咪唑并[1,2-a]吡啶-2-乙酸 | 19741-30-1

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 咪唑并[1,2-a]吡啶-2-乙酸
• 中文别名: 咪唑并[1,2-A]吡啶-2-乙酸
• 英文名称: 2-(imidazo[1,2-a]pyridin-2-yl)acetic acid
• 英文别名: 2-(H-imidazo[1,2-α]pyridin-2-yl)acetic acid；Imidazo[1,2-a]pyridin-2-yl-acetic acid；2-imidazo[1,2-a]pyridin-2-ylacetic acid
• CAS: 19741-30-1
• 化学式: C₉H₈N₂O₂
• 分子量: 176.175
• InChiKey: NYYYTUHPAJSTQV-UHFFFAOYSA-N

物化性质

• 熔点：
  207-208 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 储存条件：
  2-8°C

制备方法与用途

咪唑并[1,2-A]吡啶-2-乙酸主要用于作为研究用化合物。

反应信息

• 作为反应物：
  描述：

  咪唑并[1,2-a]吡啶-2-乙酸 在 盐酸 、 亚磷酸 、 三氯化磷 作用下， 生成 <1-hydroxy-2-(imidazo<1,2-a>pyridin-2-yl)ethylidene>bisphosphonic acid
  参考文献：
  名称：

  Studies on Novel Bone Resorption Inhibitors. II. Synthesis and Pharmacological Activities of Fused Aza-heteroarylbisphosphonate Derivatives.

  摘要：

  我们合成了两个新系列的融合杂己基双膦酸盐（5、8），它们在结构上与incadronate（YM175）和相关化合物有很大不同，并利用甲状旁腺激素（PTH）诱导的大鼠高钙血症模型（PIH 模型）对它们的抗骨吸收活性进行了评估。在这些化合物中，有几种表现出比帕米膦酸钠更强的抗骨吸收活性。其中，[1-羟基-2-（咪唑并[1，2-α]吡啶-3-基）亚乙基]双膦酸（5b，minodronate）不仅在 PIH 模型中，而且在大鼠固定骨萎缩模型（DA 模型）中的活性都比帕米膦酸高出 100 倍，因此被选中用于临床开发。本文讨论了这些新系列双膦酸盐的结构-活性关系。

  DOI：

  10.1248/cpb.46.1703
• 作为产物：
  描述：

  4-溴乙酰乙酸乙酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以10.6 g的产率得到咪唑并[1,2-a]吡啶-2-乙酸
  参考文献：
  名称：

  Imidazo[1,2-a]pyridin-2-ylacetic acid and two pairs of isomorphous ML2(H2O)2 dihydrates (M=Ni, Co and Mn, Cd) based on its anion: Syntheses, crystal structures and properties

  摘要：

  Imidazo[1,2-a]pyridin-2-ylacetic acid (HL, 1) and four ML2(H2O)(2)center dot 2H(2)O (M = Ni (2), Co (3), Mn (4), Cd (5)) complexes formed by its anion were synthesized, structurally characterized by single-crystal X-ray diffraction and investigated in terms of their thermal stability. In addition, magnetic properties of 2-4 are reported and the NIR-Vis-UV spectra of 2 and 3 are discussed in details. The crystal of 1 comprises 20 hydrogen bonded networks held in the crystal lattice by weak C-H center dot center dot center dot O and pi-pi contacts. The ML2(H2O)(2)center dot 2H(2)O complexes crystallize as isomorphous pairs (2, 3 and 4, 5) with slightly distorted hexa-coordinated environment around M(II) ion formed by two N,O-chelated imidazo[1,2-a]pyridin-2-ylacetate anions and two water molecules. In all 2-5, coordinated and lattice water molecules join discrete octahedral complexes into 2D hydrogen-bonded networks, held in the crystal lattice by weak C-H center dot center dot center dot O and pi-pi contacts.The Co(II) and Ni(II) complexes (2 and 3) are thermally less stable than Mn(II) and Cd(II) complexes (4 and 5). These differences are discussed in view of Hirshfeld surface analysis of reported compounds. The magnetic properties of 2 and 3 are largely determined by a tetragonal distortion of coordinated polyhedron, which stays in good agreement with observed and calculated transitions energies and their assignments in the electronic spectra of both compounds. Compound 4 displays almost ideal Curie-Weiss paramagnetism over the whole temperature range. Additionally, in all 2-4, weak magnetic exchange interactions mediated by H-bonds play a role with absolute values off coupling parameter increasing in the order: Mn < Co < Ni. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.03.004

文献信息

• XANTHINE DERIVATIVES, THEIR USE AS A MEDICAMENT, AND PHARMACEUTICAL PREPARATIONS COMPRISING THE SAME
  申请人：Max-Delbrück-Centrum für Molekulare Medizin

  公开号：EP3275885A1

  公开（公告）日：2018-01-31

  The invention relates to a xanthine derivative defined by chemical formula I or a salt thereof, its use as a medicament, especially for use in the treatment of serotonin-related diseases or disorders, and a pharmaceutical preparation comprising the xanthine derivative. The novel xanthine compounds are capable of inhibiting tryptophan hydroxylases (TPH) involved in the biosynthesis of serotonin and are effective in influencing the serotonin level in the body.

  本发明涉及一种由化学公式I定义的嘌呤衍生物或其盐，其用作药物，特别用于治疗与血清素相关的疾病或失调，以及包含该嘌呤衍生物的药物制剂。 这些新型的嘌呤化合物能够抑制参与血清素生物合成的色氨酸羟化酶（TPH），并且在影响体内的血清素水平方面有效。
• MCL-1 INHIBITORS
  申请人：Gilead Sciences, Inc.

  公开号：US20190352271A1

  公开（公告）日：2019-11-21

  The present disclosure generally relates to compounds and pharmaceutical compositions that may be used in methods of treating cancer.

  本公开涉及通常用于治疗癌症的化合物和药物组合物。
• Access to Unnatural α-Amino Acids via Visible-Light-Mediated Decarboxylative Conjugate Addition to Dehydroalanine
  作者：Akshay A. Shah、Michael J. Kelly、James J. Perkins

  DOI：10.1021/acs.orglett.0c00371

  日期：2020.3.20

  An expedient synthesis of β-alkyl α-amino acids is reported via application of decarboxylative photocatalysis. The method utilizes abundant, diverse, and inexpensive carboxylic acids to provide radicals for conjugate addition to dehydroalanine ester. High-throughput experimentation revealed an acridinium-based photocatalyst, tetraMeO-Acri-N-diMeOPh, to be the optimal choice enabling a general method

  据报道，通过应用脱羧光催化可以方便地合成β-烷基α-氨基酸。该方法利用丰富，多样且廉价的羧酸来提供用于共轭加成至脱氢丙氨酸酯的基团。高通量实验表明，基于a啶的光催化剂tetraMeO-Acri-N-diMeOPh是实现通用方法的最佳选择，该方法可耐受多种官能团。描述了用于访问各种非天然α-氨基酸的可扩展批处理方案和并行库合成。
• Photorearrangement of dihetarylethenes as a tool for the benzannulation of heterocycles
  作者：Andrey G. Lvov、Alexey M. Kavun、Vadim V. Kachala、Konstantin A. Lyssenko、Valerii Z. Shirinian

  DOI：10.1039/c9ob00690g

  日期：——

  provides C-, N-, O- or S-substituents in the benzoheterocycles obtained. The photochemical step is a metal-, acid-, and oxidant-free reaction, which requires non-inert conditions, and can be easily monitored by NMR spectroscopy. Applicability of the proposed strategy was tested in the synthesis of a wide range of substituted carbazoles and benzo[b]thiophenes as well as on a gram-scale benzannulation of 3-indoleacetic

  首次提出了通过1,2-二杂芳烃的光环化制备芳香族杂环的一般方法。该策略包括两个步骤，即从广泛可用的3-杂戊酸和2-溴-1-杂蒽酮中组装二甲基蒽的模块，以及后续的制备性光重排（使用365 nm的紫外灯作为光源）。这种方法对于各种杂环的环化都是有效的，并提供C-，N-，O-或S获得的苯并杂环中的-取代基。光化学步骤是无金属，无酸和无氧化剂的反应，这需要非惰性条件，并且可以通过NMR光谱轻松监控。在广泛取代的咔唑和苯并[ b ]噻吩的合成以及克级的3-吲哚乙酸的苯环上，测试了所提出策略的适用性。我们的研究揭示了如何克服成功地对二芳硫醚进行光重排的两个显着障碍：与光生单重态氧相关的不良反应以及所需产物的不稳定性。第一个问题通过添加DABCO成功解决，同时现场开发 捕获不稳定光产物的烷基化方案使我们能够克服第二个问题。
• Process for the preparation of biphosphonic acids
  申请人：Danda Subba Reddy

  公开号：US20070173645A1

  公开（公告）日：2007-07-26

  An improved process for bisphosphonylation of acids, substituted acids to obtain compounds with the formula using phosphorus trihalide, phosphorus acid, in presence of phenolic compounds as diluent/solvent.

  一种改进的方法用于通过磷三卤化物、磷酸在苯酚化合物作为稀释剂/溶剂的存在下对酸、取代酸进行双膦酸化反应，以获得具有以下公式的化合物。