4-(benzo[d]imidazo[2,1-b]thiazol-2-yl)benzonitrile | 1282523-57-2

• 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-(benzo[d]imidazo[2,1-b]thiazol-2-yl)benzonitrile
• 英文别名: 4-(imidazo[2,1-b]benzothiazol-2-yl)benzonitrile；4-Imidazo[2,1-b][1,3]benzothiazol-2-ylbenzonitrile
• CAS: 1282523-57-2
• 化学式: C₁₆H₉N₃S
• 分子量: 275.334
• InChiKey: WDFOFMVFXHPWRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(benzo[d]imidazo[2,1-b]thiazol-2-yl)benzonitrile 在 sodium hydroxide 、 盐酸 、 水 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 以96%的产率得到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
• 作为产物：
  描述：

  2-氨基苯并噻唑 、 2-溴-4'-氰基苯乙酮 以 水 、 异丙醇 为溶剂， 100.0 ℃ 、1.5 MPa 条件下， 以96%的产率得到4-(benzo[d]imidazo[2,1-b]thiazol-2-yl)benzonitrile
  参考文献：
  名称：

  微波辐照下无水催化剂合成苯并[d]咪唑并[2,1-b]噻唑和新型N-烷基化2-氨基苯并[d]恶唑

  摘要：

  开发了一种前所未有的高效无催化剂微波辅助方法，用于在绿色介质中合成苯并[ d ]咪唑并[ 2,1- b ]噻唑和N-烷基化 2-氨基苯并[ d ]恶唑。该转化提供了在温和的无过渡金属条件下从 2-氨基苯并噻唑和N-烷基化 2-氨基苯并[ d ]恶唑快速获得功能化苯并[ d ]咪唑[ 2,1- b ]噻唑的途径。这种合成操作有望极大地扩展杂环化学中反应类型的全部内容，并为生物活性化合物的新合成铺平道路。

  DOI：

  10.1039/c9ra08929b

文献信息

• On water catalyst-free synthesis of benzo[<i>d</i>]imidazo[2,1-<i>b</i>] thiazoles and novel <i>N</i>-alkylated 2-aminobenzo[<i>d</i>]oxazoles under microwave irradiation
  作者：Narasimharao Mukku、Barnali Maiti

  DOI：10.1039/c9ra08929b

  日期：——

  unprecedented catalyst-free microwave-assisted procedure for synthesizing benzo[d]imidazo[2,1-b]thiazoles and N-alkylated 2-aminobenzo[d]oxazol in green media was developed. The transformation provided rapid access to functionalized benzo[d]imidazo[2,1-b]thiazoles from 2-aminobenzothiazole and N-alkylated 2-aminobenzo[d]oxazole from 2-aminobenzoxazole scaffolds under mild transition-metal-free conditions. This

  开发了一种前所未有的高效无催化剂微波辅助方法，用于在绿色介质中合成苯并[ d ]咪唑并[ 2,1- b ]噻唑和N-烷基化 2-氨基苯并[ d ]恶唑。该转化提供了在温和的无过渡金属条件下从 2-氨基苯并噻唑和N-烷基化 2-氨基苯并[ d ]恶唑快速获得功能化苯并[ d ]咪唑[ 2,1- b ]噻唑的途径。这种合成操作有望极大地扩展杂环化学中反应类型的全部内容，并为生物活性化合物的新合成铺平道路。
• Oxidative annulation of acetophenones and 2-aminobenzothiazoles catalyzed by reusable nickel-doped LaMnO₃ perovskites
  作者：Phuong T. Pham、Duyen K. Nguyen、Nam T. S. Phan、Minh-Vien Le、Tung T. Nguyen

  DOI：10.1039/d2ra08045a

  日期：——

  report a method for direct coupling of acetophenones and 2-aminobenzothiazoles in the presence of reusable perovskites, namely LaMn0.95Ni0.05O3. Imidazole[2,1-b]benzothiazoles were obtained in moderate to good yields and contained an array of useful functionalities. Control experiments indicated that the perovskites played pivotal roles in halogenation and condensation steps.

  咪唑 [2,1- b ] 苯并噻唑的合成通常受到使用预功能化底物和/或均相、不可回收催化系统的影响。在此，我们报告了一种在可重复使用的钙钛矿（即 LaMn 0.95 Ni 0.05 O 3）存在下直接偶联苯乙酮和 2-氨基苯并噻唑的方法。咪唑 [2,1- b ] 苯并噻唑以中等到良好的产率获得，并包含一系列有用的功能。对照实验表明，钙钛矿在卤化和缩合步骤中起着关键作用。
• Organophotoredox-Catalyzed C(sp²)–H Difluoromethylenephosphonation of Imidazoheterocycles
  作者：Mukta Singsardar、Susmita Mondal、Sudip Laru、Alakananda Hajra

  DOI：10.1021/acs.orglett.9b01954

  日期：2019.7.19

  A mild and efficient method for the direct difluoromethylenephosphonation of imidazopyridines has been developed using rose bengal (RB) as a photoredox catalyst. Bis(pinacolato)diboron (B(2)pin(2)) is found to be a crucial additive in the present reaction. The present methodology is also applicable to other heterocycles like imidazo[2,1-b]thiazole, benzo[d]imidazo-[2,1-b]thiazole, and indole. The reaction possibly proceeds through a single electron transfer (SET) process.
• 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.
• 10.1002/aoc.7555
  作者：Gao, Song、Cao, Chuan-Qi、Luo, Yu-Zhou、Yao, Zi-Jian

  DOI：10.1002/aoc.7555

  日期：——

  highly efficient carbonylation of aryl halides using half-sandwich iridium catalysis was developed, providing a new avenue for synthesizing carboxylic ester derivatives and yielding consistently impressive results. These iridium complexes demonstrated remarkable catalytic performance in the coupling reaction using phenyl formate derivatives as the source of CO, phenol, and aryl halides as the starting

  开发了使用半夹心铱催化的芳基卤化物的高效羰基化反应，为合成羧酸酯衍生物提供了新途径，并始终产生令人印象深刻的结果。这些铱配合物在空气存在下以甲酸苯酯衍生物为CO源、苯酚和芳基卤化物为起始原料的偶联反应中表现出显着的催化性能，并具有良好的空气和湿气稳定性。在低反应温度下合成具有不同取代基的酯产物，无需惰性气氛，从而实现高产率。广泛的底物范围、令人印象深刻的催化活性和温和的反应条件表明该催化体系具有广阔的工业应用前景。衰减全反射傅里叶变换红外 (ATR-FTIR)、核磁共振 (NMR) 和元素分析 (EA) 充分证明了所需的金属配合物 1-4。通过X射线晶体学证明了环金属化铱配合物2和3的分子结构。此外，密度泛函理论（DFT）研究进一步支持了这种 Ir 催化过程的可能机制。