N⁴-(N-p-chlorophenyl-carbamoyl)-2'-deoxycytidine | 922713-76-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N⁴-(N-p-chlorophenyl-carbamoyl)-2'-deoxycytidine
• 英文别名: N-[(4-Chlorophenyl)carbamoyl]-2'-deoxycytidine；1-(4-chlorophenyl)-3-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]urea
• CAS: 922713-76-6
• 化学式: C₁₆H₁₇ClN₄O₅
• 分子量: 380.788
• InChiKey: RQDBTIVRPVYYSR-OUCADQQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N⁴-(N-p-chlorophenyl-carbamoyl)-3',5'-di-O-acetyl-2'-deoxycytidine 在 sodium hydroxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.08h， 以48%的产率得到N⁴-(N-p-chlorophenyl-carbamoyl)-2'-deoxycytidine
  参考文献：
  名称：

  Biomarkers for Isocyanate Exposure:  Synthesis of Isocyanate DNA Adducts

  摘要：

  Isocyanates are important intermediates in industrial manufacturing. DNA adducts and protein adducts are important tools to biomonitor people exposed to xenobiotics. In the present work, the formation of DNA adducts deriving from 4-chlorophenyl isocyanate (4CPI) and 4-methylphenyl isocyanate (4MPI) were explored. The adducts of 4CPI and/or 4MPI with 2'-deoxyadenosine, 2'-deoxyguanosine, and 2'-deoxycytidine were synthesized and characterized by NMR and MS. For low level detection, an LC-MS/MS method was developed. The formation of DNA adducts was confirmed in in vitro reactions with DNA.

  DOI：

  10.1021/tx0600853

文献信息

• Biomarkers for Isocyanate Exposure:  Synthesis of Isocyanate DNA Adducts
  作者：Armin Beyerbach、Peter B. Farmer、Gabriele Sabbioni

  DOI：10.1021/tx0600853

  日期：2006.12.1

  Isocyanates are important intermediates in industrial manufacturing. DNA adducts and protein adducts are important tools to biomonitor people exposed to xenobiotics. In the present work, the formation of DNA adducts deriving from 4-chlorophenyl isocyanate (4CPI) and 4-methylphenyl isocyanate (4MPI) were explored. The adducts of 4CPI and/or 4MPI with 2'-deoxyadenosine, 2'-deoxyguanosine, and 2'-deoxycytidine were synthesized and characterized by NMR and MS. For low level detection, an LC-MS/MS method was developed. The formation of DNA adducts was confirmed in in vitro reactions with DNA.