2-acetylamino-4H-3,1-benzothiazin-4-one | 134241-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 2-acetylamino-4H-3,1-benzothiazin-4-one
• 英文别名: N-(4-oxo-4H-benzo[d][1,3]thiazin-2-yl)acetamide；N-(4-oxo-3,1-benzothiazin-2-yl)acetamide
• CAS: 134241-00-2
• 化学式: C₁₀H₈N₂O₂S
• 分子量: 220.252
• InChiKey: DJXXLEZEWGGCJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  83.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻羧基苯基硫脲 在 硫酸 作用下， 生成 2-acetylamino-4H-3,1-benzothiazin-4-one
  参考文献：
  名称：

  Guetschow, M.; Neumann, U.; Leistner, S., Archiv der Pharmazie, 1991, vol. 324, # 9, p. 661

  摘要：

  DOI：

文献信息

• Benzothiazinones: A Novel Class of Adenosine Receptor Antagonists Structurally Unrelated to Xanthine and Adenine Derivatives
  作者：Michael Gütschow、Miriam Schlenk、Jürgen Gäb、Minka Paskaleva、Mohamad Wessam Alnouri、Silvia Scolari、Jamshed Iqbal、Christa E. Müller

  DOI：10.1021/jm300029s

  日期：2012.4.12

  related thienothiazinones were identified as structurally novel antagonists at adenosine receptors (ARs). 6-Methyl-2-benzoylamino-4H-3,1-benzothiazin-4-one (10d) was found to be a balanced AR antagonist with affinity for all human (h) subtypes (Ki hA1 65.6 nM; hA2A 120 nM; hA2B 360 nM; hA3 30.4 nM), while in rat (r), 10d was a highly potent A1-selective antagonist (rA1 7.7 nM; rA2A 546 nM; rA2B 679 nM, rA3

  2-（酰基）氨基-4 H -3,1-苯并噻嗪-4-酮和相关的噻吩并噻嗪酮被认为是腺苷受体（ARs）上结构上新颖的拮抗剂。发现6-甲基-2-苯甲酰氨基-4 H -3,1-苯并噻嗪-4-酮（10d）是一种平衡的AR拮抗剂，对所有人类（h）亚型均具有亲和力（K i hA 1 65.6 nM; hA 2A 120 nM； hA 2B 360 nM； hA 3 30.4 nM），而在大鼠（r）中，10d是一种高效的A 1选择性拮抗剂（rA 1 7.7 nM； rA 2A 546 nM； rA 2B 679 nM，rA 3> 10000 nM）。发现2-（4-甲基苯甲酰氨基）-4 H -3,1-苯并噻嗪-4-酮（10 g）是对人A 2A（68.8 nM）和A 3 AR（23.0 nM）的有效拮抗剂，相对于其他人类AR亚型。与A 1和A 3 AR相比，A 2A和A 2B AR可以容忍庞大的2-酰基取代基。叔丁基（4-oxo-4
• Use of dodecanoyl isothiocyanate as building block in synthesis of target benzothiazine, quinazoline, benzothiazole and thiourea derivatives
  作者：Magdy M. Hemdan、Eman A. El-Bordany

  DOI：10.1515/chempap-2016-0042

  日期：2016.1.1

  anthranilic acid to afford derivatives of thiourea II and benzothiazine IIIin a one-pot reaction. The cyclisation of thiourea II was achieved using acetic anhydride to form quinazoline derivative IV. The heating of quinazoline IV in acetic anhydride or butan-1-ol gave quinazoline derivatives V or VI, respectively. Benzothiazine III underwent trans-acylation to benzothiazine VII in boiling acetic anhydride

  十二烷酰基异硫氰酸酯（I）与邻氨基苯甲酸加成反应，以一锅法反应得到硫脲II和苯并噻嗪III的衍生物。硫脲II的环化反应是通过使用乙酸酐形成喹唑啉衍生物IV来实现的。在乙酸酐或丁-1-醇中加热喹唑啉IV，分别得到喹唑啉衍生物V或VI。苯并噻嗪III在沸腾的乙酸酐中进行反酰化为苯并噻嗪VII。用水合肼，邻氨基苯甲酸或氨基甲酸乙酯处理IV，得到三唑并喹唑啉衍生物VIII分别是喹唑啉代喹唑啉XI或硫代氨基脲X。I与2-氨基苯酚或2-氨基苯硫酚反应，分别得到硫脲衍生物XIII或苯并噻唑衍生物XIV。大多数合成的化合物带有月桂酰基（十二烷酰基）（烃部分）。通过显微分析和光谱数据证实了合成化合物的结构。
• 3,1-Benzothiazin-4-ones and 3,1-Benzoxazin-4-ones: Highly Different Activities in Chymotrypsin Inactivation
  作者：U. Neumann、M. Gutschow

  DOI：10.1006/bioo.1995.1006

  日期：1995.3

  3,1-Benzothiazin-4-ones are suIfur analogs of the potent serine protease inactivators of the 3, l-benzoxazin-4-one type, which acylate the serine residue within the active site of the enzymes. A series of 2-amino-3,1-benzothiazinones was synthesized, but these compounds showed only very little inhibitory activity toward chymotrypsin, a model serine protease. Detailed investigations revealed that benzothiazinones and benzoxazinones react with identical mechanisms, but benzothiazinones acylate chymotrypsin with much lower rate constants. Investigations of nonenzymatic hydrolysis showed the benzothiazinones to be intrinsically more stable than benzoxazinones. It was concluded from spectroscopic results, that benzoxazinones are highly activated due to the absence of ester-like resonance. 2-Benzoylamino-4H-3,1-benzoxazin-4-one was found to be a new, highly active chymotrypsin inactivator. In contrast, benzothiazinones were found to be resonance stabilized. The contribution of a resonance structure with an exocyclic oxanion to the overall structure of the benzothiazinones and its nonproductive binding to the active site explained their low reactivity toward chymotrypsin. (C) 1995 Academic Press, Inc.
• Guetschow, M.; Neumann, U.; Leistner, S., Archiv der Pharmazie, 1991, vol. 324, # 9, p. 661
  作者：Guetschow, M.、Neumann, U.、Leistner, S.

  DOI：——

  日期：——