6-(二乙基氨基)吡啶-3-甲醛 | 578726-67-7

• 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 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 6-(二乙基氨基)吡啶-3-甲醛
• 中文别名: 6-(二乙胺基)-3-吡啶基醛
• 英文名称: 6-(diethylamino)nicotinaldehyde
• 英文别名: 6-(Diethylamino)pyridine-3-carbaldehyde
• CAS: 578726-67-7
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: PCISUIMHLSRKGR-UHFFFAOYSA-N

物化性质

• 沸点：
  313.6±27.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

SDS

Name:	6-(Diethylamino)-3-pyridinylaldehyde Material Safety Data Sheet
Synonym:	None Known
CAS:	578726-67-7

Section 1 - Chemical Product MSDS Name:6-(Diethylamino)-3-pyridinylaldehyde Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
578726-67-7	6-(Diethylamino)-3-pyridinylaldehyde	97+	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38 42

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin. May cause sensitization by inhalation.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Causes respiratory tract irritation. Harmful if inhaled. May cause respiratory sensitization.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Store under an inert atmosphere.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 578726-67-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: green
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 61-63 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H14N2O
Molecular Weight: 178.23

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents, bases, amines.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 578726-67-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
6-(Diethylamino)-3-pyridinylaldehyde - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
R 42 May cause sensitization by inhalation.
Safety Phrases:
S 22 Do not breathe dust.
S 24/25 Avoid contact with skin and eyes.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 578726-67-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 578726-67-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 578726-67-7 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  6-(二乙基氨基)吡啶-3-甲醛 在 sodium metabisulfite 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 16.0h， 生成 N,N-diethyl-5-(1-((2-methyloxazol-4-yl)methyl)-1H-benzo[d]imidazol-2-yl)pyridin-2-amine
  参考文献：
  名称：

  基于细胞的药物发现：降低细胞中 c-MYC 蛋白水平的小分子的鉴定和优化

  摘要：

  c -MYC癌基因的表达升高是人类癌症中最常见的异常之一。不幸的是，由于蛋白质中缺乏任何已知的小分子结合口袋，鉴定直接靶向 MYC 的药理学抑制剂的努力尚未产生类似药物的分子，这可以用来破坏 MYC 功能。我们最近描述了一种间接靶向 MYC 的策略，其中一项筛选工作旨在鉴定可以快速降低 MYC 扩增细胞系中内源性c -MYC蛋白水平的化合物，从而发现了一个化合物系列-通过 siRNA 敲低 MYC。在这里，我们描述了我们的药物化学计划，该计划导致发现了有效的、口服生物可利用的c -MYC 还原化合物。将重点介绍基于经验结构活性关系的最小药效团模型的开发以及用于调节药代动力学特性的基于特性的方法。

  DOI：

  10.1021/acs.jmedchem.1c01416
• 作为产物：
  描述：

  6-氟烟酸 在 lithium aluminium tetrahydride 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.75h， 生成 6-(二乙基氨基)吡啶-3-甲醛
  参考文献：
  名称：

  [EN] ANTIBACTERIAL COMPOUNDS AND USES THEREOF
  [FR] COMPOSÉS ANTIBACTÉRIENS ET UTILISATIONS DE CEUX-CI

  摘要：

  本发明涉及式(I)的化合物，包括其任何立体化异构体或其药学上可接受的盐，用于治疗结核病。

  公开号：

  WO2017155909A1

文献信息

• [EN] 5-(1 H-BENZO[D]IMIDAZO-2-YL)-PYRIDIN-2-AMINE AND 5-(3H-IMIDAZO[4,5-B]PYRIDIN-6-YL)-PYRIDIN-2-AMINE DERIVATIVES AS C-MYC AND P300/CBP HISTONE ACETYLTRANSFERASE INHIBITORS FOR TREATING CANCER<br/>[FR] DÉRIVÉS DE 5-(1 H-BENZO[D]IMIDAZO-2-YL)-PYRIDIN-2-AMINE ET DE 5-(3H-IMIDAZO[4,5-B]PYRIDIN-6-YL)-PYRIDIN-2-AMINE UTILISÉS EN TANT QU'INHIBITEURS D'HISTONE ACÉTYLTRANSFÉRASE DE C-MYC ET P300/CBP POUR LE TRAITEMENT DU CANCER
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2019049061A1

  公开（公告）日：2019-03-14

  The invention is directed to substituted 5-(1H-benzo[d]imidazo-2-yl)- pyridin-2-amine and 5-(3H-imidazo[4,5-b]pyridin-6-yl)-pyridin-2-amine derivatives. Specifically, the invention is directed to compounds according to Formula (lb) wherein R', R2', R3', R4', Rs', R6', R7', and X1' are as defined herein; or a salt thereof including a pharmaceutically acceptable salt thereof. The compounds of the invention decrease MYC protein (c-MYC) in cells and/or inhibit p300/CBP histone acetyltransferase and can be useful in the treatment of cardiac hypertrophy, diabetes, obesity & nonalcoholic fatty liver disease, HIV, polycystic kidney disease, inflammatory diseases, ankylosing spondylitis, psoriasis, psoriatic arthritis, rheumatoid arthritis, Crohn's disease, multiple sclerosis, cancer and pre-cancerous syndromes, and diseases associated with dysregulation of Myc or inhibition of p300/CBP histone acetyltransferase. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention still further discloses methods of reducing MYC protein (c-MYC) in cells and inhibiting p300/CBP histone acetyltransferase activity, and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  本发明涉及取代的5-(1H-苯并[d]咪唑-2-基)-吡啶-2-胺和5-(3H-咪唑[4,5-b]吡啶-6-基)-吡啶-2-胺衍生物。具体而言，本发明涉及根据公式(lb)的化合物，其中R'、R2'、R3'、R4'、Rs'、R6'、R7'和X1'按本说明书中定义；或其盐，包括药用可接受的盐。本发明的化合物能够降低细胞中的MYC蛋白（c-MYC）和/或抑制p300/CBP组蛋白乙酰转移酶，可用于治疗心肌肥大、糖尿病、肥胖和非酒精性脂肪肝疾病、HIV、多囊肾疾病、炎症性疾病、强直性脊柱炎、银屑病、银屑病关节炎、类风湿性关节炎、克罗恩病、多发性硬化症、癌症和前癌症综合症，以及与Myc失调或p300/CBP组蛋白乙酰转移酶抑制相关的疾病。因此，本发明进一步涉及包含本发明化合物的药物组合物。本发明还进一步公开了使用本发明的化合物或包含本发明化合物的药物组合物，降低细胞中MYC蛋白（c-MYC）和抑制p300/CBP组蛋白乙酰转移酶活性的方法，以及治疗与之相关的疾病的方法。
• Synthesis and evaluation of analogues of the tuberculosis drug bedaquiline containing heterocyclic B-ring units
  作者：Peter J. Choi、Hamish S. Sutherland、Amy S.T. Tong、Adrian Blaser、Scott G. Franzblau、Christopher B. Cooper、Manisha U. Lotlikar、Anna M. Upton、Jerome Guillemont、Magali Motte、Laurence Queguiner、Koen Andries、Walter Van den Broeck、William A. Denny、Brian D. Palmer

  DOI：10.1016/j.bmcl.2017.10.042

  日期：2017.12

  bedaquiline where the phenyl B-unit was replaced with monocyclic heterocycles of widely differing lipophilicity (thiophenes, furans, pyridines) were synthesised and evaluated. While there was an expected broad positive correlation between lipophilicity and anti-TB activity, the 4-pyridyl derivatives appeared to have an additional contribution to antibacterial potency. The majority of the compounds were (desirably)

  合成并评估了苯达喹啉的类似物，其中苯B单元被亲脂性差异很大的单环杂环（噻吩，呋喃，吡啶）取代。虽然亲脂性和抗结核活性之间存在广泛的正相关关系，但4-吡啶基衍生物似乎对抗菌效力具有额外的贡献。与贝达喹啉相比，大多数化合物的极性更大（清除率更高），清除率更高，并显示出可接受的口服生物利用度，但其hERG耐受性的改善有限（且无法预测）。
• Synthesis and Structure−Activity Relationship of a New Series of COX-2 Selective Inhibitors:  1,5-Diarylimidazoles
  作者：Carmen Almansa、José Alfón、Alberto F. de Arriba、Fernando L. Cavalcanti、Ignasi Escamilla、Luis A. Gómez、Agustí Miralles、Robert Soliva、Javier Bartrolí、Elena Carceller、Manuel Merlos、Julián García-Rafanell

  DOI：10.1021/jm030765s

  日期：2003.7.1

  The synthesis and the pharmacological activity of a series of 1,5-diarylimidazoles developed as potent and selective cyclooxygenase-2 (COX-2) inhibitors are described. The new compounds were evaluated both in vitro (COX-1 and COX-2 inhibition in human whole blood) and in vivo (carrageenan-induced paw edema, air-pouch, and hyperalgesia tests). Modification of all the positions of two regioisomeric imidazole

  描述了开发为有效和选择性环氧合酶2（COX-2）抑制剂的一系列1,5-二芳基咪唑的合成和药理活性。在体外（在人全血中对COX-1和COX-2的抑制）和在体内（对角叉菜胶引起的爪水肿，气袋和痛觉过敏测试）均对新化合物进行了评估。修饰两个区域异构咪唑核的所有位置导致鉴定出最佳的4- [4-氯-5-（3-氟-4-甲氧基苯基）咪唑-1-基]苯磺酰胺（UR-8880，51f）候选者，目前正在进行I期临床试验。
• Cell-Based Drug Discovery: Identification and Optimization of Small Molecules that Reduce <i>c</i>-MYC Protein Levels in Cells
  作者：Jesús R. Medina、Xinrong Tian、William H. Li、Dominic Suarez、James F. Mack、Louis LaFrance、Cuthbert Martyr、James Brackley、Christina Di Marco、Ralph Rivero、Dirk A. Heerding、Charles McHugh、Elisabeth Minthorn、Aishwarya Bhaskar、Jacob Rubin、Michael Butticello、Christopher Carpenter、Eldridge N. Nartey、Thomas J. Berrodin、Lorena A. Kallal、Biju Mangatt

  DOI：10.1021/acs.jmedchem.1c01416

  日期：2021.11.11

  pharmacological inhibitors that directly target MYC have not yet yielded a drug-like molecule due to the lack of any known small molecule binding pocket in the protein, which could be exploited to disrupt MYC function. We have recently described a strategy to target MYC indirectly, where a screening effort designed to identify compounds that can rapidly decrease endogenous c-MYC protein levels in a MYC-amplified

  c -MYC癌基因的表达升高是人类癌症中最常见的异常之一。不幸的是，由于蛋白质中缺乏任何已知的小分子结合口袋，鉴定直接靶向 MYC 的药理学抑制剂的努力尚未产生类似药物的分子，这可以用来破坏 MYC 功能。我们最近描述了一种间接靶向 MYC 的策略，其中一项筛选工作旨在鉴定可以快速降低 MYC 扩增细胞系中内源性c -MYC蛋白水平的化合物，从而发现了一个化合物系列-通过 siRNA 敲低 MYC。在这里，我们描述了我们的药物化学计划，该计划导致发现了有效的、口服生物可利用的c -MYC 还原化合物。将重点介绍基于经验结构活性关系的最小药效团模型的开发以及用于调节药代动力学特性的基于特性的方法。
• Highly specific detection of Aβ oligomers in early Alzheimer's disease by a near-infrared fluorescent probe with a “V-shaped” spatial conformation
  作者：Jian Yang、Fantian Zeng、Xiaofang Li、Chongzhao Ran、Yungen Xu、Yuyan Li

  DOI：10.1039/c9cc08894f

  日期：——

  In this report, we demonstrate a "V-shaped" NIRF probe PTO-29, which can monitor Aβ oligomers with high selectivity. PTO-29 was designed and showed significant response to Aβ oligomers in the fluorescence spectral tests and good properties. In vivo imaging results indicate that 4 month APP/PS1 AD mice have higher signals in the brain than age-matched wild type mice.

  在本报告中，我们演示了“ V形” NIRF探针PTO-29，它可以以高选择性监测Aβ低聚物。PTO-29经过设计，在荧光光谱测试中显示出对Aβ低聚物的显着响应，并具有良好的性能。体内成像结果表明，与年龄匹配的野生型小鼠相比，4个月的APP / PS1 AD小鼠在大脑中具有更高的信号。