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53-96-3 N-(2-芴基)乙酰胺

N-(2-芴基)乙酰胺

英文名称:2-Acetamidofluorene
CAS:

53-96-3

分子式:C15H13NO
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N-(2-芴基)乙酰胺简介

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.

N-(2-芴基)乙酰胺基本信息

中文名称 N-(2-芴基)乙酰胺 英文名称 2-Acetamidofluorene
中文别名

2-乙酰氨基氟; N-2-芴基乙酰胺; 2-乙酰氨基芴;

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英文别名

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

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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

N-(2-芴基)乙酰胺编号系统

MDL号 MFCD00001116

N-(2-芴基)乙酰胺物化性质

外观与性状:
白色粉末
密度:
1.23g/cm3
沸点:
303ºC
熔点:
192-196 °C(lit.)
闪点:
277.2ºC
折射率:
1.656

安全信息

RTECS号:
AB9450000
安全说明:
S53-S36/37/39-S45
危险类别码:
R23/24/25; R46
WGK Germany:
3
海关编码:
2924299090
危险品运输编码:
UN 3077 9/PG 3
危险类别:
6.1(b)
包装等级:
III
危险品标志:
T

生产方法及用途

用途

1.有机合成。芳香胺类致癌性和诱变性研究。

SDS 1.0 中文 展开
SDS 1.0 英文 展开
MSDS 中文 展开
1H NMR : Predict展开

核磁图谱 1H NMR : Predict

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国家名称 海关编码 海关数据更新时间 操作
中国 2924299090 2019-03 申报要素
美国 2924297690 2019-03 概述
印度 29242990 2019-03 概述
欧盟 29242998 2019-03 概述
英国 2924299899 2019-03 概述
日本 292429090 2019-03 概述
韩国 2924299090 2019-03 概述
加拿大 2924290030 2019-03 概述
N-(2-芴基)乙酰胺
CAS号:53-96-3 分子式:C15H13NO 分子量:223.27000

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