N,N-bis(3,4-dihydro-1H-imidazol-2-yl)-1,4-bis(aminomethyl)benzene diiodide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-bis(3,4-dihydro-1H-imidazol-2-yl)-1,4-bis(aminomethyl)benzene diiodide
• 英文别名: N,N'-bis(4,5-dihydro-1H-imidazol-2-yl)-1,4-benzenedimethanamine dihydroiodide；MSX-133 Hydroiodic acid；N-[[4-[(4,5-dihydro-1H-imidazol-2-ylamino)methyl]phenyl]methyl]-4,5-dihydro-1H-imidazol-2-amine;hydroiodide
• 化学式: C₁₄H₂₀N₆*2HI
• 分子量: 528.178
• InChiKey: ACQXCICIMSRVGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.8
• 氢给体数：
  5
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,4-苯二甲胺 、 2-甲硫基-2-咪唑啉 以 甲醇 为溶剂， 以53%的产率得到N,N-bis(3,4-dihydro-1H-imidazol-2-yl)-1,4-bis(aminomethyl)benzene diiodide
  参考文献：
  名称：

  [EN] TRICYCLIC AMINO CONTAINING COMPOUNDS FOR TREATMENT OR PREVENTION OF SYMPTOMS ASSOCIATED WITH ENDOCRINE DYSFUNCTION
  [FR] COMPOSÉS CONTENANT DES ACIDES AMINÉS TRICYCLIQUES POUR LE TRAITEMENT OU LA PRÉVENTION DE SYMPTÔMES ASSOCIÉS À UN DYSFONCTIONNEMENT ENDOCRINIEN

  摘要：

  本公开提供了使用某些化合物治疗内分泌紊乱的某些症状的方法，特别是与潮热相关的症状的方法。

  公开号：

  WO2013070660A1

文献信息

• Discovery of Small Molecule CXCR4 Antagonists
  作者：Weiqiang Zhan、Zhongxing Liang、Aizhi Zhu、Serdar Kurtkaya、Hyunsuk Shim、James P. Snyder、Dennis C. Liotta

  DOI：10.1021/jm070679i

  日期：2007.11.1

  In light of a proposed molecular mechanism for the C-X-C chemokine receptor type 4 (CXCR4) antagonist 1 (AMD3100), a template with the general structure 2 was designed, and 15 was identified as a lead by means of an affinity binding assay against the ligand-mimicking CXCR4 antagonist 3 (TN14003). Following a structure-activity profile around 15, the design and synthesis of a series of novel small molecular CXCR4 antagonists led to the discovery of 32 (WZ811). The compound shows subnanomolar potency (EC50 = 0.3 nM) in an affinity binding assay. In addition, when subjected to in vitro functional evaluation, 32 efficiently inhibits CXCR4/stromal cell-derived factor-1 (SDF-1)-mediated modulation of cyclic adenosine monophophate (CAMP) levels (EC50 = 1.2 nM) and SDF-1 induced Matrigel invasion (EC50 = 5.2 nM). Molecular field topology analysis (MFTA), a 2D quantitative structure-activity relationship (QSAR) approach based on local molecular properties (Van der Waals radii (VdW), atomic charges, and local lipophilicity), applied to the 32 series suggests structural modifications to improve potency.
• Thermodynamic Aspects of Dicarboxylate Recognition by Simple Artificial Receptors
  作者：Brian R. Linton、M. Scott Goodman、Erkang Fan、Scott A. van Arman、Andrew D. Hamilton

  DOI：10.1021/jo010413y

  日期：2001.11.1

  Recognition of dicarboxylates by bis-functional hydrogen-bonding receptors displays divergent thermodynamics in different solvent systems. NMR titration and isothermal titration calorimetry indicated that neutral bis-urea and bis-thiourea receptors form exothermic complexes with dicarboxylates in DMSO, with a near zero entropic contribution to binding. The increased binding strength of bis-guanidinium receptors precluded quantitative measurement of binding constants in DMSO, but titration calorimetry offered a qualitative picture of the association. Formation of these 1:1 complexes was also exothermic, but additional endothermic events occurred at both lower and higher host-guest ratios. These events indicated multiple binding equilibria but did not always occur at a discrete 2:1 or 1:2 host-guest molar ratio, suggesting higher aggregates. With increasing amounts of methanol as solvent, bis-guanidinium receptors form more endothermic complexes with dicarboxylates, with a favorable entropy of association. This switch from association driven by enthalpy to one driven by entropy may reflect a change from complexation involving the formation of hydrogen bonds to that promoted by solvent liberation from binding sites.
• Molecular recognition: hydrogen-bonding receptors that function in highly competitive solvents
  作者：Erkang Fan、Scott A. Van Arman、Scott Kincaid、Andrew D. Hamilton

  DOI：10.1021/ja00054a066

  日期：1993.1