tert-butyl 3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1(15),11,13-triene-6-acetate | 353246-09-0

• 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 3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1(15),11,13-triene-6-acetate
• 英文别名: tert-butyl 2-(3,6,9-triaza-1(2,6)-pyridinacyclodecaphane-6-yl)acetate；Tert-butyl 2-(3,6,9,15-tetrazabicyclo[9.3.1]pentadeca-1(15),11,13-trien-6-yl)acetate；tert-butyl 2-(3,6,9,15-tetrazabicyclo[9.3.1]pentadeca-1(15),11,13-trien-6-yl)acetate
• CAS: 353246-09-0
• 化学式: C₁₇H₂₈N₄O₂
• 分子量: 320.435
• InChiKey: BNSLBWRRTNILSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1(15),11,13-triene-6-acetate 在 盐酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 48.0h， 生成 6-(carboxymethyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1(15),11,13-triene-3,9-dipropanoic acid
  参考文献：
  名称：

  Regioselective synthesis of N-functionalized 12-membered azapyridinomacrocycles bearing trialkylcarboxylic acid side chains

  摘要：

  Selective protection of primary amine moieties of diethylenetriamine by 2-nitrophenylsulfonyl chloride followed by alkylation of the central N atom generates functionalized disulfonamide building blocks. When reacted with 2,6-bis(bromomethyl)pyridine following the Richman-Atkins methodology, such compounds yield the corresponding pyridine-containing azamacrocycles. Smooth removal of the N-sulfonyl groups provides versatile azamacrocyclic intermediates with transannular secondary amine functions. Subsequent N-alkylation regioselectively leads to tri N-functionalized 12-membered azapyridinomacrocycles bearing a sequence of N-acetate and N-propionate side chains. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00328-3
• 作为产物：
  描述：

  tert-butyl 3,9-bis(2-nitrophenylsulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1(15),11,13-triene-6-acetate 在 sodium carbonate 、 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以0.835 g的产率得到tert-butyl 3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1(15),11,13-triene-6-acetate
  参考文献：
  名称：

  MACROCYLIC LIGANDS WITH PICOLINATE GROUP(S), COMPLEXES THEREOF AND ALSO MEDICAL USES THEREOF

  摘要：

  本发明涉及在医学成像和/或治疗中有用的化合物、配体和/或络合物，特别是在癌症治疗中有用的化合物、配体和/或络合物。本发明还涉及一种包含上述化合物、配体和/或络合物的药物组合物，用于医学成像、靶向和/或治疗癌症。本发明还涉及一种制备这些化合物、配体和/或络合物的方法。

  公开号：

  US20190023705A1

文献信息

• [EN] PYCLEN-BASED MACROCYCLIC LIGANDS, CHELATES THEREOF AND USES THEREOF<br/>[FR] LIGANDS MACROCYCLIQUES À BASE DE PYCLEN, LEURS CHÉLATES ET LEURS UTILISATIONS
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2019185901A1

  公开（公告）日：2019-10-03

  The present invention relates to a ligand of Formula (A): or a carboxylate salt thereof; wherein Y1, Y2 and Y3 each independently represents -COOH or a picolinate of Formula (i): wherein each R1 independently represents a chromophore group; L1, L2 and L3 each independently represents a single bond or a linker; and X1, X2 and X3 each independently represents a hydrogen atom, a coupling function or a bio -vectorizing group. The present invention further relates to a process for manufacturing the ligand and to a process for manufacturing a chelate by means of complexation by the ligand of a rare-earth cation, preferably a lanthanide cation. The present invention further relates to the use of the ligand and/or the chelate in biological imaging and/or photoluminescence imaging.

  本发明涉及化合物配体的公式（A）：或其羧酸盐；其中Y1、Y2和Y3分别独立地代表-COOH或公式（i）的吡啶酸盐，其中每个R1独立地代表一个色团基团；L1、L2和L3分别独立地代表一个单键或一个连接基团；X1、X2和X3分别独立地代表氢原子、偶联功能或生物矢量化基团。本发明还涉及一种制备该配体的方法，以及通过该配体与稀土阳离子，优选为镧系阳离子，形成络合物的方法。本发明还涉及该配体和/或络合物在生物成像和/或光致发光成像中的应用。
• Pyclen-Based Ln(III) Complexes as Highly Luminescent Bioprobes for <i>In Vitro</i> and <i>In Vivo</i> One- and Two-Photon Bioimaging Applications
  作者：Nadège Hamon、Amandine Roux、Maryline Beyler、Jean-Christophe Mulatier、Chantal Andraud、Christophe Nguyen、Marie Maynadier、Nadir Bettache、Alain Duperray、Alexei Grichine、Sophie Brasselet、Magali Gary-Bobo、Olivier Maury、Raphaël Tripier

  DOI：10.1021/jacs.0c03496

  日期：2020.6.3

  In addition to the already described ligand L-4a, two pyclen-based lanthanide chelators, L-4b and L-4c, bearing two specific picolinate two-photon antennas (tailor-made for each targeted metal) and one acetate arm arranged in a dissymmetrical manner, have been synthesized, to form a complete family of lanthanide luminescent bioprobes: [EuL4a], [SmL4a], [YbL4b], [TbL4c], and [DyL4c]. Additionally, the symmetrically arranged regioisomer L-4a' was also synthesized as well as its [EuL4a'] complex to highlight the astonishing positive impact of the dissymmetrical N-distribution of the functional chelating arms. The investigation clearly shows the high performance of each bioprobe, which, depending on the complexed lanthanide, could be used in various applications. Each presents high brightness, quantum yields, and lifetimes. Staining of the complexes into living human breast cancer cells was observed. In addition, in vivo two-photon microscopy was performed for the first time on a living zebrafish model with [EuL4a]. No apparent toxicity was detected on the growth of the zebrafish, and images of high quality were obtained.
• PYCLEN-BASED MACROCYCLIC LIGANDS, CHELATES THEREOF AND USES THEREOF
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US20210017180A1

  公开（公告）日：2021-01-21

  A ligand of Formula (A): or a carboxylate salt thereof; wherein Y 1 , Y 2 and Y 3 each independently represents —COOH or a picolinate of Formula (i): wherein each R 1 independently represents a chromophore group; L 1 , L 2 and L 3 each independently represents a single bond or a linker; and X 1 , X 2 and X 3 each independently represents a hydrogen atom, a coupling function or a bio-vectorizing group. Also, a process for manufacturing the ligand and to a process for manufacturing a chelate by complexation by the ligand of a rare-earth cation, preferably a lanthanide cation. Further, a use of the ligand and/or the chelate in biological imaging and/or photoluminescence imaging.