1-[4-[2-[2-(2-Prop-2-ynoxyethoxy)ethoxy]ethoxy]benzoyl]azetidin-2-one | 1145938-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1-[4-[2-[2-(2-Prop-2-ynoxyethoxy)ethoxy]ethoxy]benzoyl]azetidin-2-one
• CAS: 1145938-06-2
• 化学式: C₁₉H₂₃NO₆
• 分子量: 361.395
• InChiKey: CVQSZJXZABCSDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[4-[2-[2-(2-Prop-2-ynoxyethoxy)ethoxy]ethoxy]benzoyl]azetidin-2-one 、 2-((2S,5R,8S,11S)-8-(1-azido-10,13-dioxo-3,6-dioxa-9,14-diazaoctadecan-18-yl)-5-benzyl-11-(3-guanidinopropyl)-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentaazacyclopentadecan-2-yl)acetic acid 在 Cu(I):TBTA complex (1:2) 作用下， 以 乙腈 为溶剂， 以92%的产率得到
  参考文献：
  名称：

  β-Lactam-based approach for the chemical programming of aldolase antibody 38C2

  摘要：

  Irreversible chemical programming of monoclonal aldolase antibody (mAb) 38C2 has been accomplished with beta-lactam-equipped targeting modules. A model study was first performed with beta-lactam conjugated to biotin. This conjugate efficiently and selectively modified the catalytic site lysine (LysH93) of mAb 38C2. We then conjugated a beta-lactam to a cyclic-RGD peptide to chemically program mAb 38C2 to target integrin receptors alpha(nu)beta(3) and alpha(nu)beta(5). The chemically programmed antibody bound specifically to the isolated integrin receptor proteins as well as the integrins expressed on human melanoma cells. This approach provides an efficient and versatile solution to irreversible chemical programming of aldolase antibodies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.028
• 作为产物：
  描述：

  2-氮杂环丁酮 、 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 1-[4-[2-[2-(2-Prop-2-ynoxyethoxy)ethoxy]ethoxy]benzoyl]azetidin-2-one
  参考文献：
  名称：

  双特异性抗体和高价抗体的有效化学方法

  摘要：

  单克隆醛缩酶抗体 (mAb) 38C2 的不可逆化学编程已通过配备单功能和双功能靶向模块的 β-内酰胺完成，包括连接到肽 ( d -Lys 6 )-LHRH 或另一个环状 RGD 单元的环状 RGD肽以及与 ( d -Lys 6 )LHRH结合的小分子整联蛋白抑制剂 SCS-873 。我们还准备了包含环状 RGD 或 ( d -Lys 6)-LHRH 肽。评估了化学程序化抗体与整联蛋白受体 α(v)β(3) 和 α(v)β(5) 以及促黄体激素释放激素受体的结合。双功能和二价 c-RGD/LHRH 和 SCS-783/LHRH、单功能和四价 c-RGD/c-RGD 和单功能二价 c-RGD 化学程序化抗体与分离的整联蛋白受体蛋白特异性结合以及在人黑色素瘤 M-21 细胞上表达的整合素。c-RGD/LHRH、SCS-783/LHRH 和 LHRH 化学程序化抗体与人卵巢癌细胞上表达的 LHRH

  DOI：

  10.1016/j.bmcl.2009.05.047

文献信息

• An efficient chemical approach to bispecific antibodies and antibodies of high valency
  作者：Julia I. Gavrilyuk、Ulrich Wuellner、Syed Salahuddin、Rajib K. Goswami、Subhash C. Sinha、Carlos F. Barbas

  DOI：10.1016/j.bmcl.2009.05.047

  日期：2009.7

  bifunctional targeting modules, including a cyclic-RGD peptide linked to either the peptide (d-Lys6)-LHRH or another cyclic RGD unit and a small-molecule integrin inhibitor SCS-873 conjugated to (d-Lys6)LHRH. We also prepared monofunctional targeting modules containing either cyclic RGD or (d-Lys6)-LHRH peptides. Binding of the chemically programmed antibodies to integrin receptors α(v)β(3) and α(v)β(5) and

  单克隆醛缩酶抗体 (mAb) 38C2 的不可逆化学编程已通过配备单功能和双功能靶向模块的 β-内酰胺完成，包括连接到肽 ( d -Lys 6 )-LHRH 或另一个环状 RGD 单元的环状 RGD肽以及与 ( d -Lys 6 )LHRH结合的小分子整联蛋白抑制剂 SCS-873 。我们还准备了包含环状 RGD 或 ( d -Lys 6)-LHRH 肽。评估了化学程序化抗体与整联蛋白受体 α(v)β(3) 和 α(v)β(5) 以及促黄体激素释放激素受体的结合。双功能和二价 c-RGD/LHRH 和 SCS-783/LHRH、单功能和四价 c-RGD/c-RGD 和单功能二价 c-RGD 化学程序化抗体与分离的整联蛋白受体蛋白特异性结合以及在人黑色素瘤 M-21 细胞上表达的整合素。c-RGD/LHRH、SCS-783/LHRH 和 LHRH 化学程序化抗体与人卵巢癌细胞上表达的 LHRH
• Chemically Programmed Vaccination
  申请人：Barbas, III Carlos F.

  公开号：US20110311516A1

  公开（公告）日：2011-12-22

  Provided herein is a method for chemically programmed vaccination. Methods include inducing a covalent-binding polyclonal antibody response in a subject and programming the polyclonal response with a targeting compound.
• US8518927B2
  申请人：——

  公开号：US8518927B2

  公开（公告）日：2013-08-27
• β-Lactam-based approach for the chemical programming of aldolase antibody 38C2
  作者：Julia I. Gavrilyuk、Ulrich Wuellner、Carlos F. Barbas

  DOI：10.1016/j.bmcl.2009.01.028

  日期：2009.3

  Irreversible chemical programming of monoclonal aldolase antibody (mAb) 38C2 has been accomplished with beta-lactam-equipped targeting modules. A model study was first performed with beta-lactam conjugated to biotin. This conjugate efficiently and selectively modified the catalytic site lysine (LysH93) of mAb 38C2. We then conjugated a beta-lactam to a cyclic-RGD peptide to chemically program mAb 38C2 to target integrin receptors alpha(nu)beta(3) and alpha(nu)beta(5). The chemically programmed antibody bound specifically to the isolated integrin receptor proteins as well as the integrins expressed on human melanoma cells. This approach provides an efficient and versatile solution to irreversible chemical programming of aldolase antibodies. (C) 2009 Elsevier Ltd. All rights reserved.