toluene-4-sulfonic acid 2-tert-butoxycarbonylamino-3-(4-nitrophenyl)propyl ester | 1005484-22-9

• 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: toluene-4-sulfonic acid 2-tert-butoxycarbonylamino-3-(4-nitrophenyl)propyl ester
• 英文别名: [2-[(2-Methylpropan-2-yl)oxycarbonylamino]-3-(4-nitrophenyl)propyl] 4-methylbenzenesulfonate
• CAS: 1005484-22-9
• 化学式: C₂₁H₂₆N₂O₇S
• 分子量: 450.513
• InChiKey: WKIQKWFBBDJMJC-UHFFFAOYSA-N

物化性质

• 沸点：
  625.7±55.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  toluene-4-sulfonic acid 2-tert-butoxycarbonylamino-3-(4-nitrophenyl)propyl ester 在 sodium 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到tert-butyl 2-(4-nitrobenzyl)aziridine 1-carboxylate
  参考文献：
  名称：

  Rational Design and Generation of a Bimodal Bifunctional Ligand for Antibody-Targeted Radiation Cancer Therapy

  摘要：

  An antibody-targeted radiation therapy (radioimmunotherapy, RIT) employs a bifunctional ligand that can effectively hold a cytotoxic metal with clinically acceptable complexation kinetics and stability while being attached to a tumor-specific antibody. Clinical exploration of the therapeutic potential of RIT has been challenged by the absence of adequate ligand, a critical component for enhancing the efficacy of the cancer therapy. To address this deficiency, the bifunctional ligand C-NETA in a unique structural class possessing both a macrocyclic cavity and a flexible acyclic moiety was designed. The practical, reproducible, and readily scalable synthetic route to C-NETA was developed, and its potential as the chelator of Bi-212, Bi-213, and Lu-177 for RIT was evaluated in vitro and in vivo. C-NETA rapidly binds both Lu(III) and Bi(III), and the respective metal complexes remain extremely stable in serum for 14 days. Lu-177-C-NETA and Bi-205/6-C-NETA possess an excellent or acceptable in vivo biodistribution profile.

  DOI：

  10.1021/jm070401q
• 作为产物：
  描述：

  tert-butyl [2-hydroxy-1-(4-nitrobenzyl)ethyl]carbamate 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以96%的产率得到toluene-4-sulfonic acid 2-tert-butoxycarbonylamino-3-(4-nitrophenyl)propyl ester
  参考文献：
  名称：

  Rational Design and Generation of a Bimodal Bifunctional Ligand for Antibody-Targeted Radiation Cancer Therapy

  摘要：

  An antibody-targeted radiation therapy (radioimmunotherapy, RIT) employs a bifunctional ligand that can effectively hold a cytotoxic metal with clinically acceptable complexation kinetics and stability while being attached to a tumor-specific antibody. Clinical exploration of the therapeutic potential of RIT has been challenged by the absence of adequate ligand, a critical component for enhancing the efficacy of the cancer therapy. To address this deficiency, the bifunctional ligand C-NETA in a unique structural class possessing both a macrocyclic cavity and a flexible acyclic moiety was designed. The practical, reproducible, and readily scalable synthetic route to C-NETA was developed, and its potential as the chelator of Bi-212, Bi-213, and Lu-177 for RIT was evaluated in vitro and in vivo. C-NETA rapidly binds both Lu(III) and Bi(III), and the respective metal complexes remain extremely stable in serum for 14 days. Lu-177-C-NETA and Bi-205/6-C-NETA possess an excellent or acceptable in vivo biodistribution profile.

  DOI：

  10.1021/jm070401q

文献信息

• Methods and Compositions for F-18 Labeling of Proteins, Peptides and Other Molecules
  申请人：McBride William J.

  公开号：US20090155166A1

  公开（公告）日：2009-06-18

  The present application discloses compositions and methods of synthesis and use of F-18 labeled molecules of use, for example, in PET imaging techniques. The labeled molecules may be peptides or proteins, although other types of molecules may be labeled by the described methods. Preferably, the F-18 may be conjugated to a targeting molecule by formation of a metal complex and binding of the F-18-metal complex to a chelating moiety. Alternatively, the metal may first be conjugated to the chelating group and subsequently the F-18 bound to the metal. In other embodiments, the F-18 labeled moiety may comprise a targetable construct used in combination with a bispecific or multi specific antibody to target F-18 to a disease-associated antigen, such as a tumor-associated antigen. The F-18 labeled targetable construct peptides are stable in serum at 37° C. for a sufficient time to perform PET imaging analysis.
• US7993626B2
  申请人：——

  公开号：US7993626B2

  公开（公告）日：2011-08-09
• Rational Design and Generation of a Bimodal Bifunctional Ligand for Antibody-Targeted Radiation Cancer Therapy
  作者：Hyun-Soon Chong、Xiang Ma、Thien Le、Baidoo Kwamena、Diane E. Milenic、Erik D. Brady、Hyun A. Song、Martin W. Brechbiel

  DOI：10.1021/jm070401q

  日期：2008.1.1

  An antibody-targeted radiation therapy (radioimmunotherapy, RIT) employs a bifunctional ligand that can effectively hold a cytotoxic metal with clinically acceptable complexation kinetics and stability while being attached to a tumor-specific antibody. Clinical exploration of the therapeutic potential of RIT has been challenged by the absence of adequate ligand, a critical component for enhancing the efficacy of the cancer therapy. To address this deficiency, the bifunctional ligand C-NETA in a unique structural class possessing both a macrocyclic cavity and a flexible acyclic moiety was designed. The practical, reproducible, and readily scalable synthetic route to C-NETA was developed, and its potential as the chelator of Bi-212, Bi-213, and Lu-177 for RIT was evaluated in vitro and in vivo. C-NETA rapidly binds both Lu(III) and Bi(III), and the respective metal complexes remain extremely stable in serum for 14 days. Lu-177-C-NETA and Bi-205/6-C-NETA possess an excellent or acceptable in vivo biodistribution profile.