3-methylthio-1,1-dioxopyrido[4,3-e]-1,4,2-dithiazine | 1078159-96-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-methylthio-1,1-dioxopyrido[4,3-e]-1,4,2-dithiazine
• 英文别名: 3-Methylsulfanylpyrido[4,3-e][1,4,2]dithiazine 1,1-dioxide；3-methylsulfanylpyrido[4,3-e][1,4,2]dithiazine 1,1-dioxide
• CAS: 1078159-96-2
• 化学式: C₇H₆N₂O₂S₃
• 分子量: 246.335
• InChiKey: NMCJRQUQEMCNPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-methylthio-1,1-dioxopyrido[4,3-e]-1,4,2-dithiazine 在 氨 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 196.0h， 生成 9,9-dioxo-2,3-di(thien-2-yl)-1H-9-thia-1,4,4a,7,10-pentaazaphenanthrene-2-ol
  参考文献：
  名称：

  Synthesis and structure determination of 2,3-diaryl-9,9-dioxo-1 H -9-thia-1,4,4a,7,10-pentaazaphenanthrene-2-ols

  摘要：

  3-Amino-1,1-dioxopyrido[4,3-e]-1,4,2-dithiazine has been synthesized and applied to the synthesis of 3-amino-2-(4-thioxo-1,4-dihydropyridin-3-ylsulfonyl)guanidine. The reaction of the aminoguanidine with the appropriate 1,2-diarylethane-1,2-diones afforded 2,3-diaryl-9,9-dioxo-1H-9-thia-1,4,4a,7,10-pentaazaphenanthrene-2-ol derivatives. The structure of these compounds, which represent a novel heterocyclic ring system, was confirmed on the basis of elemental analysis and spectroscopic data including COSY, NOESY, ROESY, HSQC, and HMBC. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.006
• 作为产物：
  描述：

  7H-1,1-dioxopyrido[4,3-e]-1,4,2-dithiazolium-3-thiolate 、 碘甲烷 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以88%的产率得到3-methylthio-1,1-dioxopyrido[4,3-e]-1,4,2-dithiazine
  参考文献：
  名称：

  1,1-二氧吡啶并[4,3- e ] -1,4,2-二噻嗪-3-硫醇钾的合成及其在具有潜在生物活性的新型磺酰胺类化合物的合成中的应用

  摘要：

  1,1-二氧吡啶并[4,3- e ] -1,4,2-二噻嗪-3-硫醇钾2已经合成并用于7 H -1,1-二氧并吡啶[4,3- e ]的合成-1,4,2-二噻唑-3-硫醇盐3和3-甲基硫代吡啶并[4,3- e ] -1,4,2-二噻嗪1,1-二氧化物4可轻松获得其各种3-氨基衍生5-10。的肼解7,8和10，得到相应的3-氨基-2-（1,4-二氢-4- thioxopyrid -3-基磺酰基）胍11-13。随后12与4-氯苯甲醛反应，得到缩合产物14。1,4-二氢-2- thioxopyridine -3-磺酰胺15还从钾盐制备2在碱性水解，而15烷基化，得到适当š取代的衍生物16-19或S，N二取代的化合物20-21。

  DOI：

  10.1002/jhet.5570450525

文献信息

• Synthesis of Novel Pyrido[4,3-e][1,2,4]triazino[3,2-c][1,2,4]thiadiazine 6,6-dioxide Derivatives with Potential Anticancer Activity
  作者：Jarosław Sławiński、Aleksandra Grzonek、Beata Żołnowska、Anna Kawiak

  DOI：10.3390/molecules21010041

  日期：——

  A series of novel 3-/2,3-substituted pyrido[4,3-e][1,2,4]triazino[3,2-c][1,2,4]thiadiazine 6,6-dioxides 4-28 have been synthesized by the reaction of 3-amino-2-(4-thioxo-1,4-dihydropyridin-3-yl-sulfonyl)guanidine with either 2-oxoalkanoic acids and its esters, or phenylglyoxylic hydrates in glacial acetic acid. Some of them exhibited reasonable or moderate anticancer activity toward human cancer cell

  一系列新颖的3- / 2,3-取代的吡啶并[4,3-e] [1,2,4]三嗪[3,2-c] [1,2,4]噻二嗪6,6-二氧化物4-通过3-氨基-2-（4-硫代氧杂1,4-二氢吡啶基-3-基-磺酰基）胍与2-氧代链烷酸及其酯或苯基乙醛酸水合物在冰醋酸中的反应合成了28种。其中一些对人癌细胞HCT-116，MCF-7和HeLa表现出合理或中等的抗癌活性。通过1D-NMR和2D-NMR光谱数据，包括COSY，ROESY和HMBC，元素分析和MS光谱，证实了这种新型杂环系统的结构。
• 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
• Carbonic anhydrase inhibitors: Synthesis and inhibition of the human cytosolic isozymes I and II and transmembrane isozymes IX, XII (cancer-associated) and XIV with 4-substituted 3-pyridinesulfonamides
  作者：Zdzisław Brzozowski、Jarosław Sławiński、Franciszek Sączewski、Alessio Innocenti、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2010.02.020

  日期：2010.6

  A series of novel 4-substituted-3-pyridinesulfonamides (2-27 and 31-33) have been synthesized and investigated as inhibitors of five isoforms of zinc enzyme carbonic anhydrase (CA, EC 42 11), that is, the cytosolic, ubiquitous isozymes CA I and II, and transmembrane isozymes CA IX, XII (cancer-associated) and XIV. Against the human isozymes hCA I, the new compounds showed inhibition constants in the range of 0.078-11.7 mu M, against hCA II in the range of 9.9-140 nM, against hCA IX in the range of 4.6-313 nM, against hCA XII in the range of 3.4-21.6 nM, and against hCA XIV in the range of 50.9-160 nM, respectively. Compounds 4, 6, 7, 9, 11-14, 19, 20, 22-24, 26, 27, 31 and 32 showed excellent hCA IX inhibitory efficacy, with inhibition constants of 4.6-12 0 nM, being much more effective as compared to the clinically used sulfonamides AAZ, MZA, EZA, DCP and IND 4-[N'-(6-Chloro-7-cyano-1,1-dioxo-1,4,2-benzodithiazin-3-yl)hydrazino]-3-pyridinesulfonamide (31) is the prominent of the compounds due to its remarkable inhibitory activity toward hCA I (K(I)s = 0.078 mu M), hCA IX (K(I)s = 7.2 nM) and hCA XII (K(I)s = 3.4 nM).
• Syntheses of potassium 1,1-dioxopyrido[4,3-<i>e</i>]-1,4,2-dithiazine-3-thiolate and its application to the synthesis of novel sulfonamides with potential biological activity
  作者：Zdzislaw Brzozowski、Franciszek Sâczewski、Jaroslaw Slawiński

  DOI：10.1002/jhet.5570450525

  日期：2008.9

  Potassium 1,1-dioxopyrido[4,3-e]-1,4,2-dithiazine-3-thiolate 2 has been synthesized and applied to the syntheses of 7H-1,1-dioxopyrido[4,3-e]-1,4,2-dithiazolium-3-thiolate 3 and 3-methylthiopyrido[4,3-e]-1,4,2-dithiazine 1,1-dioxide 4 which provided easy access to a variety of its 3-amino derivatives 5-10. Hydrazinolysis of 7, 8 and 10 afforded the corresponding 3-amino-2-(1,4-dihydro-4-thioxopyri

  1,1-二氧吡啶并[4,3- e ] -1,4,2-二噻嗪-3-硫醇钾2已经合成并用于7 H -1,1-二氧并吡啶[4,3- e ]的合成-1,4,2-二噻唑-3-硫醇盐3和3-甲基硫代吡啶并[4,3- e ] -1,4,2-二噻嗪1,1-二氧化物4可轻松获得其各种3-氨基衍生5-10。的肼解7,8和10，得到相应的3-氨基-2-（1,4-二氢-4- thioxopyrid -3-基磺酰基）胍11-13。随后12与4-氯苯甲醛反应，得到缩合产物14。1,4-二氢-2- thioxopyridine -3-磺酰胺15还从钾盐制备2在碱性水解，而15烷基化，得到适当š取代的衍生物16-19或S，N二取代的化合物20-21。
• Synthesis and structure determination of 2,3-diaryl-9,9-dioxo-1 H -9-thia-1,4,4a,7,10-pentaazaphenanthrene-2-ols
  作者：Jarosław Sławiński、Aneta Pogorzelska、Beata Żołnowska、Tomasz Laskowski、Paweł Sowiński

  DOI：10.1016/j.tet.2013.08.006

  日期：2013.10

  3-Amino-1,1-dioxopyrido[4,3-e]-1,4,2-dithiazine has been synthesized and applied to the synthesis of 3-amino-2-(4-thioxo-1,4-dihydropyridin-3-ylsulfonyl)guanidine. The reaction of the aminoguanidine with the appropriate 1,2-diarylethane-1,2-diones afforded 2,3-diaryl-9,9-dioxo-1H-9-thia-1,4,4a,7,10-pentaazaphenanthrene-2-ol derivatives. The structure of these compounds, which represent a novel heterocyclic ring system, was confirmed on the basis of elemental analysis and spectroscopic data including COSY, NOESY, ROESY, HSQC, and HMBC. (C) 2013 Elsevier Ltd. All rights reserved.