7-methoxyimidazo[1,2-a]pyridine-3-carbaldehyde | 896722-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 7-methoxyimidazo[1,2-a]pyridine-3-carbaldehyde
• CAS: 896722-39-7
• 化学式: C₉H₈N₂O₂
• mdl: MFCD10698072
• 分子量: 176.175
• InChiKey: DEMNJFUBUDMCDH-UHFFFAOYSA-N

物化性质

• 熔点：
  142.1 °C
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-methoxyimidazo[1,2-a]pyridine-3-carbaldehyde 在 manganese(IV) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.33h， 生成 (7-methoxy-imidazo[1,2-a]pyridin-3-yl)-(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Scaffold-Hopping Strategy: Synthesis and Biological Evaluation of 5,6-Fused Bicyclic Heteroaromatics To Identify Orally Bioavailable Anticancer Agents

  摘要：

  Utilizing scaffold-hopping drug-design strategy, we sought to identify a backup drug candidate for BPR0L075 (1), an indole-based anticancer agent. For this purpose, 5,6-fused bicyclic heteroaromatic scaffolds were designed and synthesized through shuffling of the nitrogen from the N-1 position or by insertion of one or two nitrogen atoms into the indole core of 1. Among these, 7-azaindole core 12 showed potent in vitro anticancer activity and improved oral bioavailability (F = 35%) compared with 1 (F < 10%).

  DOI：

  10.1021/jm101027s
• 作为产物：
  描述：

  4-甲氧基吡啶-2-甲酸甲酯 在 碳酸氢钠 、 肼 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 15.0h， 生成 7-methoxyimidazo[1,2-a]pyridine-3-carbaldehyde
  参考文献：
  名称：

  Scaffold-Hopping Strategy: Synthesis and Biological Evaluation of 5,6-Fused Bicyclic Heteroaromatics To Identify Orally Bioavailable Anticancer Agents

  摘要：

  Utilizing scaffold-hopping drug-design strategy, we sought to identify a backup drug candidate for BPR0L075 (1), an indole-based anticancer agent. For this purpose, 5,6-fused bicyclic heteroaromatic scaffolds were designed and synthesized through shuffling of the nitrogen from the N-1 position or by insertion of one or two nitrogen atoms into the indole core of 1. Among these, 7-azaindole core 12 showed potent in vitro anticancer activity and improved oral bioavailability (F = 35%) compared with 1 (F < 10%).

  DOI：

  10.1021/jm101027s

文献信息

• Anti-tumor compounds
  申请人：Hsieh Hsing-Pang

  公开号：US20060148801A1

  公开（公告）日：2006-07-06

  Compounds of the following formula: wherein A, D, Q, T, U, V, W, X, Y, Z, R 1 , and ---- are as defined herein. This invention also relates to a method of inhibiting tubulin polymerization, or treating cancer or an angiogenesis-related disorder with one of these compounds.

  以下化合物的结构如下： 其中A、D、Q、T、U、V、W、X、Y、Z、R1和----在此处定义。本发明还涉及一种通过其中一种化合物抑制微管聚合，或治疗癌症或血管生成相关疾病的方法。
• [EN] COLONY STIMULATING FACTOR-1 RECEPTOR (CSF-1R) INHIBITORS<br/>[FR] INHIBITEURS DU RÉCEPTEUR DE FACTEUR-1 DE STIMULATION DE COLONIES (CSF-1R)
  申请人：GENZYME CORP

  公开号：WO2017015267A1

  公开（公告）日：2017-01-26

  Compounds of the formulas I and XIII, which are useful as colony stimulating factor-1 receptor inhibitors ("CSF 1R inhibitors").

  I和XIII式化合物，可用作促细胞增殖因子-1受体抑制剂（"CSF 1R抑制剂"）。
• Cu-Catalyzed Synthesis of 3-Formyl Imidazo[1,2-<i>a</i>]pyridines and Imidazo[1,2-<i>a</i>]pyrimidines by Employing Ethyl Tertiary Amines as Carbon Sources
  作者：Changqing Rao、Shaoyu Mai、Qiuling Song

  DOI：10.1021/acs.orglett.7b02015

  日期：2017.9.15

  A highly efficient synthesis of 3-formyl imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrimidine, under Cu-catalyzed aerobic oxidative conditions and by utilizing ethyl tertiary amines as carbon sources, is disclosed. A novel activation mode of ethyl tertiary amines in which simultaneous selective cleavage of C–C bond and C–N bond of ethyl group with molecular oxygen as terminal oxidant in this one-pot

  公开了在Cu催化的需氧氧化条件下并利用乙基叔胺作为碳源的3-甲酰基咪唑并[1,2- a ]吡啶和咪唑并[1,2- a ]嘧啶的高效合成方法。首次报道了一种乙基叔胺的新型活化方式，其中在此一锅操作方案中首次报道了用分子氧作为末端氧化剂同时选择性地裂解乙基的C–C键和C–N键。该反应具有广泛的底物范围，良好的官能团耐受性以及多样化且有价值的产品。
• Colony stimulating factor-1 receptor (CSF-1R) inhibitors
  申请人：Genzyme Corporation

  公开号：US11274108B2

  公开（公告）日：2022-03-15

  Compounds of the formulas which are useful as colony stimulating factor-1 receptor inhibitors (“CSF-1R inhibitors”).

  下列式子的化合物 可用作集落刺激因子-1 受体抑制剂（"CSF-1R 抑制剂"）。
• ANTI-TUMOR COMPOUNDS
  申请人：National Health Research Institutes

  公开号：EP1838711A2

  公开（公告）日：2007-10-03