2-哌嗪基-1,3-苯并恶唑 | 111628-39-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 哌嗪类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 2-哌嗪基-1,3-苯并恶唑
• 中文别名: 2-哌嗪-1-苯并噁唑
• 英文名称: 2-(1-piperazinyl)-1,3-benzoxazole
• 英文别名: 2-(piperazin-1-yl)benzo[d]oxazole；2-(piperazin-1-yl)-benzoxazole；2-(1-piperazinyl)-benzoxazole；2-piperazin-1-yl-1,3-benzoxazole；2-Piperazin-1-yl-benzooxazole
• CAS: 111628-39-8
• 化学式: C₁₁H₁₃N₃O
• mdl: MFCD04035522
• 分子量: 203.244
• InChiKey: HLKHIJZYKGDCJM-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70 °C
• 沸点：
  345.1±52.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  41.3
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  2-8°C

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2-Piperazin-1-Yl-1,3-Benzoxazole
: MNO000204
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 4), H302
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazard none
Statements
Other hazards
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 203,24 g/mol
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
2-Piperazin-1-Yl-1,3-Benzoxazole
Acute Tox. 4; H302 <= 100 %
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
2-Piperazin-1-Yl-1,3-Benzoxazole
Xn, R22 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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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
Flush eyes with water as a precaution.
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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting 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 vapours, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
For personal protection see section 8.
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.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Storage class (TRGS 510): Non Combustible Solids
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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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).
Control of environmental exposure
Do not let product enter drains.

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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- No data available
octanol/water
p) Auto-ignition 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
Stable under recommended storage conditions.
Possibility of hazardous reactions
No data available
Conditions to avoid
No data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
In the event of fire: see section 5

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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 sensitisation
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
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
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
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
No data available
Chemical Safety Assessment

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-哌嗪基-1,3-苯并恶唑 在 potassium fluoride on basic alumina 、 锌 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 6.33h， 生成 4-(5-(3-(4-(benzo[d]oxazol-2-yl)piperazin-1-yl)propylthio)-1,3,4-oxadiazol-2-yl)phenol
  参考文献：
  名称：

  Synthesis of piperazinyl benzothiazole/benzoxazole derivatives coupled with 1,3,4-oxadiazole-2-thiol: novel hybrid heterocycles as anticancer agents

  摘要：

  The synthesis of a series of substituted 2-(piperazin-1-yl)benzothiazole/benzoxazole coupled with 1,3,4-oxadiazole-2-thiol pharmacophore (8a-t) is described using a three carbon spacer (Jones and Helm, Drugs 69:1903-1910, 2009). The structures of the compounds were confirmed by NMR and mass spectral data. All the synthesized compounds have been evaluated for their cytotoxicity towards five human cancer cell lines of different origins, viz. MCF-7 (Breast), HeLa (Cervical), HepG(2) (Liver), A431 (Skin) and A549 (Lung), and IC50 values were determined. Among the compounds tested, 8j and 8t displayed maximum cytotoxic activity. A431 was the most sensitive cell line against the compounds studied, followed by MCF7, A549, HepG(2) and HeLa.

  DOI：

  10.1007/s00044-013-0510-y
• 作为产物：
  描述：

  2-氯苯并恶唑 在 盐酸 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 12.0h， 生成 2-哌嗪基-1,3-苯并恶唑
  参考文献：
  名称：

  WO2023/283608

  摘要：

  公开号：
• 作为试剂：
  描述：

  哌嗪 、 三乙胺 、 2-氯苯并恶唑 、 水 在 ice 、 二氯甲烷 、 碳酸氢钠 、 Brine 、 magnesium sulfate 、 silica gel 、 甲醇 、 2-哌嗪基-1,3-苯并恶唑 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以to obtain the title compound 2-(1-piperazinyl)benzoxazole (4.751 g) in the form of yellow crystalline powder的产率得到2-哌嗪基-1,3-苯并恶唑
  参考文献：
  名称：

  Serotonin 5-HT3 receptor partial activator

  摘要：

  该发明提供了一种5-HT3受体部分激动剂，具有5-HT3受体激活作用，除了5-HT3受体拮抗作用外，不会引起便秘等副作用。特别地，基于新合成的苯并噁唑衍生物的发现，该衍生物以以下公式（2）的化合物为代表，具有强烈的5-HT3受体拮抗作用和5-HT3受体激活作用，该发明提供这些苯并噁唑衍生物作为5-HT3受体部分激动剂。在上述公式中，R1至R4可以相同或不同，每个代表氢原子、卤素原子、取代或未取代的低级烷基、取代或未取代的低级烯基或取代或未取代的氨基，或R1和R2的两个基团可以连接在一起形成环结构，即苯环；R5代表氢原子、取代或未取代的低级烷基或取代或未取代的低级烯基；m是1到4的整数。

  公开号：

  US20030013730A1

文献信息

• 2-Benzazolyl-4-Piperazin-1-Ylsulfonylbenzenecarbohydroxamic Acids as Novel Selective Histone Deacetylase-6 Inhibitors with Antiproliferative Activity
  作者：Lei Wang、Marina Kofler、Gerald Brosch、Jelena Melesina、Wolfgang Sippl、Elisabeth D. Martinez、Johnny Easmon

  DOI：10.1371/journal.pone.0134556

  日期：——

  e ring was replaced by the isosteric heterocycles benzimidazole, benzoxazole, and benzothiazole and the position of the hydroxamic acid substituent on the phenyl ring was varied. Whereas compounds bearing a para substituted hydroxamic acid (9a-d) were active HDAC inhibitors, the meta substituted analogues (8a-d) were appreciably inactive. Compounds 9a-d selectively inhibited HDAC6 (IC50 = 0.1-1.0 μM)

  我们已经在建立的基于细胞的测定法中筛选了我们的化合物集合，该测定法测量表观遗传沉默的转基因的去阻抑，即基因座去阻抑测定。该筛选导致鉴定出4- [4-（1-（甲基苯并咪唑-2-基）哌嗪-1-基]磺酰基苯碳氧肟酸（9b）作为抑制HDAC1的活性物质。在初始结构活性关系研究中，1-甲基苯并咪唑环被等位杂环苯并咪唑，苯并恶唑和苯并噻唑取代，并且异羟肟酸取代基在苯环上的位置也有所变化。带有对位取代的异羟肟酸（9a-d）的化合物是活性HDAC抑制剂，而间位取代的类似物（8a-d）则无活性。与HDAC1（IC50 = 0）相比，化合物9a-d选择性抑制HDAC6（IC50 = 0.1-1.0μM）。而且，与患者匹配的正常细胞相比，也有选择性地抑制了肺癌细胞（9-6μM）的生长。与对照组相比，该化合物在S期诱导细胞周期停滞，而细胞凋亡的诱导则可忽略。分子模型研究发现，9a-d与HDAC6相互作用的MM-G
• Pd-Catalyzed Synthesis of Piperazine Scaffolds Under Aerobic and Solvent-Free Conditions
  作者：Sean W. Reilly、Robert H. Mach

  DOI：10.1021/acs.orglett.6b02591

  日期：2016.10.21

  A facile Pd-catalyzed methodology providing an efficient synthetic route to biologically relevant arylpiperazines under aerobic conditions is reported. Electron donating and sterically hindered aryl chlorides were aminated to afford yields up to 97%, with examples using piperazine as solvent, illustrating an ecofriendly, cost-effective synthesis of these privileged structures.

  据报道，一种简便的钯催化方法为有氧条件下生物相关的芳基哌嗪提供了有效的合成路线。给电子和位阻芳基氯化物被胺化，产率高达 97%，其中使用哌嗪作为溶剂的例子，说明了这些特殊结构的生态友好、经济有效的合成。
• REMEDIES OR PREVENTIVES FOR AIDS
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0878194A1

  公开（公告）日：1998-11-18

  The present invention is to provide the combined use of one kind or two or more kinds of a quinolone carboxylic acid having anti-HIV activity and one kind or two or more kinds of a reverse transcriptase inhibitor or HIV protease inhibitor, and an AIDS therapeutic agent or preventive agent containing as its active ingredients one kind or two or more kinds of a quinolone carboxylic acid having anti-HIV activity and one kind or two or more kinds of a reverse transcriptase inhibitor or HIV protease inhibitor.

  本发明提供了一种或两种或两种以上具有抗HIV活性的喹诺酮羧酸与一种或两种或两种以上的逆转录酶抑制剂或HIV蛋白酶抑制剂的联合使用，以及一种包含作为其活性成分的抗HIV活性的喹诺酮羧酸和一种或两种或两种以上的逆转录酶抑制剂或HIV蛋白酶抑制剂的艾滋病治疗剂或预防剂。
• [EN] PIPERIDINE OR PIPERAZINE LINKED IMIDAZOLE AND TRIAZOLE DERIVATIVES AND METHODS OF USE THEREOF FOR IMPROVING THE PHARMACOKINETICS OF A DRUG<br/>[FR] DÉRIVÉS D'IMIDAZOLE ET DE TRIAZOLE LIÉS À LA PIPÉRIDINE OU LA PIPÉRAZINE ET LEURS PROCÉDÉS D'UTILISATION POUR AMÉLIORER LA PHARMACOCINÉTIQUE D'UN MÉDICAMENT
  申请人：MERCK SHARP & DOHME

  公开号：WO2015070367A1

  公开（公告）日：2015-05-21

  The piperidine or piperazine linked imidazole and triazole derivatives, compositions comprising said compounds, alone or in combination with other drugs, and methods of using the compounds for improving the pharmacokinetics of a drug are provided. The compounds of the invention are useful in human and veterinary medicine for inhibiting CYP3A4 and for improving the pharmacokinetics of a therapeutic compound that is metabolized by CYP3A4.

  提供了与哌啶或哌嗪连接的咪唑和三唑衍生物，包括所述化合物的组合物，单独或与其他药物结合使用的方法，以及用于改善药物的药代动力学的化合物的方法。该发明的化合物在人类和兽医学中用于抑制CYP3A4并改善由CYP3A4代谢的治疗化合物的药代动力学。
• Design, Synthesis and Antiviral Activity of 2-(3-Amino-4-piperazinylphenyl)chromone Derivatives
  作者：Mi Kyoung Kim、Hyunjun Yoon、Dale Lynn Barnard、Youhoon Chong

  DOI：10.1248/cpb.c12-01050

  日期：——

  to the chromone scaffold and evaluated the antiviral activities of the resulting chromone derivatives. The synthesized 2-(3-amino-4-piperazinylphenyl)-chromones showed severe acute respiratory syndrome-corona virus (SARS-CoV)-specific antiviral activity. In particular, the 2-pyridinylpiperazinylphenyl substituents provided the resulting chromone derivatives with selective antiviral activity. Taken

  以前，我们已经确认色酮衍生物的抗病毒活性受色酮核心结构上取代基的类型和位置控制。在我们不断努力优化色酮衍生物的抗病毒活性的过程中，我们一直在尝试通过引入各种取代基来衍生色酮支架。在此概念验证研究中，我们将3-氨基-4-哌嗪基苯基官能团引入色酮支架，并评估了所得色酮衍生物的抗病毒活性。合成的2-（3-氨基-4-哌嗪基苯基）色酮显示出严重的急性呼吸综合征-冠状病毒（SARS-CoV）特异性抗病毒活性。特别是，2-吡啶基哌嗪基苯基取代基为所得色酮衍生物提供了选择性的抗病毒活性。两者合计，这个结果表明2-吡啶基哌嗪功能连接到色酮支架上可能的药理作用，这值得进一步深入的结构-活性关系研究。