3-(三氟甲基)苯甲酸酰肼 | 22227-25-4

• 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: 3-(三氟甲基)苯甲酸酰肼
• 中文别名: 3-三氟甲基苯甲酰肼；3-(三氟甲基)苯甲酸肼；3-三氟甲基苯-1-羧肼
• 英文名称: 3-(trifluoromethyl)benzohydrazide
• 英文别名: 3-trifluoromethyl-benzoic acid hydrazide
• CAS: 22227-25-4
• 化学式: C₈H₇F₃N₂O
• mdl: MFCD00221476
• 分子量: 204.152
• InChiKey: HGUSYNBASYGAMC-UHFFFAOYSA-N

物化性质

• 熔点：
  111 °C
• 密度：
  1.356±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  <p><b></b></p>

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2928000090
• 安全说明：
  S26,S36/37/39
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312+P330,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  <p><br></p>

SDS

Name:	3-(Trifluoromethyl)benzene-1-carbohydrazide 95+% Material Safety Data Sheet
Synonym:
CAS:	22227-25-4

Section 1 - Chemical Product MSDS Name:3-(Trifluoromethyl)benzene-1-carbohydrazide 95+% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
22227-25-4	3-(Trifluoromethyl)benzene-1-carbohydr	95+%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 22227-25-4: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 108 - 110 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H7F3N2O
Molecular Weight: 204

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents, acids, bases, acid chlorides.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, fluorine, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 22227-25-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-(Trifluoromethyl)benzene-1-carbohydrazide - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 22227-25-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 22227-25-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 22227-25-4 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

合成制备方法 用途

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请根据具体内容填充上述空格。

反应信息

• 作为反应物：
  描述：

  3-(三氟甲基)苯甲酸酰肼 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 生成 4-乙基-5-[3-(三氟甲基)苯基]-2,4-二氢-3H-1,2,4-三唑-3-酮
  参考文献：
  名称：

  2,4-Dihydro-3H-1,2,4-triazol-3-ones as anticonvulsant agents

  摘要：

  A series of 5-aryl-2,4-dihydro-3H-1,2,4-triazol-3-ones was evaluated for anticonvulsant activity. In general the members of this series were prepared by the alkaline cyclization of 1-aroyl-4-alkylsemicarbazides. The resulting 2-unsubstituted 3H-1,2,4-triazol-3-ones were then alkylated, yielding 2,4-dialkyl-3H-1,2,4-triazol-3-ones. Approximately one-third of the compounds examined exhibited activity against both maximal electroshock- and pentylenetetrazole-induced seizures in mice. Receptor-binding studies suggest that this activity was not a consequence of activity at either benzodiazepine or NMDA-type glutamate receptors. From this series, compound 45 was selected for further evaluation where it was also found to be active against 3-mercaptopropionic acid, bicuculline, and quinolinic acid induced seizures in mice. In addition, 45 also protected gerbils from hippocampal neuronal degeneration produced by either hypoxia or intrastriatal quinolinic acid injection.

  DOI：

  10.1021/jm00172a015
• 作为产物：
  描述：

  3-(三氟甲基)苯甲酰氯 在 一水合肼 、 sodium hydroxide 作用下， 生成 3-(三氟甲基)苯甲酸酰肼
  参考文献：
  名称：

  设计杂环查耳酮、苯甲酰/磺酰腙：深入了解它们的生物活性和分子对接研究

  摘要：

  摘要 本研究的目的是研究一些查耳酮、苯甲酰和磺酰腙的抗氧化、抗胆碱酯酶和抗增殖活性。抗氧化活性通过四个互补试验进行研究，抗胆碱酯酶活性通过埃尔曼方法研究。使用BrdU细胞增殖ELISA测定确定化合物的抗增殖活性。化合物 32 (IC50: 15.58 ± 0.01 μg/mL) 对脑 (C6) 和 29 (IC50: 5.02 ± 0.05 μg/mL) 对宫颈 (HeLa) 癌细胞系表现出比其他化合物更高的抗增殖活性。两种磺酰腙衍生物 45 和 47 表现出非常好的抗氧化活性。抗胆碱酯酶活性结果表明，9种化合物3、8、10、14、24、25、27、38、和 45 显着抑制乙酰胆碱酯酶，33 种化合物 1-4、7-14、22-28、32-41、44-47 比加兰他敏更能抑制丁酰胆碱酯酶 (BChE)。此外，基于对 BChE 具有最佳活性的配体 45 的虚拟筛选方法用于定义新的人类 BChE

  DOI：

  10.1016/j.molstruc.2020.128059

文献信息

• Design, synthesis, insecticidal activity and 3D-QSR study for novel trifluoromethyl pyridine derivatives containing an 1,3,4-oxadiazole moiety
  作者：F. Z. Xu、Y. Y. Wang、D. X. Luo、G. Yu、S. X. Guo、H. Fu、Y. H. Zhao、J. Wu

  DOI：10.1039/c8ra00161h

  日期：——

  A series of trifluoromethyl pyridine derivatives containing 1,3,4-oxadiazole moiety was designed, synthesized and bio-assayed for their insecticidal activity. The result of bio-assays indicated the synthesized compounds exhibited good insecticidal activity against Mythimna separata and Plutella xylostella, most of the title compounds show 100% insecticidal activity at 500 mg L−1 and >80% activity at

  设计、合成了一系列含有1,3,4-恶二唑部分的三氟甲基吡啶衍生物，并对其杀虫活性进行了生物测定。生物测定结果表明，合成的化合物对Mythimna separata和Plutella xylostella表现出良好的杀虫活性，大多数标题化合物在 500 mg L -1 时表现出 100% 的杀虫活性，在250 mg L -1时表现出大于 80% 的杀虫活性。两种害虫。化合物E18和E27对Mythimna separata的LC 50值分别为38.5和30.8 mg L -1，接近阿维菌素（29.6 mg L -1); 化合物E5、E6、E9、E10、E15、E25、E26和E27在 250 mg L -1下显示出 100% 的活性，优于毒死蜱 (87%)。提出了具有良好可预测性的 CoMFA 和 CoMSIA 模型，表明苯环 2 位和 4 位具有适当体积的吸电子基团可以增强杀虫活性。
• Polycyclic N-Benzamido Imides with Potent Activity against Vaccinia Virus
  作者：Eva Torres、María D. Duque、Pelayo Camps、Lieve Naesens、Teresa Calvet、Mercè Font-Bardia、Santiago Vázquez

  DOI：10.1002/cmdc.201000306

  日期：2010.12.3

  The synthesis and antiviral activity of a series of novel polycyclic analogues of the orthopoxvirus egress inhibitor tecovirimat (ST-246) is presented. Several of these compounds display sub-micromolar activity against vaccinia virus, and were more potent than cidofovir (CDV). The more active compounds were about 10-fold more active than CDV, with minimum cytotoxic concentrations above 100 μM. Chemical

  介绍了正痘病毒出口抑制剂 tecovirimat (ST-246) 的一系列新型多环类似物的合成和抗病毒活性。其中一些化合物对牛痘病毒表现出亚微摩尔活性，并且比西多福韦 (CDV) 更有效。活性更高的化合物的活性比 CDV 高约 10 倍，最小细胞毒性浓度高于 100 μM。对化合物中存在的两个碳-碳双键进行化学操作，以进一步探索这些新型多环酰亚胺的构效关系。两个碳-碳双键的氢化降低了抗病毒活性，而双键的环丙烷化或环氧化完全消除了抗病毒活性。
• [EN] [1,2,4]TRIAZOLO[1,5-C]QUINAZOLIN-5-AMINES<br/>[FR] [1,2,4]TRIAZOLO[1,5-C]QUINAZOLIN-5-AMINES
  申请人：BAYER AG

  公开号：WO2021028382A1

  公开（公告）日：2021-02-18

  The present invention covers [1,2,4]triazolo[1,5-c]quinazolin-5-amine compounds of general formula (I) in which R1, R2, R3, R4, R5, R6, R7 and R8 are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of cancer or conditions with dysregulated immune responses or other disorders associated with aberrant AHR signaling, as a sole agent or in combination with other active ingredients.

  本发明涵盖了通式（I）中R1、R2、R3、R4、R5、R6、R7和R8如所定义的[1,2,4]三唑并[1,5-c]喹唑啉-5-胺化合物，以及制备所述化合物的方法，用于制备所述化合物的有用中间体化合物，包含所述化合物的药物组合物和组合物，以及利用所述化合物制造用于治疗或预防疾病的药物组合物，特别是癌症或与异常AHR信号传导相关的疾病，或与失调免疫反应或其他与异常AHR信号传导相关的疾病有关的情况，作为唯一药剂或与其他活性成分组合使用。
• 4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors
  作者：Laurent Gavara、Alice Legru、Federica Verdirosa、Laurent Sevaille、Lionel Nauton、Giuseppina Corsica、Paola Sandra Mercuri、Filomena Sannio、Georges Feller、Rémi Coulon、Filomena De Luca、Giulia Cerboni、Silvia Tanfoni、Giulia Chelini、Moreno Galleni、Jean-Denis Docquier、Jean-François Hernandez

  DOI：10.1016/j.bioorg.2021.105024

  日期：2021.8

  (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs

  在革兰氏阴性菌中，对 β-内酰胺类抗生素产生耐药性的主要机制是产生一种或多种 β-内酰胺酶 (BLs)，包括令人担忧的碳青霉烯酶。尽管这些酶的抑制剂最近上市，但它们仅针对丝氨酸-碳青霉烯酶（例如 KPC 型），尚无临床上有用的抑制剂来中和金属-β-内酰胺酶 (MBL) 类。我们正在开发基于 1,2,4-三唑-3-硫酮支架的化合物，该支架以原始方式与 MBL 的二锌催化位点结合，我们之前报道了其产生广谱抑制剂的潜力。然而，到目前为止，在微生物测定中只能观察到适度的抗生素增强作用，需要进一步探索以改善外膜渗透。这里，我们合成并表征了一系列在杂环的 4 位具有不同官能化烷基链的化合物。我们发现在烷基链末端存在羧基会产生有效的 VIM 型酶抑制剂K i值在 μM 到亚 μM 范围内，并且该烷基链必须更长或等于丙基链。该结果证实了羧基官能团对 1,2,4-三唑-3-硫酮杂环的 4-取代基的重要性。如
• 4-Amino-1,2,4-triazole-3-thione-derived Schiff bases as metallo-β-lactamase inhibitors
  作者：Laurent Gavara、Laurent Sevaille、Filomena De Luca、Paola Mercuri、Carine Bebrone、Georges Feller、Alice Legru、Giulia Cerboni、Silvia Tanfoni、Damien Baud、Giuliano Cutolo、Benoît Bestgen、Giulia Chelini、Federica Verdirosa、Filomena Sannio、Cecilia Pozzi、Manuela Benvenuti、Karolina Kwapien、Marina Fischer、Katja Becker、Jean-Marie Frère、Stefano Mangani、Nohad Gresh、Dorothée Berthomieu、Moreno Galleni、Jean-Denis Docquier、Jean-François Hernandez

  DOI：10.1016/j.ejmech.2020.112720

  日期：2020.12

  potent, they represented a promising basis for the development of broad-spectrum MBL inhibitors. Here, we synthesized and characterized a large number of 4-amino-1,2,4-triazole-3-thione-derived Schiff bases. Compared to the previous series, the presence of an aryl moiety at position 4 afforded an average 10-fold increase in potency. Among 90 synthetic compounds, more than half inhibited at least one

  产生金属β-内酰胺酶（MBL）的革兰氏阴性菌对β-内酰胺抗生素的耐药性代表着重大的医学威胁，并且迫切需要开发临床上有用的抑制剂。我们先前报道了MBL催化位点中的5个取代的4-氨基/ H-1,2,4-三唑-3-硫酮化合物的原始结合模式。此外，我们表明，尽管具有中等效力，但它们代表了广谱MBL抑制剂开发的有希望的基础。在这里，我们合成和表征了大量的4-氨基-1,2,4-三唑-3-硫酮衍生的席夫碱。与先前的系列相比，在4位上存在芳基部分可使效力平均提高10倍。在90种合成化合物中，超过一半的化合物抑制了至少六个被测MBL（L1，VIM-4，VIM-2，NDM-1，IMP-1，K i的值在μM至亚μM范围内。几种是广谱抑制剂，也可以抑制临床上最相关的VIM-2和NDM-1。活性化合物通常在位置5处包含卤代，双环芳基或酚基部分，以及在邻苯甲酸，2,4-二羟基苯基，对苄氧基苯基或3-（m-苯甲酰基）-