5-ethyl-2,6-dihydroxy-4-methyl-nicotinonitrile | 39621-05-1

• 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: 5-ethyl-2,6-dihydroxy-4-methyl-nicotinonitrile
• 英文别名: 5-Aethyl-2,6-dihydroxy-4-methyl-nicotinonitril；2,6-Dihydroxy-5-ethyl-4-methylnicotinonitril；5-ethyl-6-hydroxy-4-methyl-2-oxo-1H-pyridine-3-carbonitrile
• CAS: 39621-05-1
• 化学式: C₉H₁₀N₂O₂
• 分子量: 178.191
• InChiKey: PEIIEYSAKQLFMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  334.7±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-ethyl-2,6-dihydroxy-4-methyl-nicotinonitrile 在 三氯氧磷 作用下， 生成 5-ethyl-4-methylnicotinonitrile
  参考文献：
  名称：

  Govindachari et al., Journal of the Chemical Society, 1957, p. 545

  摘要：

  DOI：
• 作为产物：
  描述：

  氰乙酰胺 、 2-乙基乙酰乙酸乙酯 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以47%的产率得到5-ethyl-2,6-dihydroxy-4-methyl-nicotinonitrile
  参考文献：
  名称：

  Design of Novel Potent Inhibitors of Human Uridine Phosphorylase-1: Synthesis, Inhibition Studies, Thermodynamics, and in Vitro Influence on 5-Fluorouracil Cytotoxicity

  摘要：

  Uridine (Urd) is a promising biochemical modulator to reduce host toxicity caused by 5-fluorouracil (5-FU) without impairing its antitumor activity. Elevated doses of Urd are required to achieve a protective effect against 5-FU toxicity, but exogenous administration of Urd is not well-tolerated. Selective inhibitors of human uridine phosphorylase (hUP) have been proposed as a strategy to increase Urd levels. We describe synthesis and characterization of a new class of ligands that inhibit hUP type 1 (hUP1). The design of ligands was based on a possible S(N)1 catalytic mechanism and as mimics of the carbocation in the transition state of hUP1. The kinetic and thermodynamic profiles showed that the ligands here presented are the most potent in vitro hUP1 inhibitors developed to date. In addition, a lead compound improved the antiproliferative effects of 5-FU on colon cancer cells, accompanied by a reduction of in vitro 5-FU cytotoxicity in aggressive SW-620 cancer cells.

  DOI：

  10.1021/jm401389u

文献信息

• Reactive dye composition
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0127456A2

  公开（公告）日：1984-12-05

  A reactive dye composition comprising (1) a dye having the formula, wherein D is an organic dye residue having at least one sulfo group, R, and R2 are independently a hydrogen atom or an unsubstitute or substituted lower alkyl group, A is an unsubstituted or substituted phenylene or naphthylene group, X is a halogen atom, and Y is a group, -S02CH=CH2 or -S02CH2CH2Z, in which Z is a group capable of being split by the action of an alkali, and (2) a buffer, the amount of the buffer being from 3 through 80% by weight based on the weight of the dye, and the pH value of an aqueous solution prepared from the dye composition and water of 20 times as much as the weight of the dye composition being from 3.5 through 7.5, which is superior in storage stability, and useful for dyeing or printing fiber materials to give dyed or printed products having superior fastness with high reproducibility.

  一种活性染料组合物，包括(1)具有以下式子的染料、 其中 D 是具有至少一个磺基的有机染料残基，R 和 R2 独立地为氢原子或未取代或取代的低级烷基，A 是未取代或取代的亚苯基或亚萘基，X 是卤素原子，Y 是基团 -S02CH=CH2 或 -S02 Z、其中 Z 是能在碱作用下分裂的基团，以及 (2) 缓冲剂，缓冲剂的量为染料重量的 3 至 80%（按重量计），由染料组合物和染料组合物重量 20 倍的水制备的水溶液的 pH 值为 3.这种水溶液具有优异的贮存稳定性，可用于纤维材料的染色或印花，使染色或印花产品具有优异的牢度和较高的再现性。
• On the methylation of 3-cyano-6-hydroxypyridine-2(1H)-ones
  作者：Yves Louis Janin、Jaouad Chiki、Michel Legraverend、Christiane Huel、Emile Bisagni

  DOI：10.1016/s0040-4020(99)00755-3

  日期：1999.10

  In order to prepare new heterocyclic derivatives as building block for compounds with potential biological activities, we were led to study the O-methylation of 3-cyano-6-hydroxypyridine-2(1H)-ones such as 1. This enabled us to develop a new two steps method to prepare the corresponding 2,6-dimethoxy derivative 5 in 80 % yield. It consisted first in heating 1 in trimethylorthoformate, with or without an acidic catalyst, which gave a mixture of the two mono-methoxy isomers, then a classical methylation of the second hydroxy moiety led almost exclusively to 5. In this paper we present this "methylation" method and various unexpected results recorded when we attempted to extend it to related derivatives or to other heterocycle containing lactim-lactam functions. An intramolecular transetherification mechanism requiring the simultaneous transfer of a hydrogen and a methyl is suggested. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Gibson; Simonsen, Journal of the Chemical Society, 1929, p. 1075
  作者：Gibson、Simonsen

  DOI：——

  日期：——
• Guareschi, Chemische Berichte, 29 Ref. <1896>, 656
  作者：Guareschi

  DOI：——

  日期：——
• Guareschi, vol. <2> 57, p. 297
  作者：Guareschi

  DOI：——

  日期：——

表征谱图