1,4,7-triazacyclononane-1-acetic acid | 120703-02-8

• 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: 1,4,7-triazacyclononane-1-acetic acid
• 英文别名: 2-(1,4,7-Triazonan-1-yl)acetic acid
• CAS: 120703-02-8
• 化学式: C₈H₁₇N₃O₂
• 分子量: 187.242
• InChiKey: SQWPTEOHBLSZQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  64.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4,7-triazacyclononane-1-acetic acid 、 copper dichloride 在 NaOH 作用下， 以 甲醇 为溶剂， 以77%的产率得到[(1,4,7-triazacyclononane-N-acetate)CuCl]
  参考文献：
  名称：

  Schulz, Daniela; Weyhermueller, Thomas; Wieghardt, Karl, Inorganica Chimica Acta, 1996, vol. 246, # 1-2 SPEC. ISSUE, p. 387 - 394

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4,7-三氮杂环壬烷 在 N,N-二甲基甲酰胺二甲基缩醛 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 77.0h， 生成 1,4,7-triazacyclononane-1-acetic acid
  参考文献：
  名称：

  The Influence of the Combination of Carboxylate and Phosphinate Pendant Arms in 1,4,7-Triazacyclononane-Based Chelators on Their 68Ga Labelling Properties

  摘要：

  为了比较带有不同数量的膦酸/羧酸悬垂基团的 1,4,7-三氮杂环壬烷（tacn）衍生物对 68Ga 的配位性质，研究人员利用曼尼希反应合成了 1,4,7-三氮杂环壬烷-7-乙酸-1,4-双(亚甲基膦酸)（NOPA）和 1、1,4,7- 三氮杂环壬烷-4,7-二乙酸-1-[亚甲基（2-羧乙基）膦酸]（NO2AP）是以三价或五价形式的 H-膦酸作为磷组分，通过曼尼希反应合成的。经电位测定，NOPA 的阶跃质子化常数 logK1-3 为 12.06、3.90 和 1.95，与 GaIII 和 CuII 的稳定性常数 logKGaL 为 24.01，logKCuL 为 16.66。用 68Ga 标记了这两种配体，并将其与 NOTA（tacn-N,N′,N″-三乙酸）和 NOPO（一种 TRAP 型[tacn-N,N′,N″-三（亚甲基膦酸）]螯合剂）进行了比较。在 pH 值为 3 时，与 NO2AP 和 NOTA 相比，NOPO 和 NOPA 在室温和 95 ℃ 下的标记效率更高（以较低的配体过量结合）。pH = 0-3 时的标记效率与膦酸悬臂的数量有关：NOPO >> NOPA >> NO2AP >> NOTA；不过，在 95 °C 时比室温时更明显。相比之下，与含膦酸的配体相比，NOTA 在 pH > 4 时的标记效率更高。总的来说，用羧酸盐取代单一的膦酸盐供体不会对 TRAP 型螯合剂的 68Ga 标记造成挑战。不过，羧酸盐的存在有利于在中性或弱酸性 pH 下进行标记。

  DOI：

  10.3390/molecules200713112

文献信息

• A general synthesis of mono- and disubstituted 1,4,7-triazacyclononanes
  作者：Zoltan Kovacs、A. Dean Sherry

  DOI：10.1016/0040-4039(95)02009-e

  日期：1995.12

  1,4,7-Triazacyclononane reacts selectively with 2-(t-butoxycarbonyloxyimino)- and 2-(benzyloxycarbonyloxyimino)-2-phenylacetonitrile to give 1,4-diprotected derivatives which could be converted to mono and disubstituted triazacyclononanes.

  1,4,7-三氮杂环壬烷与2-（叔丁氧羰基氧基亚氨基）-和2-（苄氧羰基氧基亚氨基）-2-苯基乙腈选择性反应，生成1,4-二保护的衍生物，可将其转化为单和二取代的三氮杂环壬烷。
• Peptide purification by means of hard metal ion affinity chromatography
  申请人：Hearn Milton Thomas William

  公开号：US20090143529A1

  公开（公告）日：2009-06-04

  A polymer substrate functionalized with a functionality comprising at least one cyclic, metal ion coordinating ligand group which comprises at least 3 nitrogen donor atoms in the ring of the cyclic group, at least one of the nitrogen atoms having an optionally substituted carboxy(lower alkyl) or optionally substituted phosphono(lower alkyl) group covalently attached thereto, is well suited for use in conjunction with “hard” metal ions of low toxicity (such as Ca 2+ , Mg 2+ or Fe 3+ ) in the separation/purification of appropriately “tagged” polypeptides by Immobilized Metal ion Affinity Chromatography (IMAC).

  一种聚合物基底，其功能化包括至少一个环状金属离子配位配体基团，该基团在环状结构中至少包含3个氮供体原子，其中至少一个氮原子具有可选择性取代的羧酸（较低烷基）或可选择性取代的膦酸（较低烷基）基团共价连接，非常适合与低毒性的“硬”金属离子（例如Ca2+，Mg2+或Fe3+）一起在固定金属离子亲和层析（IMAC）中用于分离/纯化适当“标记”的多肽。
• Aza macrocycles and processes for their preparation
  申请人：CELLTECH THERAPEUTICS LIMITED

  公开号：EP0382583A1

  公开（公告）日：1990-08-16

  Aza macrocycles of the formula (1) wherein A is a group -(CH₂)p- or -(CH₂)p N(R)(CH₂)q- where R is a group -CH(R⁴)X⁴; m, n, p, and q, which may be the same or different, is each an integer 2 or 3; R¹, R², R³ and R⁴, which may be the same or different, is each a group -CO₂H, -P(R⁵)O₂H (where R⁵ is a hydrogen atom or an alkyl or alkoxy group), -PO₃H₂ or -CONR⁶R⁷ (where R⁶ and R⁷, which may be the same or different is each a hydrogen atom or an alkyl group); X¹, X², X³ and X⁴, which may be the same or different, is each a hydrogen atom or an alkyl group, or a linker group, with the proviso that at least one of X¹, X², X³ or X⁴ is a linker group; and protected derivatives and metal complexes and/or salts thereof; are described together with processes for their preparation and compositions containing them. The compounds are useful for imaging and in the treatment of abnormal cell disorders, such as in the treatment of tumours, and may be coupled to other molecules such as proteins for use in diagnosis and therapy.

  式(1)的氮杂大环 其中 A 是基团 -(CH₂)p- 或 -(CH₂)p N(R)(CH₂)q- 其中 R 是基团 -CH(R⁴)X⁴； m、n、p 和 q（可以相同或不同）均为 2 或 3 的整数； R¹、R²、R³ 和 R⁴（可以相同或不同）各自是基团 -CO₂H、-P(R⁵)O₂H（其中 R⁵ 是氢原子或烷基或烷氧基）、-PO₃H₂或-CONR⁶R⁷（其中 R⁶ 和 R⁷ 可以相同或不同，各自为氢原子或烷基）； X¹、X²、X³和 X⁴（可以相同或不同）各自是氢原子或烷基或连接基，但 X¹、X²、X³或 X⁴ 中至少有一个是连接基；以及受保护的衍生物和金属配合物和/或其盐；这些化合物连同其制备工艺和含有它们的组合物一起进行了描述。这些化合物可用于成像和异常细胞疾病的治疗，如肿瘤的治疗，也可与其他分子如蛋白质结合用于诊断和治疗。
• Toward Protein-Cleaving Catalytic Drugs: Artificial Protease Selective for Myoglobin
  作者：Joong Won Jeon、Sang Jun Son、Chang Eun Yoo、In Seok Hong、Junghun Suh

  DOI：10.1016/s0968-0896(03)00216-5

  日期：2003.7

  A protein-cleaving catalyst highly selective for a disease-related protein can be used as a catalytic drug. As the first protein-cleaving catalyst selective for a protein substrate, a catalyst for myoglobin (Mb) was designed by attaching the Cu(II) or Co(III) complex of cyclen to a binding site searched by a combinatorial method using peptide nucleic acid monomers as building units. Various linkers were inserted between the catalytic Co(III) center and the binding site of the Mb-cleaving catalyst. Kinetic data revealed catalytic turnover of the Mb cleavage by the Cu(II) or Co(III) complex. MALDI-TOF MS revealed cleavage of the polypeptide backbone of Mb at selected positions. N-Terminal sequencing of the cleavage products identified the cleavage site and provided evidence for the hydrolytic nature of the Mb cleavage. Various chelating ligands were tested as the ligand for the Co(III) center of the Mb-cleaving catalyst. Among the nine chelating ligands examined, only cyclen and its triaza-monooxo analogue manifested catalytic activity. (C) 2003 Elsevier Science Ltd. All rights reserved.
• SYNTHESIS OF POLYAZAMACROCYCLES WITH MORE THAN ONE TYPE OF SIDE-CHAIN CHELATING GROUPS
  申请人：BOARD OF REGENTS THE UNIVERSITY OF TEXAS SYSTEM

  公开号：EP0618910A1

  公开（公告）日：1994-10-12