Amino-acetic acid 4-nitro-benzyl ester; compound with trifluoro-acetic acid | 733-71-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Amino-acetic acid 4-nitro-benzyl ester; compound with trifluoro-acetic acid
• 英文别名: (4-Nitrophenyl)methyl 2-aminoacetate;2,2,2-trifluoroacetic acid
• CAS: 733-71-1
• 化学式: C₂HF₃O₂*C₉H₁₀N₂O₄
• 分子量: 324.213
• InChiKey: CIVCOTBMSNNOBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Amino-acetic acid 4-nitro-benzyl ester; compound with trifluoro-acetic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Synthesis and evaluation of a novel 99mTc-labeled bioreductive probe for tumor hypoxia imaging

  摘要：

  Tumor hypoxia is closely associated with the malignant progression and/or the high metastatic ability of tumors and often induces resistance to chemo- and/or radiotherapy. Thus, the detection and evaluation of hypoxia is important for the optimization of cancer therapy. We designed a novel Tc-99m-labeled probe for tumor hypoxia imaging that utilizes bioreductive reactions in hypoxic cells. This probe, which contains a 4-nitrobenzyl ester group, is reduced in hypoxic cells to produce a corresponding carboxylate anion that cannot penetrate cell membranes because of its hydrophilicity and negative charge; therefore, it is expected to be trapped inside hypoxic cells. Based on this unique strategy, we synthesized the Technetium-99m ( Tc-99m)-labeled probe Tc-99m-SD32. The uptake of Tc-99m-SD32 in tumor cells was investigated under normoxic and hypoxic conditions. Tc-99m-SD32 showed sufficient accumulation and good retention in hypoxic cells. In addition, we demonstrated that Tc-99m-SD32 was subjected to bioreduction in hypoxic cells and was trapped as the corresponding carboxylate anion. These results indicated that Tc-99m-SD32 would be a promising agent for in vivo hypoxia imaging. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.022
• 作为产物：
  描述：

  对硝基苯甲醇 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 Amino-acetic acid 4-nitro-benzyl ester; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Synthesis and evaluation of a novel 99mTc-labeled bioreductive probe for tumor hypoxia imaging

  摘要：

  Tumor hypoxia is closely associated with the malignant progression and/or the high metastatic ability of tumors and often induces resistance to chemo- and/or radiotherapy. Thus, the detection and evaluation of hypoxia is important for the optimization of cancer therapy. We designed a novel Tc-99m-labeled probe for tumor hypoxia imaging that utilizes bioreductive reactions in hypoxic cells. This probe, which contains a 4-nitrobenzyl ester group, is reduced in hypoxic cells to produce a corresponding carboxylate anion that cannot penetrate cell membranes because of its hydrophilicity and negative charge; therefore, it is expected to be trapped inside hypoxic cells. Based on this unique strategy, we synthesized the Technetium-99m ( Tc-99m)-labeled probe Tc-99m-SD32. The uptake of Tc-99m-SD32 in tumor cells was investigated under normoxic and hypoxic conditions. Tc-99m-SD32 showed sufficient accumulation and good retention in hypoxic cells. In addition, we demonstrated that Tc-99m-SD32 was subjected to bioreduction in hypoxic cells and was trapped as the corresponding carboxylate anion. These results indicated that Tc-99m-SD32 would be a promising agent for in vivo hypoxia imaging. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.022

文献信息

• Synthesis of the eicosapeptide corresponding to the N-terminal amino acid sequence of the major component of human lymphoblastoid interferon.
  作者：TAKASHI ABIKO、IKUKO ONODERA、HIROSHI SEKINO

  DOI：10.1248/cpb.29.1390

  日期：——

  An eicosapeptide, H-Ser-Asp-Leu-Pro-Gln-Thr-His-Ser-Leu-Gly-Asn-Arg-Arg-Ala-Leu-Ile-Leu-Leu-Ala-Gln-OH, corresponding to the N-terminal amino acid sequence of the major component of human lymphoblastoid interferon was synthesized by a conventional method. The final deprotected peptide was purified by gel filtration on Sephadex G-25 and then by partition chromatography on Sephadex G-25. The eicosapeptide at a dose of 100 μg/ml inhibited the incorporation of 3H-thymidine into DNA of PHA-induced lymphocytes by about 15%.

  通过常规方法合成了二十肽 H-Ser-Asp-Leu-Pro-Gln-Thr-His-Ser-Leu-Gly-Asn-Arg-Arg-Ala-Leu-Ile-Leu-Leu-Ala-Gln-OH，该肽与人淋巴细胞干扰素主要成分的N端氨基酸序列相对应。通过凝胶过滤法（Sephadex G-25）和分区色谱法（Sephadex G-25）对最终去保护肽进行纯化。当剂量达到100微克/毫升时，该二十肽可抑制3H胸苷掺入PHA诱导淋巴细胞DNA的比率约15%。
• 7-Oxo-4-thia-1-azabicyclo[3,2,0]hept-2-ene derivatives
  申请人：HOECHST UK LIMITED

  公开号：EP0174561A1

  公开（公告）日：1986-03-19

  A compound of formula I with R' being an alkyl group substituted by one or more substituents and esters thereof at the 2-carboxy group or at the 8-hydroxy group or both: and salts thereof. Compounds I have antibacterial effect. Various intermediates are described. This compound of the formula I, or an ester at the 2-carboxy group or at the 8-hydroxy group or both or a salt thereof is produced by reacting a compound of formula II or of formula IX in which R represents a hydrogen atom or a carboxy protecting group, R3 represents an activated carboxylic acid group, R4 represents an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may be unsubstituteo or substituted, R15 represents a phenyl group or an alkyl group having from 1 to 4 carbon atoms, and X represents an oxygen c, sulphur with an amine of the formula III R'NH2 (III), to give a compound of formula I, or an ester therecf of formula la

  式 I 的化合物 R'为被一个或多个取代基取代的烷基及其 2-羧基或 8-羟基或两者的酯类：及其盐类。化合物 I 具有抗菌作用。描述了各种中间体。将式 II 或式 IX 的化合物与 2-羧基或 8-羟基或两者的酯或其盐反应，可制得式 I 化合物。 其中 R 代表氢原子或羧基保护基团，R3 代表活化的羧酸基团，R4 代表具有 1 至 4 个碳原子的烷基或苯基（可以是未取代的苯基或取代的苯基），R15 代表苯基或具有 1 至 4 个碳原子的烷基，X 代表氧 c、硫与式 III R'NH2 (III) 的胺反应，得到式 I 的化合物或式 la 的酯。
• US4849419A
  申请人：——

  公开号：US4849419A

  公开（公告）日：1989-07-18