2,3-二氢-1,3-苯并恶嗪-4H-2-硫酮-4-酮 | 10021-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 中文名称: 2,3-二氢-1,3-苯并恶嗪-4H-2-硫酮-4-酮
• 英文名称: 2-thioxo-2,3-dihydro-4H-benz[e]-1,3-oxazin-4-one
• 英文别名: 4-oxo-2-thioxo-3,4-dihydro-2H-1,3-benzoxazine；2-thioxo-2,3-dihydro-4H-1,3-benzoxazin-4-one；2-thioxo-3,4-dihydro-2H-1,3-benzoxazin-4-one；2-thioxo-2,3-dihydro-benzo[e][1,3]oxazin-4-one；2-thioxo-2,3-dihydro-benz[e][1,3]oxazin-4-one；2-Thioxo-2,3-dihydro-benz[e][1,3]oxazin-4-on；2-Sulfanylidene-1,3-benzoxazin-4-one
• CAS: 10021-35-9
• 化学式: C₈H₅NO₂S
• mdl: MFCD01937575
• 分子量: 179.199
• InChiKey: XCNLSOGMJQILRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2,3-二氢-1,3-苯并恶嗪-4H-2-硫酮-4-酮 在 碳酸氢钠 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 乙腈 为溶剂， 反应 7.5h， 生成 2-[pyridin-3-yl(pyridin-4-ylmethyl)amino]-4H-benz[e]-1,3-oxazin-4-one
  参考文献：
  名称：

  Synthesis, DNA-PK inhibition, anti-platelet activity studies of 2-(N-substituted-3-aminopyridine)-substituted-1,3-benzoxazines and DNA-PK and PI3K inhibition, homology modelling studies of 2-morpholino-(7,8-di and 8-substituted)-1,3-benzoxazines

  摘要：

  A number of new 2-(pyridin-3-ylamino)-4H-(substituted) benz[e]-1,3-oxazin-4-ones were synthesized 10a-g. These were then reacted with the hydro-halogen salt of 2, 3 and 4-(halo-methyl) pyridine in the presence of Cs2CO3 to give eighteen new 2-(N-substituted (pyridin-3-ylmethyl) amino)-substituted-1,3-benzoxazines (compounds 11a-i, 13a-c, and 15a-f). X-ray crystallography was used to confirm that the 2-N-substituted structures 11 and 13 were formed rather than the 3-N-substitution analogues 12 and 14. Eleven of the new compounds were tested for their effect on collagen induced platelet aggregation and it was found that the most active inhibitory compound was 8-methyl-2-(pyridin-3-yl(pyridin-3-ylmethyl) amino)-7-(pyridin-3-ylmethoxy)-4H-benz[e]-1,3-oxazin-4-one 15e with an IC50 of 10 +/- 2 mu M. DNA-dependent protein kinase (DNA-PK) inhibition data for 12 previously prepared 2-morpholino substituted-1,3-benzoxazines (compounds 19-31) were measured and showed high to moderate activity where the most active compound was compound 27 with an IC50 of 0.28 mu M. Furthermore DNA-PK inhibition data for six newly prepared 2-(N-substituted (pyridin-3-ylmethyl) amino)-substituted-1,3-benzoxazines (compounds 11b), 13a-b, 15a-b and 15e) and 8-methyl-7-(pyridin-3-ylmethoxy)-3-(pyridin-3-ylmethyl)-2H-benz[e]-1,3-oxazin-2,4(3H)-dione 17d were measured and moderate to low inhibitory activity was observed, with the most active of the compounds in this series being 8-methyl-2-(pyridin-3-yl(pyridin-3-ylmethyl)amino)-7-(pyridin-3-ylmethoxy)-4H-benz[e]-1,3-oxazin-4-one 15e with an IC50 of 2.5 mu M. PI3K inhibition studies revealed that compound 27 is highly potent (IC50 for PI3K alpha = 0.13 mu M, PI3K beta = 0.14 mu M, PI3K gamma = 0.72 mu M, PI3K delta = 2.02 mu M). Compound 22 with 7-[2-(4-methylpiperazin-1-yl)ethoxy] group shows greater inhibition of DNA-PK over PI3K.Docking of some 2-morpholino-substituted-1,3-benzoxazine compounds 19-31 within the binding pocket and structure activity relationships (SAR) analyses were performed with results agreeing well with observed activities. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.035
• 作为产物：
  描述：

  水杨酸 以70%的产率得到
  参考文献：
  名称：

  TAMURA Y.; KAWASAKI T.; TANIO M.; KITA Y., CHEM. AND IND., 1978, NO 20, 806-807

  摘要：

  DOI：

文献信息

• Generalized Method for the Production of 1,3‐Benzoxazine, 1,3‐Benzothiazine, and Quinazoline Derivatives from 2‐(Hydroxy, Thio, or Amino) Aromatic Acids Using Triphenylphosphine Thiocyanogen
  作者：Kaylene M. Pritchard、Jasim M. Al‐Rawi、Andrew B. Hughes

  DOI：10.1081/scc-200061564

  日期：2005.6.1

  derivatives has been achieved, respectively. It was also found that 3‐hydroxypyridine‐2‐carboxylic acid and 2‐hydroxynicotinic acid using a modified method gave 2‐thioxo‐2,3‐dihydro‐4H‐pyrido[2,3‐e][1,3]oxazin‐4‐one and 2‐thioxo‐2,3‐dihydro‐4H‐pyrido[3,2‐e][1,3]oxazin‐4‐one, respectively. The structures of the new compounds were confirmed by the analysis of their IR, 1H, and 13C NMR spectra.

  摘要 开发了一种改进的一锅法合成 1,3-苯并恶嗪，其中省略了不稳定硫氰的制备。发现该方法适用于取代（甲基、甲氧基、卤素和羟基）2-羟基苯甲酸和 2-羟基萘甲酸。该方法扩展到 2-硫代、2-氨基和 N-甲基氨基苯甲酸，分别实现了 1,3-苯并噻嗪和喹唑啉衍生物的合成。还发现使用改进方法的 3-羟基吡啶-2-羧酸和 2-羟基烟酸得到 2-硫代-2,3-二氢-4H-吡啶并[2,3-e][1,3]恶嗪-分别为 4-one 和 2-thioxo-2,3-dihydro-4H-pyrido[3,2-e][1,3]oxazin-4-one。新化合物的结构通过其 IR、1H 和 13C NMR 光谱的分析得到证实。
• REACTION OF STABLE TRIALKYLSILYL ESTERS WITH Ph₃P(SCN)₂: A NOVEL METHOD FOR THE PREPARATION OF ACYL AND AROYL ISOTHIOCYANATES UNDER NEUTRAL CONDITION
  作者：N. Iranpoor、H. Firouzabadi、H. R. Shaterian

  DOI：10.1081/scc-120014983

  日期：2002.1

  one-pot conversion of stable triisopropylsilyl- and tert-butyldimethylsilyl carboxylates to their corresponding acyl- or aroyl isothiocyanates using in-situ generation of Ph3P(SCN)2 at room temperature under neutral condition. This method has also been applied for the high yield preparation of 2-thioxo-3,4-dihydro-2H-1,3-benzoxazine-4-one, which has fungicidal and bactericidal activities.

  摘要描述了一种高效、温和且新颖的方法，可在中性条件下在室温下原位生成 Ph3P(SCN)2，将稳定的三异丙基甲硅烷基和叔丁基二甲基甲硅烷基羧酸酯一锅法转化为相应的酰基或芳酰基异硫氰酸酯。该方法还用于高产率制备具有杀菌和杀菌活性的2-thioxo-3,4-dihydro-2H-1,3-benzoxazine-4-one。
• Strahlungsempfindliches Gemisch und Verfahren zur Herstellung von Reliefbildern
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0006626A2

  公开（公告）日：1980-01-09

  Es wird ein strahlungsempfindliches Gemisch beschrieben, das (a) eine unter Einwirkung von aktinischer Strahlung, insbesondere UV-Licht, Säure bildende Verbindung und (b) eine Verbindung enthält, die mindestens eine N-Acyliminocarbonatgruppe enthält und deren Löslichkeit in einem flüssigen Entwickler durch Einwirkung von Säure erhöht wird. Das N-Acyliminocarbonat ist bevorzugt eine Verbindung der allgemeinen Formel I in der R, einen n-wertigen aliphatischen, cycloaliphatischen oder aromatischen Rest, R2 und R3 Alkyl- oder Aryl reste bedeuten, wobei jeweils zwei der Reste R1, R2 und R3 zu einem heterocyclischen Ring verbunden sein können, und n eine ganze Zahl von 1 bis 3 ist. Das Gemisch wird in Form einer strahlungsempfindlichen Schicht bildmäßig bestrahlt und durch Auswaschen der bestrahlten Stellen mit einem Entwickler zu einem positiven Reliefbild entwickelt.

  描述了一种辐射敏感混合物，它含有 (a) 在光辐射，特别是紫外线作用下形成酸的化合物，和 (b) 至少含有一个 N-酰基亚氨基碳酸酯基团的化合物，其在液体显影剂中的溶解度在酸的作用下会增加。N-酰亚氨基碳酸酯最好是通式 I 的化合物 其中 R 是正价脂肪族、环脂族或芳香族基、 R2 和 R3 是烷基或芳基，在每种情况下，R1、R2 和 R3 中的两个基可以连接形成杂环，以及 n 是 1 到 3 的整数。 混合物以辐射敏感层的形式进行图像辐照，然后用显影剂冲洗辐照区域，显影成正片浮雕图像。
• Rashan; Ali Al-Rawi; Nadir, Il Farmaco, 1991, vol. 46, # 5, p. 677 - 683
  作者：Rashan、Ali Al-Rawi、Nadir、Awni

  DOI：——

  日期：——
• Ukai; Hayashi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1935, vol. 55, p. 8,12; dtsch. Ref. S. 1
  作者：Ukai、Hayashi

  DOI：——

  日期：——

表征谱图