1-硝基-9H-咔唑-2-胺 | 158321-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-硝基-9H-咔唑-2-胺
• 英文名称: 2-Amino-1-nitro-9H-carbazole
• 英文别名: 1-Nitro-9H-carbazol-2-amine
• CAS: 158321-20-1
• 化学式: C₁₂H₉N₃O₂
• 分子量: 227.222
• InChiKey: VBGFPAQMPICEPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-acetylamino-9-acetylcarbazole 在 sodium tetrahydroborate 、 硝酸 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 242.0h， 生成 1-硝基-9H-咔唑-2-胺
  参考文献：
  名称：

  鼠伤寒沙门氏菌中硝基和氨基取代咔唑的致突变性。二。9H-咔唑的邻氨基硝基衍生物。

  摘要：

  The mutagenicity of 4 ortho-aminonitrocarbazoles and 2 ortho-acetamidonitrocarbazoles was assayed in Salmonella strains TA1538, TA98, TA100, TA1537 and TA1977 and in nitroreductase and acetylase deficient strains TA98NR and TA98/1,8DNP(6), with and without S9 from phenobarbital-induced rat liver. Mutagenicity of these compounds and of their monosubstituted precursors (Andre et al., Mutation Res. 299 (1993) 63-73) was tentatively correlated with various molecular descriptors. The hydrophobicity appears as an important determinant of direct mutagenicity in this series of closely related nitrocarbazoles, with a general trend of increasing mutagenicity with an increase of hydrophobicity. On the contrary; the ease of nitroreduction (depicted by electrochemical reduction potential and energy of the lowest unoccupied molecular orbitals) does not appear as a major direct determinant. The ortho-amino group does not favour mutagenic potential, except for 1-nitro-2-aminocarbazole, which is the most potent direct mutagen. Mutagenicity in the presence of S9 is attributed mainly to amine metabolism, Hydrophobicity has only a limited effect on this activity, whereas an unexpected positive correlation is found with electrochemical oxidation potential. The influence of reciprocal electronic delocalization effects of nitro and amino groups, through the modulation of the ultimate mutagenic species (nitrenium ion) reactivity, is also discussed.

  DOI：

  10.1016/0165-1218(95)90066-7

文献信息

• Mutagenicity of nitro- and amino-substituted carbazoles in Salmonella typhimurium. II. Ortho-aminonitro derivatives of 9H-carbazole
  作者：V. André、C. Boissart、F. Sichel、P. Gauduchon、J.Y. Le Talaër、J.C. Lancelot、M. Robba、C. Mercier、S. Chemtob、E. Raoult、A. Tallec

  DOI：10.1016/0165-1218(95)90066-7

  日期：1995.11

  The mutagenicity of 4 ortho-aminonitrocarbazoles and 2 ortho-acetamidonitrocarbazoles was assayed in Salmonella strains TA1538, TA98, TA100, TA1537 and TA1977 and in nitroreductase and acetylase deficient strains TA98NR and TA98/1,8DNP(6), with and without S9 from phenobarbital-induced rat liver. Mutagenicity of these compounds and of their monosubstituted precursors (Andre et al., Mutation Res. 299 (1993) 63-73) was tentatively correlated with various molecular descriptors. The hydrophobicity appears as an important determinant of direct mutagenicity in this series of closely related nitrocarbazoles, with a general trend of increasing mutagenicity with an increase of hydrophobicity. On the contrary; the ease of nitroreduction (depicted by electrochemical reduction potential and energy of the lowest unoccupied molecular orbitals) does not appear as a major direct determinant. The ortho-amino group does not favour mutagenic potential, except for 1-nitro-2-aminocarbazole, which is the most potent direct mutagen. Mutagenicity in the presence of S9 is attributed mainly to amine metabolism, Hydrophobicity has only a limited effect on this activity, whereas an unexpected positive correlation is found with electrochemical oxidation potential. The influence of reciprocal electronic delocalization effects of nitro and amino groups, through the modulation of the ultimate mutagenic species (nitrenium ion) reactivity, is also discussed.