tert-butyl-2-[(1-{4,7-bis[2-(tert-butoxy)-2-oxoethyl]-1,4,7-triazonan-1-yl}-5-[4-(hydroxyl-nitro)phenyl]-pentan-2-yl)[2-(tert-butoxy)-2-oxoethyl]amino]acetate | 1258945-99-1

• 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: tert-butyl-2-[(1-{4,7-bis[2-(tert-butoxy)-2-oxoethyl]-1,4,7-triazonan-1-yl}-5-[4-(hydroxyl-nitro)phenyl]-pentan-2-yl)[2-(tert-butoxy)-2-oxoethyl]amino]acetate
• 英文别名: tert-butyl 2-[(1-{4,7-bis[2-(tert-butoxy)-2-oxoethyl]-1,4,7-triazonan-1-yl}-5-[4-(nitro)phenyl]pentan-2-yl)[2-(tert-butoxy)-2-oxoethyl]amino]acetate；Tert-butyl 2-[4-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-5-(4-nitrophenyl)pentyl]-7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,4,7-triazonan-1-yl]acetate；tert-butyl 2-[4-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-5-(4-nitrophenyl)pentyl]-7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,4,7-triazonan-1-yl]acetate
• CAS: 1258945-99-1
• 化学式: C₄₁H₆₉N₅O₁₀
• 分子量: 792.026
• InChiKey: GIPGYDCZNMEPRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  56
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  164
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  tert-butyl-2-[(1-{4,7-bis[2-(tert-butoxy)-2-oxoethyl]-1,4,7-triazonan-1-yl}-5-[4-(hydroxyl-nitro)phenyl]-pentan-2-yl)[2-(tert-butoxy)-2-oxoethyl]amino]acetate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以100%的产率得到{4-[2-(bis-carboxymethylamino)-5-(4-nitrophenyl)entyl]-7-carboxymethyl[1,4,7]triazonan-1-yl}acetic acid
  参考文献：
  名称：

  A highly effective bifunctional ligand for radioimmunotherapy applications

  摘要：

  一种新型的双功能配体（3p-C-NETA）用于抗体靶向的90Y和177Lu放射免疫治疗，通过特定位置的环氧乙烷离子环开合反应高效合成。

  DOI：

  10.1039/c0cc05707j
• 作为产物：
  描述：

  2-amino-5-(4-nitrophenyl)pentanoic acid 在 盐酸 、 sodium tetrahydroborate 、 草酰氯 、 三乙酰氧基硼氢化钠 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 potassium iodide 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 58.83h， 生成 tert-butyl-2-[(1-{4,7-bis[2-(tert-butoxy)-2-oxoethyl]-1,4,7-triazonan-1-yl}-5-[4-(hydroxyl-nitro)phenyl]-pentan-2-yl)[2-(tert-butoxy)-2-oxoethyl]amino]acetate
  参考文献：
  名称：

  A highly effective bifunctional ligand for radioimmunotherapy applications

  摘要：

  一种新型的双功能配体（3p-C-NETA）用于抗体靶向的90Y和177Lu放射免疫治疗，通过特定位置的环氧乙烷离子环开合反应高效合成。

  DOI：

  10.1039/c0cc05707j

文献信息

• SYNTHESIS OF THERAPEUTIC AND DIAGNOSTIC DRUGS CENTERED ON REGIOSELECTIVE AND STEREOSELECTIVE RING OPENING OF AZIRIDINIUM IONS
  申请人：Chong Hyun-Soon

  公开号：US20130310555A1

  公开（公告）日：2013-11-21

  Stereoselective and regioselective synthesis of compounds via nucleophilic ring opening reactions of aziridinium ions for use in stereoselective and regioselective synthesis of therapeutic and diagnostic compounds.

  通过氮杂环丙烷离子的亲核环开反应，立体选择性和区域选择性合成化合物，用于立体选择性和区域选择性合成治疗和诊断化合物。
• Synthesis and Preclinical Evaluation of Bifunctional Ligands for Improved Chelation Chemistry of ⁹⁰Y and ¹⁷⁷Lu for Targeted Radioimmunotherapy
  作者：Chi Soo Kang、Xiang Sun、Fang Jia、Hyun A Song、Yunwei Chen、Michael Lewis、Hyun-Soon Chong

  DOI：10.1021/bc200696b

  日期：2012.9.19

  We report a practical and high-yield synthesis of a bimodal bifunctional ligand 3p-C-NETA-NCS containing the isothiocyanate group for conjugation to a tumor targeting antibody. 3p-C-NETA-NCS was conjugated to a tumor-targeting antibody, trastuzumab, and the corresponding 3p-C-NETA-trastuzumab conjugate was evaluated and compared to trastuzumab conjugates of the known bifunctional ligands C-DOTA, C-DTPA, and 3p-C-DEPA for radiolabeling kinetics with Y-90 and Lu-177. 3p-C-NETA-trastuzumab conjugate exhibited extremely rapid complexation kinetics with Y-90 and Lu-177. Y-90-3p-C-NETA-trastuzumab and Lu-177-3p-C-NETA-trastuzumab conjugates were stable in human serum for 2 weeks. A pilot biodistribution study was conducted to evaluate in vivo stability and tumor targeting of Lu-177-radiolabeled trastuzumab conjugate using nude mice bearing ZR-75-1 human breast cancer. Lu-177-3p-C-NETA-trastuzumab conjugate displayed low radioactivity level at blood (1.6%), low organ uptake (<2.2%), and high tumor-to-blood ratio (6.4) at 120 h. 3p-C-NETA possesses favorable in vitro and in vivo profiles and is an excellent bifunctional chelator that can be used for targeted RIT applications using Y-90 and Lu-177 and has the potential to replace DOTA and DTPA analogues in current clinical use.
• A highly effective bifunctional ligand for radioimmunotherapy applications
  作者：Hyun-Soon Chong、Hyun A. Song、Chi Soo Kang、Thien Le、Xiang Sun、Mamta Dadwal、Hyunbeom Lee、Xiaoli Lan、Yunwei Chen、Anzhi Dai

  DOI：10.1039/c0cc05707j

  日期：——

  A novel bifunctional ligand (3p-C-NETA) for antibody-targeted radioimmunotherapy of 90Y and 177Lu was efficiently synthesized via regiospecific ring opening of an aziridinium ion.

  一种新型的双功能配体（3p-C-NETA）用于抗体靶向的90Y和177Lu放射免疫治疗，通过特定位置的环氧乙烷离子环开合反应高效合成。