N-(3-aminopropyl)-6-hydroxymethylnicotinamide | 780781-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(3-aminopropyl)-6-hydroxymethylnicotinamide
• 英文别名: N-(3-aminopropyl)-6-(hydroxymethyl)pyridine-3-carboxamide
• CAS: 780781-62-6
• 化学式: C₁₀H₁₅N₃O₂
• 分子量: 209.248
• InChiKey: IYHZQHUZZVTBJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  88.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-aminopropyl)-6-hydroxymethylnicotinamide 在 manganese(IV) oxide 作用下， 以 氯仿 、 乙腈 、 苯 为溶剂， 反应 30.0h， 生成 (3-{[6-({(E)-(1S,3R,5S)-3,5-Bis-[(pyridin-2-ylmethyl)-amino]-cyclohexylimino}-methyl)-pyridine-3-carbonyl]-amino}-propyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and Potent Antitumor Activities of Novel 1,3,5-cis,cis-Triaminocyclohexane N-Pyridyl Derivatives

  摘要：

  The iron chelator N,N',N"-tris(2-pyridylmethyl)-cis,cis-1,3,5-triaminocyclohexane (tachpyr) was recently reported to display potent antitumor activity. The present study was focused on identifying an adequate bifunctional version of tachpyr as a lead compound for use in antibody-targeted iron depletion tumor therapy. Preparation of tachpyr derivatives having a side chain is reported, and their cytotoxic activity is evaluated in the HeLa cell line. The observed cytotoxity appears dependent on the functionalization site of the tachpyr employed for introducing the protein conjugation. Tachpyr derivatives 14 and 15 having a side chain introduced into the 5-position of the pyridyl ring display more potent cytotoxicity than tachpyr derivatives 7 and 8 having a side chain introduced onto one of the secondary amines. BOC-protected tachpyr derivative 14 exhibited the most potent cytotoxicity against this cancer cell line, which was reasonably comparable to the parent tachpyr. Tachpyr derivative 14 was further converted into bifunctional tachpyr 17 possessing a maleimide linker for conjugation with thiolated monoclonal antibodies (mAbs).

  DOI：

  10.1021/jm040076w
• 作为产物：
  描述：

  2,5-吡啶-二羧酸二甲酯 在 sodium tetrahydroborate 、 calcium chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 24.0h， 生成 N-(3-aminopropyl)-6-hydroxymethylnicotinamide
  参考文献：
  名称：

  固相合成作为发现新型钌配合物的平台，以有效释放可见光照射的光笼配体

  摘要：

  钌基光笼基团作为生物工具具有重要的应用，并显示出巨大的治疗潜力。开发了一种快速合成，筛选和鉴定基于钌的笼形基团的方法，该基团会在可见光照射下释放出腈。在聚苯乙烯树脂上合成了多样化的四齿和五齿配体库。通式[Ru（L）（MeCN）n ] m +（n = 1-3，m的钌配合物= 1-2）是从固相上的这些配体生成的，然后从树脂上裂解下来进行光化学分析。数据表明光谱调谐和与可见光的反应性范围很广。通过溶液相合成了在可见光范围内显示出强吸收性的三种配合物用于比较。溶液和固相复合物的光化学行为非常吻合，这证实了文库方法可用于在短期内鉴定具有所需光反应性的候选物，从而避免了耗时的色谱法和化合物纯化。

  DOI：

  10.1021/ic502791y

文献信息

• [EN] MULTIFUNCTIONAL CHELATORS, COMPLEXES, AND COMPOSITIONS THEREOF, AND METHODS OF USING SAME<br/>[FR] CHÉLATEURS MULTIFONCTIONNELS, COMPLEXES, ET COMPOSITIONS DE CEUX-CI, ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ILLINOIS TECHNOLOGY INST

  公开号：WO2015051362A1

  公开（公告）日：2015-04-09

  Multifunctional chelators, metal complexes thereof, compositions thereof, and methods of making and use in diagnostic imaging and treatment of cellular disorders.

  多功能螯合剂，其金属配合物，组合物以及在细胞疾病的诊断成像和治疗中的制备和使用方法。
• MULTIFUNCTIONAL CHELATORS, COMPLEXES, AND COMPOSITIONS THEREOF, AND METHODS OF USING SAME
  申请人：ILLINOIS INSTITUTE OF TECHNOLOGY

  公开号：US20160235870A1

  公开（公告）日：2016-08-18

  Multifunctional chelators, metal complexes thereof, compositions thereof, and methods of making and use in diagnostic imaging and treatment of cellular disorders.

  多功能螯合剂，其金属配合物，组合物以及在诊断成像和治疗细胞疾病方面的制备和使用方法。
• Multifunctional chelators, complexes, and compositions thereof, and methods of using same
  申请人：ILLINOIS INSTITUTE OF TECHNOLOGY

  公开号：US10441669B2

  公开（公告）日：2019-10-15

  Multifunctional chelators, metal complexes thereof, compositions thereof, and methods of making and use in diagnostic imaging and treatment of cellular disorders.

  多功能螯合剂、其金属复合物、其组合物，以及在诊断成像和治疗细胞疾病中的制造和使用方法。
• Solid-Phase Synthesis as a Platform for the Discovery of New Ruthenium Complexes for Efficient Release of Photocaged Ligands with Visible Light
  作者：Rajgopal Sharma、Jessica D. Knoll、Nicholas Ancona、Phillip D. Martin、Claudia Turro、Jeremy J. Kodanko

  DOI：10.1021/ic502791y

  日期：2015.2.16

  great potential as therapeutics. A method was developed to rapidly synthesize, screen, and identify ruthenium-based caging groups that release nitriles upon irradiation with visible light. A diverse library of tetra- and pentadentate ligands was synthesized on polystyrene resin. Ruthenium complexes of the general formula [Ru(L)(MeCN)n]m+ (n = 1–3, m = 1–2) were generated from these ligands on solid phase

  钌基光笼基团作为生物工具具有重要的应用，并显示出巨大的治疗潜力。开发了一种快速合成，筛选和鉴定基于钌的笼形基团的方法，该基团会在可见光照射下释放出腈。在聚苯乙烯树脂上合成了多样化的四齿和五齿配体库。通式[Ru（L）（MeCN）n ] m +（n = 1-3，m的钌配合物= 1-2）是从固相上的这些配体生成的，然后从树脂上裂解下来进行光化学分析。数据表明光谱调谐和与可见光的反应性范围很广。通过溶液相合成了在可见光范围内显示出强吸收性的三种配合物用于比较。溶液和固相复合物的光化学行为非常吻合，这证实了文库方法可用于在短期内鉴定具有所需光反应性的候选物，从而避免了耗时的色谱法和化合物纯化。
• Synthesis and Potent Antitumor Activities of Novel 1,3,5-<i>cis,cis</i>-Triaminocyclohexane <i>N</i>-Pyridyl Derivatives
  作者：Hyun-Soon Chong、Suzy V. Torti、Rong Ma、Frank M. Torti、Martin W. Brechbiel

  DOI：10.1021/jm040076w

  日期：2004.10.1

  The iron chelator N,N',N"-tris(2-pyridylmethyl)-cis,cis-1,3,5-triaminocyclohexane (tachpyr) was recently reported to display potent antitumor activity. The present study was focused on identifying an adequate bifunctional version of tachpyr as a lead compound for use in antibody-targeted iron depletion tumor therapy. Preparation of tachpyr derivatives having a side chain is reported, and their cytotoxic activity is evaluated in the HeLa cell line. The observed cytotoxity appears dependent on the functionalization site of the tachpyr employed for introducing the protein conjugation. Tachpyr derivatives 14 and 15 having a side chain introduced into the 5-position of the pyridyl ring display more potent cytotoxicity than tachpyr derivatives 7 and 8 having a side chain introduced onto one of the secondary amines. BOC-protected tachpyr derivative 14 exhibited the most potent cytotoxicity against this cancer cell line, which was reasonably comparable to the parent tachpyr. Tachpyr derivative 14 was further converted into bifunctional tachpyr 17 possessing a maleimide linker for conjugation with thiolated monoclonal antibodies (mAbs).