2-[(Dimethylamino)methyl]-1-(4-nitrophenyl)prop-2-en-1-one;hydrochloride | 78888-61-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(Dimethylamino)methyl]-1-(4-nitrophenyl)prop-2-en-1-one;hydrochloride
• CAS: 78888-61-6
• 化学式: C₁₂H₁₄N₂O₃*ClH
• 分子量: 270.716
• InChiKey: GZJMRZHFEGTACI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(Dimethylamino)methyl]-1-(4-nitrophenyl)prop-2-en-1-one;hydrochloride 在 重水 作用下， 以 氯仿 为溶剂， 反应 60.0h， 生成 2-(2-hydroxyethylthiomethyl)-1-(4-nitrophenyl)-prop-2-en-1-one
  参考文献：
  名称：

  .ALPHA.-Substituted 1-Aryl-3-dimethylaminopropanone Hydrochlorides: Potent Cytotoxins towards Human WiDr Colon Cancer Cells

  摘要：

  一系列1-芳基-2-二甲氨基甲基-2-丙烯酮盐酸盐1被制备出来，这些化合物对人类WiDr结肠癌细胞的IC50值小于10μM。通过水合作用形成的相关的1-芳基-2-二甲氨基甲基-3-羟基丙酮盐酸盐2，其IC50值也在低微摩尔范围内。另一方面，将2-二甲氨基甲基-1-(4-硝基苯基)-2-丙烯酮盐酸盐1c转化为相应的2-巯基乙醇加合物3c，其效力降低了37倍。本研究中制备的化合物中，有三分之二比参考药物顺铂更有效，而其中三分之一对WiDr细胞的细胞毒性比人类CRL-2522成纤维细胞更高。对每一系列1至3中的4-硝基苯基类似物在氘氧化物中的稳定性进行了研究。在1c的情况下，注意到用羟基功能团取代了二甲氨基盐酸盐基团，而在系列2中，水和二甲胺盐酸盐的损失导致了两种烯酮的混合物。巯基乙醇加合物3c经历了脱氨基作用。所获得的数据为未来扩大项目提供了指导方针。

  DOI：

  10.1248/cpb.55.511
• 作为产物：
  描述：

  三聚甲醛 、 盐酸二甲胺 、 对硝基苯乙酮 以 溶剂黄146 为溶剂， 反应 4.0h， 生成 2-[(Dimethylamino)methyl]-1-(4-nitrophenyl)prop-2-en-1-one;hydrochloride
  参考文献：
  名称：

  Gupta; Nautiyal; Jhingran, Indian journal of chemistry, 1981, vol. 20 B, # 4, p. 303 - 307

  摘要：

  DOI：

文献信息

• Synthesis and Antifungal Evaluation of 1-Aryl-2-dimethyl-aminomethyl-2-propen-1-one Hydrochlorides
  作者：Ebru Mete、Halise Inci Gul、Sinan Bilginer、Oztekin Algul、Mehmet Emin Topaloglu、Medine Gulluce、Cavit Kazaz

  DOI：10.3390/molecules16064660

  日期：——

  Mannich bases had shown remarkable antifungal activities in our previous studies led us to design and synthesize some acetophenone-derived Mannich bases, 1-8 and 2-acetylthiophene-derived Mannich base 9, 1-aryl-2-dimethylaminomethyl-2-propen-1-one hydrochloride, to evaluate their antifungal activities. The designed chemical structures have α,β-unsaturated ketone moieties, which are responsible for the bioactivities

  对当前抗真菌疗法的耐药性的发展推动了对新的有效药物的探索。在我们之前的研究中，几种苯乙酮衍生的曼尼希碱显示出显着的抗真菌活性，这一事实促使我们设计和合成了一些苯乙酮衍生的曼尼希碱，1-8 和 2-乙酰噻吩衍生的曼尼希碱 9, 1-芳基-2-二甲基氨基甲基-2-propen-1-one 盐酸盐，以评估其抗真菌活性。设计的化学结构具有 α,β-不饱和酮部分，负责曼尼希碱的生物活性。芳基部分是C 5 H 5 (1)；4-CH₃C₆H₄(2)；4-CH₃OC₆H₄ (3)；4-ClC₆H₄(4)；4-FC₆H₄ (5)；4-BrC₆H₄ (6)；4-HOC₆H₄ (7)；4-NO₂C₆H₄ (8)；和C 4 H 3 S(2-基)(9)。本研究通过常规加热法和微波辐照法合成设计的化合物，比较这些方法的反应时间和产率，寻找最佳合成方法，可用于曼尼希碱的进一步合成。学习。由于报告通过微波辐射合成曼尼希碱
• Structure-activity relationships of novel dithiocarbamates containing α,β-unsaturated ketone fragment as potent anticancer agents
  作者：Yuanqiang Wang、Ridong Li、Han Zhang、Zhiyong Zhang、Xin Wang、Zemei Ge、Runtao Li

  DOI：10.1007/s00044-019-02356-y

  日期：2019.7

  benzene ring or heteroaromatic rings greatly effect on the activity; (b) the presence of α,β-unsaturated ketone fragment is favorable for the activity; (c) the receptor cavity binding with amine moiety might be a relatively small hydrophobic cavity. These results will be valuable for the further development of this novel kind of dithiocarbamates.

  基于我们小组发现的新型铅化合物8的结构，进行了系统的结构修饰。合成了一系列化合物8的衍生物，并评估了其对人类非小细胞肺癌细胞H460的活性。其中，十二种化合物显示出显着的增殖抑制活性，IC 50值<1μM，而化合物12r是最有效的一种。对化合物12r的进一步研究表明，它对IC 50值<1μM的八种癌细胞系的生长具有明显的抑制作用。特别是对于细胞系A375和HCT116，IC 50值为12r分别达到63 nM和66 nM。同时，我们的研究结果还揭示了以下结构-活性关系：（a）苯环或杂芳环上的不同取代对活性有很大影响；（b）存在α，β-不饱和酮片段有利于该活性；（c）与胺部分结合的受体腔可能是相对小的疏水腔。这些结果对于这种新型的二硫代氨基甲酸酯的进一步开发将是有价值的。
• Synthesis, antifungal and antimycobacterial activities of new bis-imidazole derivatives, and prediction of their binding to P45014DM by molecular docking and MM/PBSA method
  作者：Daniele Zampieri、Maria Grazia Mamolo、Luciano Vio、Elena Banfi、Giuditta Scialino、Maurizio Fermeglia、Marco Ferrone、Sabrina Pricl

  DOI：10.1016/j.bmc.2007.07.023

  日期：2007.12

  New bis-imidazole derivatives have been synthesized and their antifungal and antimycobacterial activity was determined. Almost all compounds exhibited a moderate to good activity against two clinical isolates of Candida albicans 3038 and Candida glabrata 123. The same compounds showed an interesting killing activity against Mycobacterium tuberculosis H(37)Rv reference strain. Docking procedures combined with molecular dynamics simulations in the MM/PBSA framework of theory were applied to predict the binding mode of all compounds in the binding pocket of the cytochrome P450 14 alpha-sterol demethylase (14DM) of C. albicans, for which no ligand-protein crystal structure is currently available. The results obtained in silico showed that the active compounds may interact at the active site of protein, and that their binding free energy values are in agreement with the corresponding experimental activity values. (C) 2007 Elsevier Ltd. All rights reserved.
• 1-Aryl-2-dimethylaminomethyl-2-propen-1-one hydrochlorides and related adducts: A quest for selective cytotoxicity for malignant cells
  作者：Hari N. Pati、Umashankar Das、Masami Kawase、Hiroshi Sakagami、Jan Balzarini、Erik De Clercq、Jonathan R. Dimmock

  DOI：10.1016/j.bmc.2008.03.060

  日期：2008.5

  The primary objective of this study was to discover one or more clusters of compounds which are not equitoxic but display cytoselectivity toward different malignant cells. Furthermore a most important consideration is that such molecules should also display greater cytotoxic potencies to tumors than normal tissues. Two series of compounds are described which meet these criteria, namely the 1-aryl-2-dimethylaminomethyl-2-propen-1-one hydrochlorides 1a-e and 1-aryl-3-dimethylamino-2-hydroxymethyl-1-propanone hydrochlorides 2a-e. A number of these compounds possess marked cytotoxic potencies (IC(50) and CC(50) values within the 10(-6) and 10(-7) molar range) which are greater than these of the reference drug melphalan. Statistical analyses demonstrated that cytotoxic potencies are influenced by the size of the aryl substituents in series 1 and to some extent by the electronic properties of the aryl groups in series 2. The mode of action of a representative compound 1e in HL-60 cells included inducing apoptosis and activation of caspases -3, -8, and -9. (C) 2008 Elsevier Ltd. All rights reserved.
• GUPTA, R. C.;NAUTIYAL, PRAVEENA;JHINGRAN, AKHIL, G.;KAMBOJ, V. P.;SETTY, +, INDIAN J. CHEM., 1981, 20, N 4, 303-307
  作者：GUPTA, R. C.、NAUTIYAL, PRAVEENA、JHINGRAN, AKHIL, G.、KAMBOJ, V. P.、SETTY, +

  DOI：——

  日期：——