1-(5-chloro-thiophen-2-yl)-3-dimethylamino-propenone | 166196-78-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5-chloro-thiophen-2-yl)-3-dimethylamino-propenone
• 英文别名: 1-(5-Chlorothiophen-2-yl)-3-(dimethylamino)prop-2-en-1-one
• CAS: 166196-78-7
• 化学式: C₉H₁₀ClNOS
• 分子量: 215.703
• InChiKey: LURWBHIWFVQYPC-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  1-(5-chloro-thiophen-2-yl)-3-dimethylamino-propenone 在 碘苯二乙酸 、 cerium(III) chloride heptahydrate 、 ammonium acetate 、 palladium diacetate 、 sodium iodide 作用下， 以 异丙醇 、 乙腈 为溶剂， 反应 10.0h， 生成 5-chloro-2-(5-oxo-5,6,7,8-tetrahydroquinolin-2-yl)thiophen-3-yl acetate
  参考文献：
  名称：

  Pd-catalyzed site selective C–H acetoxylation of aryl/heteroaryl/thiophenyl tethered dihydroquinolinones

  摘要：

  本文描述了一种高效的选择性氧化C–H活化/乙酰氧基化协议，适用于一系列连接有2-芳基/杂芳基/噻吩基的二氢喹啉酮，使用醋酸钯作为催化剂，碘苯二乙酸作为氧化剂。所有这些反应在立体障碍较小且电子性质良好的C–H键上进行良好，生成相应的邻位乙酰氧基化衍生物，收率良好。此外，嵌入噻吩基的二氢喹啉酮的乙酰氧基化反应导致产生单一的区域异构体，乙酰氧基在噻吩基部分的C-2位上。然而，当噻吩单元的C-2位被阻塞时，乙酰氧基则会独占性地安装在C-4位上。此外，我们注意到，二氢喹啉-5(6H)-酮-肟的乙酰氧基化并未改变配体的优先性，仍然生成邻位乙酰氧基化产物。

  DOI：

  10.1039/c3ra41312h
• 作为产物：
  描述：

  1-[2-(5-Chlorothiophen-2-yl)phenyl]ethanone 、 N,N-二甲基甲酰胺二甲基缩醛 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 7.0h， 生成 1-(5-chloro-thiophen-2-yl)-3-dimethylamino-propenone
  参考文献：
  名称：

  Synthesis, in vitro, and in vivo (Zebra fish) antitubercular activity of 7,8-dihydroquinolin-5(6H)-ylidenehydrazinecarbothioamides

  摘要：

  We, herein, describe the synthesis of a series of novel aryl tethered 7,8-dihydroquinolin-5(6H)-ylidenehydrazinecarbothioamides 4a-v, which showed in vitro and in vivo antimycobacterial activity against Mycobacterium tuberculosis (Mtb) H37Rv. The intermediates dihydro-6H-quinolin-5-ones 3a-v were synthesized from beta-enaminones, reacting with cyclochexane-1,3-dione/5,5-dimethylcyclohexane-1,3-dione and ammonium acetate using a modified Bohlmann-Rahtz reaction conditions. They were further reacted with thiosemicarbazide to give the respective hydrazine carbothioamides 4a-v. All the new analogues 4a-v, were characterized by their NMR and mass spectral data analysis. Among the twenty-two compounds screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (ATCC27294), two compounds, 4e and 4j, exhibited the highest inhibition with an MIC of 0.39 mu g/mL. Compounds 4a, 4g, and 4k were found to inhibit Mtb at an MIC of 0.78 mu g/mL. Hydrazinecarbothioamides 4a-k, exhibited enhanced activity than dihydroquinolinones 3a-k. The observed increase in potency provides a clear evidence that hydrazinecarbothioamide is a potential pharmacophore, collectively imparting synergistic effect in enhancing antitubercular activity of the dihydroquinolinone core. The in vivo (Zebra fish) antimycobacterial screening of the in vitro active molecules led to the identification of a hit compound, 4j, with significant activity in the Mtb nutrient starvation model (2.2-fold reduction). Docking studies of 4j showed a hydrogen bond with the P156 residue of the protein.

  DOI：

  10.1016/j.bioorg.2020.103626

文献信息

• Anilino-pyrimidine phenyl and benzothiophene analogs
  申请人：Hu Yongbo

  公开号：US20070244140A1

  公开（公告）日：2007-10-18

  The present invention relates to compounds of formula III: wherein R 2 , R 3 , R 5 and R 6 are as defined herein.

  本发明涉及以下式III的化合物： 其中R2、R3、R5和R6如本文所定义。
• Anilino-pyrimidine analogs
  申请人：Sum Fuk-Wah

  公开号：US20060079543A1

  公开（公告）日：2006-04-13

  The present invention relates to compounds of formula I: wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are defined herein.

  本发明涉及以下式I的化合物： 其中R1、R2、R3、R4、R5和R6在此处定义。
• Novel Synthesis of 6-Substituted 2-Picolines from Aryl/heteroaryl β-Enaminones and Meldrum's Acid Using CeCl₃.7H₂O/NaI
  作者：Dinesh Addla、Srinivas Kantevari

  DOI：10.1002/jhet.1941

  日期：2014.8

  One-pot condensation of aryl/heteroaryl β-enaminones, Meldrum's acid, and ammonium acetate in the presence of CeCl3.7H2O/NaI via tandem Michael addition–cyclodehydration–elimination sequence led to the formation of novel regioselective 6-substituted 2-picolines.

  一锅缩合的芳基/杂芳基β-烯胺酮，Meldrum酸和 CeCl 3 .7H 2 O / NaI存在下，通过串联迈克尔加成-环脱水-消除序列的乙酸铵导致形成新的区域选择性6取代的2-甲基吡啶。
• Discovery of 5-(Pyrimidin-2-ylamino)-1<i>H</i>-indole-2-carboxamide Derivatives as Nur77 Modulators with Selective and Potent Activity Against Triple-Negative Breast Cancer
  作者：Jingbo Qin、Boning Niu、Xiaohui Chen、Cheng Hu、Sheng Lu、Hongsheng Li、Weihao Liu、Jiayi Li、Zihao Teng、Yinghuang Yang、Hongyu Hu、Yang Xu、Shuaidong Huo、Zhen Wu、Yingkun Qiu、Hu Zhou、Meijuan Fang

  DOI：10.1021/acs.jmedchem.3c01336

  日期：2023.12.14

  treating breast cancer. Therefore, focusing on the SAR study of the lead 8b (KDSPR(Nur77) = 354 nM), we found the active compound ja which exhibited improved Nur77-binding capability (KDSPR(Nur77) = 91 nM) and excellent antiproliferative activities against breast cancer cell lines. Interestingly, ja acted as a potent and selective Nur77 antagonist, displaying good potency against triple-negative breast

  孤儿核受体Nur77已被验证为治疗乳腺癌的潜在药物靶点。因此，重点关注先导化合物 8b ( K D SPR (Nur77) = 354 nM) 的 SAR 研究，我们发现活性化合物ja表现出改善的 Nur77 结合能力 ( K D SPR (Nur77) = 91 nM) 和优异的抗增殖活性对抗乳腺癌细胞系的活性。有趣的是， ja作为一种有效的选择性 Nur77 拮抗剂，对三阴性乳腺癌 (TNBC) 细胞系表现出良好的效力，但不抑制人类正常乳腺癌细胞系 MCF-10A (SI > 20)。例外的是， ja Nur77 依赖性引起线粒体功能障碍，并通过介导 TP53 磷酸化途径诱导 caspase 依赖性细胞凋亡。此外， ja显着抑制 MDA-MB-231 异种移植肿瘤的生长，但在小鼠和斑马鱼中没有明显的副作用。总体而言， ja被证明是第一个介导 TP53 磷酸化途径的 Nur77 调节剂，具有作为
• ANILINO-PYRIMIDINE PHENYL AND BENZOTHIOPHENE ANALOGS
  申请人：Wyeth

  公开号：EP2004638A1

  公开（公告）日：2008-12-24