N-(9,10,10-三氧代噻吨-3-基)乙酰胺 | 74134-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻喃类
• 中文名称: N-(9,10,10-三氧代噻吨-3-基)乙酰胺
• 中文别名: 9-(2,2-二丁基肼基)吖啶盐酸(1:1)
• 英文名称: N-(9,10,10-trioxothioxanthen-3-yl)acetamide
• CAS: 74134-16-0
• 化学式: C₁₅H₁₁NO₄S
• 分子量: 301.323
• InChiKey: CPEJWUGAQDQTIT-UHFFFAOYSA-N

物化性质

• 沸点：
  627.4±54.0 °C(Predicted)
• 密度：
  1.490±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-nitrothioxanthen-9-one-10,10-dioxide 在 铂 高氯酸 、 氢气 、 溶剂黄146 作用下， 以 溶剂黄146 为溶剂， 生成 N-(9,10,10-三氧代噻吨-3-基)乙酰胺
  参考文献：
  名称：

  Selective Inhibitors of Monoamine Oxidase. 2. Arylamide SAR

  摘要：

  Monoamine oxidase (MAO) exists in two forms distinguishable by substrate specificity. Inhibition of MAO A is believed to be responsible for the antidepressant activity of MAO inhibitors. A group of N-arylacetamides are highly specific inhibitors of MAO A, some with IC50 values in the 10-100 nM range. The requirements for high activity and specificity include a nearly linear tricyclic aromatic portion but a larger and a smaller central ring component. The amide group, which is best acetamido, is optimally placed para to the smaller central group. The size and shape of the aromatic moiety appear to be the major influence on activity and specificity for MAO A.

  DOI：

  10.1021/jm00039a021

文献信息

• Tricyclic compounds, processes for their preparation, compositions containing such compounds and their use in medicine
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0150891A1

  公开（公告）日：1985-08-07

  Compounds of formula (I) wherein n is 0, 1 or 2; one of R1 and R2 is hydrogen and the other is selected from carbamoyl, N-C1-4 alkylcarbamoyl, N,N-di-C1-4 alkylcarbamoyl, carbamimidoyl, N1-C1-4 alkylcarbamimidoyl, N2-C1-4 alkylcarbamimidoyl, N1-C1-4 alkyl-N2-C1-4 alkylcarbamimidoyl, N1,N1-di-C1-4 alkylcarbamimidoyl, N1,N1-di-C1-4alkyl-N2-C1-4 alkvlcarbamimidoyl, tetrazol-5-yl (optionally substituted by one or more C1-4 alky' groups) and imidaxolin-2-yl optionally substituted by one or more C1-4 alkyl groups); and R3 is selected from hydrogen, saturated and unsaturated aliphatic hydrocarbon moieties containing from 1 to 4 carbon atoms, groups OR4 (where R4 is selected from hydrogen and saturated and unsaturated aliphatic hydrocarbon moieties containing from 1 to 4 carbon atoms), halo, groups of formula -NR5R6 (where R5 and R6 are independently selected from hydrogen, C1-4 alkyl and hydroxy C1-4 alkyl, provided that the total number of carbon atoms in R5 and R6 does not exceed 4), amino C1-4 alkylamino and morpholino, provided that when R1 is carbamoyl and R2 and R3 are both hydrogen, then n is 0 or 1; and physiologically acceptable salts thereof, and their pro-drugs and metabolites are inhibitors of monoamine oxidase-A and are useful in the prophylaxis and treatment of mental disorders such as depression.

  式(I)化合物 其中 n 为 0、1 或 2；R1 和 R2 中的一个为氢，另一个选自氨基甲酰基、N-C1-4 烷基氨基甲酰基、N,N-二-C1-4 烷基氨基甲酰基、氨基亚氨酰基、N1-C1-4 烷基氨基亚氨酰基、N2-C1-4 烷基氨基亚氨酰基、N1-C1-4 烷基-N2-C1-4 烷基氨基亚氨酰基、N1,N1-二-C1-4烷基氨基甲酰亚胺、N1,N1-二-C1-4烷基-N2-C1-4烷基氨基甲酰亚胺、四唑-5-基（可选择被一个或多个 C1-4 烷基取代）和咪唑啉-2-基（可选择被一个或多个 C1-4 烷基取代）；和 R3 选自氢、含 1 至 4 个碳原子的饱和及不饱和脂肪族烃基、OR4 基团（其中 R4 选自氢、含 1 至 4 个碳原子的饱和及不饱和脂肪族烃基）、卤素、式-NR5R6（其中 R5 和 R6 独立选自氢、C1-4 烷基和羟基 C1-4 烷基，条件是 R5 和 R6 中的碳原子总数不超过 4）、氨基 C1-4 烷基氨基和吗啉基，条件是当 R1 为氨基甲酰基且 R2 和 R3 均为氢时，则 n 为 0 或 1；及其生理上可接受的盐类，它们的原药和代谢物是单胺氧化酶-A 的抑制剂，可用于预防和治疗抑郁症等精神疾病。
• Harfenist Morton, Joyner Charles T., Mize Patrick D., White Helen L., J. Med. Chem, 37 (1994) N 13, S 2085-2089
  作者：Harfenist Morton, Joyner Charles T., Mize Patrick D., White Helen L.

  DOI：——

  日期：——
• Selective Inhibitors of Monoamine Oxidase. 2. Arylamide SAR
  作者：Morton Harfenist、Charles T. Joyner、Patrick D. Mize、Helen L. White

  DOI：10.1021/jm00039a021

  日期：1994.6

  Monoamine oxidase (MAO) exists in two forms distinguishable by substrate specificity. Inhibition of MAO A is believed to be responsible for the antidepressant activity of MAO inhibitors. A group of N-arylacetamides are highly specific inhibitors of MAO A, some with IC50 values in the 10-100 nM range. The requirements for high activity and specificity include a nearly linear tricyclic aromatic portion but a larger and a smaller central ring component. The amide group, which is best acetamido, is optimally placed para to the smaller central group. The size and shape of the aromatic moiety appear to be the major influence on activity and specificity for MAO A.