5-碘吡啶-2-羧酸 | 32046-43-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 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: 5-碘吡啶-2-羧酸
• 中文别名: 5-吲哚吡啶-2-羧酸
• 英文名称: 5-Iodpicolinsaeure
• 英文别名: 5-iodopyridine-2-carboxylic acid；5-Iod-2-pyridin-carbonsaeure
• CAS: 32046-43-8
• 化学式: C₆H₄INO₂
• 分子量: 249.008
• InChiKey: VHBWDGNMKCLMCB-UHFFFAOYSA-N

物化性质

• 熔点：
  188-190 °C
• 沸点：
  355.2±27.0 °C(Predicted)
• 密度：
  2.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5-碘吡啶-2-羧酸 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 potassium [¹⁸F]fluoride 、 potassium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 间氯过氧苯甲酸 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成
  参考文献：
  名称：

  Development, Optimization, and Scope of the Radiosynthesis of 3/5-[¹⁸F]Fluoropyridines from Readily Prepared Aryl(pyridinyl) Iodonium Salts: The Importance of TEMPO and K₂CO₃

  摘要：

  A robust process for the radiosynthesis of 3/5-[F-18]fluoropyridines has been developed by radiofluorination of iodonium triflates using (KF)-F-18/(KCO3)-C-2/K-222 complex in the presence of TEMPO. Both electronically deficient and enriched iodonium salts were readily obtained from the corresponding 3/5-iodopyridines and afforded the corresponding 3/5-[F-18]fluoropyridines in 6-78% yields. The concentrations of K2CO3 and TEMPO were found to be crucial for the radiofluorination efficiency. The process was validated using two automated systems for the F-18-radiolabeling of 2-chloro and 2-carboxamido-5-fluoropyridines carried out in 10-20% yields.

  DOI：

  10.1021/acs.oprd.9b00021
• 作为产物：
  描述：

  5-氨基-2-吡啶羧酸 在 盐酸 、 尿素 、 potassium iodide 、 sodium nitrite 作用下， 生成 5-碘吡啶-2-羧酸
  参考文献：
  名称：

  Comparison of two synthetic methods to obtain [18F] N-(2-aminoethyl)-5-fluoropyridine-2-carboxamide, a potential MAO-B imaging tracer for PET

  摘要：

  化合物Ro 19-6327，即N-(2-氨基乙基)-5-氯吡啶-2-甲酰胺，已知能可逆且特异性地抑制单胺氧化酶B（MAO-B）。其123I标记的碘类似物N-(2-氨基乙基)-5-碘吡啶-2-甲酰胺（Ro 43-0463）已成功通过单光子发射断层扫描（SPET）在人体志愿者中进行了研究。因此，我们开发了相应的氟类似物N-(2-氨基乙基)-5-氟吡啶-2-甲酰胺与18F的合成及放射性标记，以进行正电子发射断层扫描（PET）研究与MAO-B相关的神经精神疾病。为此，我们采取了两种合成途径以实现18F放射性标记的亲电法和亲核法。当考虑到前体合成、束流时间、比活度和放射化学纯度等因素时，亲核法显示出优势。

  DOI：

  10.1002/jlcr.2580361005

文献信息

• Renal-selective prodrugs for control of renal sympathetic nerve activity in the treatment of hypertension
  申请人：G.D. Searle & Co.

  公开号：US20030220521A1

  公开（公告）日：2003-11-27

  Renal-selective prodrugs are described which are preferentially converted in the kidney to compounds capable of inhibiting synthesis of catecholamine-type neurotransmitters involved in renal sympathetic nerve activity. The prodrugs described herein are derived from inhibitor compounds capable of inhibiting one or more of the enzymes involved in catecholamine synthesis, such compounds being classifiable as tyrosine hydroxylase inhibitors, or as dopa-decarboxylase inhibitors, or as dopamine-&bgr;-hydroxylase inhibitors. These inhibitor compounds are linked to a chemical moiety, such as a glutamic acid derivative, by a cleavable bond which is recognized selectively by enzymes located predominantly in the kidney. The liberated inhibitor compound is then available in the kidney to inhibit one or more of the enzymes involved in catecholamine synthesis. Inhibition of renal catecholamine synthesis can suppress heightened renal nerve activity associated with sodium-retention related disorders such as hypertension. Conjugates of particular interest are glutamyl derivatives of dopamine-&bgr;-hydroxylase inhibitors, of which N-acetyl-&ggr;-glutamyl fusaric acid hydrazide (shown below) is preferred. 1

  本文描述了一种肾选择性的前药，其在肾脏中优先转化为能够抑制参与肾交感神经活动的儿茶酚型神经递质合成的化合物。本文所描述的前药来源于能够抑制儿茶酚合成中的一个或多个酶的抑制剂化合物，这些化合物可分类为酪氨酸羟化酶抑制剂，多巴脱羧酶抑制剂或多巴胺-&bgr;-羟化酶抑制剂。这些抑制剂化合物通过可被肾脏中大量存在的酶选择性识别的可裂解键与化学基团（如谷氨酸衍生物）连接。释放的抑制剂化合物然后可在肾脏中用于抑制儿茶酚合成中的一个或多个酶。抑制肾脏儿茶酚合成可抑制与钠潴留相关的疾病（如高血压）相关的增强肾脏神经活动。特别感兴趣的共轭物是多巴胺-&bgr;-羟化酶抑制剂的谷氨酰衍生物，其中N-乙酰-&ggr;-谷氨酰富萨酸肼（如下图所示）是首选。1
• Renal-selective prodrugs for control of renal smpathetic nerve activity in the treatment of hypertension
  申请人：G.D. Searle & Co.

  公开号：US20040101523A1

  公开（公告）日：2004-05-27

  Renal-selective prodrugs are described which are preferentially converted in the kidney to compounds capable of inhibiting synthesis of catecholamine-type neurotransmitters involved in renal sympathetic nerve activity. The prodrugs described herein are derived from inhibitor compounds capable of inhibiting one or more of the enzymes involved in catecholamine synthesis, such compounds being classifiable as tyrosine hydroxylase inhibitors, or as dopa-decarboxylase inhibitors, or as dopamine-&bgr;-hydroxylase inhibitors. These inhibitor compounds are linked to a chemical moiety, such as a glutamic acid derivative, by a cleavable bond which is recognized selectively by enzymes located predominantly in the kidney. The liberated inhibitor compound is then available in the kidney to inhibit one or more of the enzymes involved in catecholamine synthesis. Inhibition of renal catecholamine synthesis can suppress heightened renal nerve activity associated with sodium-retention related disorders such as hypertension. Conjugates of particular interest are glutamyl derivatives of dopamine-&bgr;-hydroxylase inhibitors, of which N-acetyl-&ggr;-glutamyl fusaric acid hydrazide (shown below) is preferred. 1

  本文描述了肾脏选择性前药，这些前药被优先转化为能够抑制与肾脏交感神经活动相关的儿茶酚类神经递质合成的化合物。所述前药源自能够抑制儿茶酚类合成中涉及的一个或多个酶的抑制剂化合物，这些化合物可分类为酪氨酸羟化酶抑制剂，或多巴脱羧酶抑制剂，或是多巴胺-β-羟化酶抑制剂。这些抑制剂化合物与化学基团（例如谷氨酸衍生物）通过可被肾脏内的酶特异性识别的可切断键连接。被释放的抑制剂化合物随后可在肾脏中抑制一个或多个涉及儿茶酚类合成的酶。抑制肾脏儿茶酚类合成可以抑制与钠潴留相关的疾病（如高血压）所伴随的过度肾脏神经活动。特别感兴趣的结合物是多巴胺-β-羟化酶抑制剂的谷氨酰衍生物，其中N-乙酰-γ-谷氨酰菌核酸酸肼（如下图所示）是首选。1
• Supramolecular Block Copolymers from Tricarboxamides. Biasing Co‐assembly by the Incorporation of Pyridine Rings
  作者：Lucía López‐Gandul、Adrián Morón‐Blanco、Fátima García、L. Luis Sánchez

  DOI：10.1002/anie.202308749

  日期：2023.9.11

  The synthesis of a series of triangular‐shaped tricarboxamides endowed with three picoline or nicotine units (compounds 2 and 3, respectively) or just one nicotine unit (compound 4) is reported, and their self‐assembling features investigated. The pyridine rings make compounds 2–4 electronically complementary with our previously reported oligo(phenylene ethynylene)tricarboxamides (OPE‐TA) 1 to form supramolecular copolymers. C₃‐symmetric tricarboxamide 2 forms highly stable intramolecular five‐membered pseudocycles that impede its supramolecular polymerization into poly‐2 and the co‐assembly with 1 to yield copolymer poly‐1‐co‐2. On the other hand, C₃‐symmetric tricarboxamide 3 readily forms poly‐3 with great stability but unable to form helical supramolecular polymers despite the presence of the peripheral chiral side chains. The copolymer poly‐1‐co‐3 can only be obtained by a previous complete disassembly of the constitutive homopolymers in CHCl₃. Helical poly‐1‐co‐3 arises in a process involving the transfer of the helicity from racemic poly‐1 to poly‐3, and the amplification of asymmetry from chiral poly‐3 to poly‐1. Importantly, C_2v‐symmetric 4, endowed with only one nicotinamide moiety and three chiral side chains, self‐assembles into a P‐type helical supramolecular polymer (poly‐4) in a thermodynamically controlled cooperative process. The combination of poly‐1 and poly‐4 generates chiral supramolecular copolymer poly‐1‐co‐4, whose blocky microstructure has been investigated by applying the previously reported supramolecular copolymerization model.

  摘要 报告合成了一系列具有三个吡啶或烟碱单元（分别为化合物 2 和 3）或只有一个烟碱单元（化合物 4）的三角形三羧酰胺，并研究了它们的自组装特征。吡啶环使化合物 2-4 与我们之前报道的低聚（苯乙炔基）三羧酰胺（OPE-TA）1 具有电子互补性，可形成超分子共聚物。C3 对称三甲酰胺 2 形成高度稳定的分子内五元假环，阻碍其超分子聚合成聚合物-2，并与 1 共同组装生成共聚物聚合物-1-co-2。另一方面，C3-对称三甲酰胺 3 很容易形成聚-3，而且非常稳定，但尽管存在外周手性侧链，却无法形成螺旋超分子聚合物。只有在 CHCl3 中完全分解构成均聚物，才能得到共聚物 poly-1-co-3。外消旋多聚物-1 的螺旋性转移到多聚物-3，手性多聚物-3 的不对称性放大到多聚物-1，螺旋多聚物-1-co-3 就这样产生了。重要的是，只有一个烟酰胺分子和三个手性侧链的 C2v 对称 4 在热力学控制的合作过程中自组装成 P 型螺旋超分子聚合物（poly-4）。聚-1 和聚-4 的结合生成了手性超分子共聚物聚-1-co-4，通过应用之前报道的超分子共聚模型对其块状微观结构进行了研究。
• X射线显影化合物及其制备方法、X射线显影栓塞材料及其制备方法
  申请人：科睿驰（深圳）医疗科技发展有限公司

  公开号：CN115490639A

  公开（公告）日：2022-12-20

  本申请涉及一种X射线显影化合物及其制备方法、X射线显影栓塞材料及其制备方法，属于X射线下可视化的栓塞技术领域。X射线显影化合物的结构式如下： 其中，X为由至少一个碘取代的C5‑12芳基或C5‑12杂芳基；Y不存在；或者，Y为C1‑6亚烷基、C2‑6亚烯基、C2‑6亚炔基、C1‑6亚烷氧基和C1‑6烷氧基亚烷基的一种。该显影化合物通过酰胺键直接或间接将咪唑基团或苯并咪唑基团与碘取代的芳基或杂芳基连接起来，形成X射线显影化合物，该显影化合物中的酰胺键处的C‑N键容易发生断裂，以便将断裂处的C与栓塞材料键接(断裂和键接可以一步反应)，以便使栓塞材料具有X射线显影功能。
• Graf, Journal fur praktische Chemie (Leipzig 1954), 1932, vol. <2> 133, p. 36,49
  作者：Graf

  DOI：——

  日期：——