5-氨基-1-(4-溴苯基)-3-甲基-1H-吡唑-4-甲腈 | 76982-35-9

• 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-氨基-1-(4-溴苯基)-3-甲基-1H-吡唑-4-甲腈
• 英文名称: 5-amino-1-(4-bromophenyl)-3-methyl-1H-pyrazole-4-carbonitrile
• 英文别名: 5-amino-1-(4-bromophenyl)-3-methylpyrazole-4-carbonitrile
• CAS: 76982-35-9
• 化学式: C₁₁H₉BrN₄
• 分子量: 277.123
• InChiKey: XNXAHPLZAJJVMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933199090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Amino-1-(4-bromophenyl)-4-cyano-3-methyl-1H-pyrazole
Synonyms: 5-Amino-1-(4-bromophenyl)-3-methyl-1H-pyrazole-4-carbonitrile

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

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Section 3. Composition/information on ingredients.
Ingredient name: 5-Amino-1-(4-bromophenyl)-4-cyano-3-methyl-1H-pyrazole
CAS number: 76982-35-9

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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.

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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.

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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.

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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:

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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.

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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: C11H9BrN4
Molecular weight: 277.1

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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, hydrogen bromide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-氨基-1-(4-溴苯基)-3-甲基-1H-吡唑-4-甲腈 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 乙醇 、 叔丁醇 为溶剂， 生成 1‐[(1,1′‐biphenyl)‐4‐yl]‐3‐methyl‐6‐phenyl‐1H‐pyrazolo[3,4‐d]pyrimidin‐4‐amine
  参考文献：
  名称：

  新型吡唑并[3,4-d]嘧啶衍生物通过产生ROS抑制人癌细胞增殖并诱导细胞凋亡

  摘要：

  缺乏成功治疗的有效抗癌药物是一个主要问题，这表明对新型治疗化合物的强烈需求。在探索新分子的过程中，本研究旨在探索吡唑并[3,4-d]嘧啶衍生物作为抗增殖剂的潜力。选定化合物的体外抗癌筛选是由美国国家癌症研究所的发育治疗计划针对 60 种癌细胞系进行的。先导化合物 PP-31d 显着抑制癌细胞的生长，如 NCI-H460（非小细胞肺癌）、OVCAR-4（卵巢癌）、786-0（肾癌）、A549（非小细胞肺癌）细胞肺癌）和 ACHN（肾癌），显示出强大的抗癌潜力，以及其他衍生物。PP-31d 对 NCI-H460 细胞的动力学研究揭示了剂量依赖性效应，IC50 为 2 µM。PP-31d 的抑制作用归因于活性氧的产生和随后的细胞凋亡诱导，如亚二倍体（subG1）群体、早期凋亡细胞群体和 caspase-3/7 活性的增加所证明的、线粒体膜电位的丧失和核 DNA 的降解。总的来说，我们的结果表明，吡唑并[3

  DOI：

  10.1002/ardp.201900296
• 作为产物：
  描述：

  (1-乙氧基乙亚基)丙二腈 、 4-溴苯肼盐酸盐 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 5-氨基-1-(4-溴苯基)-3-甲基-1H-吡唑-4-甲腈
  参考文献：
  名称：

  Pyrazolyl-Tetrazoles and Imidazolyl-Pyrazoles as Potential Anticoagulants and their Integrated Multiplex Analysis Virtual Screening

  摘要：

  本文报道了一种新颖的虚拟筛选算法，旨在合理识别新型抗凝血药物先导物。从联胺盐酸盐出发，通过三步合成路线分别以50-72%和50-85%的优良收率获得了7种5-(3-甲基-1-芳基-1H-吡咯并[1,2-b]咪唑-4-基)-1H-四氮唑和7种新型1-芳基-4-(4,5-二氢-1H-咪唑-2-基)-3-甲基-1H-吡咯并[1,2-b]咪唑。所有化合物均提交给一个基于靶点的体外虚拟筛选管道(综合多梯度分析虚拟筛选(IMA-VS))，其中包括对(i)其物理化学性质与靶点酶化学环境的契合性；(ii)靶点酶活性位点的静电势；(iii)通过分子对接对靶点活性位点的结构契合性；以及(iv)整体吸收、分布、代谢、排泄和毒性(ADMET)轮廓的评估。IMA-VS在虚拟筛选出潜在抗凝血药物候选物后,所有分子均被合成,并在体外进行了抗凝活性和溶血活性评价。由IMA-VS指向的最有望候选物1-(3',4'-二氯苯基)-4-(4,5-二氢-1H-咪唑-2-基)-3-甲基吡咯并[1,2-b]咪唑表现出体外对因子Xa(FXa)的特异性抑制活性，作用为一种非竞争性抑制剂，其抑制常数(Ki)为61.16 ± 12.96 µM，同时具有系列中最低的溶血活性。进一步的实验揭示了该化合物在由FeCl3诱导的动脉血栓形成的小鼠模型中的抗血栓活性。

  DOI：

  10.21577/0103-5053.20180150

文献信息

• Synthesis and properties of sildenafil isostere
  作者：Ziqi Su、Qi Zhang、Qieqiang Zhao、Wenyi Liu、Tao Zhao、Huiping Wang、Jiarong Li、Juan Xu

  DOI：10.1002/ardp.202100145

  日期：2021.10

  series of novel pyrazolo[3,4-d]pyrimidin-4-one derivatives were synthesized and evaluated for their anti-phosphodiesterase-5 (PDE-5) activity. A total of 28 compounds, containing alkyl and aryl groups at the 1-N and 3-C positions on the pyrazole ring, and also bearing different alkyl substituents on the piperazine ring were synthesized. Four compounds (4d, 5d, 6d, and 5o) were found to have better

  合成了一系列新型吡唑并[3,4- d ]嘧啶-4-酮衍生物，并评估了它们的抗磷酸二酯酶5 (PDE-5) 活性。共合成了 28 种化合物，它们在吡唑环的 1-N 和 3-C 位含有烷基和芳基，在哌嗪环上也带有不同的烷基取代基。发现四种化合物（4d、5d、6d和5o）对 PDE-5 具有更好的抑制活性（IC 50  < 10 nM）。所有四种最活跃的化合物都在 N1 位包含一个苯环。含有 3,5-二甲基哌嗪基的化合物比其他化合物表现出更好的活性。这些结果表明化合物5o可用作开发新的 PDE-5 抑制剂的先导结构。
• Antimykotische Wirkstoffe, 11. Mitt. 4-Amino-3-methylpyrazolo[3,4-d]pyrimidine
  作者：Alfred Kreutzberger、Klemens Burgwitz

  DOI：10.1002/ardp.19803131103

  日期：——

  Der zu den 4‐Amino‐3‐methylpyrazolo[3,4‐d]pyrimidinen 6a‐e führende Ringschluß an den 5‐Amino‐4‐cyan‐3‐methylpyrazolen 4a‐e hat sich mittels Formamid (5) realisieren lassen. Struktur‐typ 4 (4a‐h) geht aus der über die Hydrazinoethylidenmalononitrile 3 erklärbaren Umsetzung des Ethoxyethylidenmalononitrile (1) mit den korrespondierenden Hydrazinderivaten 2a‐h hervor.

  5-氨基-4-氰基-3-甲基吡唑 4a-e 的环闭合，导致 4-氨基-3-甲基吡唑并 [3,4-d] 嘧啶 6a-e，可以用甲酰胺实现 (5) . 结构类型 4 (4a-h) 来自乙氧基亚乙基丙二腈 (1) 与相应的肼衍生物 2a-h 的反应，这可以通过肼基亚乙基丙二腈 3 来解释。
• Synthesis and activity of novel tetrazole compounds and their pyrazole-4-carbonitrile precursors against Leishmania spp
  作者：Jéssica V. Faria、Maurício S. dos Santos、Alice M.R. Bernardino、Klaus M. Becker、Gérzia M.C. Machado、Raquel F. Rodrigues、Marilene M. Canto-Cavalheiro、Leonor L. Leon

  DOI：10.1016/j.bmcl.2013.09.062

  日期：2013.12

  e derivatives (4a–m) and their precursor 1-aryl-3-methyl-1H-pyrazole-4-carbonitriles (3a–m) were synthesized and evaluated as antileishmanials against Leishmania braziliensis and Leishmania amazonensis promastigotes in vitro. In parallel, the cytotoxicity of these compounds was evaluated on the RAW 264.7 cell line. The results showed that among the assayed compounds the substituted 3-chlorophenyl (4a)

  一系列新的5-（1-芳基-3-甲基-1 H-吡唑-4-基）-1 H-四唑衍生物（4a – m）及其前体1-芳基-3-甲基-1 H-吡唑合成-4-腈（3a – m）并作为抗疟药对巴西利什曼原虫和亚马逊利什曼原虫前鞭毛体进行了评价。同时，在RAW 264.7细胞系上评估了这些化合物的细胞毒性。结果表明，在待测化合物中，取代的3-氯苯基（4a）（IC 50/24 h = 15±0.14μM）和3,4-二氯苯基四唑（4d）（IC 50 /24小时= 26±0.09μM）反对的最有力的L. bRAziliensis前鞭毛体，与参考药物喷他脒，其中提出IC 50  = 13±0.04μM。此外，4a和4d衍生物的细胞毒性低于喷他idine。然而，这些四唑衍生物（4）和吡唑-4-甲腈的前体（3）针对不同每种测试物种的和反对更有效的巴西利什曼原虫比亚马逊利什曼原虫。
• Design and synthesis of pyrazolo[3,4- d ]pyrimidines: Nitric oxide releasing compounds targeting hepatocellular carcinoma
  作者：Yaseen A.M.M. Elshaier、Mohamed A. Shaaban、Mohammed K. Abd El Hamid、Mostafa H. Abdelrahman、Mahrous A. Abou-Salim、Sara M. Elgazwi、Fathi Halaweish

  DOI：10.1016/j.bmc.2017.03.002

  日期：2017.6

  pyrazolo[3,4-d]pyrimidines tethered with nitric oxide (NO) producing functionality was designed and synthesized. Sulforhodamine B (SRB) protein assay revealed that NO releasing moiety in the synthesized compounds significantly decreased the cell growth more than the des-NO analogues. Compounds 7C and 7G possessing N-para-substituted phenyl group, released the highest NO concentration of 4.6% and 4.7%

  设计并合成了一系列新的与一氧化氮（NO）连接的吡唑并[3,4-d]嘧啶类化合物。Sulforhodamine B（SRB）蛋白测定表明，合成的化合物中的NO释放部分比des-NO类似物明显减少了细胞生长。具有N-对位取代苯基的化合物7C和7G释放的最高NO浓度分别为4.6％和4.7％。与厄洛替尼作为参考药物（IC50）相比，合成化合物对HepG2细胞系的抗增殖活性分别将化合物7h，7p，14a和14b鉴定为IC50 = 3、5、3和5μM系列中最具细胞毒性的化合物。 =25μM）。流式细胞仪研究表明，7h使细胞处于细胞周期的G0 / G1期，而7p使细胞处于S期。而且，
• An unexpected formation of pyrazolopyrimidines during the attempted to obtain 5-substituted tetrazoles from carbonitriles
  作者：Jéssica Venância Faria、Maurício Silva dos Santos、Percilene Fazolin Vegi、Julio Cesar Borges、Alice M.R. Bernardino

  DOI：10.1016/j.tetlet.2013.08.033

  日期：2013.10

  1H-pyrazolo[3,4-d]pyrimidine derivatives 6a–c from 5-amino-1-aryl-3-methyl-1H-pyrazole-4-carbonitriles 4a–c, instead of 5-(5-amino-1-aryl-3-methyl-1H-pyrazole-4-yl)-1H-tetrazoles 5a–c as desired. In an attempt to obtain these tetrazole derivatives containing the methyl group at C3-position in the pyrazole ring, the amino group in 5-amino-1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile 4c was protected

  在该信中，我们描述的新的5-（5-氨基-1-芳基- 1合成H-吡唑-4-基）-1- ħ -tetrazoles 2A - Ç从5-氨基-1-芳基- 1 H ^ -吡唑-4-腈1a – c以及意外的1 H-吡唑并[3,4- d ]嘧啶衍生物6a – c来自5-氨基-1-芳基-3-甲基-1 H-吡唑-4-腈4a – c，而不是5-（5-氨基-1-芳基-3-甲基-1 H-吡唑-4-基）-1 H-四唑5a – c如预期的。为了获得这些在吡唑环的C 3位上含有甲基的四唑衍生物，尝试了5-氨基-1-（4-甲氧基苯基）-3-甲基-1 H-吡唑-4-腈4c中的氨基。通过用氢化钠和二-反应保护叔丁基-二碳酸酯（BOC）。使用类似方法从受保护的化合物7c合成四唑衍生物5c，得到2a – c和6a – c。