6-Amino-1-bromo-5,6-dihydro-cyclopenta[c]thiophen-4-one; hydrochloride

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Amino-1-bromo-5,6-dihydro-cyclopenta[c]thiophen-4-one; hydrochloride
• 英文别名: 4-Amino-3-bromo-4,5-dihydrocyclopenta[c]thiophen-6-one;hydrochloride
• 化学式: C₇H₆BrNOS*ClH
• 分子量: 268.562
• InChiKey: RWXAUAOLYWHNCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  71.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Amino-1-bromo-5,6-dihydro-cyclopenta[c]thiophen-4-one; hydrochloride 在 溶剂黄146 、 sodium nitrite 作用下， 反应 6.0h， 以70%的产率得到1-Bromo-6-hydroxy-5,6-dihydro-cyclopenta[c]thiophen-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of cyclopenta[ c ]thiophene related compounds as new antitumor agents

  摘要：

  A series of 22 cyclopenta[c]thiophene related compounds was obtained by the pharmacomodulation of 6-amino-5,6- dihydro-4H-cyclopenta[c]thiophen-4-ones 1a-g. All compounds were evaluated for potential anticancer activity in the NCI's in vitro human disease-oriented tumor cell line screening panel that consisted of 60 human tumor cell lines arranged in nine subpanels, representing diverse histologies. Among these tested compounds. seven were found to be cytotoxic, especially against leukemia cell lines, allowing us to point out some structure activity relationships. These derivatives were further evaluated for potential in vivo anticancer activity in the hollow fiber assay developed at the NCI, which selected two compounds. If and 3a for standard xenograft testing. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00070-6
• 作为产物：
  描述：

  1-bromo-6-trifluoroacetylamino-5,6-dihydro-4H-cyclopentathiophen-4-one 在 盐酸 作用下， 反应 12.0h， 生成 6-Amino-1-bromo-5,6-dihydro-cyclopenta[c]thiophen-4-one; hydrochloride
  参考文献：
  名称：

  Synthesis and biological evaluation of cyclopenta[ c ]thiophene related compounds as new antitumor agents

  摘要：

  A series of 22 cyclopenta[c]thiophene related compounds was obtained by the pharmacomodulation of 6-amino-5,6- dihydro-4H-cyclopenta[c]thiophen-4-ones 1a-g. All compounds were evaluated for potential anticancer activity in the NCI's in vitro human disease-oriented tumor cell line screening panel that consisted of 60 human tumor cell lines arranged in nine subpanels, representing diverse histologies. Among these tested compounds. seven were found to be cytotoxic, especially against leukemia cell lines, allowing us to point out some structure activity relationships. These derivatives were further evaluated for potential in vivo anticancer activity in the hollow fiber assay developed at the NCI, which selected two compounds. If and 3a for standard xenograft testing. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00070-6

文献信息

• Synthesis and biological evaluation as AChE inhibitors of new indanones and thiaindanones related to donepezil
  作者：Ziad Omran、Thomas Cailly、Elodie Lescot、Jana Sopkova-de Oliveira Santos、Jean-Hugues Agondanou、Vincent Lisowski、Frédéric Fabis、Anne-Marie Godard、Silvia Stiebing、Guillaume Le Flem、Michel Boulouard、François Dauphin、Patrick Dallemagne、Sylvain Rault

  DOI：10.1016/j.ejmech.2005.07.009

  日期：2005.12

  Sixty-four new indanones and thiaindanones related to donepezil were synthesized and evaluated in vitro as potential AChE inhibitors. Among them, 11 derivatives were found to inhibit the enzyme in the submicromolar range; the best compound revealed its inhibitory activity with an IC50 in the same range (0.06 microM) than the reference compound, donepezil (IC50=0.02 microM).

  合成了与多奈哌齐有关的六十四种新的茚满酮和硫丹酮，并在体外评估了其作为潜在的AChE抑制剂。其中，发现了11种衍生物在亚微摩尔范围内抑制该酶。最好的化合物显示出其抑制活性，其IC50与参考化合物多奈哌齐（IC50 = 0.02 microM）处于相同范围（0.06 microM）。