53-96-3,N-(2-芴基)乙酰胺, 98%

CAS号：53-96-3

分子式：C15H13NO

分子量：223.27

N-(2-芴基)乙酰胺

英文名：2-Acetamidofluorene

53-96-3,N-(2-芴基)乙酰胺, 98%化合物描述

2-Acetylaminofluorene (AAF, 2-AAF) is a carcinogenic and mutagenic derivative of fluorene. It is used as a biochemical tool in the study of carcinogenesis. It induces tumors in a number of species in the liver, bladder and kidney. The metabolism of this compound in the body by means of biotransformation reactions is the key to its carcinogenicity. 2-AAF is a substrate for cytochrome P-450 (CYP) enzyme, which is a part of a super family found in almost all organisms. This reaction results in the formation of N-hydroxy-2-acetylaminofluorene which is a proximal carcinogen and is more potent than the parent molecule. The N-hydroxy metabolite undergoes several enzymatic and non-enzymatic rearrangements. It can be O-acetylated by cytosolic N-acetyltransferase enzyme to yield N-acetyl-N-acetoxyaminofluorene. This intermediate can spontaneously rearrange to form the arylamidonium ion and a carbonium ion which can interact directly with DNA to produce DNA adducts. In addition to esterification by acetylation, the N-hydroxy derivative can be O-sulfated by cytosolic sulfur transferase enzyme giving rise to the N-acetyl-N-sulfoxy product.
In addition, the cytosolic N,O-aryl hydroxamic acid acyltransferase enzyme catalyzes the transfer of the acetyl group from the N atom of the N-OH-2-AAF to the O atom of the N-OH group to produce N-acetoxy-2-aminofluorene (N-OH-2-AF). This reactive metabolite spontaneously decomposes to form a nitrenium ion which will also react with DNA. However, the product of this latter reaction is the deacetylated aminofluorene adduct. The interconversion of amide and amine metabolites of 2-AAF can further occur via the microsomal enzyme deacetylase producing the N-hydroxy metabolite of the amine derivative. Subsequent esterification of the aryl hydroxylamine by sulfur transferase yields the sulfate ester which also spontaneously decompose to form nitrenium ion. The reactive nitrenium, carbonium and arylamidonium ion metabolites of 2-AAF react with the nucleophilic groups in DNA, proteins and endogenous thiols like glutathione. Other metabolites such as the N,O-glucuronide, although not directly activated products, can be important in the carcinogenic process because they are capable of degradation to proximal N-hydroxy metabolites. This metabolite is presumed to be involved in formation of bladder tumors. The mechanism for this is thought to involve degradation of glucuronide in the bladder due to acidic pH of urine.

53-96-3,N-(2-芴基)乙酰胺, 98%基本信息

• 中文名称：

  N-(2-芴基)乙酰胺

• 中文别名：

  2-乙酰氨基芴;
  2-乙酰氨基氟;
  N-2-芴基乙酰胺;
  

• 英文名称：

  2-Acetamidofluorene

• 英文别名：

  N-(2-Fluorenyl)acetamide;
  N-2-Fluorenylacetamide;
  N-(9H-fluoren-2-yl)acetamide;
  

• CAS号：

  53-96-3

• 分子式：

  C15H13NO

• 分子量：

  223.27000

• 精确质量：

  223.10000

• PSA：

  29.10000

• LogP：

  3.28920

物化性质

• 外观与性状：

  白色粉末

• 密度：

  1.23g/cm3

• 熔点：

  192-196 °C(lit.)

• 沸点：

  303oC

• 闪点：

  277.2oC

• 折射率：

  1.656

安全信息

• 危险类别：

  6.1(b)

• 安全说明：

  S53-S36/37/39-S45

• 危险品运输编码：

  UN 3077 9/PG 3

• 包装等级：

  III

• 危险品标志：

  T

• 危险类别码：

  R23/24/25; R46

• 海关编码：

  2924299090

• RTECS号：

  AB9450000

• WGK Germany：

  3

生产方法及用途

• 53-96-3,N-(2-芴基)乙酰胺, 98%用途

  1.有机合成。芳香胺类致癌性和诱变性研究。