostaglandin by lipopolysaccharide (LPS) in aspirin-treated macrophages and murine macropharge cell. Some of synthesized 1,2-benzothiazine derivatives were shown to be effective as selective COX-2 inhibitory activity. Others exhibited a preferential inhibition of COX-2, although some COX-1 inhibitory activity was still present. As a conclusion, simple monomer derivatives were more active than dimer derivatives. Substitution of halogen (Br, C1) on the benzothiazine nucleus slightly enhanced inhibition activity.

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Synthesis and COX-2 Inhibitory Activity of Benzothiazine-3-carboxamide Derivatives (Benzothiazine-3-carboxamide 유도체의 합성과 COX-2 저해효과)

  • 신혜순;최희전;권순경
    • YAKHAK HOEJI
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    • v.46 no.6
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    • pp.375-380
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    • 2002
  • In this study, newly designed COX-2 inhibitors, synthetic derivatives of benzothiazine-3-carboxamide, were screened in vitro for selectivity of COX-1 and COX-2 inhibition properties. 7-Bromo-1,2-benzoisothiazine derivatives were obtained from 4-bromotoluene over the chlorosulfonation, amination and oxidation. And benzothiazine ring was synthesized through Gabriel-Colmann rearrangement reaction. To evaluate inhibitory effect of COX-2, synthetic derivatives of benzothiazine-3-carboxamide were tested with accumulation of prostaglandin by lipopolysaccharide in aspirin-treated murine macropharge cell. Some of the synthesized lead compounds have potentially shown the structure-activity relationship for selectivity of COX-2 inhibition activity.

Synthesis of Antiinflammatory Novel 3-Pyrrolidinyl 1,2-Benzothiazine Derivatives (항염작용이 기대되는 새로운 피롤리딘닐 1,2-벤조티아진 유도체의 합성)

  • Park, Myung-Sook
    • YAKHAK HOEJI
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    • v.41 no.6
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    • pp.724-729
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    • 1997
  • New 7-Halo-4-hydroxy-2-allyl-N-3-(4-methoxy-2-carboxylic acid pyrrolidinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide derivatives were synthesized through the condensation of 7-halo-4-hydroxy-2-allyl-1,2-benzothiazine-3-carboxylic acid methyl ester 1,1-dioxide with 4-methoxy L-proline.

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Synthesis and Analgesic and Anti-inflammatory Activities of 1,2-Benzothiazine Derivatives

  • Lee, Eun-Bang;Kwon, Soon-Kyoung;Kim, Sang-Geon
    • Archives of Pharmacal Research
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    • v.22 no.1
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    • pp.44-47
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    • 1999
  • Three 1,2-benzothiazine derivatives were synthesized, and their analgesic / anti-inflammatory efficacy and their effect s of gastric irritation were evaluated. Among the three compounds, 39 exhibited the most potent anlagesic action, but the effect was weaker than that of piroxicam. Nonetheless, the compound showed 4 times more potent analgesic action with less gastric damage than did ibuprofen. These compounds did not show anti-inflammatory effect at an oral dose of 5 mg/kg.

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The Synthesis of 1,2-Benzothiazine-3-carboxamidylhydantoin Derivatives and their Antiinflammatory and Analgesic Activities

  • Kwon, Sonn-Kyoung;Park, Myoung-Suk
    • Archives of Pharmacal Research
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    • v.15 no.3
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    • pp.251-255
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    • 1992
  • A number of 4-hydroxy-2H (or alkyl)-N-(3-aralkyl-2-thio-1-hydantoinyl)-1, 2-benzothiazine3-carboxamide 1, 1-dioxides were synthesized through the reaction of 4-hydroxy-2H (or alkyl)1, 2-benzothiazine-3-carboxylic methyl ester 1, 1-dioxide and 1-amino-2-thio-3-aralkyl-4-imidazolones in xylene. The compounds synthesized were screened for antinflammatory effect on carrageenin-induced edema in rat and for analgesic effect on acetic acid-induced Writhing syndrome in mice. Most compounds were inhibots of carrageenin-induced rat foot edema and some showed significant antinflammatory activity comparable to that of indomethacin and significant analgesic activity comparable to that of indomethacin and aspirin.

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Synthesis of 1,2-Benzothiazine Derivatives as Oxicam Family (옥시캄 계열의 1,2-벤조티아진 유도체의 합성)

  • Park, Myung-Sook
    • YAKHAK HOEJI
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    • v.44 no.6
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    • pp.494-498
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    • 2000
  • Noble 7,7'-substituted (or unsubstituted) 4-oxo-1,1',2,2'-dibenzothiazine-3,3'-dicarboxylic acid methyl ester 1,1,1',1'-tetraoxide 3,4'-yl ethers 2a-h were synthesized through the dehydration of 7-substituted (or unsubstituted) 4-hydroxy-1,2-benzothiazine-3-carboxylic acid methyl ester 1,1-dioxides 1a-h using silver(I) oxide for the development of new nonsteroidal antiinflammatory drugs (NSAIDs). Optimal reaction was proceeded through stirring of distilled acetone using 100 mol% of silver(I) oxide at room temperature for 24-68 hrs.

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Synthesis of Novel 3-Aminohydantoinyl-1.2-benzothiazine Derivatives for the COX-2 inhibitors

  • Park, Myung-Sook;Lee, Myung-Sook;Shin, Hae-Soon;Kwon, Soon-Kyoung
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.344.1-344.1
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    • 2002
  • We report the synthesis of several new 3-aminohydantoinyl-1.2-benzothiazine derivatives and propose an another mechanism of the cyclization to the hydantoins for the development candidates of COX-2 inhibitors. 3-Aminohydantoins 3a-d were prepared through cyclization of the condensation products that were formed by heating amino acids and tert-bytyl carbazate in quinoline according to the method of Lalezari. (omitted)

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