7-oxo-5-thia-3,6,11b-triaza-benzo[c]fluorene-5,5-dioxide | 1206768-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑啉
• 英文名称: 7-oxo-5-thia-3,6,11b-triaza-benzo[c]fluorene-5,5-dioxide
• 英文别名: 7-oxa-5-thia-3,6,11b-triazabenzo[c]fluorene 5,5-dioxide；7-Oxa-5-thia-3,11b-triaza-benzo[c]fluorene 5,5-dioxide；11-oxa-8λ6-thia-1,5,9-triazatetracyclo[8.7.0.02,7.012,17]heptadeca-2(7),3,5,9,12,14,16-heptaene 8,8-dioxide
• CAS: 1206768-84-4
• 化学式: C₁₂H₇N₃O₃S
• 分子量: 273.272
• InChiKey: SOLJZWMVHYJCPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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：
  80.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-oxo-5-thia-3,6,11b-triaza-benzo[c]fluorene-5,5-dioxide 、 4-(2-氨乙基)苯磺酰胺 以 四氢呋喃 为溶剂， 反应 6.0h， 以89.7%的产率得到4-(2-hydroxyphenyl)-3-[2-(4-sulfamoylphenyl)ethylamino]-4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxide
  参考文献：
  名称：

  Synthesis of a new series of N4-substituted 4-(2-aminoethyl)benzenesulfonamides and their inhibitory effect on human carbonic anhydrase cytosolic isozymes I and II and transmembrane tumor-associated isozymes IX and XII

  摘要：

  A series of novel N(4)-substituted 4-(2-aminoethyl)benzenesulfonamides 5-17 have been synthesized and investigated as inhibitors of four isoforms of zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), that is the cytosolic CA I and II, and tumor-associated isozymes CA IX and XII. Against the human CA I investigated compounds displayed KI values from 96.3 to 3520 nM, toward hCA II at range of 18.1-2055 nM, while against hCA IX ranging from 5.9 to 419 nM and against hCA XII in the range of 4.0-414 nM. The very good inhibitory activity against tumor-associated hCA IX and hCA XII was found. The six new compounds displayed a powerful inhibitory potency toward hCA IX (K(I) = 5.9-10.7 nM) in comparison with the clinically used CAIs AAZ, MZA, EZA, DCP and IND (24-50 nM). The most potent hCA IX and hCA XII inhibitors 11 and 12 (K(I): 5.9 and 6.2 nM for hCA IX and 4.3 and 4.0 nM for hCA XII, respectively) belonged to the compounds with cationic character and presented meaningful affinity to the transmembrane isoforms hCA IX and XII than to physiologically dominant isozymes hCA I and II with the selectivity ratios hCA IX versus hCA II and hCA XII versus hCA II for 11 and 12 in the range of 10-15.

  DOI：

  10.1016/j.ejmech.2014.06.074
• 作为产物：
  描述：

  3-methylthio-1,1-dioxopyrido[4,3-e]-1,4,2-dithiazine 、 2-氨基苯酚 以 1,4-二氧六环 为溶剂， 以50%的产率得到7-oxo-5-thia-3,6,11b-triaza-benzo[c]fluorene-5,5-dioxide
  参考文献：
  名称：

  3-甲基硫代吡啶并[4,3-e] -1,4,2-噻二嗪1,1-二氧化物在新系列4H-吡啶并[4,3-e] -1,2,4-噻二嗪的合成中的应用具有潜在生物活性的衍生物

  摘要：

  两个系列4的ħ吡啶并[4,3- ë ] -1,2,4-噻二嗪衍生物3，4，5和7，8，9，10，11，12，通过3-methylthiopyrido的反应合成[ 4,3 - e ] -1,4,2-二噻嗪1,1-二氧化物1分别带有2-或6-肼基嗪和2-氨基苯酚或2-氨基硫酚。氨解8（R = Me，Y = O）得到相应的3-（R-氨基）-4-（2-羟基-5-甲基苯基）-4- H-吡啶基[4,3- e ] -1,2 ，4-噻二嗪1,1-二氧化物13，14，15，16，17，18。这些化合物的结构是根据元素分析，光谱数据和X射线晶体学确定的。化合物3，4，5，7，8，9，10，12，13，14，15，和17，18进行了筛选的体外抗菌活性。此外，初步体外是为化合物进行抗癌测定3，7，10，11，12，13，和17，18在国家癌症研究所（贝塞斯达，MD）在单次剂量（10μ中号在全NCI 60细胞组）。J

  DOI：

  10.1002/jhet.272

文献信息

• Application of 3-methylthiopyrido[4,3-<i>e</i>]-1,4,2-dithiazine 1,1-dioxide to the synthesis of novel series of 4<i>H</i>-pyrido[4,3-<i>e</i>]-1,2,4-thiadiazine derivatives with potential biological activity
  作者：Zdzisław Brzozowski、Jarosław Sławiński、Anna Kędzia、Ewa Kwapisz、Maria Gdaniec

  DOI：10.1002/jhet.272

  日期：2009.11

  1‐dioxides 13, 14, 15, 16, 17, 18. The structures of these compounds were confirmed on the basis of elemental analysis, spectral data, and X‐ray crystallography. Compounds 3, 4, 5, 7, 8, 9, 10, 12, 13, 14, 15, and 17, 18 were screened in vitro for antibacterial activity. Moreover, preliminary in vitro anticancer assay was performed for compounds 3, 7, 10, 11, 12, 13, and 17, 18 at the National Cancer

  两个系列4的ħ吡啶并[4,3- ë ] -1,2,4-噻二嗪衍生物3，4，5和7，8，9，10，11，12，通过3-methylthiopyrido的反应合成[ 4,3 - e ] -1,4,2-二噻嗪1,1-二氧化物1分别带有2-或6-肼基嗪和2-氨基苯酚或2-氨基硫酚。氨解8（R = Me，Y = O）得到相应的3-（R-氨基）-4-（2-羟基-5-甲基苯基）-4- H-吡啶基[4,3- e ] -1,2 ，4-噻二嗪1,1-二氧化物13，14，15，16，17，18。这些化合物的结构是根据元素分析，光谱数据和X射线晶体学确定的。化合物3，4，5，7，8，9，10，12，13，14，15，和17，18进行了筛选的体外抗菌活性。此外，初步体外是为化合物进行抗癌测定3，7，10，11，12，13，和17，18在国家癌症研究所（贝塞斯达，MD）在单次剂量（10μ中号在全NCI 60细胞组）。J
• Synthesis of a new series of N4-substituted 4-(2-aminoethyl)benzenesulfonamides and their inhibitory effect on human carbonic anhydrase cytosolic isozymes I and II and transmembrane tumor-associated isozymes IX and XII
  作者：Jarosław Sławiński、Zdzisław Brzozowski、Beata Żołnowska、Krzysztof Szafrański、Aneta Pogorzelska、Daniela Vullo、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2014.06.074

  日期：2014.9

  A series of novel N(4)-substituted 4-(2-aminoethyl)benzenesulfonamides 5-17 have been synthesized and investigated as inhibitors of four isoforms of zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), that is the cytosolic CA I and II, and tumor-associated isozymes CA IX and XII. Against the human CA I investigated compounds displayed KI values from 96.3 to 3520 nM, toward hCA II at range of 18.1-2055 nM, while against hCA IX ranging from 5.9 to 419 nM and against hCA XII in the range of 4.0-414 nM. The very good inhibitory activity against tumor-associated hCA IX and hCA XII was found. The six new compounds displayed a powerful inhibitory potency toward hCA IX (K(I) = 5.9-10.7 nM) in comparison with the clinically used CAIs AAZ, MZA, EZA, DCP and IND (24-50 nM). The most potent hCA IX and hCA XII inhibitors 11 and 12 (K(I): 5.9 and 6.2 nM for hCA IX and 4.3 and 4.0 nM for hCA XII, respectively) belonged to the compounds with cationic character and presented meaningful affinity to the transmembrane isoforms hCA IX and XII than to physiologically dominant isozymes hCA I and II with the selectivity ratios hCA IX versus hCA II and hCA XII versus hCA II for 11 and 12 in the range of 10-15.