methyl 4-hydroxy-2-n-propyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide | 35511-19-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: methyl 4-hydroxy-2-n-propyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide
• 英文别名: 3-Propyl-4-hydroxy-2H-1,2-benzothiazin-3-Carbonsaeuremethylester-1,1-dioxid；1,1,4-trioxo-2-propyl-1,2,3,4-tetrahydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester；methyl 2-n-propyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide；Methyl 4-hydroxy-2-propyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide；methyl 4-hydroxy-1,1-dioxo-2-propyl-1λ6,2-benzothiazine-3-carboxylate
• CAS: 35511-19-4
• 化学式: C₁₃H₁₅NO₅S
• 分子量: 297.332
• InChiKey: KCFPYFVAMPODIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-hydroxy-2-n-propyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide 、 3-氯苯胺 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1,1,4-trioxo-2-propyl-1,2,3,4-tetrahydro-1λ6-benzo[e][1,2]thiazine-3-carboxylic acid 3-chloro-anilide
  参考文献：
  名称：

  2-烷基-4-羟基-2H-1,2-苯并噻嗪1,1-二氧化物的某些3-甲酰胺的合成和抗炎活性。

  摘要：

  DOI：

  10.1021/jm00294a008
• 作为产物：
  描述：

  4-羟基-2H-1,2-苯并噻嗪-3-羧酸甲酯1,1-二氧化物 、 1-碘代丙烷 以21%的产率得到
  参考文献：
  名称：

  LOMBARDINO J. G., ORG. PREP. AND PROCED. INT., 1980, 12, NO 5, 269-274

  摘要：

  DOI：

文献信息

• Antithrombotic
  申请人：Dr. Karl Thomae Gesellschaft mit beschrankter Haftung

  公开号：US04533664A1

  公开（公告）日：1985-08-06

  Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, methyl, methoxy, fluorine or chlorine; and R.sub.2 is hydrogen, methyl, ethyl or n-propyl; and non-toxic, pharmacologically acceptable salts thereof formed with an inorganic or organic base. The compounds as well as the salts are useful as antithrombotics.

  式为##STR1##的化合物，其中R.sub.1是氢、甲基、甲氧基、氟或氯；R.sub.2是氢、甲基、乙基或正丙基；以及与无机或有机碱形成的非毒性、药理学上可接受的盐。这些化合物以及盐可用作抗血栓药物。
• Anticancer Ruthenium(η⁶-<i>p</i>-cymene) Complexes of Nonsteroidal Anti-inflammatory Drug Derivatives
  作者：Farhana Aman、Muhammad Hanif、Waseeq Ahmad Siddiqui、Adnan Ashraf、Lukas K. Filak、Jóhannes Reynisson、Tilo Söhnel、Stephen M. F. Jamieson、Christian G. Hartinger

  DOI：10.1021/om500825h

  日期：2014.10.13

  Oxicams are a versatile family of heterocyclic compounds and the two representatives meloxicam and piroxicam are widely used drugs for the treatment of a variety of inflammatory and rheumatic diseases in humans. As cancer-associated inflammation is known to occur in carcinogenesis, we aimed to combine compounds carrying bioactive oxicam moieties with ruthenium(arene) fragments, known for anticancer activity. Ru-II(arene) complexes withe methyl ester derivatives of the oxicam scaffold were prepared and characterized by standard methods and crystallographically. The organoruthenium compounds formed from Ru-II(eta(6)-p-cymene) chlorido moieties and oxicam-based ligands were subjected to bioanalytical investigations to establish their physicochemical properties with regard to stability in DMSO and water as well as reactivity toward the amino acids L-histidine (His), L-methionine (Met), and L-crysteine (Cys) and the DNA model compound guanosine 5'-monophosphate (5'GMP). The compounds hydrolyzed rapidly in water to give the respective aqua complexes, formed amino acid complexes with Met and His, but decompose with Cys, while interaction with 5'-GMP was through its phosphate residue. The anticancer activity of the complexes against the colon carcinoma HCT116 and breast cancer MDA MB 231 cancer cell lines was established using an in vitro assay. the cytotoxicity was found strongly dependent on the lipophilicity of the compound, as was shown through correlation with low k(w) and clog P values of the ligands. the most lipophilic compound [chlorido (methyl 4-oxido-2-benzyl-2H-1,2benzothiazine-3-carboxylate-1,1-dioxide) (eta(6)-p-cymene)ruthenium (II)] was the most active in the cell assays, with an IC50 of 80 mu M in HCT116 cells.
• US4533664A
  申请人：——

  公开号：US4533664A

  公开（公告）日：1985-08-06