(E)-3-(3-(dimethylamino)phenyl)acrylaldehyde | 1260372-11-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (E)-3-(3-(dimethylamino)phenyl)acrylaldehyde
• 英文别名: 3-[3-(Dimethylamino)phenyl]prop-2-enal；(E)-3-[3-(dimethylamino)phenyl]prop-2-enal
• CAS: 1260372-11-9
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: OLFLXBDTBRJGFW-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (E)-3-(3-(dimethylamino)phenyl)acrylaldehyde 在 sodium tetrahydroborate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium sulfate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 tert-butyl 2-(7-acetyl-9-(3-(dimethylamino)phenyl)-3-oxo-1H-pyrrolo[3,4-β]indolizin-2(3H)-yl)ethylcarbamate
  参考文献：
  名称：

  Emission Wavelength Prediction of a Full-Color-Tunable Fluorescent Core Skeleton, 9-Aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one

  摘要：

  In this paper we report on a novel fluorescent core skeleton, 9-aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one, which we named Seoul-Fluor, having tunable and predictable photophysical properties. Using a concise and practical one-pot synthetic procedure, a 68-member library of new fluorescent compounds was synthesized with diverse substituents. In Seoul-Fluor, the electronic characteristics of the substituents, as well as their positional changes, have a close correlation with their photophysical properties. The systematic perturbation of electronic densities on the specific positions of Seoul-Fluor, guided with the Hammett constant, allows emission wavelength tunability covering the full color range. On the basis of these observations and a computational analysis, we extracted a simple first-order correlation of photophysical properties with the theoretical calculation and accurately predicted the emission wavelength of Seoul-Fluors through the rational design. In this study, we clearly demonstrate that Seoul-Fluor can provide a powerful gateway for the generation of desired fluorescent probes without the need for a tiresome synthesis and trial-and-error process.

  DOI：

  10.1021/ja110766a
• 作为产物：
  描述：

  methyl (E)-3-[3-(dimethylamino)phenyl]acrylate 在 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-3-(3-(dimethylamino)phenyl)acrylaldehyde
  参考文献：
  名称：

  Emission Wavelength Prediction of a Full-Color-Tunable Fluorescent Core Skeleton, 9-Aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one

  摘要：

  In this paper we report on a novel fluorescent core skeleton, 9-aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one, which we named Seoul-Fluor, having tunable and predictable photophysical properties. Using a concise and practical one-pot synthetic procedure, a 68-member library of new fluorescent compounds was synthesized with diverse substituents. In Seoul-Fluor, the electronic characteristics of the substituents, as well as their positional changes, have a close correlation with their photophysical properties. The systematic perturbation of electronic densities on the specific positions of Seoul-Fluor, guided with the Hammett constant, allows emission wavelength tunability covering the full color range. On the basis of these observations and a computational analysis, we extracted a simple first-order correlation of photophysical properties with the theoretical calculation and accurately predicted the emission wavelength of Seoul-Fluors through the rational design. In this study, we clearly demonstrate that Seoul-Fluor can provide a powerful gateway for the generation of desired fluorescent probes without the need for a tiresome synthesis and trial-and-error process.

  DOI：

  10.1021/ja110766a

文献信息

• Anticancer activity of newly synthesized 1,1‐disubstituted cyclohexane‐1‐carboxamides: in vitro caspases mediated apoptosis activators in human cancer cell lines and their molecular modeling
  作者：Walaa Hamada Abd‐Allah、Asmaa Salman、Samah Sabry Saad

  DOI：10.1002/ddr.21573

  日期：2019.11

  Novel 1,1‐disubstituted cyclohexane‐1‐carboxamides 6a‐h, 7a‐e, and 8a‐b were designed and synthesized as apoptotic inducers. Cytotoxicity test revealed that some compounds have strong to moderate effect, while others displayed weak action against different cancer cell lines including, MCF‐7, HepG2, A549, and HTC‐116. A549 carcinoma cell line exhibited higher sensitivity toward all synthesized candidates

  设计并合成了新颖的1,1-二取代环己烷-1-羧酰胺6a-h，7a-e和8a-b作为凋亡诱导剂。细胞毒性测试表明，某些化合物具有强至中度的作用，而另一些化合物对包括MCF-7，HepG2，A549和HTC-116在内的不同癌细胞系则显示出弱的作用。相对于IC 50值为3.01μM的阳性对照阿霉素，A549癌细胞系对所有合成候选物，尤其是化合物6a和8a的敏感性更高，分别具有最低的IC 50值3.03和5.21μM 。与阿霉素治疗相比，化合物6a和8a诱导A549癌细胞系中的caspases-3，-8和-9活性和G2 / M生长停滞。p53（由TP53基因编码的人类肿瘤抑制蛋白），Bax（由bax基因编码的人类细胞凋亡调节蛋白）和Bax / Bcl-2的表达水平均高于阿霉素。经治疗的细胞（Bcl-2，B细胞淋巴瘤2，由Bcl-2基因在人体内编码）。此外，化合物6a和8a对MCF-10人乳腺正常
• Detection of uronium salts
  申请人：Almog Joseph

  公开号：US20060084176A1

  公开（公告）日：2006-04-20

  Methods and kits for colorimetric identification of uronium salts, such as explosives.

  用比色法鉴别炸药等脲盐的方法和试剂盒。
• 1,8-NAPHTHYRIDINONE COMPOUNDS AND USES THEREOF
  申请人：Nuvation Bio Inc.

  公开号：EP3654982A1

  公开（公告）日：2020-05-27
• [EN] 1,8-NAPHTHYRIDINONE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE 1,8-NAPHTHYRIDINONE ET LEURS UTILISATIONS
  申请人：GIRAFPHARMA LLC

  公开号：WO2019018583A1

  公开（公告）日：2019-01-24

  1,8-naphthyridinone compounds as modulators of an adenosine receptor are provided. The compounds may find use as therapeutic agents for the treatment of diseases mediated through a G-protein-coupled receptor signaling pathway and may find particular use in oncology.