1-(4-(cholesterylcarbonylamino)benzyl)uracil | 339985-31-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 1-(4-(cholesterylcarbonylamino)benzyl)uracil
• 英文别名: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-[4-[(2,4-dioxopyrimidin-1-yl)methyl]phenyl]carbamate
• CAS: 339985-31-8
• 化学式: C₃₉H₅₅N₃O₄
• 分子量: 629.883
• InChiKey: OQLSNNXLMBIPDK-PNFBIEMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-(cholesterylcarbonylamino)benzyl)uracil 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以67%的产率得到1-(4-(cholesterylcarbonyl(methyl)amino)benzyl)-3-methyluracil
  参考文献：
  名称：

  Organogels of a nucleobase-bearing gelator and the remarkable effects of nucleoside derivatives and a porphyrin derivative on the gel stability

  摘要：

  An organogelator, which has a nucleobase group at its terminus, features one-dimensional, cholesteric-helical organization: the gel was remarkably destabilized by the addition of nucleoside derivatives (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00095-8
• 作为产物：
  描述：

  1-(4-nitrobenzyl)uracil 在 三乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 7.0h， 生成 1-(4-(cholesterylcarbonylamino)benzyl)uracil
  参考文献：
  名称：

  Gel formation properties of a uracil-appended cholesterol gelator and cooperative effects of the complementary nucleobases

  摘要：

  We designed and synthesized a uracil-appended cholesterol gelator (1) in order to control the gel stability and the gel morphology by addition of the complementary and non-complementary nucleobase derivatives. Compound 1 forms columnar stacks in cyclohexane due to the van der Waals interaction (cholesterol-cholesterol interaction) and the intergelator hydrogen bonding between uracil moieties. Addition of a 'monomeric' adenosine (3) into the gel only decreases the stability with increasing the concentration. The destabilization is ascribed to a lack of intergelator hydrogen bonding accompanied with forming the complementary base pairs between 1 and 3. In contrast, addition of adenine-appended cholesterol (7) induces a different behavior; with increasing 7 concentration the mixed gel is initially stabilized and then destabilized, giving rise to a maximum at the ratio of 1/7= 1:1 for the T-gel plot. One may consider, therefore, that when the additive has a common, column-forming cholesterol moiety, the cholesterol-cholesterol interaction can operate cooperatively with the complementary base pairing. In addition, the gel fiber structure is clearly changed by the addition of 7. Taking the fact that there is no report for such an additive effect inducing a structural change with maintaining the gel stability into consideration, our attempt combining cholesterol columnar stacks with the nucleobase additives provides a new methodology to control the stability and the morphology of organogels. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01059-1

文献信息

• Organogels of a nucleobase-bearing gelator and the remarkable effects of nucleoside derivatives and a porphyrin derivative on the gel stability
  作者：Erwin Snip、Seiji Shinkai、David N Reinhoudt

  DOI：10.1016/s0040-4039(01)00095-8

  日期：2001.3

  An organogelator, which has a nucleobase group at its terminus, features one-dimensional, cholesteric-helical organization: the gel was remarkably destabilized by the addition of nucleoside derivatives (C) 2001 Elsevier Science Ltd. All rights reserved.
• Gel formation properties of a uracil-appended cholesterol gelator and cooperative effects of the complementary nucleobases
  作者：Erwin Snip、Kazuya Koumoto、Seiji Shinkai

  DOI：10.1016/s0040-4020(02)01059-1

  日期：2002.10

  We designed and synthesized a uracil-appended cholesterol gelator (1) in order to control the gel stability and the gel morphology by addition of the complementary and non-complementary nucleobase derivatives. Compound 1 forms columnar stacks in cyclohexane due to the van der Waals interaction (cholesterol-cholesterol interaction) and the intergelator hydrogen bonding between uracil moieties. Addition of a 'monomeric' adenosine (3) into the gel only decreases the stability with increasing the concentration. The destabilization is ascribed to a lack of intergelator hydrogen bonding accompanied with forming the complementary base pairs between 1 and 3. In contrast, addition of adenine-appended cholesterol (7) induces a different behavior; with increasing 7 concentration the mixed gel is initially stabilized and then destabilized, giving rise to a maximum at the ratio of 1/7= 1:1 for the T-gel plot. One may consider, therefore, that when the additive has a common, column-forming cholesterol moiety, the cholesterol-cholesterol interaction can operate cooperatively with the complementary base pairing. In addition, the gel fiber structure is clearly changed by the addition of 7. Taking the fact that there is no report for such an additive effect inducing a structural change with maintaining the gel stability into consideration, our attempt combining cholesterol columnar stacks with the nucleobase additives provides a new methodology to control the stability and the morphology of organogels. (C) 2002 Elsevier Science Ltd. All rights reserved.