6-dimethylaminomethylene-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one | 135274-43-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-dimethylaminomethylene-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one
• 英文别名: 2-dimethylaminomethylene-1-benzosuberone；6-(dimethylaminomethylidene)-8,9-dihydro-7H-benzo[7]annulen-5-one
• CAS: 135274-43-0
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: MVQFCMRATNPGQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-dimethylaminomethylene-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one 、 间硝基苯胺 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 、 乙醇 为溶剂， 以84%的产率得到
  参考文献：
  名称：

  芳基偶氮苯并亚砜的合成，互变异构和抗菌，抗HCV，抗SSPE，抗氧化剂和抗肿瘤活性

  摘要：

  将2-二甲基氨基亚甲基-1-苯并亚砜1与重氮化苯胺衍生物偶联，可获得一系列迄今未报道的2-芳基偶氮-1-苯并亚砜3a - i。讨论了互变异构结构和取代基对产物3a – i互变异构形式的影响。烯胺酮1与杂环胺的重氮盐的类似偶联产生了相应的稠合的三唑并三嗪-苯并亚砜。一些新合成的化合物显示出有效的抗微生物，抗HCV，抗氧化剂，抗肿瘤作用（作为拓扑异构酶I抑制剂）和抗微生物活性。

  DOI：

  10.1016/j.bmc.2009.10.012
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 1-苯并环庚酮 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 生成 6-dimethylaminomethylene-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one
  参考文献：
  名称：

  Synthesis and biological evaluation of tricyclic anilinopyrimidines as IKKβ inhibitors

  摘要：

  A series of tricyclic anilinopyrimidines were synthesized and evaluated as IKK beta inhibitors. Several analogues, including tricyclic phenyl (10, 18a, 18c, 18d, and 18j) and thienyl (26 and 28) derivatives were shown to have good in vitro enzyme potency and excellent cellular activity. Pharmaceutical profiling of a select group of tricyclic compounds compared to the non-tricyclic analogues suggested that in some cases, the improved cellular activity may be due to increased clog P and permeability. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.022

文献信息

• Lewis-Acid-Catalyzed Regioselective Construction of Diversely Functionalized Polycyclic Fused Furans
  作者：Sana Jamshaid、Yong Rok Lee

  DOI：10.1021/acs.orglett.2c00019

  日期：2022.2.18

  A novel, facile, and efficient Lewis-acid-catalyzed [4 + 1] annulation protocol for the construction of functionalized polycyclic-fused furans is developed. This methodology is free of transition metals and ligands and provides a rapid synthetic route to divergently orientated polycyclic furans in good yields. In addition, this protocol can also be used to synthesize multisubstituted furans.

  开发了一种用于构建功能化多环稠合呋喃的新型、简便且高效的路易斯酸催化 [4 + 1] 环化方案。该方法不含过渡金属和配体，并提供了一种快速合成途径，以良好的收率获得发散取向的多环呋喃。此外，该协议还可用于合成多取代呋喃。
• [EN] SUBSTITUTED PYRAZOLO [3, 4-B] PYRIDINE COMPOUNDS<br/>[FR] COMPOSÉS DE PYRAZOLO[3,4-B]PYRIDINE SUBSTITUÉS
  申请人：ARQULE INC

  公开号：WO2010078427A1

  公开（公告）日：2010-07-08

  The present invention relates to substituted imidazoly 1-5,6- dihydrobenzo[n]isoquinoline compounds and methods of synthesizing these compounds. The present invention also relates to pharmaceutical compositions containing substituted imidazolyl-5,6-dihydrobenzo[n]isoquinoline compounds and methods of treating cell proliferative disorders, such as cancer, by administering these compounds and pharmaceutical compositions to subjects in need thereof.

  本发明涉及替代咪唑基-5,6-二氢苯并[ｎ]异喹啉化合物及合成这些化合物的方法。本发明还涉及含有替代咪唑基-5,6-二氢苯并[ｎ]异喹啉化合物的药物组合物，以及通过向需要的受试者投予这些化合物和药物组合物来治疗细胞增殖性疾病，如癌症的方法。
• SUBSTITUTED IMIDAZOLYL-5,6-DIHYDROBENZO[N]ISOQUINOLINE COMPOUNDS
  申请人：Ali Syed M.

  公开号：US20100239526A1

  公开（公告）日：2010-09-23

  The present invention relates to substituted imidazolyl-5,6-dihydrobenzo[n]isoquinoline compounds and methods of synthesizing these compounds. The present invention also relates to pharmaceutical compositions containing substituted imidazolyl-5,6-dihydrobenzo[n]isoquinoline compounds and methods of treating cell proliferative disorders, such as cancer, by administering these compounds and pharmaceutical compositions to subjects in need thereof.

  本发明涉及取代的咪唑基-5,6-二氢苯并[n]异喹啉化合物及其合成方法。本发明还涉及含有取代的咪唑基-5,6-二氢苯并[n]异喹啉化合物的制药组合物，以及通过向需要治疗细胞增殖性疾病（如癌症）的受试者施用这些化合物和制药组合物来治疗的方法。
• Facile access to the 2,2-difluoro-2,3-dihydrofuran skeleton without extra additives: DMF-promoted difluorocarbene formation of ClCF₂CO₂Na
  作者：Zunsheng Chen、Xin Xie、Weiming Chen、Nianhua Luo、Xiaoning Li、Fuchao Yu、Jiuzhong Huang

  DOI：10.1039/d2ob01542k

  日期：——

  A practical and facile difluorocarbene-triggered cycloaddition reaction of enaminones was developed, which delivered 2,2-difluoro-2,3-dihydrofurans without any extra additives.

  一种实用且容易的二氟卡宾触发的烯酰胺环加成反应被开发出来，可以在不添加任何额外添加剂的情况下得到2,2-二氟-2,3-二氢呋喃。
• Novel 6,7,8-trihydrobenzo[6',7']cyclohepta[2',1'-e]pyrazolo[2,3-a]pyrimidine derivatives as Topo IIα inhibitors with potential cytotoxic activity
  作者：Thoraya A. Farghaly、Hanan Gaber Abdulwahab、Hanadi Y. Medrasi、Mariam A. Al-sheikh、Dina F. Katowah、Amani M.R. Alsaedi

  DOI：10.1016/j.bioorg.2022.106043

  日期：2022.11

  18 µM). Among the tested compounds, aminopyrazolopyrimidine derivatives 6a (IC50 = 3.44 µM) and 6c (IC50 = 2.35 µM) were comparable/ equipotent to Doxorubicin (IC50 = 2.71 µM) against Topo II. The most active compounds in Topo II assay were further investigated in vitro for their cytotoxic potential. The oxo-pyrazolopyrimidine derivative 15c; was the most potent possessing one-digit IC50 values (HCT116

  新型四环吡唑并[1,5- a ]嘧啶衍生物；即苯并[3]、[4]环庚[1,2 -e ]吡唑并[1,5 - a ]嘧啶-2-胺6a-e和苯并[3]、[4]环庚[1,2 -e ] pyrazolo[1,5 - a ]pyrimidin-2(6H)-ones 15a-d被设计和合成为具有潜在抗癌活性的拓扑异构酶 IIα 抑制剂。基于光谱数据和 DFT 计算，讨论并确认了结构及其机理路径。化合物6a、6c、15b、15c和15d在一位数 IC 50下表现出有效的 Topo II 抑制活性值 (2.35 – 7.18 µM)。在测试的化合物中，氨基吡唑并嘧啶衍生物6a (IC 50 = 3.44 µM) 和6c (IC 50 = 2.35 µM) 与多柔比星 (IC 50 = 2.71 µM) 对 Topo II相当/等效。在体外进一步研究了 Topo II 测定中最活跃的化合物的细胞毒性潜力。氧代