(2S,5S,8S,11S)-1,4,7,10-tetrabenzyl-2,5,8,11-tetrakis(4-methoxybenzyl)-1,4,7,10-tetraazacyclododecane | 1160293-95-7

• 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: (2S,5S,8S,11S)-1,4,7,10-tetrabenzyl-2,5,8,11-tetrakis(4-methoxybenzyl)-1,4,7,10-tetraazacyclododecane
• 英文别名: (2S,5S,8S,11S)-1,4,7,10-tetrabenzyl-2,5,8,11-tetrakis[(4-methoxyphenyl)methyl]-1,4,7,10-tetrazacyclododecane
• CAS: 1160293-95-7
• 化学式: C₆₈H₇₆N₄O₄
• 分子量: 1013.38
• InChiKey: IWJHPZPYLIFNIB-VPUOQKLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.1
• 重原子数：
  76
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,5S,8S,11S)-1,4,7,10-tetrabenzyl-2,5,8,11-tetrakis(4-methoxybenzyl)-1,4,7,10-tetraazacyclododecane 在 氯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以94%的产率得到
  参考文献：
  名称：

  Synthesis of Water-Soluble Chiral DOTA Lanthanide Complexes with Predominantly Twisted Square Antiprism Isomers and Circularly Polarized Luminescence

  摘要：

  One-step cyclization of a tetraazamacrocycle 5 with 70% yield in a 25-g scale was performed. Its chiral DOTA derivatives, L4, has similar to 93% of TSAP coordination isomer in its Eu(III) and Yb(III) complexes in aqueous solution. [GdL4](5-) exhibits a high relaxivity, making it a promising and efficient MRI contrast agent. High luminescence dissymmetry factor (g(lum)) values of 0.285 (Delta J = 1) for [TbL3](-) and 0.241 (Delta J = 1) for [TbL4](5-) in buffer solutions were recorded.

  DOI：

  10.1021/acs.inorgchem.9b01799
• 作为产物：
  描述：

  N-苄氧羰基-L-酪氨酸 在 甲醇 、 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 对甲苯磺酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 176.0h， 生成 (2S,5S,8S,11S)-1,4,7,10-tetrabenzyl-2,5,8,11-tetrakis(4-methoxybenzyl)-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  Synthesis of Water-Soluble Chiral DOTA Lanthanide Complexes with Predominantly Twisted Square Antiprism Isomers and Circularly Polarized Luminescence

  摘要：

  One-step cyclization of a tetraazamacrocycle 5 with 70% yield in a 25-g scale was performed. Its chiral DOTA derivatives, L4, has similar to 93% of TSAP coordination isomer in its Eu(III) and Yb(III) complexes in aqueous solution. [GdL4](5-) exhibits a high relaxivity, making it a promising and efficient MRI contrast agent. High luminescence dissymmetry factor (g(lum)) values of 0.285 (Delta J = 1) for [TbL3](-) and 0.241 (Delta J = 1) for [TbL4](5-) in buffer solutions were recorded.

  DOI：

  10.1021/acs.inorgchem.9b01799

文献信息

• Synthesis of chiral polyazamacrocycles of variable ring size
  作者：Seiji Kamioka、Sakae Sugiyama、Takashi Takahashi、Takayuki Doi

  DOI：10.1039/c001228a

  日期：——

  Synthesis and structure elucidation of optically active tri-, tetra-, and penta-azamacrocycles having 4-methoxyphenyl pendants are described. Regioselective ring opening of a nosylaziridine with secondary benzyl amines was repeatedly performed to afford the cyclization precursors. Intramolecular N-alkylation of N-(ω-haloalkyl) nosylamide provided tri-, tetra-, and penta-azamacrocycles. On the basis

  描述了具有4-甲氧基苯基侧基的旋光的三，四和五氮杂大环的合成和结构阐明。重复进行具有仲苄基胺的Nosylaziridine的区域选择性开环，以提供环化前体。N-（ω-卤代烷基）壬基酰胺的分子内N-烷基化提供了三，四和五氮杂ama环。根据我们先前通过X射线单晶分析阐明的四氮杂二十环的研究以及在NMR分析的溶液的基础上，我们得出结论，由于三氟氮杂六环的空间位阻，其主要不是花瓶型构象。 4-甲氧基苯基，但五氮杂双环在CDCl 3和CD 2 Cl 2。但是，五-金刚花环的花瓶型构象不如四-金刚花环中观察到的那样稳定，因为在氘代中观察到了五-金刚花环的构象柔性。苯。
• Chiral cyclen compounds and their uses
  申请人：THE HONG KONG POLYTECHNIC UNIVERSITY

  公开号：US11357873B2

  公开（公告）日：2022-06-14

  The present invention relates to the preparation of a series of chiral DOTA, DO3A, DO2A, DO1A, cyclen and their metal complexes, which display properties superior to those of previous DOTA-based compounds, and hence are potentially valuable as a platform for diagnostic applications. The chiral DOTAs reveal a high abundance of twisted square antiprism (TSA) geometry favoring them to be used as potential MRI contrast agents, whereas their rapid labelling properties at mild conditions make them excellent candidates for use as radiometal chelators.

  本发明涉及一系列手性 DOTA、DO3A、DO2A、DO1A、cyclen 及其金属配合物的制备，这些配合物显示出优于以往 DOTA 类化合物的特性，因此具有作为诊断应用平台的潜在价值。手性 DOTAs 显示出高丰度的扭曲方形反棱柱（TSA）几何形状，有利于它们用作潜在的核磁共振成像造影剂，而它们在温和条件下的快速标记特性使它们成为放射性金属螯合剂的绝佳候选化合物。
• WO2018051197A5
  申请人：——

  公开号：WO2018051197A5

  公开（公告）日：2022-06-01
• Chiral Tetraazamacrocycles Having Four Pendant-Arms
  作者：Seiji Kamioka、Takashi Takahashi、Susumu Kawauchi、Hiroaki Adachi、Yusuke Mori、Kotaro Fujii、Hidehiro Uekusa、Takayuki Doi

  DOI：10.1021/ol9005954

  日期：2009.6.4

  chiral tetraazamacrocycle 9 having four pendant-arms was synthesized by repeating ring opening of an Ns-aziridine with secondary amines, followed by macrocyclization. The structure of 9 has been determined by single crystal X-ray diffraction analysis and NMR studies. Sugar-hybrid molecules 12a-12f were synthesized based on the scaffold 9. NMR study showed that 12a-12f keep the similar conformation as 9 in solution.
• CHIRAL CYCLEN COMPOUNDS AND THEIR USES
  申请人：THE HONG KONG POLYTECHNIC UNIVERSITY

  公开号：US20210283278A1

  公开（公告）日：2021-09-16

  The present invention relates to the preparation of a series of chiral DOTA, DO3A, DO2A, DO1A, cyclen and their metal complexes, which display properties superior to those of previous DOTA-based compounds, and hence are potentially valuable as a platform for diagnostic applications. The chiral DOTAs reveal a high abundance of twisted square antiprism (TSA) geometry favoring them to be used as potential MRI contrast agents, whereas their rapid labelling properties at mild conditions make them excellent candidates for use as radiometal chelators.