2-benzoylamino-6,7-dimethoxy-4H-3,1-benzothiazin-4-one | 135509-76-1

• 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-benzoylamino-6,7-dimethoxy-4H-3,1-benzothiazin-4-one
• 英文别名: 2-benzoylamino-6,7-dimethoxy-3,1-benzothiazin-4-one；N-(6,7-dimethoxy-4-oxo-3,1-benzothiazin-2-yl)benzamide
• CAS: 135509-76-1
• 化学式: C₁₇H₁₄N₂O₄S
• 分子量: 342.375
• InChiKey: KTABESZSOYKGKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氨基-4,5-二甲氧基苯甲酸甲酯 在 硫酸 作用下， 以 丙酮 为溶剂， 反应 48.0h， 生成 2-benzoylamino-6,7-dimethoxy-4H-3,1-benzothiazin-4-one
  参考文献：
  名称：

  Mehrcyclische Azine mit Heteroatomen in 1- und 3-Stellung, 30. Mitt.1): Zur Synthese 6,7-dimethoxysubstituierter 3,1-Benzothiazin-4-one

  摘要：

  AbstractIn vorherigen Mitt.2,3) berichteten wir über die Synthese von 2‐Amino‐ bzw. Benzoylamino‐3,1‐benzothiazin‐4‐on (5 bzw. 4) sowie deren 6‐methyl‐ und 6‐Chlor‐Derivaten durch Einwirkung von konz. Schwefelsäure auf die ggf. 5‐substituierten 2‐(3‐Benzoylthioureido)benzoesäuren oder deren Methylester 1.

  DOI：

  10.1002/ardp.19913240712

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
• 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.
• 2-Benzoylamino-6,7-dimethoxy-4H-3,1-benzoxazin-4-one: Synthesis and investigation of serine protease inactivation
  作者：M. G�tschow、U. Neumann

  DOI：10.1007/bf00811383

  日期：1995.10

  2-Benzoylamino-6,7-dimethoxy-4H-3,1-benzoxazin-4-one was prepared by thermal treatment of 2-(3-benzoylthioureido)-4,5-dimethoxybenzoic acid and by benzoylation of 2-amino-6,7-dimethoxy-4H-3,1-benzoxazin-4-one. The inactivation of chymotrypsin and human leukozyte elastase by the title compound and 2-benzoylamino-4H-3,1-benzoxazin-4-one is reported.
• GUTSCHOW, MICHAEL;HEINECKE, KRISTINA;THIEL, WILFRIED;LEISTNER, SIEGFRIED, ARCH. PHARM., 324,(1991) N, C. 465-466
  作者：GUTSCHOW, MICHAEL、HEINECKE, KRISTINA、THIEL, WILFRIED、LEISTNER, SIEGFRIED

  DOI：——

  日期：——
• Mehrcyclische Azine mit Heteroatomen in 1- und 3-Stellung, 30. Mitt.1): Zur Synthese 6,7-dimethoxysubstituierter 3,1-Benzothiazin-4-one
  作者：Michael Gütschow、Kristina Heinecke、Wilfried Thiel、Siegfried Leistner

  DOI：10.1002/ardp.19913240712

  日期：——

  AbstractIn vorherigen Mitt.2,3) berichteten wir über die Synthese von 2‐Amino‐ bzw. Benzoylamino‐3,1‐benzothiazin‐4‐on (5 bzw. 4) sowie deren 6‐methyl‐ und 6‐Chlor‐Derivaten durch Einwirkung von konz. Schwefelsäure auf die ggf. 5‐substituierten 2‐(3‐Benzoylthioureido)benzoesäuren oder deren Methylester 1.