2H-<1,2>-Benzothiazin-4(3H)-oxo-1,1-dioxid-4- | 5510-31-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 2H-<1,2>-Benzothiazin-4(3H)-oxo-1,1-dioxid-4-
• 英文别名: 2H-<1,2>-Benzothiazin-4(3H)-on-1,1-dioxid-4-；2,3-dihydro-spiro[benzo[e][1,2]thiazine-4,2'-[1,3]dioxolane] 1,1-dioxide；3,4-dihydro-2H-1,2-benzothiazin-4-one 1,1-dioxide ethylene acetal；2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide ethylene ketal；spiro[1,3-dioxolane-2,4'-2,3-dihydro-1λ6,2-benzothiazine] 1',1'-dioxide
• CAS: 5510-31-6
• 化学式: C₁₀H₁₁NO₄S
• 分子量: 241.268
• InChiKey: OXMUEARBOZEKBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  73
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2H-<1,2>-Benzothiazin-4(3H)-oxo-1,1-dioxid-4- 在 盐酸 、 palladium 10% on activated carbon 、 水 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 反应 22.0h， 生成 2-[2-(2-fluorobenzyl)-1,1-dioxido-2H-1,2-benzothiazin-4(3H)-ylidene]acetic acid methyl ester
  参考文献：
  名称：

  1,2-Benzothiazine 1,1-dioxide carboxylate derivatives as novel potent inhibitors of aldose reductase

  摘要：

  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 mu M to 10.42 mu M, 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 alpha,beta-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. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2011.07.051
• 作为产物：
  描述：

  saccharin sodium salt 在 盐酸 、 甲醇 、 水 、 sodium 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 2H-<1,2>-Benzothiazin-4(3H)-oxo-1,1-dioxid-4-
  参考文献：
  名称：

  1,2-Benzothiazine 1,1-dioxide carboxylate derivatives as novel potent inhibitors of aldose reductase

  摘要：

  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 mu M to 10.42 mu M, 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 alpha,beta-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. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2011.07.051

文献信息

• Benzothiazine derivative
  申请人：Suntory Limited

  公开号：US05874429A1

  公开（公告）日：1999-02-23

  Disclosed are benzothiazine derivatives represented by the following formula (I): ##STR1## The benzothiazine derivatives (I) and their salts according to the present invention have strong serotonin-2 blocking action, have excellent selectivity to this action against .alpha..sub.1 blocking action and have high safety. Accordingly, the present invention has made it possible to provide pharmaceuticals making use of antagonistic action against serotonin-2 receptors, for example, therapeutics for various circulatory diseases such as ischemic heart diseases, cerebrovascular disturbances and peripheral circulatory disturbances.

  以下是翻译结果： 揭示了由以下式(I)表示的苯并噻嗪衍生物：苯并噻嗪衍生物(I)及其盐根据本发明具有强大的5-羟色胺-2阻滞作用，对此作用具有出色的选择性，而对α1阻滞作用具有很高的安全性。因此，本发明使得可以提供利用对5-羟色胺-2受体的拮抗作用的药物，例如，用于各种循环系统疾病的治疗药物，如缺血性心脏病、脑血管障碍和外周循环障碍的治疗药物。
• Alkylenediamine derivatives
  申请人：Nippon Chemiphar Co., Ltd.

  公开号：US05773437A1

  公开（公告）日：1998-06-30

  The present invention relates to alkylenediamine derivatives which relieve urinating contraction and therefore are of value as active ingredients of therapeutic agents for treating dysuria.

  本发明涉及缓解排尿收缩的烷二胺衍生物，因此可作为治疗排尿困难的药物的有效成分。
• Synthesis and antiinflammatory activity of some 3-carboxamides of 2-alkyl-4-hydroxy-2H-1,2-benzothiazine 1,1-dioxide
  作者：Joseph G. Lombardino、Edward H. Wiseman、W. M. McLamore

  DOI：10.1021/jm00294a008

  日期：1971.12
• Synthesis and in vitro evaluation of novel small molecule inhibitors of bacterial arylamine N-acetyltransferases (NATs)
  作者：Edward W. Brooke、Stephen G. Davies、Andrew W. Mulvaney、Minoru Okada、Frédérique Pompeo、Edith Sim、Richard J. Vickers、Isaac M. Westwood

  DOI：10.1016/s0960-894x(03)00484-0

  日期：2003.8

  The synthesis and inhibitory activity of a series of 5-substituted-(1,1-dioxo-2,3-dihydro-1H-1lambda(6)-benzo[e][1,2]thiazin-4-ylidene)-thiazolidine-2,4-dione derivatives as competitive inhibitors of recombinant bacterial arylamine-N-acetyltransferases (NATs) are described. The most potent NAT inhibitors are those that contain planar hydrophobic substituents on the sultam nitrogen. (C) 2003 Elsevier Ltd. All rights reserved.
• 1,2-Benzothiazines. IV.¹ The Synthesis of 7,8-Dihydropyrido[1,2-<i>b</i>][1,2]benzothiazine-10,11(9H,10aH)-dione 5,5-Dioxides as 1,2-Benzothiazine Analogs of Partial Tetracycline Structures
  作者：Harold. Zinnes、Roger A. Comes、John. Shavel

  DOI：10.1021/jm00314a020

  日期：1967.3