N-(3-溴苯基)-3-[(六氢-1H-氮杂卓-1-基)磺酰基]-苯甲酰胺 | 420831-40-9

• 物质功能分类: 化学试剂 - 有机试剂 - 酰胺
• 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: N-(3-溴苯基)-3-[(六氢-1H-氮杂卓-1-基)磺酰基]-苯甲酰胺
• 英文名称: 3-(1-azepanylsulfonyl)-N-(3-bromphenyl)benzamide
• 英文别名: AK-7；3-(azepane-1-sulfonyl)-N-(3-bromo-phenyl)-benzamide；3-(azepan-1-ylsulfonyl)-N-(3-bromophenyl)benzamide
• CAS: 420831-40-9
• 化学式: C₁₉H₂₁BrN₂O₃S
• mdl: MFCD03140195
• 分子量: 437.357
• InChiKey: IYAYHZZWYNXHEQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.469±0.06 g/cm3(Predicted)
• 溶解度：
  在DMSO中的溶解度≥15mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.315
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 危险标志：
  GHS07
• 危险性描述：
  H319
• 危险性防范说明：
  P305 + P351 + P338
• 储存条件：
  2-8℃

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : AK-7
CAS-No. : 420831-40-9
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]
Eye irritation (Category 2)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H319 Causes serious eye irritation.
Precautionary statement(s)
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)
R36 Irritating to eyes.
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
Synonyms : N-(3-Bromophenyl)-3-[(hexahydro-1H-azepin-1-yl)sulfonyl]-benzamide
Formula : C19H21BrN2O3S
Molecular Weight : 437,35 g/mol
Component Concentration
N-(3-Bromophenyl)-3-[(hexahydro-1H-azepin-1-yl)sulfonyl]-benzamide
CAS-No. 420831-40-9 -

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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), Sulphur oxides, Hydrogen bromide 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. 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.
Recommended storage temperature: 2 - 8 °C
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
impervious clothing, 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: 3,886
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
no data available
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
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause 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

生物活性

AK-7 是一种可透过细胞及血脑屏障的 SIRT2 抑制剂，IC50 值为 15.5 μM。

靶点

| SIRT2 | 15.5 μM (IC₅₀) |

体外研究

AK-7（10 μM）可降低未培养的 N2a 神经母细胞瘤细胞和野生型小鼠海马切片中的胆固醇水平。在纹状体亨廷顿病（HD）神经元中，AK-7（1 μM）表现出神经保护作用。此外，AK-7（12.5 μM）可减少原代中脑培养物中多巴胺神经元的比例。

体内研究

AK-7（每剂量 15 mg/kg 腹腔注射）在野生型和 HD 小鼠中的大脑渗透性良好。在 R6/2 HD 小鼠中，AK-7（10、20 mg/kg 腹腔注射）可改善行为和神经病理表型，并延长生存期。此外，AK-7（20 mg/kg）能够减轻 R6/2 小鼠的亨廷顿病神经病理学。AK-7 还可以减少 R6/2 大脑中的聚谷氨酰胺聚集。另外，接受 AK-7 治疗的 140CAG 小鼠表现出与未治疗野生型小鼠相似的运动表现变化，其中 20 mg/kg 剂量最为有效，并且显著不同于未治疗的 140CAG 小鼠。

反应信息

• 作为反应物：
  描述：

  N-(3-溴苯基)-3-[(六氢-1H-氮杂卓-1-基)磺酰基]-苯甲酰胺 、 3-甲氧基苯硼酸 在 nickel(II) chloride hexahydrate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三[3,4-双(三氟甲基)苯基]膦 作用下， 以 2-甲基四氢呋喃 、 甲醇 为溶剂， 反应 21.0h， 以55%的产率得到3-(azepan-1-ylsulfonyl)-N-(3'-methoxy-[1,1'-biphenyl]-3-yl)benzamide
  参考文献：
  名称：

  Advancing Base-Metal Catalysis: Development of a Screening Method for Nickel-Catalyzed Suzuki–Miyaura Reactions of Pharmaceutically Relevant Heterocycles

  摘要：

  DOI：

  10.1021/acs.oprd.1c00210
• 作为产物：
  描述：

  3-氯磺酰苯甲酰氯 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成 N-(3-溴苯基)-3-[(六氢-1H-氮杂卓-1-基)磺酰基]-苯甲酰胺
  参考文献：
  名称：

  化学合成和连续合成间氨基磺酰基苯甲酰胺类似物。

  摘要：

  为了合成以其生物活性而闻名的小分子氨磺酰基苯甲酰胺类似物，已从间氯磺酰基苯甲酰氯开始开发了一种化学选择性方法。尽管已经报道了分批进行化学选择的方法，但是连续流方法显示出在较高温度下且没有催化剂的情况下选择性的提高。在相似的条件下，总共合成了15种类似物，产率在65％至99％之间。这是间氨基磺酰基苯甲酰胺类似物的首次自动化和化学选择性合成。

  DOI：

  10.3762/bjoc.13.33

文献信息

• Benzamide Compounds and Related Methods of Use
  申请人：Northwestern University

  公开号：US20150025235A1

  公开（公告）日：2015-01-22

  Benzamide compounds and derivatives thereof, as can be used for selective inhibition of the SIRT2 enzyme and/or therapeutic use in the treatment of Huntington's disease.

  苯甲酰胺化合物及其衍生物可用于选择性抑制SIRT2酶和/或治疗亨廷顿病。
• Methods for production of functional beta cells
  申请人：Janssen Biotech, Inc.

  公开号：US10633635B2

  公开（公告）日：2020-04-28

  The invention provides for methods of differentiating pancreatic endocrine cells into pancreatic beta cells expressing PDX1, NKX6.1, MAFA, UCN3 and SLC2A. These pancreatic beta cells may be obtained by step-wise differentiation of pluripotent stem cells. The pancreatic beta cells exhibit glucose-dependent mitochondrial respiration and glucose-stimulated insulin secretion similar to islet cells.

  本发明提供了将胰腺内分泌细胞分化成表达PDX1、NKX6.1、MAFA、UCN3和SLC2A的胰腺β细胞的方法。这些胰腺β细胞可通过多能干细胞的逐步分化获得。胰岛β细胞表现出与胰岛细胞相似的葡萄糖依赖性线粒体呼吸和葡萄糖刺激的胰岛素分泌。
• Expansion and differentiation of inner ear supporting cells and methods of use thereof
  申请人：Massachusetts Eye and Ear Infirmary

  公开号：US11466252B2

  公开（公告）日：2022-10-11

  This disclosure relates to methods for expanding inner ear supporting cells (e.g., Lgr5+ inner ear supporting cells) and differentiating inner ear supporting cells (e.g., Lgr5+ inner ear supporting cells) to inner ear hair cells (e.g., atonal homolog 1 (Atoh1)+ inner ear hair cells) and the use of the inner hear supporting cells and hair cells, e.g., for identifying candidate therapeutic compounds for the treatment of hearing loss and balance loss. Additionally, the methods described herein can be used in the treatment of a subject having hearing loss and balance loss that would benefit from increased proliferation and differentiation of inner ear supporting cells (e.g., Lgr5+ inner ear supporting cells).

  本公开涉及扩增内耳支持细胞（如Lgr5+内耳支持细胞）和将内耳支持细胞（如Lgr5+内耳支持细胞）分化为内耳毛细胞（如阿托纳同源物1（Atoh1）+内耳毛细胞）的方法，以及内耳支持细胞和毛细胞的用途，如用于鉴定治疗听力损失和平衡损失的候选治疗化合物。此外，本文所述的方法还可用于治疗听力损失和平衡失调患者，这些患者将受益于内耳支持细胞（如Lgr5+内耳支持细胞）的增殖和分化。
• EXPANSION AND DIFFERENTIATION OF INNER EAR SUPPORTING CELLS AND METHODS OF USE THEREOF
  申请人：Massachusetts Eye & Ear Infirmary

  公开号：EP3407901B1

  公开（公告）日：2021-07-21
• Compositions and methods for modulating sirtuin activity
  申请人：Kazantsev Aleksey G.

  公开号：US20080021063A1

  公开（公告）日：2008-01-24

  The present invention is based, in part, on our discovery of compounds that inhibit an activity of a sirtuin (e.g., compounds that inhibit or preferentially inhibit an activity of SIRT2) and are therefore believed useful in the treatment or prevention of diseases associated with sirtuin activity. These diseases include, but are not limited to, neurological disorders such as Parkinson's Disease (PD).