ethyl 2-acetylamino-6-bromo-7-hydroxybenzo[b]thiophene-3-carboxylate | 113407-93-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethyl 2-acetylamino-6-bromo-7-hydroxybenzo[b]thiophene-3-carboxylate
• 英文别名: Ethyl 2-(acetylamino)-6-bromo-7-hydroxy-1-benzothiophene-3-carboxylate；ethyl 2-acetamido-6-bromo-7-hydroxy-1-benzothiophene-3-carboxylate
• CAS: 113407-93-5
• 化学式: C₁₃H₁₂BrNO₄S
• mdl: MFCD00426585
• 分子量: 358.213
• InChiKey: LVQQTDJOVUGDGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-acetylamino-6-bromo-7-hydroxybenzo[b]thiophene-3-carboxylate 在 tripotassium phosphate "n" hydrate 、 二氯双[二叔丁基-(4-二甲基氨基苯基)膦]钯(II) 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 25.0h， 生成 ethyl 2-amino-7-[2-(N,N-diethylamino)ethyloxy]-6-(4-methoxyphenyl)benzo[b]thiophene-3-carboxylate
  参考文献：
  名称：

  BENZOTHIOPHENE COMPOUND, ALTERNATIVE AUTOPHAGY-INDUCING AGENT AND ANTICANCER DRUG INCLUDING BENZOTHIOPHENE COMPOUND AS ACTIVE INGREDIENT

  摘要：

  公开号：

  EP2813226B1
• 作为产物：
  描述：

  乙基 2-(乙酰基氨基)-4,5,6,7-四氢-1-苯并噻吩-3-羧酸 在 potassium dichromate 、 溴 、 potassium carbonate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 氯仿 、 水 为溶剂， 反应 43.5h， 生成 ethyl 2-acetylamino-6-bromo-7-hydroxybenzo[b]thiophene-3-carboxylate
  参考文献：
  名称：

  BENZOTHIOPHENE COMPOUND, ALTERNATIVE AUTOPHAGY-INDUCING AGENT AND ANTICANCER DRUG INCLUDING BENZOTHIOPHENE COMPOUND AS ACTIVE INGREDIENT

  摘要：

  公开号：

  EP2813226B1

文献信息

• BENZOTHIOPHENE COMPOUND, ALTERNATIVE AUTOPHAGY-INDUCING AGENT AND ANTICANCER AGENT INCLUDING THE COMPOUND AS ACTIVE INGREDIENT, AND METHOD FOR SCREENING FOR COMPOUND HAVING ANTICANCER ACTIVITY
  申请人：National University Corporation Tokyo Medical and Dental University

  公开号：US20150056141A1

  公开（公告）日：2015-02-26

  It has been found that efficient screening for a compound having anticancer activity can be achieved by selecting a compound having activity to induce alternative autophagy using, as an index, formation of fluorescent bright spots due to aggregation of a lysosomal protein to which a fluorescent protein is attached in cells expressing the lysosomal protein. In addition, it has been found that a benzothiophene compound represented by the following general formula (1) has alternative autophagy-inducing activity and anticancer activity:

  已经发现，通过选择具有诱导替代自噬活性的化合物作为指标，在细胞中表达溶酶体蛋白质的情况下，通过形成荧光亮点聚集溶酶体蛋白质，可以实现高效筛选具有抗癌活性的化合物。此外，已经发现以下通式（1）所表示的苯并噻吩化合物具有替代自噬诱导活性和抗癌活性：
• BENZOTHIOPHENE COMPOUND, ALTERNATIVE AUTOPHAGY-INDUCING AGENT AND ANTICANCER DRUG INCLUDING BENZOTHIOPHENE COMPOUND AS ACTIVE INGREDIENT, AND METHOD FOR SCREENING FOR COMPOUNDS HAVING ANTICANCER ACTIVITY
  申请人：National University Corporation Tokyo Medical and Dental University

  公开号：EP2813226A1

  公开（公告）日：2014-12-17

  It has been found that efficient screening for a compound having anticancer activity can be achieved by selecting a compound having activity to induce alternative autophagy using, as an index, formation of fluorescent bright spots due to aggregation of a lysosomal protein to which a fluorescent protein is attached in cells expressing the lysosomal protein. In addition, it has been found that a benzothiophene compound represented by the following general formula (1) has alternative autophagy-inducing activity and anticancer activity:

  研究发现，以表达溶酶体蛋白的细胞中附着荧光蛋白的溶酶体蛋白聚集形成荧光亮点为指标，选择具有诱导替代自噬活性的化合物，可以有效筛选出具有抗癌活性的化合物。此外，还发现由以下通式（1）代表的苯并噻吩化合物具有替代自噬诱导活性和抗癌活性：
• Benzothiophene compound, alternative autophagy-inducing agent and anticancer agent including the compound as active ingredient, and method for screening for compound having anticancer activity
  申请人：National University Corporation Tokyo Medical and Dental University

  公开号：US10954222B2

  公开（公告）日：2021-03-23

  It has been found that efficient screening for a compound having anticancer activity can be achieved by selecting a compound having activity to induce alternative autophagy using, as an index, formation of fluorescent bright spots due to aggregation of a lysosomal protein to which a fluorescent protein is attached in cells expressing the lysosomal protein. In addition, it has been found that a benzothiophene compound represented by the following general formula (1) has alternative autophagy-inducing activity and anticancer activity:

  研究发现，以表达溶酶体蛋白的细胞中附着荧光蛋白的溶酶体蛋白聚集形成荧光亮点为指标，选择具有诱导替代自噬活性的化合物，可以有效筛选出具有抗癌活性的化合物。此外，还发现由以下通式（1）代表的苯并噻吩化合物具有替代自噬诱导活性和抗癌活性：
• Synthesis and antitubercular activity of benzothieno[2,3-d]pyrimidines
  作者：M. V. Kapustina、O. Yu. Amel'kin、I. A. Kharizomenova、V. I. Shvedov、L. N. Filitis

  DOI：10.1007/bf00772002

  日期：1991.7
• Synthesis of derivatives of 2-acylamino-7-oxybenzo[b]thiophene. Bromination and nitration
  作者：A. N. Grinev、I. A. Kharizomenova、M. V. Kapustina、Yu. N. Sheinker、L. M. Alekseeva、N. M. Rubtsov

  DOI：10.1007/bf00546729

  日期：1987.4