1,1'-(hexane-1,6-diyl)bis(3-((7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)urea) | 1448805-64-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,1'-(hexane-1,6-diyl)bis(3-((7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)urea)
• 英文别名: 1,1'-(hexane-1,6-diyl)bis(3-{[(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl]methyl}urea)；1-[[(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methyl]-3-[6-[[(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methylcarbamoylamino]hexyl]urea
• CAS: 1448805-64-8
• 化学式: C₄₈H₇₄N₄O₂
• 分子量: 739.141
• InChiKey: XUHNHAFPJKQDKC-FTVGNFKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.2
• 重原子数：
  54
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  82.3
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  dehydroabietylamine 、 1,6-己二异氰酸酯 以 乙醇 为溶剂， 以98%的产率得到1,1'-(hexane-1,6-diyl)bis(3-((7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)urea)
  参考文献：
  名称：

  Synthesis of Supramolecular Organogels Derived from Urea and Bisurea Derivatives of Dehydroabietylamine

  摘要：

  The gelation ability of diterpenes was investigated by applying aromatic linker steroid strategy. Four new mono (1) and bis-urea (2-4) derivatives of dehydroabietylamine (DAA) (a tricyclic diterpene amine) were synthesized on reaction of respective isocyanates with DAA and characterized through spectroscopic data. Three of these (1, 2, and 4) were obtained as low-molecular-weight organogelators that can form thermally reversible organogels. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for full experimental and spectral details.

  DOI：

  10.1080/00397911.2012.745157

文献信息

• Dehydroabietylamine Ureas and Thioureas as Tyrosyl-DNA Phosphodiesterase 1 Inhibitors That Enhance the Antitumor Effect of Temozolomide on Glioblastoma Cells
  作者：Kseniya Kovaleva、Olga Oleshko、Evgeniya Mamontova、Olga Yarovaya、Olga Zakharova、Alexandra Zakharenko、Alena Kononova、Nadezhda Dyrkheeva、Sergey Cheresiz、Andrey Pokrovsky、Olga Lavrik、Nariman Salakhutdinov

  DOI：10.1021/acs.jnatprod.8b01095

  日期：2019.9.27

  A new class of tyrosyl-DNA phosphodiesterase 1 (TDP1) inhibitors was found among resin acid derivatives. Several novel ureas and thioureas derived from dehydroabietylamine were synthesized and tested for TDP1 inhibition. The synthesized compounds showed IC50 values in the range of 0.1 to 3.7 μM and demonstrated low cytotoxicity against the human tumor cell lines U-937, U-87MG, MDA-MB, SK-Mel8, A-549

  在树脂酸衍生物中发现了一类新型的酪氨酰-DNA磷酸二酯酶1（TDP1）抑制剂。合成了几种衍生自脱氢松香胺的新型脲和硫脲，并测试了其对TDP1的抑制作用。合成的化合物的IC50值在0.1至3.7μM的范围内，并且对人肿瘤细胞系U-937，U-87MG，MDA-MB，SK-Mel8，A-549，MCF7，T98G和SNB19的细胞毒性较低。几种化合物显示出在GBM细胞系U-87MG和SNB19中用作抗胶质母细胞瘤（GBM）的一线疗法的烷基化剂替莫唑胺的细胞毒活性增强。
• Synthesis of Supramolecular Organogels Derived from Urea and Bisurea Derivatives of Dehydroabietylamine
  作者：Afshan Aslam、Imran Ali Hashmi、Viqar-uddin Ahmed、Firdous Imran Ali

  DOI：10.1080/00397911.2012.745157

  日期：2013.10.18

  The gelation ability of diterpenes was investigated by applying aromatic linker steroid strategy. Four new mono (1) and bis-urea (2-4) derivatives of dehydroabietylamine (DAA) (a tricyclic diterpene amine) were synthesized on reaction of respective isocyanates with DAA and characterized through spectroscopic data. Three of these (1, 2, and 4) were obtained as low-molecular-weight organogelators that can form thermally reversible organogels. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for full experimental and spectral details.