6-[2-(叔丁氧羰基)肼基]烟酸 | 133081-25-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他氨基酸衍生物
• 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
• 中文名称: 6-[2-(叔丁氧羰基)肼基]烟酸
• 英文名称: 6-BOC-hydrazinopyridine-3-carboxylic acid
• 英文别名: 6-(2-(tert-butoxycarbonyl)hydrazinyl)nicotinic acid；Boc-6-hydrazinonicotinic acid；6-Boc-hydrazinonicotinic acid；6-(tert-butoxycarbonyl)-hydrazinopyridine-3-carboxylic acid；6-(N′-Boc-hydrazino)nicotinic acid；N-Boc 4-hydrazino nicotinic acid；6-[2-[(2-methylpropan-2-yl)oxycarbonyl]hydrazinyl]pyridine-3-carboxylic acid
• CAS: 133081-25-1
• 化学式: C₁₁H₁₅N₃O₄
• 分子量: 253.258
• InChiKey: DBNGJNCAXKNLLQ-UHFFFAOYSA-N

物化性质

• 熔点：
  126 °C
• 密度：
  1.312
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  温度：2-8°C，保持在惰性气体氛围中。

反应信息

• 作为反应物：
  描述：

  6-[2-(叔丁氧羰基)肼基]烟酸 在 盐酸 作用下， 反应 16.0h， 生成 6-肼基烟酸
  参考文献：
  名称：

  Trifluoroacetyl-HYNIC Peptides:  Synthesis and ^99mTc Radiolabeling

  摘要：

  Fmoc-lys(HYNIC-Boc)-OH, a precursor for solid-phase synthesis of Tc-99m-labeled peptides, was synthesized efficiently without HPLC purification. HPLC-ESMS showed that deprotection and decoupling of peptide from the resin with trifluoroacetic acid gave initially HYNIC-peptide, which was trifluoroacetylated upon prolonged incubation. The trifluoroacetyl-HYNIC group was hydrolyzed during Tc-99m labeling, rendering deprotection unnecessary. Trifluoroacetyl-HYNIC peptide was Tc-99m-labeled as efficiently, producing the same product, as HYNIC-peptide. These modifications enhance the versatility of HYNIC for Tc-99m peptide labeling.

  DOI：

  10.1021/jm061274l
• 作为产物：
  描述：

  6-氯烟酸 在 一水合肼 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-[2-(叔丁氧羰基)肼基]烟酸
  参考文献：
  名称：

  四氢ac啶衍生物作为乙酰胆碱酯酶抑制剂的合成及生物活性

  摘要：

  医学的当前状态不允许治疗神经退行性疾病，例如阿尔茨海默氏病（AD）。目前，AD的治疗受到严格限制。AD中使用的主要药物是乙酰胆碱酯酶抑制剂（AChEI），例如他克林，多奈哌齐，加兰他敏和卡巴拉汀，这些都不能促进认知和行为功能的长期改善。 在这项工作中，我们报告了他克林-6-肼基烟酰胺的新杂种的合成和生物学评估。该合成基于他克林衍生物与烟酸肼部分（HYNIC）之间的缩合反应。所有获得的化合物都对两种胆碱酯酶都具有亲和力，并且相对于丁酰胆碱酯酶（BChE）具有高选择性。

  DOI：

  10.1016/j.bioorg.2011.05.001

文献信息

• Synthesis and Stability Evaluation of New HYNIC Derivatives as Ligands for Technetium-99m
  作者：Yoann Joyard、Laurent Bischoff、Vincent Levacher、Cyril Papamicael、Pierre Vera、Pierre Bohn

  DOI：10.2174/15701786113106660087

  日期：2014.2

  An efficient synthetic route to prepare two new HYNIC derivatives with a 2-nitroimidazole moiety designed for tumor hypoxia imaging is described. During the course of the synthesis, the optimization of N-alkylation reaction of 2- nitroimidazole with propargyl bromide is reported to favor the formation of the terminal alkyne versus allene. Thereafter, the two ligands were used with tricine/EDDA to complex 99mTc. However, decomposition of these ligands was observed and we suggest a reasonable explanation based on LC-MS analysis.

  描述了一种高效的合成路线，用于制备两种新型HYNIC衍生物，它们含有2-硝基咪唑结构，设计用于肿瘤乏氧显像。在合成过程中，报道了对2-硝基咪唑与丙炔基溴的N-烷基化反应的优化，这有利于形成末端炔烃而非丙二烯。随后，这两种配体与tricine/EDDA一起用于络合99mTc。然而，观察到了这些配体的分解现象，我们基于LC-MS分析给出了一个合理的解释。
• [EN] TRI-FUNCTIONAL CROSSLINKING REAGENTS<br/>[FR] RÉACTIFS DE RÉTICULATION TRIFONCTIONNELS
  申请人：ETH ZUERICH

  公开号：WO2017081069A1

  公开（公告）日：2017-05-18

  The present invention relates to tri-functional crosslinking reagents carrying (i) a ligand-reactive group for conjugation to a ligand of interest having at least one binding site on a target glycoprotein receptor, (ii) a hydrazone group for the capturing of oxidized receptor-glycoproteins and (iii) an affinity group selected from azides and aklynes for the detection, isolation and purification of captured glycoproteins; as well as their manufacturing. The invention further provides for improved methods of detecting, identifying and characterizing interactions between ligands and their corresponding target glycoproteins on living cells and in biological fluids. The invention further provides for new uses of catalysts in such methods.

  本发明涉及携带（i）与感兴趣的配体结合的配体反应性基团，该配体在目标糖蛋白受体上至少具有一个结合位点，（ii）用于捕获氧化受体-糖蛋白的缩醛基团，以及（iii）从叠氮化物和炔烃中选择的亲和基团，用于检测、分离和纯化捕获的糖蛋白的三功能交联试剂；以及它们的制造。本发明还提供了改进的方法，用于检测、识别和表征配体与其相应目标糖蛋白在活细胞和生物体液中的相互作用。本发明还提供了在这些方法中使用催化剂的新用途。
• [EN] IMMUNOMODULATORY CONJUGATES<br/>[FR] CONJUGUÉS IMMUNOMODULATEURS
  申请人：ASCEND BIOPHARMACEUTICALS PTY LTD

  公开号：WO2013067597A1

  公开（公告）日：2013-05-16

  The present invention provides an immunomodulatory compound comprising a carbohydrate polymer comprising mannose, wherein the carbohydrate polymer is conjugated to at least one immune modulator. The present invention also provides for the use of this compound in immunomodulatory compositions for vaccination and gene therapy methods, together with processes for its preparation.

  本发明提供了一种免疫调节化合物，包括一种含有甘露糖的碳水化合物聚合物，其中该碳水化合物聚合物与至少一种免疫调节剂结合。本发明还提供了将该化合物用于免疫调节组合物、疫苗和基因治疗方法的用途，以及其制备方法。
• Melanoma Uptake of ^99mTc Complexes Containing the <i>N</i>-(2-Diethylaminoethyl)benzamide Structural Element
  作者：Michael Eisenhut、Ashour Mohammed、Walter Mier、Frank Schönsiegel、Matthias Friebe、Ashfaq Mahmood、Alun G. Jones、Uwe Haberkorn

  DOI：10.1021/jm021026z

  日期：2002.12.1

  benzamides by melanoma cells, (99m)Tc complexes containing the structural elements of N-(dialkylaminoalkyl)benzamide pharmacophores have been synthesized and evaluated in vitro and in vivo for melanoma uptake. One of the complexes Tc-12 containing the ligand 4-(S-benzoyl-2-thioacetyl-glycyl-glycylamido)-N-(2-diethylaminoethyl)benzamide (11) displayed the highest melanoma uptake. The 1-h melanoma uptake values

  基于黑色素瘤细胞对放射性碘化苯甲酰胺的摄取，已合成了含有N-（二烷基氨基烷基）苯甲酰胺药效团的结构元素的（99m）Tc复合物，并在体内和体外评估了其对黑色素瘤的摄取。含有配体4-（S-苯甲酰基-2-硫代乙酰基-甘氨酰-甘氨酰胺基）-N-（2-二乙基氨基乙基）苯甲酰胺的配合物Tc-12之一（11）显示出最高的黑素瘤摄取。1-h黑色素瘤摄取值和相应的血液计数表明，肿瘤摄取与（99m）Tc复合物的生物利用度具有相互依赖性。
• Synthesis and evaluation of a^99mTc-labeled tubulin-binding agent for tumor imaging
  作者：Mostafa Erfani、Mojtaba Shamsaei、Faiyaz Mohammadbaghery、Seyed Pezhman Shirmardi

  DOI：10.1002/jlcr.3200

  日期：2014.5.30

  Cholchicine and its derivatives are very potent tubulin-binding compounds and can be used as a potential tumor targeting agents. In this study, colchicine was labeled with 99mTc via hydrazinonicotinic acid (HYNIC) and was investigated further. HYNIC/cholchicine was synthesized and labeling with 99mTc was performed at 95 °C for 15 min and radiochemical analysis included HPLC method. The stability of radiconjugate was checked in the presence of human serum at 37 °C up to 24 h. Biodistribution was studied in breast tumor-bearing mice. Labeling yield of 95.8 ± 0.54% was obtained corresponding to a specific activity of 54 MBq/µmol. Radioconjugate showed good stability in the presence of human serum. Biodistribution studies in tumor-bearing mice showed that 99mTc/HYNIC/colchicine conjugate accumulated in tumor with good uptake (3.17 ± 0.14% g/g at 1 h post-injection). The radioconjugate was cleared fast from normal organs and showed clearance through urinary and hepatobiliary systems with accumulation of activity in kidneys and intestine. This radioconjugate may be useful to assess the presence of tumor by imaging.

  秋水仙碱及其衍生物是非常有效的微管蛋白结合化合物，可用作潜在的肿瘤靶向剂。在本研究中，秋水仙碱通过肼基烟酸（HYNIC）标记了99mTc，并进一步进行了研究。合成了HYNIC/秋水仙碱并在95°C下进行15分钟的99mTc标记，放射化学分析包括HPLC方法。在37°C下，在人血清存在下检查了放射性偶联物的稳定性，最长可达24小时。在携带乳腺癌的小鼠中研究了生物分布。获得了95.8±0.54%的标记产率，对应于54MBq/µmol的特定活性。放射性偶联物在人血清存在下显示出良好的稳定性。在肿瘤携带的小鼠中进行的生物分布研究表明，99mTc/HYNIC/秋水仙碱偶联物在肿瘤中积累，摄取良好（注射后1小时为3.17±0.14% g/g）。放射性偶联物从正常器官中快速清除，并通过泌尿和肝胆系统清除，在肾脏和肠道中积累活性。这种放射性偶联物可能有助于通过成像评估肿瘤的存在。