6,12-Dihydro-1-benzopyrano<3,4-b><1,4>benzothiazin-6-one | 75908-14-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6,12-Dihydro-1-benzopyrano<3,4-b><1,4>benzothiazin-6-one
• 英文别名: 6,12-dihydro<1>benzopyrano<3,4-b><1,4>benzothiazin-6-one；3-demethoxyestrothiazine；Chromeno(3,4-b)(1,4)benzothiazin-6(12H)-one；12H-chromeno[3,4-b][1,4]benzothiazin-6-one
• CAS: 75908-14-4
• 化学式: C₁₅H₉NO₂S
• 分子量: 267.308
• InChiKey: BUPPVTUKPWAYCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,12-Dihydro-1-benzopyrano<3,4-b><1,4>benzothiazin-6-one 在 高氯酸四乙基铵 作用下， 以 乙腈 为溶剂， 以73%的产率得到6,12-dihydro<1>benzopyrano<3,4-b><1,4>benzothiazin-6-one-5-oxide
  参考文献：
  名称：

  Synthesis and electrochemical study of benzothiazine and phenothiazine derivatives

  摘要：

  DOI：

  10.1021/jo00227a021
• 作为产物：
  描述：

  2-氨基苯硫醇 、 4-氯-3-硝基香豆素 以 乙腈 为溶剂， 反应 2.0h， 以74%的产率得到6,12-Dihydro-1-benzopyrano<3,4-b><1,4>benzothiazin-6-one
  参考文献：
  名称：

  Tabakovic, Ibro; Tabakovic, Katmerka; Grujic, Radoslaw, Heterocycles, 1985, vol. 23, # 10, p. 2539 - 2542

  摘要：

  DOI：

文献信息

• Substituted benzopyranobenzothiazinones. Synthesis and estrogenic activity on MCF-7 breast carcinoma cells
  作者：Yves Jacquot、Laurent Bermont、Hervé Giorgi、Bernard Refouvelet、Gerard.L Adessi、Edwige Daubrosse、Alain Xicluna

  DOI：10.1016/s0223-5234(00)01207-1

  日期：2001.2

  compounds was evaluated by the inhibition of their effect by ICI 182,780, an antiestrogenic compound. Among the compounds tested, 6,12-dihydro-3-methoxy-1-benzopyrano[3,4-b][1,4]benzothiazin-6-one 3e and 6,12-dihydro-3-hydroxy-1-benzopyrano[3,4-b][1,4]benzothiazin-6-one 3f exhibited an ER-dependent proliferation and a high binding affinity to ER, but a moderate capacity to activate the transcription of a reporter

  在寻找由雌激素受体（ER）介导的具有雌激素活性的新药物中，合成了六个6,12-二氢-1-苯并吡喃并[3,4-b] [1,4]苯并噻嗪-6-酮3a-f。通过将2-氨基硫酚2加到取代的4-羟基香豆素衍生物1a-e中，可以容易地制备这些化合物。已评估了对MCF-7乳腺癌细胞增殖的雌激素作用，并通过ICI 182,780（一种抗雌激素化合物）抑制了其作用，从而评估了所描述化合物的特异性。在测试的化合物中，6,12-二氢-3-甲氧基-1-苯并吡喃并[3,4-b] [1,4]苯并噻嗪-6-one 3e和6,12-二氢-3-羟基-1-苯并吡喃[3,4-b] [1,4]苯并噻嗪-6-one 3f表现出ER依赖性增殖和对ER的高结合亲和力，但具有中等能力激活报告基因的转录。
• Synthesis of 4-hydroxycoumarin and 2,4-quinolinediol derivatives and evaluation of their effects on the viability of HepG2 cells and human hepatocytes culture
  作者：Bernard Refouvelet、Catherine Guyon、Yves Jacquot、Corinne Girard、Hervé Fein、Françoise Bévalot、Jean-François Robert、Bruno Heyd、Georges Mantion、Lysiane Richert、Alain Xicluna

  DOI：10.1016/j.ejmech.2004.07.006

  日期：2004.11

  We report here the synthesis of aromatic coumarins and aromatic alpha-quinolones which were evaluated in vitro for their protective potentialities against tert-butyl hydroperoxide (t-BHP)-induced oxidative damage on human liver cell death, i.e., human hepatoma HepG2 cell line and human hepatocytes in primary culture. We found that the presence of a benzylidene at the 3-position or a heterocycle with N and S heteroatoms on the benzopyrone or quinolone system was essential for the protective effect of these compounds against t-BHP-induced decrease in viability of cells. We found also that a methoxy group on the aromatic ring systems decreased this potential. t-BHP-induced cytotoxicity in primary cultures of human hepatocytes could be therefore prevented by these compounds suggesting that they could display hepatoprotective effects in humans. (C) 2004 Elsevier SAS. All rights reserved.
• Reddy, B. Sucharita; Darbarwar, Malleshwar, Journal of the Indian Chemical Society, 1985, vol. 62, # 5, p. 377 - 379
  作者：Reddy, B. Sucharita、Darbarwar, Malleshwar

  DOI：——

  日期：——
• Tabakovic, K.; Tabakovic, I.; Trkovnik, M., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 801 - 803
  作者：Tabakovic, K.、Tabakovic, I.、Trkovnik, M.、Juric, A.、Trinajstic, N.

  DOI：——

  日期：——
• TABAKOVIC K.; TABAKOVIC I.; TRKOVNIK M.; JURIC A.; TRINAJSTIC N., J. HETEROCYCL. CHEM., 1980, 17, NO 4, 801-803
  作者：TABAKOVIC K.、 TABAKOVIC I.、 TRKOVNIK M.、 JURIC A.、 TRINAJSTIC N.

  DOI：——

  日期：——