3-苯基吡唑-5-羧酸水合物 | 5071-61-4

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-苯基吡唑-5-羧酸水合物
• 中文别名: 5-苯基-1H-吡唑-3-羧酸；3-苯基-1H-吡唑-5-羧酸
• 英文名称: 5-phenyl-1H-pyrazole-3-carboxylic acid
• 英文别名: 5-phenyl-1H-pyrazol-1-ium-3-carboxylate
• CAS: 5071-61-4
• 化学式: C₁₀H₈N₂O₂
• mdl: MFCD05170017
• 分子量: 188.186
• InChiKey: QBPUOAJBMXXBNU-UHFFFAOYSA-N

物化性质

• 熔点：
  238-242 °C (dec.)(lit.)
• 沸点：
  496.5±33.0 °C(Predicted)
• 密度：
  1.355±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存于室温下，密封保存，并保持环境干燥。

SDS

3-Phenylpyrazole-5-carboxylic Acid Hydrate Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 3-Phenylpyrazole-5-carboxylic Acid Hydrate

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
Not classified
HEALTH HAZARDS
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols None
No signal word
Signal word
Hazard statements None
None
Precautionary statements:

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 3-Phenylpyrazole-5-carboxylic Acid Hydrate
Percent: >97.0%(LC)(T)
CAS Number: 5071-61-4
Chemical Formula: C10H8N2O2·xH2O

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.

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Section 5. FIRE-FIGHTING MEASURES
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: Crystal- Powder
Colour: White - Slightly pale yellow
Odour: No data available
pH: No data available
Melting point/freezing point:233°C (dec.)
No data available
Boiling point/range:
Flash point: No data available
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
No data available
Relative density:
Solubility(ies):
No data available
[Water]
[Other solvents] No data available
2.06
Log Pow:

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx)
products:

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Section 11. TOXICOLOGICAL INFORMATION
ipr-mus LDLo:1 g/kg
Acute Toxicity:
Skin corrosion/irritation: No data available
No data available
Serious eye
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
No data available
Reproductive toxicity:
RTECS Number: UQ6437000

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
2.06
Log Pow:
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Does not correspond to the classification standard of the United Nations
Hazards Class:
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-苯基吡唑-5-羧酸水合物 在 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N-(3-aminopropyl)-5-phenyl-1H-pyrzole-3-carboxamide hydrochloride
  参考文献：
  名称：

  ISOXAZOLE ANALOGS AS MEDIATORS OF TRANSCRIPTIONAL INDUCTION OF E-CADHERIN

  摘要：

  在一个方面，该发明涉及N-((芳基氨基)烷基)-5-芳基异噁唑-3-羧酰胺类似物，其衍生物和相关化合物，这些化合物可用作E-钙粘蛋白的转录诱导介质；制备这些化合物的合成方法；包含这些化合物的药物组合物；以及使用这些化合物和组合物治疗与E-钙粘蛋白活性相关的疾病的方法。本摘要旨在作为在特定领域搜索的扫描工具，并不意味着对本发明的限制。

  公开号：

  US20160052896A1
• 作为产物：
  描述：

  2,4-二氧代-4-苯基-丁酸 在 sodium hydroxide 、 硫酸肼 作用下， 生成 3-苯基吡唑-5-羧酸水合物
  参考文献：
  名称：

  Knorr, Justus Liebigs Annalen der Chemie, 1894, vol. 279, p. 253 Anm. 3

  摘要：

  DOI：
• 作为试剂：
  描述：

  (R)-tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate 、 5-(4-氯苯基)-1H-吡唑-3-羧酸 在 (S)-tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate 、 5-(4-氯苯基)-1H-吡唑-3-羧酸 、 3-苯基吡唑-5-羧酸水合物 作用下， 生成 (R)-3-(4-chlorophenyl)-N-(4-(morpholin-2-yl)phenyl)-1H-pyrazole-5-carboxamide hydrochloride
  参考文献：
  名称：

  PYRAZOLE DERIVATIVES

  摘要：

  本发明涉及式IA和式IB的化合物，其中R1、R2、R3、R4和Z如本文所定义，或其药学上适宜的酸加盐。式IA和式IB的化合物对微量胺相关受体（TAARs）具有良好的亲和力，特别是对TAAR1。这些化合物可用于治疗抑郁症、焦虑症、双相情感障碍、注意力缺陷多动障碍（ADHD）、应激相关障碍、精神疾病如精神分裂症、神经疾病如帕金森病、神经退行性疾病如阿尔茨海默病、癫痫、偏头痛、高血压、物质滥用和代谢性疾病如进食障碍、糖尿病、糖尿病并发症、肥胖症、脂质代谢异常、能量消耗和吸收障碍、体温稳态障碍和功能障碍、睡眠和昼夜节律障碍，以及心血管疾病。

  公开号：

  US20120316172A1

文献信息

• [EN] 3-PHOSPHOGLYCERATE DEHYDROGENASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE LA 3-PHOSPHOGLYCÉRATE DÉSHYDROGÉNASE) ET LEURS UTILISATIONS
  申请人：RAZE THERAPEUTICS INC

  公开号：WO2016040449A1

  公开（公告）日：2016-03-17

  The present invention provides compounds, compositions and methods useful for treating a variety of diseases, disorders or conditions, associated with PHGDH.

  本发明提供了一种用于治疗与PHGDH相关的各种疾病、疾病或病况的化合物、组合物和方法。
• Synthesis and anticancer activity of heteroaromatic linked 4β-amido podophyllotoxins as apoptotic inducing agents
  作者：Ahmed Kamal、Jaki R. Tamboli、M.V.P.S. Vishnuvardhan、S.F. Adil、V. Lakshma Nayak、S. Ramakrishna

  DOI：10.1016/j.bmcl.2012.10.099

  日期：2013.1

  17a–i and 18a–d) were synthesized and evaluated for anticancer activity against five human cancer cell lines. Among the series, one of the compound 17g showed significant antiproliferative activity in A549 (lung cancer) cell line. Flow cytometric analysis showed that 17g arrested the cell cycle in the G2/M phase leading to caspase-3 dependent apoptotic cell death. Further, Hoechst 33258 staining and DNA

  合成了一系列不同的杂芳族连接的4β-酰胺基鬼臼毒素偶联物（16a – i，17a – i和18a – d），并评估了其对五种人类癌细胞系的抗癌活性。在该系列中，一种化合物17g在A549（肺癌）细胞系中显示出显着的抗增殖活性。流式细胞仪分析表明，17g细胞在G2 / M期停滞，导致caspase-3依赖性凋亡细胞死亡。此外，Hoechst 33258染色和DNA片段化分析还表明17g通过凋亡诱导细胞死亡。
• [EN] PYRAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS DE PYRAZOLE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2012168260A1

  公开（公告）日：2012-12-13

  The invention relates to compounds of formula wherein R1 is hydrogen or phenyl, optionally substitutes by halogen, CN or lower alkoxy or lower alkoxy substituted by halogen; R2 is hydrogen or lower alkyl; R3 is hydrogen or lower alkyl or is phenyl optionally substituted by one or more substituents, selected from halogen, cyano or lower alkoxy substituted by halogen, or is pyridinyl, optionally substituted by halogen or lower alkyl substituted by halogen, or is pyrimidinyl, optionally substituted by lower alkyl substituted by halogen, or is pyrazinyl, optionally substituted by halogen, cyano or lower alkyl substituted by halogen; R4 is hydrogen, lower alkyl or phenyl; Z is a bond, -CH2- or -O-; or to a pharmaceutically suitable acid addition salt thereof. It has now been found that the compounds of formulas IA and IB have a good affinity to the trace amine associated receptors (TAARs), especially for TAAR1. The compounds may be used for the treatment of depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  该发明涉及以下式中的化合物，其中R1是氢或苯基，可选择由卤素、CN或较低的烷氧基或由卤素取代的较低的烷氧基取代；R2是氢或较低的烷基；R3是氢或较低的烷基或是苯基，可选择由卤素、氰基或由卤素取代的较低的烷氧基取代，或是吡啶基，可选择由卤素或由卤素取代的较低的烷基取代，或是嘧啶基，可选择由较低的烷基取代的较低的烷基取代，或是吡嗪基，可选择由卤素、氰基或由卤素取代的较低的烷基取代；R4是氢、较低的烷基或苯基；Z是键，-CH2-或-O-；或其药学上适宜的酸盐。现已发现，IA和IB式的化合物对痕量胺相关受体（TAARs）具有良好的亲和力，特别是对TAAR1。这些化合物可用于治疗抑郁症、焦虑症、躁郁症、注意力缺陷多动障碍（ADHD）、与压力有关的疾病、如精神分裂症等精神疾病、帕金森病等神经系统疾病、阿尔茨海默病等神经退行性疾病、癫痫、偏头痛、高血压、物质滥用和代谢性疾病，如进食障碍、糖尿病、糖尿病并发症、肥胖症、血脂异常、能量消耗和吸收障碍、体温稳态障碍、睡眠和昼夜节律障碍以及心血管疾病。
• Fragment-Based Lead Generation of 5-Phenyl-1H-pyrazole-3-carboxamide Derivatives as Leads for Potent Factor Xia Inhibitors
  作者：Qunchao Wei、Zhichao Zheng、Shijun Zhang、Xuemin Zheng、Fancui Meng、Jing Yuan、Yongnan Xu、Changjiang Huang

  DOI：10.3390/molecules23082002

  日期：——

  FXIa is suggested as a major target for anticoagulant drug discovery because of reduced risk of bleeding. In this paper, we defined 5-phenyl-1H-pyrazole-3-carboxylic acid derivatives as privileged fragments for FXIa inhibitors’ lead discovery. After replacing the (E)-3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acrylamide moiety in compound 3 with 5-(3-chlorophenyl)-1H-pyrazole-3-carboxamide, we traveled from FXIa inhibitor3 to a scaffold that fused the privileged fragments into a pharmacophore for FXIa inhibitors. Subsequently, we synthesized and assessed the FXIa inhibitory potency of a series of 5-phenyl-1H-pyrazole-3-carboxamide derivatives with different P1, P1′ and P2′moiety. Finally, the SAR of them was systematically investigated to afford the lead compound 7za (FXIa Ki = 90.37 nM, 1.5× aPTT in rabbit plasma = 43.33μM) which exhibited good in vitro inhibitory potency against FXIa and excellent in vitro coagulation activities. Furthermore, the binding mode of 7za with FXIa was studied and the results suggest that the 2-methylcyclopropanecarboxamide group of 7za makes 2 direct hydrogen bonds with Tyr58B and Thr35 in the FXIa backbone, making 7za binds to FXIa in a highly efficient manner.

  FXIa被认为是抗凝药物发现的主要靶点，因为减少了出血风险。在这篇论文中，我们将5-苯基-1H-吡唑-3-羧酸衍生物定义为FXIa抑制剂的引物片段，用于引物发现。在将化合物3中的(E)-3-(5-氯-2-(1H-四唑-1-基)苯基)丙烯酰胺基团替换为5-(3-氯苯基)-1H-吡唑-3-羧酰胺后，我们从FXIa抑制剂3转变为将引物片段融合成FXIa抑制剂的药效团的支架。随后，我们合成并评估了一系列具有不同P1、P1'和P2'基团的5-苯基-1H-吡唑-3-羧酰胺衍生物的FXIa抑制活性。最后，对它们的结构活性关系进行了系统研究，得到了引物化合物7za（FXIa Ki = 90.37 nM，在兔血浆中1.5× aPTT = 43.33μM），该化合物表现出良好的体外抑制FXIa活性和优秀的体外凝血活性。此外，研究了7za与FXIa的结合方式，结果表明7za的2-甲基环丙烷甲酰胺基团与FXIa骨架中的Tyr58B和Thr35直接形成两个氢键，使7za以高效的方式结合到FXIa上。
• NOVEL PIPERAZINE DERIVATIVES AS INHIBITORS OF STEAROYL-CoA DESATURASE
  申请人：Bischoff Alexander

  公开号：US20100160323A1

  公开（公告）日：2010-06-24

  The present invention relates to piperazine derivatives that act as inhibitors of stearoyl-CoA desaturase. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.

  本发明涉及作为硬脂酰辅酶A去饱和酶抑制剂的哌嗪衍生物。该发明还涉及制备这些化合物的方法、含有这些化合物的组合物，以及使用这些化合物进行治疗的方法。

表征谱图