2-chloromethyl-1H-benzimidazole hydrochloride | 91862-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-chloromethyl-1H-benzimidazole hydrochloride
• 英文别名: 2-Chlormethyl-1H-benzimidazol; Hydrochlorid；2-chloromethyl-benzimidazole, hydrochloride；2-(Chloromethyl)benzimidazolium chloride；2-(chloromethyl)-1H-benzimidazol-3-ium;chloride
• CAS: 91862-40-7
• 化学式: C₈H₇ClN₂*ClH
• mdl: MFCD00159934
• 分子量: 203.071
• InChiKey: IIXABTCJZHHRFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  28.7
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Fluoro-5-(3-trifluoromethylimidazo[1,2-b][1,2,4]triazin-7-yl)phenol 、 2-chloromethyl-1H-benzimidazole hydrochloride 以to give the title compound as a yellow solid (23 mg, 21%)的产率得到7-[3-(1H-Benzimidazol-2-ylmethoxy)-4-fluorophenyl]-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine
  参考文献：
  名称：

  Imidazopyridines pyrimidines and triazines for enhancing cognition as gaba-a-alphas 5 receoptor subtype ligands

  摘要：

  本发明提供了一种制药组合物，其中包含式I的化合物或其药学上可接受的盐，以及药学上可接受的载体：（I），其中：X和Y独立地表示CH或N，但如果X是CH，则Y也是CH；R1表示氢、碳氢化合物、杂环基、卤素、氰基、三氟甲基、硝基、—ORa、—SRa、—SORa、—SO2Ra、—SO2NRaRb、—NRaRb、—NRaCORb、—NRaCO2Rb、—CORa、—CO2Ra、—CONRaRb或CRa═NORb；Ra和Rb独立地表示氢、碳氢化合物或杂环基；V和W独立地选自H、卤素、C11-6烷基、OH和C-1-6烷氧基；Z表示H、卤素、CN、NO2、CF3、OCF3、CF2H、SCF3、R2、OR3、SR3、（CH2）pN（R3）2、O（CH2）pN（R3）2、SO2R2、SO2N（R3）2、COR4、CO2R3、CON（R3）2、NHCOR4、NR1（CH2）n杂环基或O（CH2）n杂环基，其中杂环基可选地被来自C1-6烷基、苯甲基、（CH2）pN（R3）2、卤素和CF3的一个、两个或三个基团取代，R1是C1-6烷基，其中n为1或2，p为0、1或2；但要求V、W和Z中至少有一个不是H；R2表示C1-6烷基、C3-6环烷基、C3-6环烷基C1-4烷基、C2-6烯基、C2-6炔基或杂环基，其中任何一种可以携带来自卤素、CN、NO2、CF3、OCF3、CF2H、SCF3、OH、C1-4烷氧基、C1-4烷氧羰基、氨基、C1-4烷基氨基或二（C1-4烷基）氨基的取代基；R3表示H或R2；或者两个结合到同一氮原子上的R3基团可以形成一个5-7成员非芳香杂环环；R4表示R3或杂环基；这些化合物是GABA-A受体的配体，包含α5亚型，因此对于患有阿尔茨海默病等疾病的个体，有助于增强认知能力。

  公开号：

  US20060040940A1
• 作为产物：
  描述：

  氯乙酸 、 邻苯二胺 在 盐酸 作用下， 以 水 为溶剂， 反应 24.0h， 生成 2-chloromethyl-1H-benzimidazole hydrochloride
  参考文献：
  名称：

  Molecular structure of 2-chloromethyl-1H-benzimidazole hydrochloride: Single crystal, spectral, biological studies, and DFT calculations

  摘要：

  In the present work, structural studies on 2-chloromethyl-1H-benzimidazole hydrochloride have been performed extensively by X-ray crystallography, H-1 NMR, FT-IR, UV/vis, and elemental analysis. The title compound crystallizes in a monoclinic space group P2(1)/c with a = 7.1982 (3)angstrom, b = 9.4513(5)angstrom, c = 14.0485 (7) angstrom and beta = 102.440 (3)degrees forming an infinite chain structure parallel to "b" axis through the intermolecular hydrogen bond. Optimized geometrical structure, harmonic vibrational frequencies, natural bonding orbital (NBO) and frontier molecular orbitals (FMO) were obtained by DFT/B3LYP method combined with 6-31G(d) basis set. TD-DFT calculations help to assign the electronic transitions. The 1H NMR chemical shifts were computed at the B3LYP/6-311 + G(2d,p) level of theory in different solvents by applying CIAO method using the polarizable continuum model (PCM). The title compound was screened for its antibacterial activity referring to Tetracycline as a standard antibacterial agent. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2011.11.024

文献信息

• Retroviral protease inhibiting compounds
  申请人：ABBOTT LABORATORIES

  公开号：EP0486948A2

  公开（公告）日：1992-05-27

  A retroviral protease inhibiting compound of the formula A -X- B is disclosed. Also disclosed are a composition and method for inhibiting a retroviral protease and for treating an HIV infection. Also disclosed are processes and intermediates useful for the preparation of the retroviral protease inhibitors.

  本发明公开了一种式 A -X- B 的逆转录病毒蛋白酶抑制化合物。还公开了一种抑制逆转录病毒蛋白酶和治疗 HIV 感染的组合物和方法。还公开了用于制备逆转录病毒蛋白酶抑制剂的工艺和中间体。
• Intermediates for preparing retroviral protease inhibiting compounds
  申请人：Abbott Laboratories

  公开号：EP0997459A1

  公开（公告）日：2000-05-03

  An intermediate of the formula: and an intermediate of the formula: or an acid addition salt thereof.

  公式的中间体： 和 式的中间体 或其酸加成盐。
• Structure, spectra and redox behaviour of copper(II) complexes of bis(benzimidazolyl)diamine ligands
  作者：Thangarasu Pandiyan、Mallayan Palaniandavar、M. Lakshminarayanan、Hattikudur Manohar

  DOI：10.1039/dt9920003377

  日期：——

  The linear quadridentate ligand N,N'-bis(benzimidazol-2-ylethyl)ethane-1,2-diamine (L1) and its 1-methylbenzimidazole analogue (L2) and homologues form 1:1 complexes with Cu (ClO4)2; L1 also forms complexes of the types CuL1X2 where X = NO3, PF6, Br or Cl and CuL1(X)Y where X = Cl or Br and Y = ClO4 or Br. Deep blue CuL1Br2.2H2O crystallizes in the monoclinic space group C2/c with Z = 4, a = 9.919(2), b = 16.626(3), c = 14.102(3) angstrom and beta = 94.39(2)-degrees. The structure was solved by Patterson and Fourier difference methods and refined by the least-squares technique to R = 0.064 for 2195 independent reflections with / > 1.5sigma(/). The molecule lies on a two-fold axis symmetrically around Cu(II). The co-ordination around Cu(II) is found to be square planar with two amino nitrogens and two benzimidazole nitrogens forming the equatorial plane [Cu-N 1.983(3) and 2.037(4) angstrom]. The bromides are at longer distances [3.349(1) angstrom] in axial sites. Ligand field and EPR spectra indicate that one bromide or chloride ion is axially co-ordinated to Cu(II) in [CuL1]2+. This ion exhibits quasi-reversible redox behaviour. Electrochemical studies of the dihalides in methanol have established the presence of [CuL1X2], [CuL1(X)]+ and [CuL1]2+ in equilibrium. In complexes with 565 [CuL4]2+ [L4 = N,N'-bis(benzimidazol-2-ylmethyl)ethane-1,2-diamine] and 555 [CuL3]2+ [L3 = N,N'-bis(1-methylbenzimidazol-2-ylmethyl)propane-1,3-diamine] chelate rings, Cu(II) does not seem to lie in the N4 square plane, as revealed by their low A(parallel-to) values and irreversible electrochemical behaviour. The Cu(II)-Cu(I) redox potentials in methanol are in the order [CuL1]2+ < [CuL3]2+ < [CuL4]2+; this illustrates that six-membered chelate rings are suitable to stabilize Cu(II), when Cu-N sigma interactions are favourable.
• IMIDAZOPYRIDINES, PYRIMIDINES AND TRIAZINES FOR ENHANCING COGNITION AS GABA-A ALPHA 5 RECEPTOR SUBTYPE LIGANDS
  申请人：Merck Sharp & Dohme Limited

  公开号：EP1451161A1

  公开（公告）日：2004-09-01
• US5354866A
  申请人：——

  公开号：US5354866A

  公开（公告）日：1994-10-11