苯并[H][1,6]萘啶-5-甲醛 | 69164-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 苯并[H][1,6]萘啶-5-甲醛
• 英文名称: benzo[h][1,6]naphthyridine-5-carbaldehyde
• 英文别名: benzo[h][1,6]naphthyridine-5-carbaldehyde；<1,6>Phenanthrolin-5-carbaldehyd
• CAS: 69164-27-8
• 化学式: C₁₃H₈N₂O
• mdl: MFCD03085770
• 分子量: 208.219
• InChiKey: PNCCXVYVMZWAQH-UHFFFAOYSA-N

物化性质

• 熔点：
  144 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

SDS

Name:	Benzo[h][1 6]naphthyridine-5-carbaldehyde Material Safety Data Sheet
Synonym:	None Known
CAS:	69164-27-8

Section 1 - Chemical Product MSDS Name:Benzo[h][1 6]naphthyridine-5-carbaldehyde Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
69164-27-8	Benzo[h][1,6]naphthyridine-5-carbaldeh	95+	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# 69164-27-8: 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: orange
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 143-144 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: C13H8N2O
Molecular Weight: 208.22

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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: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 69164-27-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Benzo[h][1,6]naphthyridine-5-carbaldehyde - 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# 69164-27-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 69164-27-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 69164-27-8 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：

  4,4-二甲基-3-氨基硫脲单水合物 、 苯并[H][1,6]萘啶-5-甲醛 以 异丙醇 为溶剂， 反应 0.42h， 以88%的产率得到2-(benzo[h][1,6]naphthyridin-5-ylmethylene)-N,N-dimethylhydrazinecarbothioamide
  参考文献：
  名称：

  A Series of α-Heterocyclic Carboxaldehyde Thiosemicarbazones Inhibit Topoisomerase IIα Catalytic Activity

  摘要：

  A series of novel thiosemicarbazone derivatives bearing condensed heterocyclic carboxaldehyde moieties were designed and synthesized. Among them, TSC24 exhibited broad antiproliferative activity in a panel of human tumor cells and suppressed tumor growth in mice. The mechanism research revealed that TSC24 was not only an iron chelator but also a topoisomerase II alpha catalytic inhibitor. Its inhibition on topoisomerase II alpha was due to direct interaction with the ATPase domain of topoisomerase I la which led to the block of ATP hydrolysis. Molecular docking predicted that TSC24 might bind at the ATP binding site, which was confirmed by the competitive inhibition assay. These results about the mechanisms involved in the anticancer activities of thiosemicarbazones will aid in the rational design of novel topoisomerase II-targeted drugs and will provide insights into the discovery and development of novel cancer therapeutics based on the dual activity to chelate iron and to inhibit the catalytic activity of topoisomerase II alpha.

  DOI：

  10.1021/jm9014394
• 作为产物：
  描述：

  5-methylbenzo[h]-1,6-naphthyridine 、 二氧化硒 、 1,4-二氧六环 以70%的产率得到
  参考文献：
  名称：

  TAKENCHI I.; OZAWA I.; OCAKI T.; HAMADA Y.; ITO T., YAKUGAKU DZASSI, YAKUGAKU ZASSNI, J. PHARM. SOS., JAR., 1978, 98, NO 9, 1+

  摘要：

  DOI：

文献信息

• Design, synthesis, and evaluation of fluorine and Naphthyridine–Based half-sandwich organoiridium/ruthenium complexes with bioimaging and anticancer activity
  作者：JuanJuan Li、Zhenzhen Tian、Xingxing Ge、Zhishan Xu、Yaqian Feng、Zhe Liu

  DOI：10.1016/j.ejmech.2018.12.021

  日期：2019.2

  addition, the self-luminescence of the complex 1C was also successfully used in confocal microscopy images for elucidating the subcellular localization. Complex 1C specifically targeted to lysosomes in A549 cancer cells and caused lysosomal damages and promote cathepsin B released. Flow cytometry studies confirmed that the biological effects of this type of complexes induced apoptosis, especially late

  合成了一系列基于氟和萘啶的半夹心铱（III）和钌（II）配合物。铱配合物具有优异的抗增殖性能，与顺铂相比有显着提高，尤其是最好的含氟原子的1C和含萘啶的2C。相反，钌配合物显示出少得多的抗增殖活性。确定了两个X射线晶体结构。可以通过调节金属中心和辅助配体灵活地改变复合物的细胞毒性。最好的复合1C选择进一步研究其作用机理。研究了化学反应性，例如水解，与核碱基的反应，谷胱甘肽和NADH向NAD +的催化转化。配合物1C可以与9-乙基鸟嘌呤（9-EtG）反应并催化NADH的氧化。此外，复合物1C的自发光也已成功用于共聚焦显微镜图像中，以阐明亚细胞定位。1C综合楼专门针对A549癌细胞中的溶酶体，引起溶酶体损伤并促进组织蛋白酶B的释放。流式细胞术研究证实，这种复合物的生物学效应诱导了细胞凋亡，尤其是晚期细胞凋亡。我们的结果表明，线粒体膜电位的变化与细胞凋亡有关。化学和生物学研究表明，这类金属配合物对于新型抗癌药物的设计值得进一步探索。
• GANGLIOSIDE GD2 AS A MARKER AND TARGET ON CANCER STEM CELLS
  申请人：Board of Regents , The University of Texas System

  公开号：US20150044233A1

  公开（公告）日：2015-02-12

  Methods for determining the presence of cancer stem cells by detecting GD2 expression. Also provided are methods for reducing proliferation of cancer stem cells by contacting the cells with a GD2 targeting agent, such as an anti-GD2 antibody or a GD3 synthase inhibitor. GD3 synthase inhibitor compounds are also provided.
• US9846160B2
  申请人：——

  公开号：US9846160B2

  公开（公告）日：2017-12-19
• [EN] GANGLIOSIDE GD2 AS A MARKER AND TARGET ON CANCER STEM CELLS<br/>[FR] GANGLIOSIDE GD2 EN TANT QUE MARQUEUR ET CIBLE SUR DES CELLULES SOUCHES CANCÉREUSES
  申请人：UNIV TEXAS

  公开号：WO2013130603A1

  公开（公告）日：2013-09-06

  Methods for determining the presence of cancer stem cells by detecting GD2 expression. Also provided are methods for reducing proliferation of cancer stem cells by contacting the cells with a GD2 targeting agent, such as an anti-GD2 antibody or a GD3 synthase inhibitor. GD3 synthase inhibitor compounds are also provided.
• A Series of α-Heterocyclic Carboxaldehyde Thiosemicarbazones Inhibit Topoisomerase IIα Catalytic Activity
  作者：He Huang、Qin Chen、Xin Ku、Linghua Meng、Liping Lin、Xiang Wang、Caihua Zhu、Yi Wang、Zhi Chen、Ming Li、Hualiang Jiang、Kaixian Chen、Jian Ding、Hong Liu

  DOI：10.1021/jm9014394

  日期：2010.4.22

  A series of novel thiosemicarbazone derivatives bearing condensed heterocyclic carboxaldehyde moieties were designed and synthesized. Among them, TSC24 exhibited broad antiproliferative activity in a panel of human tumor cells and suppressed tumor growth in mice. The mechanism research revealed that TSC24 was not only an iron chelator but also a topoisomerase II alpha catalytic inhibitor. Its inhibition on topoisomerase II alpha was due to direct interaction with the ATPase domain of topoisomerase I la which led to the block of ATP hydrolysis. Molecular docking predicted that TSC24 might bind at the ATP binding site, which was confirmed by the competitive inhibition assay. These results about the mechanisms involved in the anticancer activities of thiosemicarbazones will aid in the rational design of novel topoisomerase II-targeted drugs and will provide insights into the discovery and development of novel cancer therapeutics based on the dual activity to chelate iron and to inhibit the catalytic activity of topoisomerase II alpha.