2-(乙酰基氨基)-3-羟基吡啶 | 31354-48-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-(乙酰基氨基)-3-羟基吡啶
• 中文别名: 2-乙酰氨基-3-羟基吡啶
• 英文名称: N-(3-hydroxypyridin-2-yl)acetamide
• 英文别名: 2-acetamido-3-hydroxypyridine；2-acetylamino-pyridin-3-ol；N-(3-hydroxy-[2]pyridyl)-acetamide；N-(3-Hydroxy-[2]pyridyl)-acetamid；2-Acetamino-3-hydroxy-pyridin；2-(Acetylamino)-3-pyridinol
• CAS: 31354-48-0
• 化学式: C₇H₈N₂O₂
• mdl: MFCD09757484
• 分子量: 152.153
• InChiKey: RNNMBUAVVIZMMX-UHFFFAOYSA-N

物化性质

• 熔点：
  101-102 °C
• 沸点：
  485.3±30.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090
• WGK Germany：
  3
• 危险标志：
  GHS07
• 危险性描述：
  H302
• 危险性防范说明：
  P280,P305+P351+P338
• 储存条件：
  存储条件为2-8°C，并需保存在惰性气体中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Acetamido-3-hydroxypyridine
Synonyms: N-(3-Hydroxypyridin-2-yl)acetamide

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Acetamido-3-hydroxypyridine
CAS number: 31354-48-0

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C7H8N2O2
Molecular weight: 152.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-(乙酰基氨基)-3-羟基吡啶 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 锌 作用下， 以 N,N-二甲基乙酰胺 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.0h， 生成 3,4-dihydro-2H-pyrido-[3,2-b][1,4]oxazine-7-carbonitrile
  参考文献：
  名称：

  Acridone-Based Inhibitors of Inosine 5‘-Monophosphate Dehydrogenase:  Discovery and SAR Leading to the Identification of N-(2-(6-(4-Ethylpiperazin-1-yl)pyridin-3-yl)propan-2-yl)-2- fluoro-9-oxo-9,10-dihydroacridine-3-carboxamide (BMS-566419)

  摘要：

  Inosine monophosphate dehydrogenase (IMPDH), a key enzyme in the de novo synthesis of guanosine nucleotides, catalyzes the irreversible nicotinamide-adenine dinucleotide dependent oxidation of inosine-5'-monophosphate to xanthosine-5'-monophosphate. Mycophenolate Mofetil (MMF), a prodrug of mycophenolic acid, has clinical utility for the treatment of transplant rejection based on its inhibition of IMPDH. The overall clinical benefit of MMF is limited by what is generally believed to be compound-based, dose-limiting gastrointestinal (GI) toxicity that is related to its specific pharmacokinetic characteristics. Thus, development of an IMPDH inhibitor with a novel structure and a different pharmacokinetic profile may reduce the likelihood of GI toxicity and allow for increased efficacy. This article will detail the discovery and SAR leading to a novel and potent acridone-based IMPDH inhibitor 4m and its efficacy and GI tolerability when administered orally in a rat adjuvant arthritis model.

  DOI：

  10.1021/jm070299x
• 作为产物：
  描述：

  3-乙酰氧基-1-乙酰基-2-乙酰亚氨基-1,2-二氢-吡啶 在 ammonium hydroxide 作用下， 生成 2-(乙酰基氨基)-3-羟基吡啶
  参考文献：
  名称：

  Takahashi; Yoneda, Pharmaceutical Bulletin, 1957, vol. 5, p. 350,352

  摘要：

  DOI：

文献信息

• NMR studies of new heterocycles tethered to purine moieties with anticancer activity
  作者：Nerea Fernández-Sáez、Joaquín M. Campos、María Encarnación Camacho、María Dora Carrión

  DOI：10.1002/mrc.4871

  日期：2019.6

  study reports the unambiguous assignment of each signal in the H and C NMR spectra in benzoxazine derivatives (3a–d), including elongation of the side chain, tetrahydroquinolines (5a–d), and pyridoxazine derivatives (11a–b) in which a pyridine ring is merged to the oxazine heterocycle, using one‐ and two‐dimensional resonance techniques. The assignment of derivatives 1, 2, 4, and 6–10, the precursors

  癌症是我们社会面临的最大威胁之一，因为它是导致死亡的主要原因之一。近年来已经开发了许多活性化合物来解决这个问题。一些具有有趣的抗增殖活性的嘌呤衍生物先前已通过将苯并稠合杂环与取代的嘌呤相结合而合成。为了提高活性并更深入地了解构效关系，获得了新的化合物。这些变化包括一些生物等排置换，如杂环氧原子的消除或六元杂环和取代嘌呤之间连接链的延长。通过这种方式，这些新型嘌呤衍生物家族的合成和生物学评价与六元杂环部分 3a-d、5a-d 和 11a-b 相连，已经描述了它们被设计和评估为抗癌剂。这些新化合物的结构已通过 H 和 C 核磁共振 (NMR) 和质谱法确定。为了通过使用二维技术证实它们的骨架，对其中的一些进行了更详细的研究，并对所有最终化合物进行了元素分析。本研究报告了苯并恶嗪衍生物 (3a-d) 的 H 和 C NMR 光谱中每个信号的明确分配，包括侧链的伸长、四氢喹啉 (5a-d) 和吡哆嗪衍生物
• [EN] HETEROCYCLIC AMIDE DERIVATIVES AS INHIBITORS OF GLYCOGEN PHOSPHORYLASE<br/>[FR] DERIVES D'AMIDES HETEROCYCLIQUES COMME INHIBITEURS DE LA GLYCOGENE PHOSPHORYLASE
  申请人：ASTRAZENECA AB

  公开号：WO2003074532A1

  公开（公告）日：2003-09-12

  Heterocyclic amides of formula (1) wherein: X is N or CH; R4 and R5 together are either -S-C(R6)=C(R7)- or -C(R7)=C(R6)-S-; R6 and R7 are independently selected from, for example hydrogen, halo and C1-4alkyl; A is phenylene or heteroarylene; n is 0, 1 or 2; R1 is selected from for example halo, nitro, cyano, hydroxy, carboxy; R2 is hydrogen, hydroxy or carboxy; R3 is selected from for example hydrogen, hydroxy, aryl, heterocyclyl and C1-4alkyl (optionally substituted by 1 or 2 R8 groups); R8 is selected from for example hydroxy, -COCOOR9, -C(O)N(R9)(R10), -NHC(O)R9, (R9)(R10)N- and -COOR9; R9 and R10 are selected from for example hydrogen, hydroxy, C1-4alkyl (optionally substituted by 1 or 2 R13); R13 is selected from hydroxy, halo, trihalomethyl and C1-4alkoxy; or a pharmaceutically acceptable salt or pro-drug thereof; possess glycogen phosphorylase inhibitory activity and accordingly have value in the treatment of disease states associated with increased glycogen phosphorylase activity. Processes for the manufacture of said heterocyclic amide derivatives and pharmaceutical compositions containing them are described.

  式（1）的杂环酰胺，其中：X为N或CH；R4和R5一起是-S-C（R6）=C（R7）-或-C（R7）=C（R6）-S-；R6和R7可独立地选择自氢、卤素和C1-4烷基；A为苯基或杂芳基；n为0、1或2；R1可从卤素、硝基、氰基、羟基、羧基中选择；R2为氢、羟基或羧基；R3可从氢、羟基、芳基、杂环烷基和C1-4烷基中选择（可选地由1或2个R8基取代）；R8可从羟基、-COCOOR9、-C（O）N（R9）（R10）、-NHC（O）R9、（R9）（R10）N-和-COOR9中选择；R9和R10可从氢、羟基、C1-4烷基（可选地由1或2个R13取代）中选择；R13可从羟基、卤素、三卤甲基和C1-4烷氧基中选择；或其药学上可接受的盐或前药；具有糖原磷酸化酶抑制活性，因此在治疗与糖原磷酸化酶活性增加相关的疾病状态中具有价值。描述了制备所述杂环酰胺衍生物和含有它们的药物组合物的方法。
• Benzazole compounds and pharmaceutical composition comprising the same
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05047411A1

  公开（公告）日：1991-09-10

  The benzazole compounds of this invention can be represented by the following formula [I]: ##STR1## wherein R.sup.1 is aryl or a heterocyclic group, each of which may have suitable substitutent(s), R.sup.2 is hydroxy, mercapto, lower alkylthio, sulfo, lower alkyl, amino or substituted amino, R.sup.3 is hydrogen, halogen or lower alkoxy, A is lower alkenylene, lower alkylene optionally substituted with hydroxy, or a group of the formula: --A'--Q--A"--, in which A' is lower alkylene, A" is lower alkylene or a single bond, and Q is O or S, and X is O, S, NH or N--R.sup.4, in which R.sup.4 is lower alkyl, More particularly, it relates to benzazole compounds and pharmaceutically acceptable salts thereof which have antiulcer activity and H.sub.2 -receptor antagonism, to processes for the preparation thereof, to a pharmaceutical composition comprising the same and to a method for the treatment of ulcers in human being or animals.

  本发明的苯唑化合物可以用以下公式[I]表示：其中R.sup.1是芳基或杂环基，每个基上可能有适当的取代基，R.sup.2是羟基、巯基、较低的烷硫基、磺酰基、较低的烷基、氨基或取代氨基，R.sup.3是氢、卤素或较低的烷氧基，A是较低的烯烃基、较低的烷基，可选择地取代羟基，或者是下述式的基团：--A'--Q--A"--，其中A'是较低的烷基，A"是较低的烷基或单键，Q是O或S，X是O、S、NH或N--R.sup.4，其中R.sup.4是较低的烷基。具体地，它涉及具有抗溃疡活性和H.sub.2-受体拮抗作用的苯唑化合物及其药学上可接受的盐，其制备方法，包括其制剂组合物以及治疗人类或动物溃疡的方法。
• METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS
  申请人：Duke University

  公开号：US20140371194A1

  公开（公告）日：2014-12-18

  This invention relates generally to the discovery of a method of inhibiting, preventing or treating bacterial infections. The invention also relates to a method of inhibiting bacterial capsule biogenesis.

  这项发明通常涉及发现一种抑制、预防或治疗细菌感染的方法。该发明还涉及一种抑制细菌胶囊生物合成的方法。
• The first enantioselective synthesis of 4-acetyl-3( R) - and 3( S )-(hydroxymethyl)-3,4-dihydro-2 H -pyrido[3,2- b ]oxazine
  作者：N. Henry、G. Guillaumet、M.D. Pujol

  DOI：10.1016/j.tetlet.2003.12.030

  日期：2004.2

  A novel short and enantioselective synthetic approach to pyridobenzoxazines is reported in which (R)- and (S)-3-(hydroxymethyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine were first synthesized from readily available chiral glycidyl derivatives.

  报道了一种新颖的短对映选择性合成吡啶并苯并恶嗪的方法，其中（R）-和（S）-3-（羟甲基）-3,4-二氢-2 H-吡啶[3,2- b ] [1,4]首先从容易获得的手性缩水甘油基衍生物合成恶嗪。