4,7-dimethoxy-2-mercaptobenzimidazole | 95306-53-9

• 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: 4,7-dimethoxy-2-mercaptobenzimidazole
• 英文别名: 4,7-dimethoxy-1,3-dihydrobenzimidazole-2-thione
• CAS: 95306-53-9
• 化学式: C₉H₁₀N₂O₂S
• 分子量: 210.257
• InChiKey: WCMTVWLAEJYDMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,7-dimethoxy-2-mercaptobenzimidazole 在 四磷十氧化物 、 磷酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5,8-dimethoxy-3-p-bromophenylthiazolo<3,2-a>benzimidazole
  参考文献：
  名称：

  Narayan, Sat; Kumar, Vinod; Pujari, H. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 267 - 270

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-二甲氧基-2,3-二硝基苯 在 镍 一水合肼 作用下， 生成 4,7-dimethoxy-2-mercaptobenzimidazole
  参考文献：
  名称：

  Narayan, Sat; Kumar, Vinod; Pujari, H. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 267 - 270

  摘要：

  DOI：

文献信息

• 1-aza-1,3-enynes in synthesis of substituted 4H-[1,3]thiazino[3,2-a]benzimidazol-4-ols
  作者：M. V. Karpov、A. V. Eremin、A. I. Fisher、A. N. Belyaev、M. D. Stadnichuk

  DOI：10.1134/s1070363211010208

  日期：2011.1

  Reaction of N-tert-butyl-1-aza-1,3-enynes with symmetrically substituted 2-mercaptobenzimidazoles in water-alcohol solutions afford 4H-[1,3]thiazino[3,2-a]benzimidazol-4-ols. The structure of compounds obtained was proved by the H-1 and C-13 NMR spectroscopy and X-ray diffraction data.
• <i>N</i>-Methylation of Heterocycles with Dimethylformamide Dimethyl Acetal
  作者：Richard W. Middleton、Hugh Monney、John Parrick

  DOI：10.1055/s-1984-30953

  日期：——
• Synthesis and antiproliferative activity of some benzimidazole-4,7-dione derivatives
  作者：Laura Garuti、Marinella Roberti、Monica Malagoli、Tiziana Rossi、Mario Castelli

  DOI：10.1016/s0960-894x(00)00429-7

  日期：2000.10

  A series of benzimidazole-4,7-diones bearing at the 2-position the thiomethyl group or the 2-pyridyl moiety has been synthesized and tested in vitro on three tumor cell lines. Two of them show a very good antiproliferative effect. Compounds 1 and 2d are more active or equiactive, respectively, than MMC against human lymphoblastic leukemia. Both compounds exhibit high activity on human non-Hodgkin lymphoma. Compound a is non toxic at all the concentrations used in the antiproliferative assay and 2d is toxic only at high concentration. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Rational Design of Novel Immunosuppressive Drugs:  Analogues of Azathioprine Lacking the 6-Mercaptopurine Substituent Retain or Have Enhanced Immunosuppressive Effects
  作者：Duncan J. K. Crawford、John L. Maddocks、D. Neville Jones、Paul Szawlowski

  DOI：10.1021/jm960132w

  日期：1996.1.1

  Clinical use of the immunosuppressive drug azathioprine is limited by potentially serious toxic effects related to depression of bone marrow function. The immunosuppressive and toxic properties of azathioprine are regarded as being properties of the cytotoxicity of its metabolite, 6-mercaptopurine (6-MP). However, azathioprine has an immunosuppressive effect additional to that attributable to 6-MP alone, and we propose that this is associated with an action of the methylnitroimidazolyl substituent. This suggests a route to the rational design of nontoxic immunosuppressants by replacing the 6-MP component of azathioprine with nontoxic thiols. We have synthesized and tested in vitro 24 such analogues, with two being further tested in vivo. In the human mixed lymphocyte reaction, virtually all compounds showed some degree of activity, 10 compounds being more active than azathioprine. In vivo, two compounds were more effective than azathioprine at prolonging graft survival in mice. In an oral toxicity study in male CD1 mice at doses equivalent to those at which azathioprine caused severe bone marrow depression both analogues had no toxic effects. Our results show that the immunosuppressive effects and bone marrow toxicity of azathioprine are not a consequence of release of 6-MP alone, and with appropriate modification can be separated, an approach which may lead to less toxic immunosuppressive drugs.
• MIDDLETON, R. W.;MONNEY, H.;PARRICK, J., SYNTHESIS, BRD, 1984, N 9, 740-743
  作者：MIDDLETON, R. W.、MONNEY, H.、PARRICK, J.

  DOI：——

  日期：——