{tert-butoxycarbonylmethyl-[1-hydroxymethyl-4-(4-nitrophenyl)butyl]amino}acetic acid tert-butyl ester | 1142811-83-3

• 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-butoxycarbonylmethyl-[1-hydroxymethyl-4-(4-nitrophenyl)butyl]amino}acetic acid tert-butyl ester
• 英文别名: tert-butyl 2-{[2-(tert-butoxy)-2-oxoethyl]({1-hydroxy-5-[4-nitrophenyl]pentan-2-yl})amino}acetate；Tert-butyl 2-[[1-hydroxy-5-(4-nitrophenyl)pentan-2-yl]-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]acetate
• CAS: 1142811-83-3
• 化学式: C₂₃H₃₆N₂O₇
• 分子量: 452.548
• InChiKey: JDERSESLPQGVEC-UHFFFAOYSA-N

物化性质

• 沸点：
  551.3±50.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  {tert-butoxycarbonylmethyl-[1-hydroxymethyl-4-(4-nitrophenyl)butyl]amino}acetic acid tert-butyl ester 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到1,1-bis[2-(tert-butoxy)-2-oxoethyl]-2-[3-(4-nitrophenyl)propyl]aziridin-1-ium bromide
  参考文献：
  名称：

  稳定的阿兹立丁鎓盐作为多种中间体：分离，区域和立体选择性开环和重排

  摘要：

  岩石捕获和勘探：在N，N-二羧甲基化的β-氨基醇的溴化过程中偶然发现了氮丙啶鎓盐。区域特异性的开环和重排，分离出的稳定的叠氮鎓盐可产生有用的分子，包括C-官能化的吗啉和α，β-不饱和胺。

  DOI：

  10.1002/anie.200805244
• 作为产物：
  描述：

  2-amino-5-(4-nitrophenyl)pentanoic acid 在 盐酸 、 sodium tetrahydroborate 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 乙腈 为溶剂， 反应 1.0h， 生成 {tert-butoxycarbonylmethyl-[1-hydroxymethyl-4-(4-nitrophenyl)butyl]amino}acetic acid tert-butyl ester
  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。
• 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。
• 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：US20160052894A1

  公开（公告）日：2016-02-25

  Substituted 1,4,7-triazacyclononane-N,N′,N″-triacetic acid and 1,4,7,10-tetraazacycicododecane-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.

  替代了带有氨基或羟基侧链的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，其金属配合物，组合物以及制备和在诊断成像和治疗细胞疾病中的使用方法。
• 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：US10189803B2

  公开（公告）日：2019-01-29

  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.

  通过氮丙啶离子的亲核开环反应立体选择性和区域选择性合成化合物，用于治疗和诊断化合物的立体选择性和区域选择性合成。
• 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.