2-(chloroacetylamino)-4,4'-diaminobiphenyl | 223768-64-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(chloroacetylamino)-4,4'-diaminobiphenyl
• 英文别名: N-[5-amino-2-(4-aminophenyl)phenyl]-2-chloroacetamide
• CAS: 223768-64-7
• 化学式: C₁₄H₁₄ClN₃O
• 分子量: 275.738
• InChiKey: CGODWIGYLCMLOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  81.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(chloroacetylamino)-4,4'-diaminobiphenyl 在 盐酸 、 potassium carbonate 、 potassium iodide 、 sodium nitrite 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 5,5'-{1,1'-biphenyl-2-[N-[2-(triphenylmethylmercapto)ethyl]-N-[N-(2-(triphenylmethylmercapto)ethyl)-carbamoylmethyl]aminoacetamido]-4,4'-diylbis(azo)}-bis(ethyl 2-hydroxybenzoate)
  参考文献：
  名称：

  Preparation of99mTc-N2S2 conjugates of chrysamine G, potential probes for the beta-amyloid protein of Alzheimer's disease

  摘要：

  Chrysamine G is known to bind in vitro to the beta-amyloid protein (A beta 10-43) and to homogenates of several regions of brain of Alzheimer's patients. The purpose of this study was to develop a Tc-99m-labelled derivative of chrysamine G, in which the structural requirements for beta-amyloid affinity are preserved,Bis-S-trityl protected monoamide-monoaminedithiol (MAMA-Tr-2), a chelating system used to incorporate Tc-99m, was coupled with 2-(chloroacetylamino)-chrysamine G diethyl ester (4) yielding 2-(MAMA-Tr-2-acetylamino)-chrysamine G diethyl ester (5-Tr-2) To prepare 4, 4,4'-dinitro-2-biphenylamine was treated with chloroacetyl chloride to obtain 2-(chloroacetylamino)-4,4'-dinitrobiphenyl, of which the nitro functions were reduced by catalytic hydrogenation. Diazotation of 2-(chloroacetylamino)-4,4'-diaminobiphenyl, followed by coupling with ethyl salicylate provided 4 in an overall yield of 4.3 %. Alkaline hydrolysis of 5-Tr2 resulted in the monoethyl ester derivative (6-Tr-2) and diacid derivative (7-Tr-2) Detritylation acid labelling with Tc-99m was performed in the presence of Sn2+ and (TcO4-)-Tc-99m solution at pH 2-3 with heating. RP-HPLC analysis showed one peak for both the diester derivative (Tc-99m-5) and the diacid derivative (Tc-99m-7), while two peaks (A and B) were present for the monoethyl ester derivative (Tc-99m-6), probably isomers with respect to the ester position. The order of elution from RP-HPLC reflected the lipophilicity of the Tc-99m-complexes as determined by partitioning between l-octanol and phosphate buffer pH 7.4 (log P: Tc-99m-5 = 2.15, Tc-99m-6(A) = 1.79, Tc-99m-6(B) = 1.93, Tc-99m-7 = 1.08).

  DOI：

  10.1002/(sici)1099-1344(199904)42:4<309::aid-jlcr192>3.0.co;2-o
• 作为产物：
  描述：

  4,4’-二硝基-2-联苯胺 在 palladium on activated charcoal 氢气 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 20.0 ℃ 、137.8 kPa 条件下， 反应 25.0h， 生成 2-(chloroacetylamino)-4,4'-diaminobiphenyl
  参考文献：
  名称：

  Preparation of99mTc-N2S2 conjugates of chrysamine G, potential probes for the beta-amyloid protein of Alzheimer's disease

  摘要：

  Chrysamine G is known to bind in vitro to the beta-amyloid protein (A beta 10-43) and to homogenates of several regions of brain of Alzheimer's patients. The purpose of this study was to develop a Tc-99m-labelled derivative of chrysamine G, in which the structural requirements for beta-amyloid affinity are preserved,Bis-S-trityl protected monoamide-monoaminedithiol (MAMA-Tr-2), a chelating system used to incorporate Tc-99m, was coupled with 2-(chloroacetylamino)-chrysamine G diethyl ester (4) yielding 2-(MAMA-Tr-2-acetylamino)-chrysamine G diethyl ester (5-Tr-2) To prepare 4, 4,4'-dinitro-2-biphenylamine was treated with chloroacetyl chloride to obtain 2-(chloroacetylamino)-4,4'-dinitrobiphenyl, of which the nitro functions were reduced by catalytic hydrogenation. Diazotation of 2-(chloroacetylamino)-4,4'-diaminobiphenyl, followed by coupling with ethyl salicylate provided 4 in an overall yield of 4.3 %. Alkaline hydrolysis of 5-Tr2 resulted in the monoethyl ester derivative (6-Tr-2) and diacid derivative (7-Tr-2) Detritylation acid labelling with Tc-99m was performed in the presence of Sn2+ and (TcO4-)-Tc-99m solution at pH 2-3 with heating. RP-HPLC analysis showed one peak for both the diester derivative (Tc-99m-5) and the diacid derivative (Tc-99m-7), while two peaks (A and B) were present for the monoethyl ester derivative (Tc-99m-6), probably isomers with respect to the ester position. The order of elution from RP-HPLC reflected the lipophilicity of the Tc-99m-complexes as determined by partitioning between l-octanol and phosphate buffer pH 7.4 (log P: Tc-99m-5 = 2.15, Tc-99m-6(A) = 1.79, Tc-99m-6(B) = 1.93, Tc-99m-7 = 1.08).

  DOI：

  10.1002/(sici)1099-1344(199904)42:4<309::aid-jlcr192>3.0.co;2-o