1-hexyl-imidazole-2-carbaldehyde | 937664-62-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-hexyl-imidazole-2-carbaldehyde
• 英文别名: 1-Hexylimidazole-2-carbaldehyde
• CAS: 937664-62-5
• 化学式: C₁₀H₁₆N₂O
• 分子量: 180.25
• InChiKey: XSVOJWAQCTWEDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  311.7±25.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-hexyl-imidazole-2-carbaldehyde 在 盐酸羟胺 、 sodium carbonate 作用下， 以 水 为溶剂， 生成 RS113A
  参考文献：
  名称：

  New Structural Scaffolds for Centrally Acting Oxime Reactivators of Phosphylated Cholinesterases

  摘要：

  We describe here the synthesis and activity of a new series of oxime reactivators of cholinesterases (ChEs) that contain tertiary amine or imidazole protonatable functional groups. Equilibration between the neutral and protonated species at physiological pH enables the reactivators to cross the blood-brain barrier and distribute in the CNS aqueous space as dictated by interstitial and cellular pH values. Our structure-activity analysis of 134 novel compounds considers primarily imidazole aldoximes and N-substituted 2-hydroxyiminoacetamides. Reactivation capacities of novel oximes are rank ordered by their relative reactivation rate constants at 0.67 mM compared with 2-pyridinealdoxime methiodide for reactivation of four organophosphate (sarin, cyclosarin, VX, and paraoxon) conjugates of human acetylcholinesterase (hAChE). Rank order of the rates differs for reactivation of human butyrylcholinesterase (hBChE) conjugates. The 10 best reactivating oximes, predominantly hydroxyimino acetamide derivatives (for hAChE) and imidazole-containing aldoximes (for hBChE) also exhibited reasonable activity in the reactivation of tabun conjugates. Reactivation kinetics of the lead hydroxyimino acetamide reactivator of hAChE, when analyzed in terms of apparent affinity (1/K-ox) and maximum reactivation rate (k(2)), is superior to the reference uncharged reactivators monoisonitrosoacetone and 2,3-butanedione monoxime and shows potential for further refinement. The disparate pH dependences for reactivation of ChE and the general base-catalyzed oximolysis of acetylthiocholine reveal that distinct reactivator ionization states are involved in the reactivation of ChE conjugates and in conferring nucleophilic reactivity of the oxime group.

  DOI：

  10.1074/jbc.m111.230656
• 作为产物：
  描述：

  1-碘己烷 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 44.28h， 生成 1-hexyl-imidazole-2-carbaldehyde
  参考文献：
  名称：

  Halogen-bond driven self-assembly of triangular macrocycles

  摘要：

  卤素键驱动2-碘乙炔吡啶和2-碘乙炔-1-甲基咪唑的自组装成离散的超分子三角形。

  DOI：

  10.1039/c8nj00759d

文献信息

• Ionic liquids from copper(ii) complexes with alkylimidazole-containing tripodal ligands
  作者：Yusuke Funasako、Misaki Nosho、Tomoyuki Mochida

  DOI：10.1039/c3dt50976a

  日期：——

  tripodal ligands were prepared, where L = bis(2-dimethylaminoethyl)-((1-alkylimidazol-2-yl)methyl)amine and X = bis(trifluoromethanesulfonyl)amide (Tf2N) and PF6. The salts with hexyl ([1]X), propyl ([2]X), and methyl ([3]X) substituents in the ligand were prepared, of which [1]Tf2N and [2]Tf2N were ionic liquids with high viscosity at room temperature. X-ray crystal structure determination at low temperature

  制备了含烷基咪唑的三脚架配体的五配位铜（II）配合物[Cu（L）Cl] X，其中L =双（2-二甲基氨基乙基）-（（（1-烷基咪唑-2-基）甲基）胺和X ＝双（三氟甲磺酰基）酰胺（Tf 2 N）和PF 6。制备在配体中具有己基（[ 1 ] X），丙基（[ 2 ] X）和甲基（[ 3 ] X）取代基的盐，其中[ 1 ] Tf 2 N和[ 2 ] Tf 2 N为在室温下具有高粘度的离子液体。低温X射线晶体结构测定表明，[ 3] Tf 2 N扭曲为三角双锥体，而[ 2 ] PF 6中的则接近于方形锥体。这些盐的紫外可见吸收光谱与配位结构一致。
• Molecular isomerism induced Fe(<scp>ii</scp>) spin state difference based on the tautomerization of the 4(5)-methylimidazole group
  作者：Wang-Kang Han、Zhi-Hua Li、Wei Zhu、Tao Li、Zaijun Li、Xuehong Ren、Zhi-Guo Gu

  DOI：10.1039/c7dt00260b

  日期：——

  obtained via a well-designed strategy based on the tautomerization of the 4(5)-methylimidazole group. Structural investigations reveal that the two isomers are extremely similar with only differences in the methyl group position of the ligands. The iron(II) center is surrounded by three bidentate imidazole Schiff-base ligands in the face-Λ conformation, which affords a distorted [FeN6] octahedral coordination

  两种铁（II）分子异构体，即face-Λ- [Fe（L 1）3 ]（ClO 4）2（1a）（L 1 = R -1-苯基-N -（（1-己基-5-甲基-1 H-咪唑-2-基亚甲基）乙胺））和面Λ- [Fe（L 2）3 ]（ClO 4）2（1b）（L 2 = R -1-苯基-N-（1-己基） -4-甲基-1 H-咪唑-2-基亚甲基）乙胺）通过一种基于4（5）-甲基咪唑基团互变异构的精心设计的策略。结构研究表明，这两种异构体极为相似，只是配体的甲基位置不同。铁（II）中心被三个在面Λ构象的二齿咪唑席夫碱配体包围，从而提供了扭曲的[FeN 6 ]八面体配位球。1a（1.971Å）的平均Fe–N键长比1b（2.185Å ）的短。光谱分析，X射线晶体结构和磁学研究表明1a由于在咪唑基团的5位上的供电子甲基基团所赋予的强大配体场，该化合物在室温下处于低自旋状态，并经历了部分自旋转变，估计的T 1/2 =
• Structure–Activity Relationship and Pharmacokinetic Studies of 1,5-Diheteroarylpenta-1,4-dien-3-ones: A Class of Promising Curcumin-Based Anticancer Agents
  作者：Rubing Wang、Chengsheng Chen、Xiaojie Zhang、Changde Zhang、Qiu Zhong、Guanglin Chen、Qiang Zhang、Shilong Zheng、Guangdi Wang、Qiao-Hong Chen

  DOI：10.1021/acs.jmedchem.5b00470

  日期：2015.6.11

  Forty-three 1,5-diheteroaryl-1,4-pentadien-3-ones were designed as potential curcumin mimics, structurally featuring a central five-carbon dienone linker and two identical nitrogen-containing aromatic rings. They were synthesized using a Horner-Wadsworth-Emmons reaction as the critical step and evaluated for their cytotoxicity and antiproliferative activities toward both androgen-insensitive and androgen-sensitive prostate cancer cell lines and an aggressive cervical cancer cell line. Most of the synthesized compounds showed distinctly better in vitro potency than curcumin in the four cancer cell lines. The structure-activity data acquired from the study validated (1E,4E)-1,5-dihereroaryl-1,4-pentadien-3-ones as an excellent scaffold for in-depth development for clinical treatment of prostate and cervical cancers. 1-Alkyl-1H-imidazol-2-yl, ortho pyridyl, 1-alkyl-1H-benzo[d]imidazole-2-yl, 4-bromo-1-methyl-1H-pyrazol-3-yl, thiazol-2-yl, and 2-methyl-4-(trifluoromethyl)thiazol-5-yl were identified as optimal heteroaromatic rings for the promising in vitro potency. (1E,4E)-1,5-Bis(2-methyl-4-(trifluoromethyl)thiazol-5-yl)penta-1,4-dien-3-one, featuring thiazole rings and trifluoromethyl groups, was established as the optimal lead compound because of its good in vitro potency and attractive in vivo pharmacokinetic profiles.