3-(2,4-Dichloro-phenylamino)-5,5-dimethyl-cyclohex-2-enone | 145657-31-4

• 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: 3-(2,4-Dichloro-phenylamino)-5,5-dimethyl-cyclohex-2-enone
• 英文别名: 3-(2,4-Dichloroanilino)-5,5-dimethylcyclohex-2-en-1-one
• CAS: 145657-31-4
• 化学式: C₁₄H₁₅Cl₂NO
• mdl: MFCD00128467
• 分子量: 284.185
• InChiKey: LHFZLBOSEAWBHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2,4-Dichloro-phenylamino)-5,5-dimethyl-cyclohex-2-enone 在 一水合肼 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 30.83h， 生成 6,6-dimethyl-4-(2-(propan-2-ylidene)hydrazinyl)-6,7-dihydro-2H-indazole-3(5H)-thione
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular docking studies of benzyl, alkyl and glycosyl [2-(arylamino)-4,4-dimethyl-6-oxo-cyclohex-1-ene]carbodithioates, as potential immunomodulatory and immunosuppressive agents

  摘要：

  The immunomodulating properties of functionalized [2-(arylamino)-4,4-dimethyl-6-oxo-cyclohex-1-ene] carbodithioates and 6,6-dimethyl-4-(2-(propan-2-ylidene)hydrazinyl)-6,7-dihydro-2H-indazole-3(5H)-thione compounds have been investigated. Four of them, 13, 18, 19 and 20 inhibited PBMC proliferation induced by phytohemagglutinin (PHA) in a dose dependent manner with an IC50 of <= 20 mu M. The Th-1 cytokine, interleukin-2 (IL-2) in PHA/PMA-stimulated peripheral blood mononuclear cells (PBMCs) is significantly inhibited by 13, 19 and 20 with an IC50 of 8.4 +/- 0.4, 5.34 +/- 0.15 and 4.9 +/- 0.7 mu M, respectively. They also inhibited the PMA/lipopolysaccharide-induced proinflammatory cytokines, IL-1 beta and TNF-alpha production in human monocytic leukemia cells (THP-1), by 86%, 46% and 59.2% for IL-1 beta and by 83.8%, 48.2% and 58.7% for TNF-alpha, respectively. Only 20 showed significant suppressive activity against the phagocyte oxidative burst in a dose dependent manner, with an IC50 of 23.8 mu M. LPS-induced nitrites in mouse macrophages were found to be inhibited by compounds 6, 8, 13-15 and 19 with an IC50, which range between 7.7 and 63 mu M. The cytotoxicity for the active compounds was also studied on Rat Wistar Hepatocyte cell line, CC1 and the Mouse Fibroblast cell line 3T3 NIH in the presence of compounds using a standard MTT assay. Furthermore, structural-activity relationship using automated docking software revealed that active compounds 7, 13 and 19, adapted the same binding mode, however the most active compound 20 is found deeply inserted within the ligand binding site of IL-2, as multiple hydrophobic and hydrophilic key interactions stabilize the compound inside the binding site, thus contributing higher activity.[GRAPHICS]. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.003
• 作为产物：
  描述：

  2,4-二氯苯胺 、 5,5-二甲基-1,3-环己二酮 以 various solvent(s) 为溶剂， 反应 4.0h， 以82%的产率得到3-(2,4-Dichloro-phenylamino)-5,5-dimethyl-cyclohex-2-enone
  参考文献：
  名称：

  Ionic Liquid Promoted Synthesis of β-Enamino Ketones at Room Temperature

  摘要：

  通过芳香族或脂肪族胺与 1,3-二羰基化合物在离子液体中的反应，δ-埃米诺酮在室温下无需添加任何催化剂即可合成，且收率极高。离子液体可多次循环使用。

  DOI：

  10.1055/s-2006-939042

文献信息

• Metal-free syntheses of new azocines<i>via</i>addition reactions of enaminones with acenaphthoquinone followed by oxidative cleavages of the corresponding vicinal diols
  作者：S. Hekmat Mousavi、Mohammad Reza Mohammadizadeh、Satoru Arimitsu、Dariush Saberi、Samira Poorsadeghi、Kojya Genta

  DOI：10.1039/d0ra02852e

  日期：——

  A one-pot, clean and green procedure is described for the syntheses of new azocine derivatives via addition reactions of enaminones with acenaphthoquinone followed by periodic acid-mediated oxidative cleavages of the corresponding vicinal diols. Various derivatives of azocine were prepared and well characterized. The excellent yields, simple synthesis procedure, lack of a need to carry out any tedious

  描述了一种通过烯胺酮与苊醌的加成反应，然后通过高碘酸介导的相应连二醇的氧化裂解来合成新的偶氮辛衍生物的一锅法、清洁和绿色程序。制备并充分表征了偶氮辛的多种衍生物。优异的收率、简单的合成程序、不需要进行任何繁琐的后处理和柱色谱、无金属催化和温和的反应条件是该协议的重要特征。
• Synthesis and X-ray analysis of butyl and glycosyl (2-arylamino-4,4-dimethyl-6-oxocyclohex-1-ene)carbodithioates and their possible cyclization to 2-thioxo-6,7-dihydro-1H-benzo[d][1,3]thiazin-5(2H)-one derivatives
  作者：El Sayed H. El Ashry、Aly A. Aly、Mohammed R. Amer、Muhammad R. Shah、Seik W. Ng

  DOI：10.1016/j.carres.2010.11.005

  日期：2011.2

  Variety of butyl [2-arylamino-4,4-dimethyl-6-oxo-cyclohex-1-ene]carbodithioates (3a-c), 2-thioxo-6,7-dihydro-1H-benzo[d][1,3]thiazin-5(2H)-one derivatives (5a-c), and the glucosyl carbodithioates 6a-c as well as galactosyl carbodithioates 7a-c have been synthesized from the reaction of enaminone derivatives 1a-c with carbon disulfide followed by the alkylation with n-butyl bromide and alpha-d-glycosyl

  [2-芳氨基-4,4-二甲基-6-氧代-环己-1-烯]丁基碳二硫代酸酯（3a-c），2-硫代-6,7-二氢-1H-苯并[d] [1， 3]噻嗪5（2H）-一衍生物（5a-c）和葡糖基碳二硫代酸酯6a-c以及半乳糖基碳二硫代酸酯7a-c是由烯胺酮衍生物1a-c与二硫化碳反应然后合成分别用正丁基溴化物和α-d-糖基溴化物进行烷基化。二硫化碳的量在反应模式中起重要作用。通过光谱数据和X射线晶体学来阐明合成的化合物的结构。
• Synthesis, biological evaluation, and molecular docking studies of benzyl, alkyl and glycosyl [2-(arylamino)-4,4-dimethyl-6-oxo-cyclohex-1-ene]carbodithioates, as potential immunomodulatory and immunosuppressive agents
  作者：El Sayed H. El Ashry、Mohammad R. Amer、Omer M. Abdalla、Aly A. Aly、Samreen Soomro、Almas Jabeen、Sobia Ahsan Halim、M. Ahmed Mesaik、Zaheer Ul-Haq

  DOI：10.1016/j.bmc.2012.03.003

  日期：2012.5

  The immunomodulating properties of functionalized [2-(arylamino)-4,4-dimethyl-6-oxo-cyclohex-1-ene] carbodithioates and 6,6-dimethyl-4-(2-(propan-2-ylidene)hydrazinyl)-6,7-dihydro-2H-indazole-3(5H)-thione compounds have been investigated. Four of them, 13, 18, 19 and 20 inhibited PBMC proliferation induced by phytohemagglutinin (PHA) in a dose dependent manner with an IC50 of <= 20 mu M. The Th-1 cytokine, interleukin-2 (IL-2) in PHA/PMA-stimulated peripheral blood mononuclear cells (PBMCs) is significantly inhibited by 13, 19 and 20 with an IC50 of 8.4 +/- 0.4, 5.34 +/- 0.15 and 4.9 +/- 0.7 mu M, respectively. They also inhibited the PMA/lipopolysaccharide-induced proinflammatory cytokines, IL-1 beta and TNF-alpha production in human monocytic leukemia cells (THP-1), by 86%, 46% and 59.2% for IL-1 beta and by 83.8%, 48.2% and 58.7% for TNF-alpha, respectively. Only 20 showed significant suppressive activity against the phagocyte oxidative burst in a dose dependent manner, with an IC50 of 23.8 mu M. LPS-induced nitrites in mouse macrophages were found to be inhibited by compounds 6, 8, 13-15 and 19 with an IC50, which range between 7.7 and 63 mu M. The cytotoxicity for the active compounds was also studied on Rat Wistar Hepatocyte cell line, CC1 and the Mouse Fibroblast cell line 3T3 NIH in the presence of compounds using a standard MTT assay. Furthermore, structural-activity relationship using automated docking software revealed that active compounds 7, 13 and 19, adapted the same binding mode, however the most active compound 20 is found deeply inserted within the ligand binding site of IL-2, as multiple hydrophobic and hydrophilic key interactions stabilize the compound inside the binding site, thus contributing higher activity.[GRAPHICS]. (C) 2012 Elsevier Ltd. All rights reserved.
• Ionic Liquid Promoted Synthesis of β-Enamino Ketones at Room Temperature
  作者：Rajendra Pawar、Rajesh Bhosale、Padmakar Suryawanshi、Sachin Ingle、Mahendra Lokhande、Sandeep More、Sandeep Mane、Sidthanath Bhosale

  DOI：10.1055/s-2006-939042

  日期：——

  β-Enamino ketones have been synthesised in excellent yield at room temperature in the absence of any added catalyst by the reaction of aromatic or aliphatic amines with 1,3-dicarbonyl compounds in ionic liquid. The ionic liquid is recycled and reused several times.

  通过芳香族或脂肪族胺与 1,3-二羰基化合物在离子液体中的反应，δ-埃米诺酮在室温下无需添加任何催化剂即可合成，且收率极高。离子液体可多次循环使用。