烟酸乙酯-D4 | 66148-16-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 烟酸乙酯-D4
• 英文名称: 2,4,5,6-tetradeuterio-nicotinic acid ethyl ester
• 英文别名: [pyridine-D₄]ethyl nicotinate；ethyl nicotinate (2,4,5,6-[2H]4)；d4-nicotinic acid ethyl ester；ethyl [2,4,5,6-d4]nicotinate；Ethyl Nicotinate-d4；ethyl 2,4,5,6-tetradeuteriopyridine-3-carboxylate
• CAS: 66148-16-1
• 化学式: C₈H₉NO₂
• 分子量: 155.133
• InChiKey: XBLVHTDFJBKJLG-LNFUJOGGSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

制备方法与用途

3-吡啶-2,4,5,6-四甲基deen-2-基乙酸酯是一种氘标记的衍生物，源自3-吡啶-2,4,5,6-四甲基-4-羧酸乙酯[1]。

反应信息

• 作为反应物：
  描述：

  烟酸乙酯-D4 在 palladium on activated charcoal 吡啶 、 乙酸铵 、 lithium aluminium tetrahydride 、 草酰氯 、 氢气 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 33.5h， 生成 3-(3-pyridinyl)propanenitrile (2,4,5,6-[2H]4)
  参考文献：
  名称：

  Synthesis of deuterated-BCX-34 (peldesine)

  摘要：

  BCX-34 (peldesine) is a novel purine nucleoside phosphorylase inhibitor that is in human clinical trials for the treatment of T-cell cancers and for: HIV infected patients. In support of our BCX-34 clinical program, a mass spectrometric assay has been developed utilizing a deuterated-BCX-34 analog as an internal standard. The synthesis of tetra-deuterated-BCX-34 (peldesine) from ethyl nicotinate. (2,4,5,6-[H-2](4)) is,described in this report.

  DOI：

  10.1002/(sici)1099-1344(19991230)42:13<1235::aid-jlcr279>3.0.co;2-q

文献信息

• Quantitation of Pyridyloxobutyl DNA Adducts of Tobacco-Specific Nitrosamines in Rat Tissue DNA by High-Performance Liquid Chromatography−Electrospray Ionization−Tandem Mass Spectrometry
  作者：Yanbin Lao、Peter W. Villalta、Shana J. Sturla、Mingyao Wang、Stephen S. Hecht

  DOI：10.1021/tx050351x

  日期：2006.5.1

  produce pyridyloxobutyl (POB)-DNA adducts. POB-DNA adduct formation plays a critical role in NNN and NNK carcinogenicity in rodents. To further investigate the significance of this pathway, we developed a high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry (HPLC-ESI-MS/MS) method for quantitative analysis of four POB-DNA adducts with known structures. The corresponding

  烟草特有的亚硝胺 N'-亚硝基烟碱 (NNN, 1) 和 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK, 2) 是啮齿类动物的强致癌物。细胞色素 P450 酶对 NNN 和 NNK 的生物活化产生吡啶氧丁基化剂 6，它使 DNA 烷基化以产生吡啶氧丁基 (POB)-DNA 加合物。POB-DNA 加合物的形成在啮齿类动物的 NNN 和 NNK 致癌性中起着关键作用。为了进一步研究该途径的重要性，我们开发了一种高效液相色谱-电喷雾电离-串联质谱 (HPLC-ESI-MS/MS) 方法，用于定量分析四种已知结构的 POB-DNA 加合物。合成相应的氘代类似物并用作内标。掺入内标的 DNA 样本，进行中性热水解，然后进行酶水解。在 HPLC-ESI-MS/MS 分析之前，通过固相萃取部分纯化水解产物。该方法准确而精确。获得了出色的灵敏度，尤其是对于
• Syntheses of isotope-labeled tobacco-specific nitrosamines and their metabolites
  作者：Dhimant Desai、Jacek Krzeminski、Karam El-Bayoumy、Shantu Amin

  DOI：10.1002/jlcr.1508

  日期：2008.4

  and myosmine, 4-hydroxy-1-(3-[2,4,5,6-d4]pyridyl)-1-butanone, was also synthesized. The synthetic strategy reported here is similar to that reported in the literature for the preparation of corresponding unlabeled compounds. The commercially available [2,4,5,6-d4]ethylnicotinate was used as starting material. During the course of these syntheses [2,4,5,6-d4]myosmine and [2,4,5,6-d4]nornicotine were

  我们在此报告了三种氘标记的烟草特异性亚硝胺的合成，即 [2,4,5,6-d4]nitrosonornicotine([2,4,5,6-d4]NNN)、4-(methylnitrosamino)-1 -(3-[2,4,5,6-d4] 吡啶基)-1-丁酮 ([2,4,5,6-d4]NNK) 和 4-(甲基亚硝胺)-1-(3-[2 ,4,5,6-d4]吡啶基）-1-丁醇（[2,4,5,6-d4]NNAL）。还合成了 NNK 和肌胺的代谢物 4-羟基-1-(3-[2,4,5,6-d4] 吡啶基)-1-丁酮。这里报道的合成策略类似于文献中报道的用于制备相应未标记化合物的合成策略。使用市售的[2,4,5,6-d4]乙基烟酸酯作为原料。在这些合成过程中，[2,4,5,6-d4]myosmine 和 [2,4,5,6-d4]nornicotine 被作为稳定的中间体获得。这些同位素标记的化合物是在分子流行病学研究中量化吸烟者
• DEUTERATED HIV ATTACHMENT INHIBITORS
  申请人：Wang Tao

  公开号：US20130096305A1

  公开（公告）日：2013-04-18

  Deuterated piperazine and piperidine HIV attachment inhibitor compounds are set forth. The present invention provides compounds of Formula I, the pharmaceutically acceptable salts and/or solvates (e.g., hydrates) thereof, their pharmaceutical formulations, and their use in patients suffering from or susceptible to a virus such as HIV. The compounds of Formula I, their pharmaceutically acceptable salts and/or solvates are effective antiviral agents, particularly as inhibitors of HIV. They are useful for the treatment of HIV and AIDS.

  本发明提供了一种取代了氘代哌嗪和哌啶的HIV附着抑制剂化合物。本发明提供了I式化合物、其药学上可接受的盐和/或溶剂（例如水合物）、它们的制剂以及它们在患有或易感染HIV等病毒的患者中使用。I式化合物及其药学上可接受的盐和/或溶剂是有效的抗病毒剂，特别是HIV抑制剂。它们可用于治疗HIV和AIDS。
• Synthesis of Partially Deuterated N -Nitrosamines ? New Standards in Tobacco-smoke Analysis
  作者：Peter G�rtner、Katharina Bica、Christian Einzinger

  DOI：10.1007/s00706-003-0152-8

  日期：2004.5.1

  N-Nitrosamines of tobacco alkaloids contribute to the cause of tobacco related cancers and, therefore, they are important analytes. Herein the preparation of four partially deuterated N-nitrosamines from simple, commercially available, deuterated educts is described, which can serve as useful standards in tobacco-smoke analysis.
• Synthesis of deuterated-BCX-34 (peldesine)
  作者：Tracy L. Hutchison、Philip E. Morris

  DOI：10.1002/(sici)1099-1344(19991230)42:13<1235::aid-jlcr279>3.0.co;2-q

  日期：1999.12.30

  BCX-34 (peldesine) is a novel purine nucleoside phosphorylase inhibitor that is in human clinical trials for the treatment of T-cell cancers and for: HIV infected patients. In support of our BCX-34 clinical program, a mass spectrometric assay has been developed utilizing a deuterated-BCX-34 analog as an internal standard. The synthesis of tetra-deuterated-BCX-34 (peldesine) from ethyl nicotinate. (2,4,5,6-[H-2](4)) is,described in this report.