(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl) [2-(4-bromophenylamino)-4,4-dimethyl-6-oxocyclohex-1-ene]carbodithioate | 1268615-86-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl) [2-(4-bromophenylamino)-4,4-dimethyl-6-oxocyclohex-1-ene]carbodithioate
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[2-(4-bromoanilino)-4,4-dimethyl-6-oxocyclohexene-1-carbothioyl]sulfanyloxan-2-yl]methyl acetate
• CAS: 1268615-86-6
• 化学式: C₂₉H₃₄BrNO₁₀S₂
• 分子量: 700.626
• InChiKey: RXNDFTQAZXNJQP-INFWBLCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  201
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  3-(4-溴苯胺基)-5,5-二甲基环己-2-烯-1-酮 、 二硫化碳 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 24.33h， 以29%的产率得到(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl) [2-(4-bromophenylamino)-4,4-dimethyl-6-oxocyclohex-1-ene]carbodithioate
  参考文献：
  名称：

  丁基和糖基（2-芳基氨基-4,4-二甲基-6-氧代环己基-1-烯）碳二硫代酸酯的合成和X射线分析，以及可能的环化成2-硫代-6,7-二氢-1H-苯并[d] ] [1,3]噻嗪-5（2H）-一衍生物。

  摘要：

  [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。

  DOI：

  10.1016/j.carres.2010.11.005

文献信息

• 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.
• 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。