9-十六烷基嘌呤-6-胺 | 68180-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 9-十六烷基嘌呤-6-胺
• 英文名称: N-9-hexadecyladenine
• 英文别名: 9-hexadecyladenine；9-hexadecyl-9H-purin-6-ylamine；6-Amino-9-n-hexadecylpurin；9-Hexadecyl-9H-purin-6-amine；9-hexadecylpurin-6-amine
• CAS: 68180-20-1
• 化学式: C₂₁H₃₇N₅
• 分子量: 359.558
• InChiKey: XRKDUNXFMAHKGU-UHFFFAOYSA-N

物化性质

• 熔点：
  118 °C
• 沸点：
  520.4±53.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-十六烷醇 、 腺嘌呤 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到9-十六烷基嘌呤-6-胺
  参考文献：
  名称：

  Alkynyl and Phosphonyl Substituted Nucleobases: A Case of Thermally Induced Conformational Polymorphism

  摘要：

  Substituted nucleobases with alkynyl and phosphonyl groups wire investigated in the context of supramolecular interactions and possible use toward synthesis of nucleoside phosphonic acids (NPAs). The adeninyl compound (adeninyl-N-9)-CH2CH2CH2CH2C CH exhibits conformational polymorphism as revealed by X-ray structures determined at 200 and 298 K. Interestingly, in the compound (adeninyl-N-9)-(CH2)(15)CH3, the long aliphatic carbon chain does not show disorder. A rather unusual bending of alkyl chain, likely due to C center dot center dot center dot O interactions, is observed in the case of the thymine compound (thyminyl)-CH2CH2CH2C CH that possesses a terminal alkyne group. The, powerful hydrogen bond acceptor property of the phosphoryl oxygen (P=O) does not perturb (unless assisted by other hydrogen Bonding partners) the :homo base-pairing in the structures of most of the phosphonyl substituted nucleobases studied.

  DOI：

  10.1021/cg101737x

文献信息

• Biodegradable Amphiphilic Copolymer Containing Nucleobase: Synthesis, Self-Assembly in Aqueous Solutions, and Potential Use in Controlled Drug Delivery
  作者：Huihui Kuang、Suhong Wu、Zhigang Xie、Fanbo Meng、Xiabin Jing、Yubin Huang

  DOI：10.1021/bm301169x

  日期：2012.9.10

  Biodegradable nucleobase-grafted amphiphilic copolymer, the methoxyl poly (ethylene glycol)-b-poly (L-lactide-omega-2-methyl-2(3-(2,3-dihydroxylpropylthio) propyloxycarbonyl)-propylene carbonate/1-carboxymethylthymine) (mPEG-b- P(LA-co-MPT)), was synthesized. H-1 NMR titration and FT-IR spectroscopy indicated that the hydrogen-bonding could be formed between mPEG-b-P(LA-co-MPT) and 9-hexadecyladenine (A-C16). The hydrophobic microenvironment of the amphiphilic copolymer can protect the complementary multiple hydrogen bonds between mPEG-b-P(LA-co-MPT) and A-C16 from water effectively. The addition of A-C16 not only lowered the critical aggregation concentration (CAC) of mPEG-b-P(LA-co-MPT)/A-C16 nanoparticles (NPs) in aqueous solution but also induced different morphologies, which can be observed by transmission electron microscopy (TEM). Meanwhile, dynamic light scattering (DLS) and turbidometry was utilized to evaluate the effect of temperature and pH change on the stability of mPEG-b-P(LA-co-MPT)/A-C16 NPs. Cytotoxicity evaluation showed good biocompatibility of the mPEG-b-P(LA-co-MPT)/A-C16 NPs. The in vitro drug release profile showed that with the increase of A-C16 content, the doxorubiucin (DOX) release at pH 7.4 decreased, while the faster release rate was observed with the addition of A-C16 with a pH of 5.0. Importantly, DOX-loaded NPs exerted comparable cytotoxicity against MDA-MB-231 cells. This work provided a new method to stabilize NP structure using hydrogen-bonds and would have the potential to be applied in controlled drug delivery.
• Michas, J.; Paleos, C. M.; Skoulios, A., Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1994, vol. 239, p. 245 - 256
  作者：Michas, J.、Paleos, C. M.、Skoulios, A.、Weber, P.

  DOI：——

  日期：——
• Zeng, Qingdao; Wang, Chen; Zhang, Bin, Journal of the Indian Chemical Society, 2000, vol. 77, # 11-12, p. 599 - 602
  作者：Zeng, Qingdao、Wang, Chen、Zhang, Bin、Xu, Shandong、Wu, Peng、Qiu, Xiaohui、Bai, Chunli

  DOI：——

  日期：——
• BANERJEE S.; DUTTA S. K.; CHAKRABORTI S. K., INDIAN J. CHEM., 1978, B 16, NO 4, 314-316
  作者：BANERJEE S.、 DUTTA S. K.、 CHAKRABORTI S. K.

  DOI：——

  日期：——
• Alkynyl and Phosphonyl Substituted Nucleobases: A Case of Thermally Induced Conformational Polymorphism
  作者：K. C. Kumara Swamy、Srinivasarao Allu、Venu Srinivas、E. Balaraman、K. V. P. Pavan Kumar

  DOI：10.1021/cg101737x

  日期：2011.6.1

  Substituted nucleobases with alkynyl and phosphonyl groups wire investigated in the context of supramolecular interactions and possible use toward synthesis of nucleoside phosphonic acids (NPAs). The adeninyl compound (adeninyl-N-9)-CH2CH2CH2CH2C CH exhibits conformational polymorphism as revealed by X-ray structures determined at 200 and 298 K. Interestingly, in the compound (adeninyl-N-9)-(CH2)(15)CH3, the long aliphatic carbon chain does not show disorder. A rather unusual bending of alkyl chain, likely due to C center dot center dot center dot O interactions, is observed in the case of the thymine compound (thyminyl)-CH2CH2CH2C CH that possesses a terminal alkyne group. The, powerful hydrogen bond acceptor property of the phosphoryl oxygen (P=O) does not perturb (unless assisted by other hydrogen Bonding partners) the :homo base-pairing in the structures of most of the phosphonyl substituted nucleobases studied.