4-氯-2-[(6-甲氧基-3-吡啶基)氨基]苯甲酸 | 6626-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氯-2-[(6-甲氧基-3-吡啶基)氨基]苯甲酸
• 中文别名: 5-(2-羧基-5-氯苯胺基)-2-甲氧基吡啶；N-(2-羧基-5-氯苯基)-6-甲氧基-3-吡啶胺；N-(2-羧基-5-氯苯基)-6-甲氧
• 英文名称: 4-chloro-2-((6-methoxypyridin-3-yl)amino)benzoic acid
• 英文别名: 4-Chloro-2-[(6-methoxypyridin-3-yl)amino]benzoic acid
• CAS: 6626-07-9
• 化学式: C₁₃H₁₁ClN₂O₃
• 分子量: 278.695
• InChiKey: UYMKSOUAEXWFOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  71.4
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933399090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 4-CHLORO-N-(6-METHOXY-3-
PYRIDYL)ANTHRANILIC ACID
CAS-No. : 6626-07-9
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Oral (Category 4)
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C13H11ClN2O3
Molecular Weight : 278,7 g/mol
Component Concentration
4-CHLORO-N-(6-METHOXY-3-PYRIDYL)ANTHRANILIC ACID
CAS-No. 6626-07-9 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 3,952
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
Specific target organ toxicity - single exposure
May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：咯萘啶的中间体。

反应信息

• 作为反应物：
  描述：

  4-氯-2-[(6-甲氧基-3-吡啶基)氨基]苯甲酸 在 磷酸 、 三氯氧磷 作用下， 以 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 37.0h， 生成 4-[(7-氯-2-甲氧基-1,5-二氢吡啶并[3,2-b]喹啉-10-基)亚氨]-2,6-二(吡咯烷-1-基甲基)环己-2,5-二烯-1-酮磷酸盐 (1:4)
  参考文献：
  名称：

  Improved Manufacturing Process for Pyronaridine Tetraphosphate

  摘要：

  四次磷酸吡咯烷酮（1）是一种著名的抗疟药物。然而，生产四磷酸吡咯烷酮需要经过精心优化的生产工艺。我们对其生产过程的每个步骤都进行了重新研究。在将 4-氯-2-(6-甲氧基吡啶-3-基氨基)-苯甲酸 6 环化为 7,10-二氯-2-甲氧基苯并[b]-1,5-萘啶 5 的过程中，开发了一种改进的工艺，以消除关键工艺杂质（BIA）。通过重新设计三磷酸盐的形成过程，提高了原料药等级的纯度。因此，我们开发出了一种稳健的生产工艺，其工艺性能可以接受，可以生产出高质量的四磷酸吡萘啶。

  DOI：

  10.5012/bkcs.2014.35.2.521
• 作为产物：
  描述：

  2,4-二氯苯甲酸 在 戊醇 、 potassium carbonate 、 copper(II) oxide 作用下， 生成 4-氯-2-[(6-甲氧基-3-吡啶基)氨基]苯甲酸
  参考文献：
  名称：

  Besly; Goldberg, Journal of the Chemical Society, <1954> 2448, 2452

  摘要：

  DOI：

文献信息

• [EN] ACRIDIN-9-YL-AMINE, QUINOLIN-9-YL-AMINE, 1 -AMINO-9H-THIOXANTHENE-9-ONE AND BENZO[B][1,5]NAPHTHYRI DIN-10-YL-AMINE DERIVATIVES AS AUTOPHAGY INHIBITORS FOR TREATING CANCER<br/>[FR] DÉRIVÉS D'ACRIDIN-9-YL-AMINE, DE QUINOLIN-9-YL-AMINE, DE 1 -AMINO-9H-THIOXANTHÈNE-9-ONE ET DE BENZO[B][1,5]NAPHTYRIDIN-10-YL-AMINE UTILSÉS COMME INHIBITEURS DE L'AUTOPHAGIE POUR LE TRAITEMENT DU CANCER
  申请人：REYOUNG CORP

  公开号：WO2021142065A1

  公开（公告）日：2021-07-15

  This disclosure provides a cridin-9-yl-amine, quinolin-9-yl-amine, 1- amino-9H-thioxanthene-9-one and benzo[b][l,5]naphthyridin-10- yl-amine derivatives and structurally related compounds for use as autophagy inhibitors for treating cancer. The present description discloses the synthesis and characterisation of exemplary compounds as well as pharmacological data thereof (e.g. pages 77 to 155; examples 1 to 22; compound A; compounds 1 to 21; tables 1 to 3).

  本公开提供了一种脱氧胸苷-9-基胺、喹啉-9-基胺、1-氨基-9H-噻吩并[1,5]苯并并[1,5]萘啉-10-基胺衍生物和结构相关化合物，用作治疗癌症的自噬抑制剂。本描述公开了示例化合物的合成和表征，以及其药理数据（例如第77页至155页；示例1至22；化合物A；化合物1至21；表1至3）。
• Design, synthesis and biological evaluation of novel phthalazinone acridine derivatives as dual PARP and Topo inhibitors for potential anticancer agents
  作者：Qiuzi Dai、Jiwei Chen、Chunmei Gao、Qinsheng Sun、Zigao Yuan、Yuyang Jiang

  DOI：10.1016/j.cclet.2019.06.019

  日期：2020.2

  Abstract In this study, we designed and synthesized a series of phthalazinone acridine derivatives as dual PARP and Topo inhibitors. MTT assays indicated that most of the compounds significantly inhibited multiple cancer cells proliferation. In addition, all the compounds displayed Topo II inhibition activity at 10 mol/L, and also possessed good PARP-1 inhibitory activities. Subsequent mechanistic

  摘要在本研究中，我们设计和合成了一系列的酞菁酮a啶衍生物作为PARP和Topo双重抑制剂。MTT分析表明，大多数化合物显着抑制多种癌细胞的增殖。此外，所有化合物在10 mol / L时均表现出Topo II抑制活性，并且还具有良好的PARP-1抑制活性。随后的机理研究表明，化合物9a在HCT116细胞中诱导了显着的细胞凋亡并引起了显着的S细胞周期停滞。我们的研究表明9a同时抑制Topo和PARP可能是潜在的癌症治疗先导化合物。
• Highly sensitive and selective “naked eye” sensing of Cu(II) by a novel acridine-based sensor both in aqueous solution and on the test kit
  作者：Qiuzi Dai、Chunmei Gao、Yijia Liu、Haiyang Liu、Boren Xiao、Chengken Chen、Jiwei Chen、Zigao Yuan、Yuyang Jiang

  DOI：10.1016/j.tet.2018.09.027

  日期：2018.11

  A highly selective and sensitive acridine-based colorimetric sensor 2-((7-chloro-2-methoxybenzo[b][1,5]naphthyridin-10-yl)amino)phenol (NAP) was developed for detection of Cu2+ ions both in aqueous solution and on test papers. Sensor NAP responses to Cu2+ ions by changing its color from yellow to pink, which could be easily observed by the naked eyes. Furthermore, the mechanism of the binding model

  开发了一种高选择性和灵敏的a啶基比色传感器2-（（7-氯-2-甲氧基苯并[b] [1,5]萘啶-10-基）氨基）苯酚（NAP），用于检测Cu 2+离子。无论是在水溶液中还是在试纸上。传感器NAP通过将其颜色从黄色更改为粉红色来对Cu 2+离子做出响应，这可以用肉眼轻易观察到。此外，通过1 H NMR，HRMS分析和DFT计算研究了NAP -Cu 2+络合物结合模型的机理。
• Novel Synthetic Azaacridine Analogues as Topoisomerase 1 Inhibitors
  作者：Xudong Luan、Chunmei Gao、Qinsheng Sun、Chunyan Tan、Hongxia Liu、Yibao Jin、Yuyang Jiang

  DOI：10.1246/cl.2011.728

  日期：2011.7.5

  Novel azaacridine analogues were synthesized and their antiproliferative activities against K562 and HepG-2 cell lines were evaluated, among which compound 5a was found to display good cytotoxicity. UV–visible spectral absorbance measurements showed that 5a can bind with calf thymus DNA (ct DNA). A relaxation assay indicated that 5a inhibits topoisomerase 1 activity.

  合成了新型氮杂吖啶类似物，并评估了它们对 K562 和 HepG-2 细胞系的抗增殖活性，发现其中化合物 5a 具有良好的细胞毒性。紫外可见光谱吸光度测量显示，5a 能与小牛胸腺 DNA（ct DNA）结合。弛豫试验表明，5a 能抑制拓扑异构酶 1 的活性。
• 一种制备咯萘啶的方法
  申请人：上海迪赛诺药业有限公司

  公开号：CN103373995B

  公开（公告）日：2016-04-27

  本发明涉及一种制备咯萘啶的方法，具体地，本发明公开了一种高纯度的咯萘啶的制备方法，包括步骤：在惰性溶剂中，将式II化合物与式III化合物的酸式盐反应，从而形成式I咯萘啶；其中，n为1～3。本发明所述方法具有合成路线短，反应条件温和，操作简单，产品收率高、纯度高、杂质1和杂质2的含量低，成本低等特点，适合工业化生产。