1-(4-(3-(dimethylamino)propoxy)phenyl)ethan-1-one | 62416-92-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(3-(dimethylamino)propoxy)phenyl)ethan-1-one
• 英文别名: Ethanone, 1-[4-[3-(dimethylamino)propoxy]phenyl]-；1-[4-[3-(dimethylamino)propoxy]phenyl]ethanone
• CAS: 62416-92-6
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: CNWCATHDRJEQRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)quinolin-2-carbaldehyde 、 1-(4-(3-(dimethylamino)propoxy)phenyl)ethan-1-one 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 (E)-1-{4-[3-(dimethylamino)propoxy]phenyl}-3-[3-(4-methoxyphenyl)quinolin-2-yl]prop-2-en-1-one
  参考文献：
  名称：

  Discovery of 3-phenylquinolinylchalcone derivatives as potent and selective anticancer agents against breast cancers

  摘要：

  A number of 3-phenylquinolinylchalcone derivatives were synthesized and evaluated in vitro for their antiproliferative activities against three breast cancer cell lines (MCF-7, MDA-MB-231, and SKBR-3), and a non-cancer normal epithelial cell line (H184B5F5/M10). Among them, (E)-3-[3-(4-methoxyphenyl)quinolin-2-yl]-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (7) was active against the growth of MCF-7, MDA-MB-231, and SKBR-3 with IC50 values of 1.05, 0.75, and 0.78 mu M respectively without significant cytotoxicity to the normal H184B5F5/M10 cell line and therefore, was selected as a new lead for further mechanism studies. Results indicated that compound 7 inhibited the polymerization of tubulins, induced G2/M cell cycle arrest via modulation of the cyclin B1, cdk1 and CDC25. Compound 7 ultimately induced cell apoptosis by the increase of apoptotic protein Bax and the decrease of anti-apoptotic protein Bcl-2. In addition, PARP was cleaved while caspase-3 and -8 activities were induced after the treatment of compound 7 for 24 h in a concentration-dependent manner. Thus, compound 7 induces cell cycle arrest at G2/M phase via cleavage of PARP, induces caspase-3 and -8 activities and consequently to cause the cell death. Further study on the structure optimization of 7 is ongoing. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.054
• 作为产物：
  描述：

  N,N-二甲氨基氯丙烷盐酸盐 、 对羟基苯乙酮 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 1-(4-(3-(dimethylamino)propoxy)phenyl)ethan-1-one
  参考文献：
  名称：

  Discovery of 3-phenylquinolinylchalcone derivatives as potent and selective anticancer agents against breast cancers

  摘要：

  A number of 3-phenylquinolinylchalcone derivatives were synthesized and evaluated in vitro for their antiproliferative activities against three breast cancer cell lines (MCF-7, MDA-MB-231, and SKBR-3), and a non-cancer normal epithelial cell line (H184B5F5/M10). Among them, (E)-3-[3-(4-methoxyphenyl)quinolin-2-yl]-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (7) was active against the growth of MCF-7, MDA-MB-231, and SKBR-3 with IC50 values of 1.05, 0.75, and 0.78 mu M respectively without significant cytotoxicity to the normal H184B5F5/M10 cell line and therefore, was selected as a new lead for further mechanism studies. Results indicated that compound 7 inhibited the polymerization of tubulins, induced G2/M cell cycle arrest via modulation of the cyclin B1, cdk1 and CDC25. Compound 7 ultimately induced cell apoptosis by the increase of apoptotic protein Bax and the decrease of anti-apoptotic protein Bcl-2. In addition, PARP was cleaved while caspase-3 and -8 activities were induced after the treatment of compound 7 for 24 h in a concentration-dependent manner. Thus, compound 7 induces cell cycle arrest at G2/M phase via cleavage of PARP, induces caspase-3 and -8 activities and consequently to cause the cell death. Further study on the structure optimization of 7 is ongoing. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.054

文献信息

• Light‐Promoted Nickel Catalysis: Etherification of Aryl Electrophiles with Alcohols Catalyzed by a Ni ^II ‐Aryl Complex
  作者：Liu Yang、Huan‐Huan Lu、Chu‐Hui Lai、Gang Li、Wei Zhang、Rui Cao、Fengyi Liu、Chao Wang、Jianliang Xiao、Dong Xue

  DOI：10.1002/anie.202003359

  日期：2020.7.27

  highly effective C−O coupling reaction of (hetero)aryl electrophiles with primary and secondary alcohols is reported. Catalyzed by a NiII‐aryl complex under long‐wave UV (390–395 nm) irradiation in the presence of a soluble amine base without any additional photosensitizer, the reaction enables the etherification of aryl bromides and aryl chlorides as well as sulfonates with a wide range of primary

  据报道，（杂）芳基亲电试剂与伯醇和仲醇的高效C-O偶联反应。在可溶性胺碱的存在下，在没有任何其他光敏剂的情况下，在长波紫外线（390–395 nm）辐射下，由Ni II-芳基络合物催化，该反应可以使芳基溴化物和芳基氯化物以及磺酸盐与多种伯和仲脂族醇，可提供合成上重要的醚。分子内CO偶联也是可能的。该反应似乎通过Ni I -Ni III催化循环进行。
• Photoinduced Carbon−Heteroatom Cross‐Coupling Catalyzed by Nickel Naphthyridine Complexes
  作者：Janet Bahri、Shubham Deolka、Pavan K. Vardhanapu、Eugene Khaskin、Ramadoss Govindarajan、Robert R. Fayzullin、Serhii Vasylevskyi、Julia R. Khusnutdinova

  DOI：10.1002/cctc.202301142

  日期：2023.12.19

  and C‒O cross-coupling reactions catalyzed by NiII complexes supported by 2,7-dimethyl-1,8-naphthyridine ligand. Using the same Ni catalyst and visible light irradiation, both C‒O and C‒N coupling reactivity was observed without additional photocatalysts. These results demonstrate that Ni naphthyridine complexes represent a versatile catalytic motif for photoredox nickel catalysis alternative to commonly

  我们描述了由 2,7-二甲基-1,8-萘啶配体支持的 NiII 配合物催化的多功能且实用的光促进 C-N 和 C-O 交叉偶联反应。使用相同的 Ni 催化剂和可见光照射，无需额外的光催化剂即可观察到 C-O 和 C-N 偶联反应性。这些结果表明，镍萘啶配合物代表了光氧化还原镍催化的通用催化基序，可替代常用的联吡啶或多齿配体。
• METHOD FOR IDENTIFYING MYC INHIBITORS
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：EP2917203B1

  公开（公告）日：2019-04-03
• US7314937B2
  申请人：——

  公开号：US7314937B2

  公开（公告）日：2008-01-01