t-butyl (4-tert-butoxycarbonylmethyl-7-{2-[tert-butoxycarbonylmethyl-(4-nitro-benzyl)-amino]ethyl}-[1,4,7]triazonan-1-yl)acetate | 1016237-79-8

• 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: t-butyl (4-tert-butoxycarbonylmethyl-7-{2-[tert-butoxycarbonylmethyl-(4-nitro-benzyl)-amino]ethyl}-[1,4,7]triazonan-1-yl)acetate
• 英文别名: tert-butyl 2-[(2-{4,7-bis[2-(tert-butoxy)-2-oxoethyl]-1,4,7-triazonan-1-yl}ethyl)({[4-nitrophenyl]methyl})amino]acetate；Tert-butyl 2-[4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-7-[2-[[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-[(4-nitrophenyl)methyl]amino]ethyl]-1,4,7-triazonan-1-yl]acetate
• CAS: 1016237-79-8
• 化学式: C₃₃H₅₅N₅O₈
• 分子量: 649.828
• InChiKey: IHOUMQGNWPFVGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  t-butyl (4-tert-butoxycarbonylmethyl-7-{2-[tert-butoxycarbonylmethyl-(4-nitro-benzyl)-amino]ethyl}-[1,4,7]triazonan-1-yl)acetate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 14.0h， 以90%的产率得到tert-butyl 2-{[(4-aminophenyl)methyl](2-{4,7-bis[2-(tert-butoxy)-2-oxoethyl]-1,4,7-triazonan-1-yl}ethyl)amino}acetate
  参考文献：
  名称：

  Bimodal ligands with macrocyclic and acyclic binding moieties, complexes and compositions thereof, and methods of using

  摘要：

  用带有氨基或羟基的1,4,7-三氮杂环壬烷-N,N′,N″-三乙酸和1,4,7,10-四氮杂环十二烷-N,N′,N″,N′″-四乙酸化合物替代，以及它们的金属配合物、组合物、制备方法以及在诊断成像和治疗细胞疾病中的应用。

  公开号：

  US09115094B2
• 作为产物：
  描述：

  2-(p-Nitrobenzylidenamino)ethanol 在 sodium tetrahydroborate 、 草酰氯 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 二甲基亚砜 作用下， 以 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 64.2h， 生成 t-butyl (4-tert-butoxycarbonylmethyl-7-{2-[tert-butoxycarbonylmethyl-(4-nitro-benzyl)-amino]ethyl}-[1,4,7]triazonan-1-yl)acetate
  参考文献：
  名称：

  Bimodal ligands with macrocyclic and acyclic binding moieties, complexes and compositions thereof, and methods of using

  摘要：

  用带有氨基或羟基的1,4,7-三氮杂环壬烷-N,N′,N″-三乙酸和1,4,7,10-四氮杂环十二烷-N,N′,N″,N′″-四乙酸化合物替代，以及它们的金属配合物、组合物、制备方法以及在诊断成像和治疗细胞疾病中的应用。

  公开号：

  US09115094B2

文献信息

• Synthesis and Evaluation of Novel Polyaminocarboxylate-Based Antitumor Agents
  作者：Hyun-Soon Chong、Xiang Ma、Haisung Lee、Phuong Bui、Hyun A. Song、Noah Birch

  DOI：10.1021/jm701307j

  日期：2008.4.1

  Iron depletion, using iron chelators targeting transferrin receptor (TfR) and ribonucleotide reductase (RR), is proven to be effective in the treatment of cancer. We synthesized and evaluated novel polyarninocarboxylate-based chelators NETA, NE3TA, and NE3TA-Bn and their bifunctional versions C-NETA, C-NE3TA, and N-NE3TA for use in iron depletion tumor therapy. The cytotoxic activities of the novel polyaminocarboxylates were evaluated in the HeLa and HT29 colon cancer cell lines and compared to the clinically available iron depletion agent DFO and the frequently explored polyaminocarboxylate DTPA. All new chelators except C-NETA displayed enhanced cytotoxicities in both HeLa and HT29 cancer cells compared to DFO and DTPA. Incorporation of the nitro functional unit for conjugation to a targeting moiety into the two potent non-functionalized chelators NE3TA and NE3TA-Bn (C-NE3TA and N-NE3TA) was well-tolerated and resulted in a minimal decrease in cytotoxicity. Cellular uptake of C-NE3TA, examined using a confocal microscope, indicates that the chelator is taken up into HT29 cancer cells.
• US9115094B2
  申请人：——

  公开号：US9115094B2

  公开（公告）日：2015-08-25
• Bimodal ligands with macrocyclic and acyclic binding moieties, complexes and compositions thereof, and methods of using
  申请人：Chong Hyun-soon

  公开号：US09115094B2

  公开（公告）日：2015-08-25

  Substituted 1,4,7-triazacyclononane-N,N′,N″-triacetic acid and 1,4,7,10-tetraazacyclcododecane-N,N′,N″,N′″-tetraacetic acid compounds with a pendant amino or hydroxyl group, metal complexes thereof, compositions thereof, and methods of making and use in diagnostic imaging and treatment of cellular disorders.

  用带有氨基或羟基的1,4,7-三氮杂环壬烷-N,N′,N″-三乙酸和1,4,7,10-四氮杂环十二烷-N,N′,N″,N′″-四乙酸化合物替代，以及它们的金属配合物、组合物、制备方法以及在诊断成像和治疗细胞疾病中的应用。
• Novel 64Cu-radiolabeled bile acid conjugates for targeted PET imaging
  作者：Hyun-Soon Chong、Yunwei Chen、Chi Soo Kang、Xiang Sun、Ningjie Wu

  DOI：10.1016/j.bmcl.2015.01.008

  日期：2015.3

  A promising bifunctional chelate (N-NE3TA) was conjugated to bile acids, cholic acid (CA), deoxycholic acid (DCA), and chenodeoxycholic acid (CDCA) as tumor targeting vectors. Bile acid conjugates of N-NE3TA (CA-N-NE3TA, DCA-N-NE3TA, and CDCA-N-NE3TA) were comparatively evaluated for complexation with Cu-64, an imaging probe for positron emission tomography (PET). N-NE3TA-bile acid conjugates were evaluated for radiolabeling kinetics with Cu-64, and the corresponding Cu-64-radiolabeled conjugates were screened for complex stability in human serum and EDTA solution. The NE3TA-bile acid conjugates instantly bound to Cu-64 with excellent radiolabeling efficiency at room temperature. All NE3TA-bile acid conjugates radiolabeled with Cu-64 remained inert in human serum for 2 days without releasing a considerable amount of the radioactivity. The Cu-64-radiolabeled complexes were further challenged by EDTA in a 100-fold molar excess. Bile acid-N-NE3TA conjugates radiolabeled with Cu-64 were quite stable with a minimal transfer of Cu-64 to EDTA at 4 h time point. The in vitro data indicate that the bile acid-N-NE3TA conjugates deserve further biological evaluation for Cu-64-based targeted PET imaging applications. (C) 2015 Elsevier Ltd. All rights reserved.