4-(imidazo[2,1-b]benzothiazol-2-yl)benzoic acid | 79889-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(imidazo[2,1-b]benzothiazol-2-yl)benzoic acid
• 英文别名: 2-(p-carboxyphenyl)imidazo[2,1-b]benzothiazole；4-imidazo[2,1-b][1,3]benzothiazol-2-ylbenzoic acid
• CAS: 79889-93-3
• 化学式: C₁₆H₁₀N₂O₂S
• 分子量: 294.334
• InChiKey: SJVSPBJRLIELAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(imidazo[2,1-b]benzothiazol-2-yl)benzoic acid 在 lithium aluminium tetrahydride 、 三甲基硅烷化重氮甲烷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 生成 4-(imidazo[2,1-b]benzothiazol-2-yl)benzyl alcohol
  参考文献：
  名称：

  Synthesis and biological evaluation of imidazolo[2,1-b]benzothiazole derivatives, as potential p53 inhibitors

  摘要：

  Since activation of p53 in response to cytotoxic stress may have proapoptotic or protective effects depending on the nature of the injury, inhibitors of p53 may have therapeutic interest as modulators of chemotherapy toxicity or efficacy. In an attempt to identify novel p53 inhibitors, a quality collection of compounds structurally related to pifithrin-beta were designed and synthesized as potential inhibitors of p53. The biochemical and biological evaluations supported that compounds of the tetrahydrobenzothiazole series were inhibitors of the p53 transcriptional activity and were effective in enhancing paclitaxel-induced apoptosis. In contrast, in spite of the increased cytotoxic potency, selected compounds of the benzothiazole series were not able to modulate the transcriptional activity of p53, as indicated by lack of change of p21 expression. The therapeutic interest of the compounds of the former series in combination with taxanes was confirmed in a human tumor xenograft model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.039
• 作为产物：
  描述：

  2-溴-4'-氰基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 7.5h， 生成 4-(imidazo[2,1-b]benzothiazol-2-yl)benzoic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of imidazolo[2,1-b]benzothiazole derivatives, as potential p53 inhibitors

  摘要：

  Since activation of p53 in response to cytotoxic stress may have proapoptotic or protective effects depending on the nature of the injury, inhibitors of p53 may have therapeutic interest as modulators of chemotherapy toxicity or efficacy. In an attempt to identify novel p53 inhibitors, a quality collection of compounds structurally related to pifithrin-beta were designed and synthesized as potential inhibitors of p53. The biochemical and biological evaluations supported that compounds of the tetrahydrobenzothiazole series were inhibitors of the p53 transcriptional activity and were effective in enhancing paclitaxel-induced apoptosis. In contrast, in spite of the increased cytotoxic potency, selected compounds of the benzothiazole series were not able to modulate the transcriptional activity of p53, as indicated by lack of change of p21 expression. The therapeutic interest of the compounds of the former series in combination with taxanes was confirmed in a human tumor xenograft model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.039

文献信息

• 2-Phenylimidazo [2,1-b]benzothiazole derivatives
  申请人：Yamanouchi Pharmaceutical Co., Ltd.

  公开号：US04497817A1

  公开（公告）日：1985-02-05

  A novel 2-phenylimidazo[2,1-b]benzothiazole derivative shown by the following formula ##STR1## or a salt thereof which possesses an immunoregulatory action and is useful as an antiallergic agent, an antiasthmatic, and a suppressant of rejection at tissue transplantation and skin graft.

  下列式子所示的新型2-苯基咪唑[2,1-b]苯并噻唑衍生物，或其盐，具有免疫调节作用，并可用作抗过敏剂，抗哮喘剂，以及组织移植和皮肤移植的抑制剂。 ##STR1##
• Imidazo[2,1-b]benzothiazoles. 2. New immunosuppressive agents
  作者：Toshiyasu Mase、Hideki Arima、Kenichi Tomioka、Toshimitsu Yamada、Kiyoshi Murase

  DOI：10.1021/jm00153a014

  日期：1986.3

  A series of 2-phenylimidazo[2,1-b]benzothiazole derivatives was prepared and tested for immunological activities. Some of the compounds showed significant suppressive activity of delayed type hypersensitivity (DTH) without inhibition of humoral immunity in mice by oral administration. The most active compound was 2-(m-hydroxyphenyl)imidazo[2,1-b]benzothiazole (20).
• MASE, TOSHIYASU;ARIMA, HIDEKI;TOMIOKA, KENICHI;YAMADA, TOSHIMITSU;MURASE,+, J. MED. CHEM., 1986, 29, N 3, 386-394
  作者：MASE, TOSHIYASU、ARIMA, HIDEKI、TOMIOKA, KENICHI、YAMADA, TOSHIMITSU、MURASE,+

  DOI：——

  日期：——
• US4497817A
  申请人：——

  公开号：US4497817A

  公开（公告）日：1985-02-05
• Synthesis and biological evaluation of imidazolo[2,1-b]benzothiazole derivatives, as potential p53 inhibitors
  作者：Michael S. Christodoulou、Francesco Colombo、Daniele Passarella、Gabriella Ieronimo、Valentina Zuco、Michelandrea De Cesare、Franco Zunino

  DOI：10.1016/j.bmc.2011.01.039

  日期：2011.3

  Since activation of p53 in response to cytotoxic stress may have proapoptotic or protective effects depending on the nature of the injury, inhibitors of p53 may have therapeutic interest as modulators of chemotherapy toxicity or efficacy. In an attempt to identify novel p53 inhibitors, a quality collection of compounds structurally related to pifithrin-beta were designed and synthesized as potential inhibitors of p53. The biochemical and biological evaluations supported that compounds of the tetrahydrobenzothiazole series were inhibitors of the p53 transcriptional activity and were effective in enhancing paclitaxel-induced apoptosis. In contrast, in spite of the increased cytotoxic potency, selected compounds of the benzothiazole series were not able to modulate the transcriptional activity of p53, as indicated by lack of change of p21 expression. The therapeutic interest of the compounds of the former series in combination with taxanes was confirmed in a human tumor xenograft model. (C) 2011 Elsevier Ltd. All rights reserved.