5-甲基-4-苯基-2H-吡唑-3-胺 | 60419-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-甲基-4-苯基-2H-吡唑-3-胺
• 英文名称: 3-methyl-4-phenyl-1H-pyrazol-5-amine
• 英文别名: 5-amino-3-methyl-4-phenyl-1H-pyrazole；5-methyl-4-phenyl-1H-pyrazol-3-amine
• CAS: 60419-81-0
• 化学式: C₁₀H₁₁N₃
• mdl: MFCD00831955
• 分子量: 173.217
• InChiKey: UMDNRKCXSUJMCY-UHFFFAOYSA-N

物化性质

• 熔点：
  140-141°C
• 溶解度：
  18.4 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933199090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 5-Methyl-4-phenyl-2H-pyrazol-3-amine
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 5-Methyl-4-phenyl-2H-pyrazol-3-amine
CAS number: 60419-81-0

---

Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C10H11N3
Molecular weight: 173.2

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-甲基-4-苯基-2H-吡唑-3-胺 在 盐酸 、 sodium acetate 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 3.0h， 生成 2-hydroxy-8-methyl-7-phenyl-3,4-dihydro-pyrazolo[5,1-c]pyrimido[4,5-e][1,2,4]triazin-4-one
  参考文献：
  名称：

  杂环组分合成新型偶氮化合物和熔融吡唑并[5,1–c] [1,2,4]三嗪

  摘要：

  据报道，3-甲基-4-苯基-1 H-吡唑-5-胺1在盐酸中重氮化可提供相应的重氮盐2。后者与多种活性亚甲基化合物（巴比妥3a和硫代巴比妥3b酸，2-杂芳基嘧啶-4,6-二酮6a，6b，4-羟基-6-甲基吡啶2-2 （1 H）-1a 10a，4偶氮偶合-羟基-6-甲基-2- ħ -吡喃-2-酮10b中，4-羟基-1- p甲苯基- 1 H ^吡唑-3-羧酸乙酯14，1,3-噻唑烷-2,4-二酮16a，2-thioxo-1,3-thiazolidin-4-one 16b）生成新的吡唑基咪唑衍生物。稠合的吡唑并[5,1- c ^ ] [1,2,4]三嗪5，图9a，图9b，12，13是由heterocyclization反应获得。版权所有©2013 HeteroCorporation

  DOI：

  10.1002/jhet.1533
• 作为产物：
  描述：

  α-苯乙酰乙腈 在 盐酸肼 作用下， 以 乙醇 为溶剂， 生成 5-甲基-4-苯基-2H-吡唑-3-胺
  参考文献：
  名称：

  N-Acetyl-3-aminopyrazoles block the non-canonical NF-kB cascade by selectively inhibiting NIK

  摘要：

  由于击中导向优化，氨基吡唑3a是一种选择性超过44种激酶的NIK抑制剂。

  DOI：

  10.1039/c8md00068a
• 作为试剂：
  描述：

  α-苯乙酰乙腈 、 一水合肼 、 溶剂黄146 在 乙醚 、 5-甲基-4-苯基-2H-吡唑-3-胺 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以This resulted in 9.95 g (91%) of 3-methyl-4-phenyl-1H-pyrazol-5-amine as a yellow solid的产率得到5-甲基-4-苯基-2H-吡唑-3-胺
  参考文献：
  名称：

  HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

  摘要：

  本文介绍了新的杂环化合物和组合物，以及它们作为治疗疾病的药物的应用。还提供了抑制人类或动物主体中PAS激酶（PASK）活性的方法，用于治疗糖尿病等疾病。

  公开号：

  US20120277224A1

文献信息

• [EN] APELIN RECEPTOR AGONISTS AND METHODS OF USE THEREOF<br/>[FR] AGONISTES DU RÉCEPTEUR DE L'APELINE ET LEURS MÉTHODES D'UTILISATION
  申请人：SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INST

  公开号：WO2019032720A1

  公开（公告）日：2019-02-14

  Provided herein are agonists of the apelin receptor for the treatment of disease. The compounds disclosed herein are useful for the treatment of a range of cardiovascular, renal and metabolic conditions.

  本文提供了用于治疗疾病的阿普林受体激动剂。本文披露的化合物对于治疗一系列心血管、肾脏和代谢状况是有用的。
• [EN] SUBSTITUTED 5-AMINOPYRAZOLES AND USE THEREOF<br/>[FR] 5-AMINOPYRAZOLES SUBSTITUÉS ET LEUR UTILISATION
  申请人：BAYER SCHERING PHARMA AG

  公开号：WO2010020363A1

  公开（公告）日：2010-02-25

  The present application relates to novel substituted 5-aminopyrazoles, methods of production thereof, use thereof alone or in combinations for the treatment and/or prophylaxis of diseases and use thereof for the production of medicinal products for the treatment and/or prophylaxis of diseases.

  本申请涉及新型取代的5-氨基吡唑化合物，其生产方法，单独或组合使用于治疗和/或预防疾病，以及用于生产治疗和/或预防疾病的药物产品的用途。
• Inhibitors of IAP
  申请人：Cohen Frederick

  公开号：US20060014700A1

  公开（公告）日：2006-01-19

  The invention provides novel inhibitors of IAP that are useful as therapeutic agents for treating malignancies where the compounds have the general formula I: wherein X, Y, A, R 1 , R 2 , R 3 , R 4 , R 4 ′, R 5 , R 5 ′, R 6 and R 6 ′ are as described herein.

  这项发明提供了IAP的新型抑制剂，可作为治疗恶性肿瘤的治疗剂，其中化合物具有一般式I：其中X、Y、A、R1、R2、R3、R4、R4'、R5、R5'、R6和R6'如本文所述。
• Synthesis and biological evaluation of 7-(aminoalkyl)pyrazolo[1,5-a]pyrimidine derivatives as cathepsin K inhibitors
  作者：Nejc Petek、Bogdan Štefane、Marko Novinec、Jurij Svete

  DOI：10.1016/j.bioorg.2018.11.029

  日期：2019.3

  novel 7-aminoalkyl substituted pyrazolo[1,5-a]pyrimidine derivatives were synthesized and tested for inhibition of cathepsin K. The synthetic methodology comprises cyclization of 5-aminopyrazoles with N-Boc-α-amino acid-derived ynones followed by transformation of the ester and the Boc-amino functions. It allows for easy diversification of the pyrazolo[1,5-a]pyrimidine scaffold at various positions

  合成了一系列新颖的7-氨基烷基取代的吡唑并[1,5-a]嘧啶衍生物，并测试了其对组织蛋白酶K的抑制作用。合成方法包括用N-Boc-α-氨基酸衍生的炔酮环化5-氨基吡唑通过酯和Boc-氨基官能团的转化。它使得吡唑并[1，5-a]嘧啶支架易于在各种位置上多样化。还进行了与吡唑并[1,5-a]嘧啶衍生物的分子对接研究，以阐明组织蛋白酶K活性位点的结合模式。合成的化合物表现出中等的抑制活性（Ki≥77μM）。
• Design, synthesis and biological activity of pyrazolo[1,5-a]pyrimidin-7(4H)-ones as novel Kv7/KCNQ potassium channel activators
  作者：Jinlong Qi、Fan Zhang、Yi Mi、Yan Fu、Wen Xu、Diqun Zhang、Yibing Wu、Xiaona Du、Qingzhong Jia、Kewei Wang、Hailin Zhang

  DOI：10.1016/j.ejmech.2011.01.010

  日期：2011.3

  series of pyrazolo[1,5-a]pyrimidin-7(4H)-ones (PPOs) have been found to be novel activators (openers) of KCNQ2/3 potassium channels through high-throughput screening by using atomic absorption rubidium efflux assay. Based on structure–activity relationship (SAR), the substituted PPOs have been optimized. The 5-(2,6-dichloro-5-fluoropyridin-3-yl)-3-phenyl-2-(trifluoromethyl) pyrazolo[1,5-a]pyrimidin-7(4H)-one

  电压门控的Kv7 / KCNQ / M-钾通道在控制神经元兴奋性中起关键作用。突变导致KCNQ通道活性的遗传降低导致各种人类疾病，例如癫痫和心律不齐。因此，发现激活KCNQ通道的小分子是对膜兴奋性相关疾病进行临床干预的重要策略。在这项研究中，已发现一系列吡唑并[1,5-a]嘧啶-7（4H）-酮（PPO）是KCNQ2 / 3钾离子通道的新型活化剂（开启剂），通过使用原子能的高通量筛选吸收rub外排测定。基于结构-活性关系（SAR），对取代的PPO进行了优化。5-（2,6-二氯-5-氟吡啶-3-基）-3-苯基-2-（三氟甲基）吡唑并[1,5-a]嘧啶-7（4H）-one（17）通过膜片钳记录测定被鉴定为新颖，有效和选择性的KCNQ2 / 3钾通道开放剂。