1,3-dibromo-6-trifluoroacetylamino-5,6-dihydro-4H-cyclopentathiophen-4-one | 147542-31-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-dibromo-6-trifluoroacetylamino-5,6-dihydro-4H-cyclopentathiophen-4-one
• 英文别名: N-(1,3-Dibromo-4-oxo-5,6-dihydro-4H-cyclopenta[c]thiophene-6-yl)trifluoroacetamide；N-(1,3-dibromo-4-oxo-5,6-dihydrocyclopenta[c]thiophen-6-yl)-2,2,2-trifluoroacetamide
• CAS: 147542-31-2
• 化学式: C₉H₄Br₂F₃NO₂S
• 分子量: 407.005
• InChiKey: DCYNBGBFOVOEAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3-dibromo-6-trifluoroacetylamino-5,6-dihydro-4H-cyclopentathiophen-4-one 在 盐酸羟胺 、 sodium acetate 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 (E)-1,3-dibromo-6-trifluoroacetylamino-5,6-dihydro-4H-cyclopenta[c]thiophen-4-one O-formyloxime
  参考文献：
  名称：

  Khanh, Lan Pham; Dallemagne, Patrick; Alsaidi, Abdellah, Heterocycles, 1997, vol. 45, # 3, p. 527 - 535

  摘要：

  DOI：
• 作为产物：
  描述：

  3-三氟乙酰氨基-3-(噻吩-3-基)丙酸 在 三氯化铝 、 氯化亚砜 、 溴 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 0.41h， 生成 1,3-dibromo-6-trifluoroacetylamino-5,6-dihydro-4H-cyclopentathiophen-4-one
  参考文献：
  名称：

  Dallemagne, Patrick; Alsaidi, Abdellah; Boulouard, M., Heterocycles, 1993, vol. 36, # 2, p. 287 - 294

  摘要：

  DOI：

文献信息

• Design, synthesis and biological evaluation of novel indano- and thiaindano-pyrazoles with potential interest for Alzheimer's disease
  作者：David Genest、Christophe Rochais、Cédric Lecoutey、Jana Sopkova-de Oliveira Santos、Céline Ballandonne、Sabrina Butt-Gueulle、Remi Legay、Marc Since、Patrick Dallemagne

  DOI：10.1039/c3md00041a

  日期：——

  The synthesis of eighteen novel (thia)indanopyrazole derivatives was achieved starting from amino(thia)indanones. Some of them displayed a dual binding site acetylcholinesterase inhibition which makes them potentially interesting for Alzheimer's disease treatment.

  从氨基(噻)茚酮开始，合成了 18 种新型(噻)茚并吡唑衍生物。其中一些衍生物显示出双结合位点乙酰胆碱酯酶抑制作用，这使它们具有治疗阿尔茨海默病的潜在意义。
• Facile Diastereoselective Routes to Highly Functionalized Cyclopenta[c]thiophenes as Useful Scaffolds in Medicinal Chemistry
  作者：Lan Pham Khanh、Patrick Dallemagne、Sylvain Rault

  DOI：10.1055/s-2002-31960

  日期：——

  The diastereoselective access to highly functionalized cyclopenta[c]thiophene derivatives, potential useful scaffolds in medicinal chemistry, is described starting from aminocyclopenta[c]thiophenones.

  从氨基环戊并[c]噻吩酮开始，描述了非对映选择性地获得高度官能化的环戊并[c]噻吩衍生物的方法，这些衍生物是药物化学中潜在的有用支架。
• Synthesis and biological evaluation of five-Membered heterocycles fused to cyclopenta[ c ]thiophene as new antitumor agents
  作者：Patrick Dallemagne、Lan Pham Khanh、Abdellah Alsaı̈di、Isabelle Varlet、Valérie Collot、Magalie Paillet、Ronan Bureau、Sylvain Rault

  DOI：10.1016/s0968-0896(02)00654-5

  日期：2003.4

  A series of 10 derivatives 2-6 issued from the fusion of various five-membered heterocycles to cyclopenta[c]thiophene 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, four were found to be

  在由60个人类肿瘤组成的NCI体外人类疾病导向肿瘤细胞系筛选小组中，评估了由各种五元杂环与环戊[c]噻吩的融合产生的一系列10个衍生物2-6的潜在抗癌活性细胞系排列在九个子面板中，代表不同的组织学。在这些测试的化合物中，发现有四种具有细胞毒性，这使我们指出了一些构效关系。恶唑烷酮衍生物2a-c在NCI开发的中空纤维测定和标准异种移植物中显示出进一步的体内抗肿瘤活性。
• Synthesis and Cytotoxic Activity against L1210 Leukemia of New Aminocyclopenta(c)thiophenones.
  作者：Abdellah ALSAIDI、Samir AL SHARGAPI、Patrick DALLEMAGNE、Franck CARREIRAS、Pascal GAUDUCHON、Sylvain RAULT、Max ROBBA

  DOI：10.1248/cpb.42.1605

  日期：——

  Synthesis of some new hydroxyaminocyclopenta[c]thiophenones was achieved via halogenation reaction, then formation and finally cleavage of an aziridino ring. The in vitro cytotoxic activity of these compounds was evaluated against L1210 leukemia. The importance of the ketohydroxyethylamino sequence for their activities is discussed.

  通过卤化反应，然后形成并最终裂解一个氮丙啶环，合成了一些新的羟基氨基环戊并[c]噻吩酮。评估了这些化合物对 L1210 白血病的体外细胞毒性活性。讨论了酮羟乙氨基序列对其活性的重要性。
• Synthesis and biological evaluation of cyclopenta[ c ]thiophene related compounds as new antitumor agents
  作者：Patrick Dallemagne、Lan Pham Khanh、Abdellah Alsaı̈di、Olivier Renault、Isabelle Varlet、Valérie Collot、Ronan Bureau、Sylvain Rault

  DOI：10.1016/s0968-0896(02)00070-6

  日期：2002.7

  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.