4-丙基-1H-咪唑-5-羧醛 | 97749-72-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-丙基-1H-咪唑-5-羧醛
• 英文名称: 1h-Imidazole-5-carboxaldehyde, 4-propyl-
• 英文别名: 5-propyl-1H-imidazole-4-carbaldehyde
• CAS: 97749-72-9
• 化学式: C₇H₁₀N₂O
• mdl: MFCD19224437
• 分子量: 138.169
• InChiKey: AYSGWEZTYITIHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-丙基-1H-咪唑-5-羧醛 、 1,4-二乙酰基哌嗪-2,5-二酮 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationship Study of Antimicrotubule Agents Phenylahistin Derivatives with a Didehydropiperazine-2,5-dione Structure

  摘要：

  Plinabulin (11, NPI-2358) is a potent microtubule-targeting agent derived from the natural diketopiperazine "phenylahistin" (1) with a colchicine-like tubulin depolymerization activity. Compound 11 was recently developed as VDA and is now under phase II clinical trials as an anticancer drug. To develop more potent antimicrotubule and cytotoxic derivatives based on the didehydro-DKP skeleton, we performed further modification on the tert-butyl or phenyl groups of 11, and evaluated their cytotoxic and tubulin-binding activities. In the SAR study, we developed more potent derivatives 33 with 2,5-difluorophenyl and 50 with activity of 33 and 50 exhibited a lowest effective concentration The values of 33 and 50 were 5 and 10 times more potent than second-generation derivative with both vascular disrupting and a benzophenone in place of the phenyl group. The anti-HuVEC of 2 and 1 nM for microtubule depolymerization, respectively. that of CA-4, respectively. These derivatives could be a valuable cytotoxic activities.

  DOI：

  10.1021/jm2009088
• 作为产物：
  描述：

  2-氯-3-氧代己酸乙酯 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 19.5h， 生成 4-丙基-1H-咪唑-5-羧醛
  参考文献：
  名称：

  Imidazole-based pinanamine derivatives: Discovery of dual inhibitors of the wild-type and drug-resistant mutant of the influenza A virus

  摘要：

  We previously reported potent hit compound 4 inhibiting the wild-type influenza A virus A/HK/68 (H3N2) and A/M2-S31N mutant viruses A/WS/33 (H1N1), with its latter activity quite weak. To further increase its potency, a structure-activity relationship study of a series of imidazole-linked pinanamine derivatives was conducted by modifying the imidazole ring of this compound. Several compounds of this series inhibited the amantadine-sensitive virus at low micromolar concentrations. Among them, 33 was the most potent compound, which was identified as being active on an amantadine-sensitive virus through blocking of the viral M2 ion channel. Furthermore, 33 markedly inhibited the amantadine-resistant virus (IC50 = 3.4 mu M) and its activity increased by almost 24-fold compared to initial compound, with its action mechanism being not M2 channel mediated. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.013

文献信息

• Inhibitors of Tumor Progression Loci-2 (Tpl2) Kinase and Tumor Necrosis Factor α (TNF-α) Production:  Selectivity and in Vivo Antiinflammatory Activity of Novel 8-Substituted-4-anilino-6-aminoquinoline-3-carbonitriles
  作者：Neal Green、Yonghan Hu、Kristin Janz、Huan-Qiu Li、Neelu Kaila、Satenig Guler、Jennifer Thomason、Diane Joseph-McCarthy、Steve Y. Tam、Rajeev Hotchandani、Junjun Wu、Adrian Huang、Qin Wang、Louis Leung、Jefferey Pelker、Suzana Marusic、Sang Hsu、Jean-Baptiste Telliez、J. Perry Hall、John W. Cuozzo、Lih-Ling Lin

  DOI：10.1021/jm070436q

  日期：2007.9.1

  involved in diseases such as rheumatoid arthritis. Initial 4-anilino-6-aminoquinoline-3-carbonitrile leads showed poor selectivity for Tpl2 over epidermal growth factor receptor (EGFR) kinase. Using molecular modeling and crystallographic data of the EGFR kinase domain with and without an EGFR kinase-specific 4-anilinoquinazoline inhibitor (erlotinib, Tarceva), we hypothesized that we could diminish the

  肿瘤进展基因座2（Tpl2）（Cot / MAP3K8）是MAP3K家族中位于MEK上游的丝氨酸/苏氨酸激酶。最近使用Tpl2敲除小鼠的研究表明Tpl2在脂多糖（LPS）诱导的肿瘤坏死因子α（TNF-alpha）和其他与风湿性关节炎等疾病有关的促炎细胞因子的产生中具有重要作用。最初的4-苯胺基-6-氨基喹啉-3-甲腈导线显示出对Tpl2的选择性较表皮生长因子受体（EGFR）激酶差。使用和不使用EGFR激酶特异性4-苯胺基喹唑啉抑制剂（erlotinib，Tarceva）的EGFR激酶结构域的分子模型和晶体学数据，我们假设我们可以通过在C-8位置进行取代来减少对EGFR激酶的抑制作用4-苯胺基-6-氨基喹啉-3-腈引线。由适当的2-取代的4-硝基苯胺制备8-取代的4-苯胺基-6-氨基喹啉-3-甲腈。对C-6和C-8位置的修饰导致鉴定了对LPS刺激的大鼠和人类血液中TNF-α释放抑制作用增强的
• Imidazolyl- indolylpropanones as 5-HT.sub.3 receptor antagonists
  申请人：Glaxo Group Limited

  公开号：US04808581A1

  公开（公告）日：1989-02-28

  The invention relates to compounds of formula (I): ##STR1## and physiologically acceptable salts or solvates thereof, wherein Im represents an imidazolyl group of formula: ##STR2## and the various substituents are defined hereinbelow. The compounds are potent and selective antagonists of the effect of 5-HT at 5-HT.sub.3 receptors and are useful, for example, in the treatment of psychotic disorders, anxiety, and nausea and vomiting.

  本发明涉及公式(I)的化合物：##STR1##以及其生理上可接受的盐或溶剂，其中Im代表公式的咪唑基：##STR2##各种取代基在此下面定义。这些化合物是5-HT.sub.3受体5-HT效应的有效和选择性拮抗剂，并且在治疗精神病性障碍、焦虑和恶心和呕吐等方面非常有用。
• Indole derivatives, method for their preparation and pharmaceutical compositions containing them
  申请人：GLAXO GROUP LIMITED

  公开号：EP0242973B1

  公开（公告）日：1991-07-17
• Lactam derivatives
  申请人：GLAXO GROUP LIMITED

  公开号：EP0306323B1

  公开（公告）日：1994-09-21
• COATES, IAN HAROLD;NORTH, PETER CHARLES;OXLORD, ALEHANDER WILLIAM
  作者：COATES, IAN HAROLD、NORTH, PETER CHARLES、OXLORD, ALEHANDER WILLIAM

  DOI：——

  日期：——