5-丙基-1H-咪唑-4-羧酸乙酯 | 97749-91-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-丙基-1H-咪唑-4-羧酸乙酯
• 英文名称: ethyl 5-propyl-1H-imidazole-4-carboxylate
• CAS: 97749-91-2
• 化学式: C₉H₁₄N₂O₂
• 分子量: 182.222
• InChiKey: BNKOCVLXFACPNR-UHFFFAOYSA-N

物化性质

• 熔点：
  171-174 °C(Solv: isopropanol (67-63-0))
• 沸点：
  367.0±30.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-丙基-1H-咪唑-4-羧酸乙酯 在 盐酸 、 草酰氯 作用下， 以 水 、 乙腈 为溶剂， 反应 25.0h， 生成 (9ci)-5-丙基-1H-咪唑-4-羰酰氯
  参考文献：
  名称：

  Anion Binding by Fluorescent Biimidazole Diamides

  摘要：

  Six 2,2'-biimidazoles with various amide groups at the 4- and 4'-positions were prepared from 5-propyl-1H-imidazole-4-carboxylic acid ethyl ester. In the final step of the synthesis, biimidazole C2-C2' bond formation was accomplished in 33-45% yield by palladium(0)-catalyzed homocoupling of the corresponding 2-iodoimidazoles. Four of the biimidazoles were studied by X-ray diffraction. In the solid state, all display coplanar imidazole rings, an anti relationship of amide groups, and intramolecular (NHamide...N-imid) and intermolecular (NHimid...O-amide) hydrogen bonding. In CH2Cl2, the emission intensity of the biimidazoles is quenched by the presence of dihydrogenphosphate and chloride anions, but no shifts in lambda(emiss) are observed. Binding constants for 1:1 biimidazole-anion complexation (K-assoc) are on the order of 10(4) M-1 for H2PO4- and Cl-. One of the receptors (bearing 3,5-difluorobenzylamides) is selective for chloride. The participation of the amide NH atoms in anion binding was established by H-1 NMR.

  DOI：

  10.1021/jo020098v
• 作为产物：
  描述：

  丁酰乙酸乙酯 在 磺酰氯 、 水 作用下， 以 氯仿 为溶剂， 反应 7.0h， 生成 5-丙基-1H-咪唑-4-羧酸乙酯
  参考文献：
  名称：

  Imidazo[1,5-d][1,2,4]triazines as potential antiasthma agents

  摘要：

  By using inhibition of histamine release from antigen-challenged, sensitized human basophils as a means of identifying a potentially prophylactic drug for the treatment of asthma, a series of substituted imidazo[1,5-d][1,2,4]triazines were found, which were active. These compounds were prepared by treating imidazolecarboxaldehydes with excess Grignard agent and then oxidizing the resulting alcohols to ketones with Jones reagent. Pyrolysis of a mixture of ketone and methyl carbazate at 200 degrees C in diphenyl ether produced the desired imidazo[1,5-d][1,2,4]triazines. Those compounds with the greatest basophil activity were tested for in vivo activity in the mouse passive cutaneous anaphylaxis (PCA) and the guinea pig passive anaphylaxis tests. The best compounds, 1-ethyl-8-methyl-6-propylimidazo[1,5-d][1,2,4]triazin-4(3H)- one (4-17) and 1,8-dimethyl-6-propylimidazo[1,5-d][1,2,4]triazin-4-(3H)-one (4-16) were chosen for further study.

  DOI：

  10.1021/jm00149a029

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
• [EN] MICROBIOCIDAL OXADIAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'OXADIAZOLE MICROBIOCIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2017118689A1

  公开（公告）日：2017-07-13

  Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially fungicides.

  式（I）中的化合物，其中取代基如权利要求1所定义，可用作杀虫剂，特别是杀菌剂。
• Self-Assembled Helices from 2,2′-Biimidazoles
  作者：William E. Allen、Christopher J. Fowler、Vincent M. Lynch、Jonathan L. Sessler

  DOI：10.1002/1521-3765(20010202)7:3<721::aid-chem721>3.0.co;2-1

  日期：2001.2.2

  2,2'-Biimidazoles were synthesized by palladium(0)-catalyzed coupling of 2-iodoimidazoles bearing an alkyl and an ester group at the 4- and 5-positions, respectively. The products were found to be fluorescent and moderately soluble in organic solvents. Three biimidazoles were subjected to single crystal X-ray diffraction analysis. In all three instances, adjacent molecules were found to be bound together

  通过钯（0）催化分别在4位和5位带有烷基和酯基的2-碘咪唑的偶合反应合成2,2'-苯并咪唑。发现产物是荧光的，并适度溶于有机溶剂。对三种联咪唑进行单晶X射线衍射分析。在所有这三种情况下，都发现相邻的分子通过成对的NH ... N氢键结合在一起，形成类似于双螺旋的扭曲的带状柱。在这些螺旋中，相邻的联咪唑亚基之间观察到的螺旋扭曲量随烷基和酯基的不同而不同。在两种情况下约为60度，而在第三种情况下约为90度。六种不同的联咪唑的质谱显示出质量与二聚体相对应的离子。这表明这些化合物在气相中彼此保留一定的亲和力。三种最易溶解的联咪唑也显示归因于三聚体和四聚体的质谱峰。通过蒸气压渗透法研究了后三种化合物的溶液相聚集趋势。在每种情况下，在1,2-二氯乙烷溶液中的表观分子量均高于游离单体的预期分子量。
• Novel 5-Hydroxytryptamine (5-HT3) Receptor Antagonists. Synthesis and Structure-Activity Relationships of 9-Methyl-2,3,4,9-tetrahydrothiopyrano(2,3-b)indol-4-one Derivatives.
  作者：Takeshi SUZUKI、Akira MATSUHISA、Keiji MIYATA、Isao YANAGISAWA、Mitsuaki OHTA

  DOI：10.1248/cpb.45.101

  日期：——

  Novel 9-methyl-4,9-dihydrothiopyrano[2,3-b]indol-4-one derivatives 2b-e, 3-methylene-9-methyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-4-on e derivatives 3b-e and 9-methyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-4-one derivatives 4a-e were prepared. The 5-hydroxytryptamine (5-HT3) receptor-antagonistic activities of these compounds were evaluated by using the von Bezold-Jarisch reflex test (B. J.

  新型9-甲基-4,9-二氢噻喃并[2,3-b]吲哚-4-one衍生物2b-e，3-亚甲基-9-甲基-2,3,4,9-四氢噻喃并[2,3-b制备了]吲哚-4-on e衍生物3b-e和9-甲基-2,3,4,9-四氢噻喃并[2,3-b]吲哚-4-one衍生物4a-e。使用von Bezold-Jarisch反射试验（BJ反射，大鼠）和离体远端结肠（豚鼠）对5-HT的收缩反应，评估了这些化合物的5-羟色胺（5-HT3）受体拮抗活性。 。在BJ反射测试中（ID50 = 0.048微克/千克，iv），发现5-乙基-4-咪唑基衍生物4d的效力是昂丹西酮1的79倍，发现5-甲基-4-咪唑基衍生物4c在结肠收缩（IC50 = 0.0062 microM）分析中，其效力是1的126倍。
• Biimidazole diamide anion binding agents
  申请人：Allen E. William

  公开号：US20050004370A1

  公开（公告）日：2005-01-06

  Biimidazole diamide compounds that are useful for binding anions such as sulfate are described, along with the use thereof for purposes such as extracting anions from a waste stream and/or detecting anions.

  本文描述了用于结合阴离子，如硫酸的双咪唑二酰胺化合物，以及其用途，例如从废水流中提取阴离子和/或检测阴离子。