N-nicotinoyltri(hydroxymethyl)aminomethane | 6323-83-7

• 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
• 英文名称: N-nicotinoyltri(hydroxymethyl)aminomethane
• 英文别名: N-(2-hydroxy-1,1-bis-hydroxymethyl-ethyl)-nicotinamide；n-[1,3-Dihydroxy-2-(hydroxymethyl)propan-2-yl]pyridine-3-carboxamide
• CAS: 6323-83-7
• 化学式: C₁₀H₁₄N₂O₄
• 分子量: 226.232
• InChiKey: WWEDWTGXAUAFNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  103
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-nicotinoyltri(hydroxymethyl)aminomethane 在 硝酸 作用下， 反应 1.25h， 以94.3%的产率得到
  参考文献：
  名称：

  异功能系列有机硝酸盐的合成与研究

  摘要：

  N-烟酰三（羟甲基）氨基甲烷三硝酸盐，N-烟酰乙醇胺硝酸盐的类似物（抗心绞痛药物尼可地尔的活性成分），是通过相应的三醇与浓HNO3的O-硝化制备的。通过X射线结构分析确定反应产物的结构。

  DOI：

  10.1007/bf02495262
• 作为产物：
  描述：

  3-吡啶羧酸 2,5-二氧代-1-吡咯烷基酯 、 三羟甲基氨基甲烷 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 N-nicotinoyltri(hydroxymethyl)aminomethane
  参考文献：
  名称：

  Studies on the Inhibition of Moloney Murine Leukemia Virus Reverse Transcriptase by N-Tritylamino Acids and N-Tritylamino Acid-Nucleotide Compounds

  摘要：

  N-Acylated derivatives of 8-(6-aminohexyl) amino-adenosine-5'-phosphate were prepared and studied with regard to their effect on DNA synthesis by the Moloney leukemia virus reverse transcriptase. N-palmitoyl and N-nicotinyl derivatives and bis-8-(6-aminohexyl) amino-5'-AMP inhibited the enzyme partially using poly (rA).oligo d(pT)(16-18) as template-primer with [H-3]dTTP. In order to increase hydrophobicity in the acyl component tethered to the 8-(6-aminohexyl) amino group on the adenine nucleotide, N-trityl-L-phenylalanine and the N-trityl derivatives of the o, m, and p-fluoro-DL-phenylalanine were initially examined for inhibition of the enzyme using the above template-primer system. The compounds all inhibited the reverse transcriptase with IC50 values of approximately 60-80 mu M. However, when N-trityl-m-fluoro-DL-phenylalanine was coupled to the nucleotide 8-(6-aminohexyl) amino-adenosine-5'-phosphate, the inhibitory activity of this compound increased significantly (IC50 = 5 mu M).

  DOI：

  10.1080/15257770802271698

文献信息

• Transfer of a positively charged acyl group between substituted phenolate ion nucleophiles: the brønsted β for the calibrating equilibrium for N-methylisonicotinyl (4-carbonyl-N-methylpyridinium) transfer
  作者：Matthew J. Colthurst、Matilde Nanni、Andrew Williams

  DOI：10.1039/p29960002285

  日期：——

  measured for the reaction of substituted phenolate ions with aryl acetate esters and with aryl N-methylisonicotinate esters in aqueous solution. A new method is demonstrated for determining βeq for group transfer from 4-nitrophenyl esters; it employs the rate constant for the reaction of 2,6-difluorophenolate ion with substituted phenyl ester as a surrogate for the reactivity of the 4-nitrophenolate ion

  已经测量了在水溶液中取代酚盐离子与乙酸芳基酯和与芳基N-甲基异烟酸酯的反应的速率常数。一种新方法被证明用于确定β当量从4-硝基苯基酯基转移; 它采用的速率常数的反应2,6- difluorophenolate离子取代的苯基酯作为4-硝基苯酚盐离子和产量的反应性的替代β当量= 1.55为Ñ -methylisonicotinyl转移反应。苯甲酸根离子对4-硝基苯基N-甲基异烟酸根酸酯的进攻速率常数的布朗斯台德图在p K a范围内是线性的值从5.5到10，并为该反应的协调位移机制提供了很好的证据。所述的反应性Ñ -methylisonicotinate酯酚离子是比相应的乙酸酯的大约300次，但较大的β NUC值（0.90与0.74比较）提出了一种“后面”过渡结构。所述的校准β与对应的值β当量给出莱弗勒α NUC为= 0.58和0.42 Ñ -methylisonicotinate和乙酸分别，与
• Coordination-driven self-assembly of polyoxometalates into discrete supramolecular triangles
  作者：Marie-Pierre Santoni、Amlan K. Pal、Garry S. Hanan、Marie-Christine Tang、Karine Venne、Alexandra Furtos、Pierre Ménard-Tremblay、Cédric Malveau、Bernold Hasenknopf

  DOI：10.1039/c1cc16155e

  日期：——

  Pd(II)-directed self-assembly of a 3-pyridyl grafted Lindqvist hexavanadate led to the formation of a unique trimeric species, as confirmed by a variety of techniques, including pulsed-field gradient NMR spectroscopy and high-resolution ESI mass spectrometry.

  Pd（II）定向的3-吡啶基接枝的Lindqvist六钒酸盐的自组装导致形成独特的三聚体物种，这一点已通过多种技术证实，包括脉冲场梯度NMR光谱和高分辨率ESI质谱。
• New method for the synthesis of metal complexes based on PtIV and substituted nicotinamides and isonicotinamides and investigation of their antimetastatic activity
  作者：B. S. Fedorov、M. A. Fadeev、G. I. Kozub、A. N. Chekhlov、N. P. Konovalova、T. E. Sashenkova、E. N. Berseneva、O. V. Dobrokhotova、L. V. Tatyanenko

  DOI：10.1007/s11172-011-0186-8

  日期：2011.6

  Complexes of platinum tetrachloride with substituted nicotinamides and isonicotinamides were synthesized by the reactions of the corresponding amides with hexachloroplatinic acid. All these complexes are low-toxic. The strong antimetastatic activity of these complexes against Lewis lung carcinoma and B16 melanoma experimental tumors was found in an enzyme system and was then shown in experiments on animals.

  通过相应的酰胺与六氯铂酸的反应合成了四氯化铂与取代烟酰胺和异烟酰胺的配合物。所有这些复合物都是低毒的。在酶系统中发现了这些复合物对 Lewis 肺癌和 B16 黑色素瘤实验性肿瘤的强抗转移活性，并在动物实验中得到了证明。
• Studies on the Inhibition of Moloney Murine Leukemia Virus Reverse Transcriptase by N-Tritylamino Acids and N-Tritylamino Acid-Nucleotide Compounds
  作者：Arthur Hawtrey、Anton Pieterse、Johann van Zyl、Pieter Van der Bijl、Marichen Van der Merwe、William Nel、Mario Ariatti

  DOI：10.1080/15257770802271698

  日期：2008.8.28

  N-Acylated derivatives of 8-(6-aminohexyl) amino-adenosine-5'-phosphate were prepared and studied with regard to their effect on DNA synthesis by the Moloney leukemia virus reverse transcriptase. N-palmitoyl and N-nicotinyl derivatives and bis-8-(6-aminohexyl) amino-5'-AMP inhibited the enzyme partially using poly (rA).oligo d(pT)(16-18) as template-primer with [H-3]dTTP. In order to increase hydrophobicity in the acyl component tethered to the 8-(6-aminohexyl) amino group on the adenine nucleotide, N-trityl-L-phenylalanine and the N-trityl derivatives of the o, m, and p-fluoro-DL-phenylalanine were initially examined for inhibition of the enzyme using the above template-primer system. The compounds all inhibited the reverse transcriptase with IC50 values of approximately 60-80 mu M. However, when N-trityl-m-fluoro-DL-phenylalanine was coupled to the nucleotide 8-(6-aminohexyl) amino-adenosine-5'-phosphate, the inhibitory activity of this compound increased significantly (IC50 = 5 mu M).
• Synthesis and studies of organic nitrates of the heterofunctional series
  作者：A. M. Korolev、L. T. Eremenko、L. V. Meshikhina、I. L. Eremenko、S. E. Nefedov

  DOI：10.1007/bf02495262

  日期：1997.12

  N-Nicotinoyltris(hydroxymethy)aminomethane trinitrate hydronitrate, an analog ofN-nicotinoylethanolamine nitrate (the active principle of the antianginal drug nicorandil), was prepared byO-nitration of the corresponding triol with concentrated HNO3. The structure of the reaction product was established by X-ray structural analysis.

  N-烟酰三（羟甲基）氨基甲烷三硝酸盐，N-烟酰乙醇胺硝酸盐的类似物（抗心绞痛药物尼可地尔的活性成分），是通过相应的三醇与浓HNO3的O-硝化制备的。通过X射线结构分析确定反应产物的结构。