N(trimethylsilyl)nicotinamide | 1079394-06-1

• 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
• 英文名称: N(trimethylsilyl)nicotinamide
• 英文别名: Niacinamide, TMS derivative；N-trimethylsilylpyridine-3-carboxamide
• CAS: 1079394-06-1
• 化学式: C₉H₁₄N₂OSi
• 分子量: 194.308
• InChiKey: VQRBOHGTTOAYTJ-UHFFFAOYSA-N

物化性质

• 保留指数：
  2041

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N(trimethylsilyl)nicotinamide 在 磷酸三甲酯 、 三氟甲磺酸三甲基硅酯 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.08h， 生成 1-(3'-azido-3'-deoxy-β-D-ribofuranosyl)nicotinamide-5'-(butyl phosphate)
  参考文献：
  名称：

  Studies on the Synthesis of Nicotinamide Nucleoside and Nucleotide Analogues and Their Inhibitions towards CD38 NADase

  摘要：

  Nicotinamide adenine dinucleotide (NAD) analogues inhibit the NADase activity of CD38. In the current study, efficient protocols for the synthesis of substituted-nicotinamide nucleosides and nucleotides were developed. The one-pot phosphorylation esterification strategy provides a convenient way of obtaining nicotinamide nucleoside phosphodiesters from the corresponding nucleosides. Structure activity relationship information revealed that replacement of 3'-hydroxy group with F or N-3 led to the considerably decrease of activity as compared with ara-F NMN. Phosphodiesterification of nicotinamide nucleosides lowers their inhibitory activities in some extent.

  DOI：

  10.3987/com-11-12361
• 作为产物：
  描述：

  在 purine nucleoside phosphorylase 作用下， 以 重水 为溶剂， 反应 16.0h， 生成 N(trimethylsilyl)nicotinamide
  参考文献：
  名称：

  [EN] RIBOSE LINKERS AND CONJUGATES THEREOF
  [FR] LIEURS DE RIBOSE ET LEURS CONJUGUÉS

  摘要：

  The present disclosure provides a compound of Formula I: A-Rl-A' wherein A and A' are independently H or [Formula I], wherein A, A', and R1 are as described herein. Also provided are methods of making the compounds described herein, and use of the compounds, e.g., in NAD-increasing compositions.

  公开号：

  WO2023150667A2

文献信息

• [EN] BIOENERGETIC NICOTINIC ACID GLYCEROL ESTERS, COMPOSITIONS AND METHODS OF USING SAME<br/>[FR] ESTERS DE GLYCÉROL D'ACIDE NICOTINIQUE BIOÉNERGÉTIQUES, COMPOSITIONS ET PROCÉDÉS D'UTILISATION DE CEUX-CI
  申请人：UNILEVER PLC

  公开号：WO2020089236A1

  公开（公告）日：2020-05-07

  New nicotinic acid glycerol ester compound(s) (NAEs); topical personal care compositions containing NAEs; and methods for modulating or activating cellular AMPK levels; and for increasing skin cellular bioenergetics are described. Use of one or more of the nicotinic acid glycerol ester compounds for modulating or activating cellular AMPK levels; and for increasing skin cellular bioenergetics are described. Use of a skin benefit agent comprising certain nicotinic acid glycerol ester compounds in the manufacture of a topical personal care composition for modulating or activating cellular AMPK levels; and for increasing skin cellular bioenergetics are described.

  新的烟酸甘油酯化合物（NAEs）；含有NAEs的局部个人护理组合物；以及调节或激活细胞AMPK水平的方法；以及增加皮肤细胞生物能量的方法被描述。描述了利用一个或多个烟酸甘油酯化合物来调节或激活细胞AMPK水平；以及增加皮肤细胞生物能量的用途。描述了利用包含特定烟酸甘油酯化合物的皮肤益处剂在制造用于调节或激活细胞AMPK水平；以及增加皮肤细胞生物能量的局部个人护理组合物的用途。
• Scalable syntheses of traceable ribosylated NAD⁺ precursors
  作者：M. V. Makarov、N. W. Harris、M. Rodrigues、M. E. Migaud

  DOI：10.1039/c9ob01981b

  日期：——

  This work is novel as it describes scalable methods to gain efficient access to the ribosylated form of NAD⁺ precursors and to a range of isotopologues of NAD⁺ precursors, key tools to probing NAD⁺ biology.

  这项工作具有创新性，因为它描述了可扩展的方法，以高效地获得核糖基化形式的NAD⁺前体以及一系列NAD⁺前体的同位素衍生物，这些是探究NAD⁺生物学的关键工具。
• Nitrogen Atom Transfer Catalysis by Metallonitrene C−H Insertion: Photocatalytic Amidation of Aldehydes
  作者：Till Schmidt‐Räntsch、Hendrik Verplancke、Jonas N. Lienert、Serhiy Demeshko、Matthias Otte、Gerard P. Van Trieste、Kaleb A. Reid、Joseph H. Reibenspies、David C. Powers、Max C. Holthausen、Sven Schneider

  DOI：10.1002/anie.202115626

  日期：2022.2.21

  nitrogen-centered biradical character was identified as the key intermediate and was photocrystallographically, magnetically and computationally characterized. The nucleophilic metallonitrene C−H insertion step results in inverted selectivity for the net nitrene transfer catalysis.

  据报道，光催化氮原子转移成醛 C−H 键。具有氮中心双自由基特征的钯(II)金属氮烯物种被确定为关键中间体，并进行了光晶体学、磁性和计算表征。亲核金属氮烯CH插入步骤导致净氮烯转移催化的选择性反转。
• Silane: A new linker for chromophores in dye-sensitised solar cells
  作者：Katherine Szpakolski、Kay Latham、Colin Rix、Rozina A. Rani、Kourosh Kalantar-zadeh

  DOI：10.1016/j.poly.2012.07.078

  日期：2013.3

  A series of ruthenium(II) polypyridyl complexes, with novel silane functionalisation, [Ru(bipy)(2)(bipy-sil)] (PF6)(2) (3), [Ru(bipy-sil)(2)Cl-2] (6), and [Ru(bipy-sil)(2)(NCS)(2)] (7) have been synthesised and tested as chromophores (dyes) in TiO2 and WO3 based dye-sensitised solar cells (DSSCs). The performance of the respective DSSCs were compared to analogous dyes with ionic carboxylate ([Ru(bipy)(2)(dcbipy)](PF6)(2) (1), [Ru(dcbipy)(2)Cl-2] (4), [Ru(dcbipy)(2)(NCS)(2)] (5)) or phosphonate ([Ru(bipy)(2)(dpipy)](PF6)(2) (2)) linking groups. The covalent silane-metal oxide linkage offers much needed improvement to the operating conditions, and lifetime of DSSCs, in terms of pH range and choice of solvent. UV-Vis spectroscopy of the deep-red solutions showed that the bis-bipy-sil complexes absorbed more visible light than the tris-bipy complex, as indicated by the presence of two absorption bands and higher E values. The UV-Vis spectrum of (3) contained a single broad absorption at 400-600 nm with: lambda(max) = 457 nm; epsilon = 10520 +/- 440 L mol(-1) cm(-1), whereas two intense broad absorption bands were observed for novel bis-bipy-sil complexes (6): 340-370 nm (lambda(max(1)) = 365 nm, epsilon((1)) = 12716 +/- 180 L mol(-1) cm(-1)); and 440-540 nm (lambda(max(2)) = 485 nm, epsilon((2)) = 11070 +/- 150 L mol(-1) cm(-1)), and (7): 340-400 nm (lambda(max) = 371 nm epsilon((1)) = 20690 +/- 485 L mol(-1) cm(-1)), and 460-530 nm (lambda(max) = 500 nm and epsilon((2)) = 20750 +/- 487 L mol(-1) cm(-1)). The bands in (7) being significantly more defined.A 10-fold improvement in the efficiency of the bipy-sil TiO2-based DSSCs was observed from (3) to (6) to (7). This performance was lower than that of the commercial N3 dye, [Ru(dcbipy)(2)(NCS)(2)] (5), but the current of (7) on WO3, was comparable to that of the carboxylate system (4). There is considerable potential for further improvement by modification of the silyl linker, reducing the long non-conjugated propyl chain between the amide group and the silatrane (bipy-sil), to a short, conjugated link. During an extensive synthetic study, the most promising strategy was identified as direct linkage, the formation of a direct Si-C bond, using butyllithium with 4,4'-dibromo-2,2'-bipyridine and either trimethylsilane or 1-ethoxysilatrane, provided that the product can be captured and stabilised prior to binding to a metal oxide coated DSSC substrate. (C) 2012 Elsevier Ltd. All rights reserved.
• Chemical and Biochemical Reactivity of the Reduced Forms of Nicotinamide Riboside
  作者：Mikhail V. Makarov、Faisal Hayat、Briley Graves、Manoj Sonavane、Edward A. Salter、Andrzej Wierzbicki、Natalie R. Gassman、Marie E. Migaud

  DOI：10.1021/acschembio.0c00757

  日期：2021.4.16