ethyl N-(3-aminopropyl)-N-(pyridin-2-ylmethyl)glycinate | 857032-69-0

• 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: ethyl N-(3-aminopropyl)-N-(pyridin-2-ylmethyl)glycinate
• 英文别名: (N-3-aminopropyl-N-pyridin-2-ylmethyl-amino)acetic acid ethyl ester；Ethyl 2-[3-aminopropyl(pyridin-2-ylmethyl)amino]acetate
• CAS: 857032-69-0
• 化学式: C₁₃H₂₁N₃O₂
• 分子量: 251.329
• InChiKey: WPDRWNXVARRRQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(2-carbethoxyethyl)-2'-deoxyuridine 、 ethyl N-(3-aminopropyl)-N-(pyridin-2-ylmethyl)glycinate 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [(3-{3-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-propionylamino}-propyl)-pyridin-2-ylmethyl-amino]-acetic acid ethyl ester
  参考文献：
  名称：

  Mundwiler, S.; Alberto, R., Journal of Labelled Compounds and Radiopharmaceuticals, 2001, vol. 44, p. S494 - S495

  摘要：

  DOI：

文献信息

• [EN] COBALAMINE DERIVATIVES USEFUL FOR DIAGNOSIS AND TREATMENT OF ABNORMAL CELLULAR PROLIFERATION<br/>[FR] DERIVES DE LA COBALAMINE SERVANT AU DIAGNOSTIC ET AU TRAITEMENT DE LA PROLIFERATION CELLULAIRE ANORMALE
  申请人：SOLIDAGO AG

  公开号：WO2005061527A1

  公开（公告）日：2005-07-07

  The invention relates to cobalamin derivatives (a) having no binding affinity or low binding affinity to the transport protein transcobalamin II TCII) and (b) retaining activity as a vitamin B12 substitute, optionally carrying a therapeutic and/or diagnostic agent, such as a radioactive metal. These compounds have a much reduced accumulation rate in blood and benign organs, such as kidney and liver, compared to the accumulation rate in neoplastic tissues, and are more rapidly eliminated from blood. The invention further relates to a method of diagnosis and a method of treatment of a neoplastic disease or an infection by microorganisms in a mammal comprising (a) exposing the mammal to a period of a vitamin B12 - free diet, and (b) subsequently applying a cobalamin derivative of the invention carrying a diagnostic and/or therapeutic agent. By selecting cobalamin derivatives acting as vitamin B12 substitutes, the risk of the formation of resistant off­spring in neoplastic tissue is much reduced.

  该发明涉及一种钴胺衍生物（a），其与运输蛋白转钴胺II（TCII）无结合亲和力或低结合亲和力，并且（b）保留维生素B12替代物的活性，可选地携带治疗和/或诊断剂，如放射性金属。与在恶性组织中的积累速率相比，这些化合物在血液和良性器官（如肾脏和肝脏）中的积累速率大大降低，并且更快地从血液中排出。该发明还涉及一种诊断方法和治疗方法，用于治疗哺乳动物中的恶性疾病或由微生物感染引起的感染，包括（a）使哺乳动物暴露于维生素B12 - 无食物的饮食期间，以及（b）随后应用携带该发明的钴胺衍生物的诊断和/或治疗剂。通过选择作为维生素B12替代物的钴胺衍生物，大大降低了恶性组织中抵抗性后代形成的风险。
• Structures of the b‐ and d‐Acid Derivatives of Vitamin B ₁₂ and Their Complexes with [M(CO) ₃ ] ⁺ (M = ^99m Tc, Re)
  作者：Bernhard Spingler、Stefan Mundwiler、Pilar Ruiz‐Sánchez、Dave R. van Staveren、Roger Alberto

  DOI：10.1002/ejic.200601195

  日期：2007.6

  the b- and d-acid in 1 and 2, respectively. The reaction of 4 and 5 with the complex [Re(OH2)3(CO)3]+ in water gave the corresponding vitamin B12 derivatives 8 and 9, and the aqueous reaction of 4 and 5 with the complex [99mTc(OH2)3(CO)3]+ afforded the 99mTc homologues 10 and 11, respectively.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  天然维生素 B12 的酸水解产生几种产物，其中 corrin 骨架上的乙酰胺或丙酰胺侧链转化为相应的酸。这些酸可以衍生出更多的官能团。我们特别分离了 b- 和 d- 酸衍生物 1 和 2，因为在 corrin 环的这些位置上的功能化通常保持对维生素 B12 转运蛋白的亲和力完整。尽管 1H NMR 研究表明 1 和 2 的真实性似乎很明显，但它并没有得到 X 射线结构分析的支持。N-(3-氨基丙基)-N-(吡啶-2-基甲基)甘氨酸乙酯(3)通过肽合成方法与1和2中的羧酸根基团偶联，分别得到维生素B12衍生物4和5。4 和 5 的结构可以通过 X 射线分析表征，明确地证实了 1 和 2 中分别存在 b-和 d-酸。4和5与配合物[Re(OH2)3(CO)3]+在水中反应得到相应的维生素B12衍生物8和9，4和5与配合物[99mTc(OH2)3的水溶液反应得到相应的维生素B12衍生物8和9。 (CO)3]+
• Cobalamine derivatives useful for diagnosis and treatment of abnormal cellular proliferation
  申请人：Treichler Hans-Jorg

  公开号：US20070155692A1

  公开（公告）日：2007-07-05

  The invention relates to cobalamin derivatives (a) having no binding affinity or low binding affinity to the transport protein transcobalamin II TCII) and (b) retaining activity as a vitamin B12 substitute, optionally carrying a therapeutic and/or diagnostic agent, such as a radioactive metal. These compounds have a much reduced accumulation rate in blood and benign organs, such as kidney and liver, compared to the accumulation rate in neoplastic tissues, and are more rapidly eliminated from blood. The invention further relates to a method of diagnosis and a method of treatment of a neoplastic disease or an infection by microorganisms in a mammal comprising (a) exposing the mammal to a period of a vitamin B12-free diet, and (b) subsequently applying a cobalamin derivative of the invention carrying a diagnostic and/or therapeutic agent. By selecting cobalamin derivatives acting as vitamin B12 substitutes, the risk of the formation of resistant offspring in neoplastic tissue is much reduced.
• US7585852B2
  申请人：——

  公开号：US7585852B2

  公开（公告）日：2009-09-08
• Mundwiler, S.; Alberto, R., Journal of Labelled Compounds and Radiopharmaceuticals, 2001, vol. 44, p. S494 - S495
  作者：Mundwiler, S.、Alberto, R.

  DOI：——

  日期：——