ethyl 2-(1H-1,3-benzodiazol-2-ylsulfanyl)-3-oxobutanoate | 5268-66-6

• 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: ethyl 2-(1H-1,3-benzodiazol-2-ylsulfanyl)-3-oxobutanoate
• 英文别名: ethyl 2-((1H-benzo[d]imidazol-2-yl)thio)-3-oxobutanoate；ethyl 2-(2-benzimidazolylthio)acetoacetate；2-(2-Benzimidazolylthio)-acetessigsaeure-aethylester；2-(1H-benzoimidazol-2-ylsulfanyl)-3-oxo-butyric acid ethyl ester；Ethyl 2-[(1H-benzimidazol-2-yl)sulfanyl]-3-oxobutanoate；ethyl 2-(1H-benzimidazol-2-ylsulfanyl)-3-oxobutanoate
• CAS: 5268-66-6
• 化学式: C₁₃H₁₄N₂O₃S
• 分子量: 278.332
• InChiKey: JCBDJXPAGBZJFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  97.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  ethyl 2-(1H-1,3-benzodiazol-2-ylsulfanyl)-3-oxobutanoate 在 吡啶 、 乙酸酐 、 一水合肼 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  New tilomisole-based benzimidazothiazole derivatives as anti-inflammatory agents: Synthesis, in vivo, in vitro evaluation, and in silico studies

  摘要：

  DOI：

  10.1016/j.bioorg.2022.105644
• 作为产物：
  描述：

  3H-benzimidazo<2,1-c><1,2,4>dithiazol-3-thione 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 ethyl 2-(1H-1,3-benzodiazol-2-ylsulfanyl)-3-oxobutanoate
  参考文献：
  名称：

  Martin, Dieter; Tittelbach, Franz, Journal of the Chemical Society. Perkin transactions I, 1985, p. 1007 - 1014

  摘要：

  DOI：

文献信息

• Development of isatin-thiazolo[3,2-a]benzimidazole hybrids as novel CDK2 inhibitors with potent in vitro apoptotic anti-proliferative activity: Synthesis, biological and molecular dynamics investigations
  作者：Wagdy M. Eldehna、Mahmoud A. El Hassab、Mahmoud F. Abo-Ashour、Tarfah Al-Warhi、Mahmoud M. Elaasser、Nesreen A. Safwat、Howayda Suliman、Marwa F. Ahmed、Sara T. Al-Rashood、Hatem A. Abdel-Aziz、Radwan El-Haggar

  DOI：10.1016/j.bioorg.2021.104748

  日期：2021.5

  treatments that target tumor cells in a selective manner. In this regard, the present work aims at developing a new set of small molecules featuring the privileged isatin scaffold conjugated with a thiazolo[3,2-a]benzimidazole (TBI) motif through a cleavable hydrazide linker (7a-e and 10a-i) as potential anticancer CDK2 inhibitors. The large tricyclic TBI motif is anticipated to achieve a plethora of hydrophobic

  在当前的医学时代，人类健康正面临着诸多挑战，尤其是人类恶性肿瘤。因此，通过以选择性方式靶向肿瘤细胞的新疗法，将无情地增强这些恶性肿瘤的治疗手段。在这方面，目前的工作旨在开发一组新的小分子，其特征是通过可切割的酰肼接头（7a-e和10a-i）与噻唑并 [3,2- a ] 苯并咪唑 ( TBI ) 基序缀合的特权靛红支架。) 作为潜在的抗癌 CDK2 抑制剂。大三环TBI预计基序将在 CDK2 结合位点内实现大量疏水相互作用。大多数制备的杂合体在IC 50范围内显着抑制了两种检测细胞系的生长；（2.60 ± 1.47–20.90 ± 1.17 µM，针对 MDA-MB-231）和（1.27 ± 0.06–16.83 ± 0.95 µM，针对 MCF-7）。特别是，杂种7a、7d和10a对所检查的细胞系显示出强大的双重活性，因此被选中用于进一步研究。除了在 MDA-MB-231 和 MCF-7
• 苯并咪唑并噻唑甲酰胺类化合物及其应用
  申请人：沈阳药科大学

  公开号：CN108017659A

  公开（公告）日：2018-05-11

  本发明属于医药技术领域，涉及苯并咪唑并噻唑甲酰胺类化合物及其应用。苯并咪唑并噻唑甲酰胺类化合物包括苯并咪唑并噻唑甲酰胺类化合物的衍生物和药学上适用的盐，其结构通式如下所示：其中R1、R2如权利要求和说明书所述。苯并咪唑并噻唑甲酰胺类化合物以及该类化合物药学上适用的酸加成的盐可以与现有药物合并或单独使用作为表皮上生长因子酪氨酸激酶抑制剂，用于治疗表皮生长因子受体信号转导失调的相关疾病如小细胞肺癌，鳞癌，腺癌，大细胞癌，结肠直肠癌、乳腺癌，卵巢癌，肾细胞癌。
• Syntheses of heterocyclic fused thiazolecarboxylic acids I
  作者：Stanley C. Bell、Carl Gochman、Peter H. L. Wei

  DOI：10.1002/jhet.5570120622

  日期：1975.12

  A number of thiazolo 5-carboxylic acid derivatives were prepared which were fused to other heterocycles such as 1,2,4-benzothiadiazine, quinazoline, and pyrimidine rings at the 2,3-position of the thiazole ring. In several instances unexpected products were obtained, depending on the reaction conditions. The chemistry of these reactions and the identification of the products are discussed.

  制备了许多噻唑5-羧酸衍生物，它们在噻唑环的2，3-位与其他杂环如1,2,4-苯并噻二嗪，喹唑啉和嘧啶环稠合。在几种情况下，取决于反应条件，获得了意想不到的产物。讨论了这些反应的化学反应和产物的鉴定。
• Studies on New Acidic Azoles as Glucose-Lowering Agents in Obese, Diabetic db/db Mice
  作者：Kenneth L. Kees、Thomas J. Caggiano、Kurt E. Steiner、John J. Fitzgerald、Michael J. Kates、Thomas E. Christos、John M. Kulishoff、Robin D. Moore、Michael L. McCaleb

  DOI：10.1021/jm00004a008

  日期：1995.2

  Bioisosteric substitution was used as a tool to generate several new structural alternatives to the thiazolidine-2,4-dione and tetrazole heterocycles as potential antidiabetic agents. Among the initial leads that emerged from this strategy, a family of acidic azoles isoxazol-3- and -5-ones and a pyrazol-3-one, showed significant plasma glucose-lowering activity (17-42% reduction) in genetically obese, diabetic db/db mice at a dose of 100 mg/kg/day x 4. Structure-activity relationship studies determined that 5-alkyl-4-(arylmethyl)pyrazol-3-ones, which exist in solution as aromatic enol/iminol tautomers, were the most promising new class of potential antidiabetic agent (32-45% reduction at 20 mg/kg/d x 4). Included in this work are convenient syntheses for several types of acidic azoles that may find use as new acidic bioisosteres in medicinal chemistry such as the antidiabetic lead 5-(trifluoromethyl)pyrazol-3-one (hydroxy tautomer) and aza homologs of the pyrazolones, 1,2,3-triazol-5-ones (hydroxy tautomer) and 1,2,3,4-tetrazol-5-one heterocycles. log P and pK(a) data for 15 potential acidic bioisosteres, all appended to a 2-naphthalenylmethyl residue so as to maintain a similar distance between the acidic hydrogen and arene nucleus, are presented. This new data set allows comparison of a wide variety of potential acid mimetics (pK(a) 3.78-10.66; log P -0.21 to 2.76) for future drug design.
• MARTIN, D.;TITTEIBACH, F.
  作者：MARTIN, D.、TITTEIBACH, F.

  DOI：——

  日期：——