吖啶-4,9-二羧酸单水合物 | 27574-29-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 吖啶-4,9-二羧酸单水合物
• 英文名称: acridine-4,9-dicarboxylic acid
• 英文别名: 4,9-acridinedicarboxylic acid；4,9-Acridindicarbonsaeure
• CAS: 27574-29-4
• 化学式: C₁₅H₉NO₄
• 分子量: 267.241
• InChiKey: DOZKPGOIZJCCHC-UHFFFAOYSA-N

物化性质

• 沸点：
  611.0±25.0 °C(Predicted)
• 密度：
  1.518±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.5
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

SDS

Name:	Acridine-4 9-Dicarboxylic Acid Monohydrate Material Safety Data Sheet
Synonym:	None known
CAS:	27574-29-4

Section 1 - Chemical Product MSDS Name:Acridine-4 9-Dicarboxylic Acid Monohydrate Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
27574-29-4	Acridine-4, 9-Dicarboxylic Acid Monohy	ca 100	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: 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.
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 agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 27574-29-4: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: yellowish green powder
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 267 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C15H9NO4.H2O
Molecular Weight: 285.26

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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:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 27574-29-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Acridine-4, 9-Dicarboxylic Acid Monohydrate - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 37/39 Wear suitable gloves and eye/face
protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 27574-29-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 27574-29-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 27574-29-4 is not on the TSCA Inventory because it is a hydrate.
It is considered to be listed if the CAS number for the anhydrous form
is on the inventory (40CFR720.3(u)(2)).

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  吖啶-4,9-二羧酸单水合物 以 二乙二醇二甲醚 为溶剂， 反应 12.0h， 以69%的产率得到4-吖啶羧酸
  参考文献：
  名称：

  混合拓扑异构酶I / II抑制剂N- [2-（二甲基氨基）乙基]]啶-4-羧酰胺的a啶取代类似物的结构活性关系。

  摘要：

  混合拓扑异构酶I / II抑制剂N- [2-（二甲基氨基）乙基] ac啶-4-羧酰胺（DACA）目前正在临床试验中作为抗癌药物。使用新的合成路线来制备一系列of啶取代的类似物，以取代substituted啶-4-羧酸（将取代的二苯胺二酸单酸酯转化为相应的醛，然后用弱酸催化的闭环反应直接形成the啶）。在一组细胞系中评估类似物，所述细胞系包括人Jurkat白血病系的野生型（JLC）和突变体（JLA和JLD）形式。由于酶水平较低，后一种突变株对拓扑异构酶II靶向试剂具有抗性。结构活性研究表明，取代基的电子性质不会明显影响细胞毒性，但空间体积很重要，较大的群体会导致活动减少。这些化合物大致分为两类。大多数具有与DACA相似（或低于DACA自身）的细胞毒性，并且在所有Jurkat品系中均具有相同的毒性，这表明与拓扑异构酶II相比，对拓扑异构酶I的作用相对更大。大多数5-取代的衍生物和7-Ph化合物

  DOI：

  10.1021/jm970004n
• 作为产物：
  描述：

  isatin sodium salt 在 盐酸 、 copper(l) iodide 、 铜 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 生成 吖啶-4,9-二羧酸单水合物
  参考文献：
  名称：

  混合拓扑异构酶I / II抑制剂N- [2-（二甲基氨基）乙基]]啶-4-羧酰胺的a啶取代类似物的结构活性关系。

  摘要：

  混合拓扑异构酶I / II抑制剂N- [2-（二甲基氨基）乙基] ac啶-4-羧酰胺（DACA）目前正在临床试验中作为抗癌药物。使用新的合成路线来制备一系列of啶取代的类似物，以取代substituted啶-4-羧酸（将取代的二苯胺二酸单酸酯转化为相应的醛，然后用弱酸催化的闭环反应直接形成the啶）。在一组细胞系中评估类似物，所述细胞系包括人Jurkat白血病系的野生型（JLC）和突变体（JLA和JLD）形式。由于酶水平较低，后一种突变株对拓扑异构酶II靶向试剂具有抗性。结构活性研究表明，取代基的电子性质不会明显影响细胞毒性，但空间体积很重要，较大的群体会导致活动减少。这些化合物大致分为两类。大多数具有与DACA相似（或低于DACA自身）的细胞毒性，并且在所有Jurkat品系中均具有相同的毒性，这表明与拓扑异构酶II相比，对拓扑异构酶I的作用相对更大。大多数5-取代的衍生物和7-Ph化合物

  DOI：

  10.1021/jm970004n

文献信息

• SYNTHESIS OF ACRIDINE BASED THREADING INTERCALATORS
  作者：Sahar Badr、Mohamed M. El-Kerdawy、Farial A. Tanious、W. David Wilson、David W. Boykin

  DOI：10.1515/hc.2008.14.1-2.15

  日期：2008.1

  The multistep synthesis of two N,N -Bis[2[[4-[[iV-(dimethylamino)aIkyl]carbamoyl]thiazol-2yl]carbamoyl]ethyl]acridine-4,9-dicarboxamides as novel threading intercalators is reported. Preliminary studies show that the molecules exhibit moderately strong DNA affinity. Introduction DNA threading intercalators offer the potential for the development of sequence specific binding agents for a number of purposes

  报道了作为新型穿插剂的两个 N,N-双 [2[[4-[[V-(二甲氨基)烷基]氨基甲酰基]噻唑-2基]氨基甲酰基]乙基]吖啶-4,9-二甲酰胺的多步合成。初步研究表明，这些分子表现出中等强度的 DNA 亲和力。引言 DNA 穿线嵌入剂为开发用于治疗和诊断等多种用途的序列特异性结合剂提供了潜力。我们之前已经报道了基于具有两个阳离子侧链的萘并噻吩系统的平面芳香系统的合成，这些侧链被认为通过穿线嵌入模式与 DNA 结合。穿线嵌入剂是在平面芳环的相对侧具有两条侧链的分子，结合需要侧链之一滑过堆叠的碱基对，以实现碱基对和平面芳环之间的堆叠相互作用。由于它们能够选择性地与 DNA 2,3 和 RNA' 相互作用，已经研究了许多螺纹嵌入剂。已经描述了几种具有两个阳离子侧链的吖啶系统，它们通过穿线机制与 DNA 结合，包括具有治疗意义的 9-anilinoacridine-4-carboxamide 衍生化合物。”
• J. Med. Chem. 1997, 40, 1919-1929
  作者：

  DOI：——

  日期：——
• J. Med. Chem. 1987, 30, 664-669
  作者：

  DOI：——

  日期：——
• ACID-DYEABLE FIBRE
  申请人：DSM N.V.

  公开号：EP0904434B1

  公开（公告）日：2000-09-20
• US5939568A
  申请人：——

  公开号：US5939568A

  公开（公告）日：1999-08-17