1-isopropyl-3-((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)urea | 1123244-51-8

• 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-isopropyl-3-((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)urea
• 英文别名: N-nor-dehydroabietyl-N'-isopropylurea；1-[(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]-3-propan-2-ylurea
• CAS: 1123244-51-8
• 化学式: C₂₃H₃₆N₂O
• 分子量: 356.552
• InChiKey: AQAGVXXLYORIIL-YMPZKCBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  18-nordehydroabietyl isocyanate 、 异丙胺 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 1-isopropyl-3-((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)urea
  参考文献：
  名称：

  脱氢松香酸中新型不对称n，n'-取代脲的合成，结构分析和细胞毒性研究。

  摘要：

  由脱氢松香酸合成了一系列新型的不对称N，N′-取代的脲，并通过IR，1H-NMR，13C-NMR和单晶X射线衍射对它们的结构进行了表征。尿素4c的三个六元环分别表现出平面，半椅和椅构型。通过MTT（3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴化物）方法评估它们对SMMC7721肝癌细胞的细胞毒性活性。结果表明标题化合物对SMMC7721细胞表现出高度有效的细胞毒性活性。它们的IC50值在8.8和14.2 micromol / l之间。N'取代基的变化对尿素的细胞毒性活性影响不大，

  DOI：

  10.1248/cpb.56.1575

文献信息

• Synthesis, Structure Analysis and Cytotoxicity Studies of Novel Unsymmetrically N,N'-Substituted Ureas from Dehydroabietic Acid
  作者：Xiaoping Rao、Zhanqian Song、Ling He、Weihong Jia

  DOI：10.1248/cpb.56.1575

  日期：——

  A series of novel unsymmetrically N,N'-substituted ureas were synthesized from dehydroabietic acid and their structures were characterized by IR, 1H-NMR, 13C-NMR spectroscopy and single crystal X-ray diffraction. Three six-membered rings of urea 4c exhibited plane, half-chair and chair configurations, respectively. Their cytotoxicity activities against SMMC7721 liver cancer cells were evaluated by

  由脱氢松香酸合成了一系列新型的不对称N，N′-取代的脲，并通过IR，1H-NMR，13C-NMR和单晶X射线衍射对它们的结构进行了表征。尿素4c的三个六元环分别表现出平面，半椅和椅构型。通过MTT（3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴化物）方法评估它们对SMMC7721肝癌细胞的细胞毒性活性。结果表明标题化合物对SMMC7721细胞表现出高度有效的细胞毒性活性。它们的IC50值在8.8和14.2 micromol / l之间。N'取代基的变化对尿素的细胞毒性活性影响不大，
• Crystal Structure of Unsymmetrically N-nor-dehydroabietyl-N′-isopropyl Urea
  作者：Xiao-Ping Rao、Yong Wu、Zhan-Qian Song、Shi-Bin Shang

  DOI：10.1007/s10870-009-9656-3

  日期：2010.4

  The title compound (C46H72N4O2, M r  = 713.08) [systematic name: 1-isopropyl-3-((1R,4aS,10aR)-7-isopropyl-1, 4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)urea] is a new derivative of dehydroabietic acid. It crystallized in the orthorhombic system, space group P2121 21 with cell dimensions of a = 9.5950(19) Å, b = 18.740(4) Å, c = 24.654(5) Å, V = 4,433.0(16) Å3, Z = 4, D c  = 1.068 g/cm3, λ = 0.71073 Å, μ = 0.07 mm−1, F(000) = 1,568, final R = 0.0777 and wR = 0.1731 for 2,048 observed reflections with I > 2σ(I). Two crystallorgraphically independent molecules with different conformations co-exist in the structure. Each molecule exhibit classic tricyclic hydrophenanthrene structure, the two cyclohexane rings form a trans ring junction with chair and half-chair conformations, respectively. The crystal is stabilized by intermolecule hydrogen bonds and the molecules are in a head–tail zigzag arrangement. The title compound (C46H72N4O2, M r  = 713.08) [systematic name: 1-isopropyl-3-((1R,4aS,10aR)-7-isopropyl-1, 4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)urea] is a new derivative of dehydroabietic acid. It crystallized in the orthorhombic system, space group P2121 21 with cell dimensions of a = 9.5950(19) Å, b = 18.740(4) Å, c = 24.654(5) Å, V = 4,433.0(16) Å3, Z = 4, D c  = 1.068 g/cm3, λ = 0.71073 Å, μ = 0.07 mm−1, F(000) = 1,568, final R = 0.0777 and wR = 0.1731 for 2,048 observed reflections with I > 2σ(I). Two crystallorgraphically independent molecules with different conformations co-exist in the structure. Each molecule exhibit classic tricyclic hydrophenanthrene structure, the two cyclohexane rings form a trans ring junction with chair and half-chair conformations, respectively. The crystal is stabilized by intermolecule hydrogen bonds and the molecules are in a head–tail zigzag arrangement.

  标题化合物（C46H72N4O2，M r = 713.08）[系统名称：1-异丙基-3-((1R,4aS,10aR)-7-异丙基-1,4a-二甲基-1,2,3,4,4a,9,10,10a-八氢菲-1-基)脲]是脱氢松香酸的一种新衍生物。它结晶于正方晶系，空间群为 P2121 21，晶胞尺寸为 a = 9.5950(19) Å, b = 18.740(4) Å, c = 24.654(5) Å, V = 4,433.0(16) Å3, Z = 4, D c  = 1.068 g/cm3, λ = 0.71073 Å, μ = 0.07 mm-1, F(000) = 1,568, final R = 0.0777，wR = 0.1731，共观察到 2,048 次反射，I > 2σ(I)。该结构中同时存在两个不同构象的独立晶体分子。每个分子都呈现出经典的三环菲结构，两个环己烷环分别以椅状和半椅状构象形成反式环结。晶体由分子间氢键稳定，分子呈头尾之字形排列。标题化合物（C46H72N4O2，M r = 713.08）[系统名称：1-异丙基-3-((1R,4aS,10aR)-7-异丙基-1,4a-二甲基-1,2,3,4,4a,9,10,10a-八氢菲-1-基)脲]是脱氢松香酸的一种新衍生物。它结晶于正方晶系，空间群为 P2121 21，晶胞尺寸为 a = 9.5950(19) Å, b = 18.740(4) Å, c = 24.654(5) Å, V = 4,433.0(16) Å3, Z = 4, D c  = 1.068 g/cm3, λ = 0.71073 Å, μ = 0.07 mm-1, F(000) = 1,568, final R = 0.0777，wR = 0.1731，共观察到 2,048 次反射，I > 2σ(I)。该结构中同时存在两个不同构象的独立晶体分子。每个分子都呈现出经典的三环菲结构，两个环己烷环分别以椅状和半椅状构象形成反式环结。晶体由分子间氢键稳定，分子呈头尾之字形排列。