(1-甲基-1H-苯并咪唑-2-基)-肼 | 7022-37-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: (1-甲基-1H-苯并咪唑-2-基)-肼
• 英文名称: 1-methyl-2-hydrazinobenzimidazole
• 英文别名: 2-hydrazino-1-methylbenzimidazole；2-hydrazino-1-methyl-1H-benzimidazole；2-hydrazineyl-1-methyl-1H-benzo[d]imidazole；1-Methyl-2-hydrazino-benzimidazol；2-Hydrazino-1-methyl-benzimidazol；(1-methylbenzimidazol-2-yl)hydrazine
• CAS: 7022-37-9
• 化学式: C₈H₁₀N₄
• mdl: MFCD00778770
• 分子量: 162.194
• InChiKey: LKMYQGVYVQZJST-UHFFFAOYSA-N

物化性质

• 熔点：
  201-202 °C
• 沸点：
  311.1±25.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  55.9
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 储存条件：
  存储温度应保持在2-8°C，并请避免光线直射。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (1-Methyl-1h-benzoimidazol-2-yl)-hydrazine
Synonyms:

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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: (1-Methyl-1h-benzoimidazol-2-yl)-hydrazine
CAS number: 7022-37-9

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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: C8H10N4
Molecular weight: 162.2

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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.

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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：

  (1-甲基-1H-苯并咪唑-2-基)-肼 以 乙醇 为溶剂， 反应 24.0h， 生成 9-Methyl-S-triazolo<4,3-a>benzimidazol-3-thion
  参考文献：
  名称：

  N-取代-2-苯并唑-2-基肼基碳硫酰胺的合成及其抗流感活性

  摘要：

  NS Egorov，抗生素科学基础 [俄文]，第 3 版，莫斯科（1979 年），第 46-47 页~ VI ll'enko，化合物抗流感病毒抗病毒活性的测试和评估方法。方法论[俄语]，列宁格勒（1977 年）。GA Mokrushina、SK Kotovskaya 和 GA Yurchenko，有机硫化合物和含硫石油化学与技术会议。第 16 号：论文摘要 [俄文]，里加，1984 年，第 1 页。187. GA Mokrushina、SK Kotovskaya、GN Tyurenkova 等人，Khim.-farm。Zh., No. 2, 195 (1988).

  DOI：

  10.1007/bf00758277
• 作为产物：
  描述：

  N-甲基-1,2-苯二胺 在 一水合肼 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (1-甲基-1H-苯并咪唑-2-基)-肼
  参考文献：
  名称：

  Design and synthesis of prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors as anti-prostate cancer drugs

  摘要：

  A series of 1-aryl-3,4-substituted-1H-pyrazol-5-ol derivatives was synthesized and evaluated as prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors to obtain a novel anti-prostate cancer drug. After modifying 1-(1H-benzimidazol-2-yl)-3,4-dimethyl-1H-pyrazol-5-ol (1), a hit compound found during random screening using a recombinant PCA-1/ALKBH3, 1-(1H-5-methylbenzimidazol-2-yl)-4-benzyl-3-methyl-1H- pyrazol-5-ol (35, HUHS015), was obtained as a potent PCA-1/ALKBH3 inhibitor both in vitro and in vivo. The bioavailability (BA) of 35 was 7.2% in rats after oral administration. As expected, continuously administering 35 significantly suppressed the growth of DU145 cells, which are human hormone-independent prostate cancer cells, in a mouse xenograft model without untoward effects. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.008

文献信息

• 3-Aryl-[1,2,4]triazino[4,3-<i>a</i>]benzimidazol-4(10<i>H</i>)-ones:  Tricyclic Heteroaromatic Derivatives as a New Class of Benzodiazepine Receptor Ligands
  作者：Giampaolo Primofiore、Federico Da Settimo、Sabrina Taliani、Anna Maria Marini、Concettina La Motta、Ettore Novellino、Giovanni Greco、Marco Gesi、Letizia Trincavelli、Claudia Martini

  DOI：10.1021/jm991131h

  日期：2000.1.1

  A series of 3-substituted [1,2,4]triazino[4,3-c]benzimidazoles V were prepared and tested at the central benzodiazepine receptor (BzR). These compounds were designed as rigid analogues of the previously described N-benzylindolylglyoxylylamide derivatives IV. The title compounds V showed an affinity which depended directly on the presence of the N(10)-H group and an aromatic ring at position 3. Some

  制备了一系列3-取代的[1,2,4]三嗪[4,3-c]苯并咪唑V，并在中央苯并二氮杂pine受体（BzR）上进行了测试。这些化合物被设计为先前描述的N-苄基吲哚基二烯丙基乙二酰胺衍生物IV的刚性类似物。标题化合物V显示出亲和力，该亲和力直接取决于N（10）-H基团和位置3上的芳环的存在。相对于吲哚基二羟乙酰胺，它们中的一些引起了2倍或3倍的高亲和力。导数IV（R = H）。GABA比和[（35）S]-叔丁基环磷酸硫代酸酯结合数据揭示了化合物1c，e，f，j，k的部分反向激动剂/拮抗剂和2c的部分激动剂的功效谱。该最后的化合物被证明可有效拮抗戊四氮诱导的小鼠癫痫发作。
• Designing Structural Motifs for Clickamers: Exploiting the 1,2,3-Triazole Moiety to Generate Conformationally Restricted Molecular Architectures
  作者：Denise Zornik、Robert M. Meudtner、Tamer El Malah、Christina M. Thiele、Stefan Hecht

  DOI：10.1002/chem.201002491

  日期：2011.2.1

  around the single bonds attached to both the 1‐ and 4‐positions of the 1,2,3‐triazole moiety and should therefore be able to induce well‐defined conformational preferences in higher oligomers and polymers, that is, foldamers. Various compounds were synthesized and characterized with regard to their preferred conformations in all three aggregation states—that is, in the gas phase, in solution as well

  限制在一个大分子中的非共价相互作用，尤其是氢键相互作用以及静电力，是设计在溶液中采用定义明确的构型的折叠剂的关键。在三唑连接的折叠剂（即所谓的Clickamers）领域近期的重要活动中，我们提出了一项基础研究，比较了带有相邻N-，O-或F-杂原子取代基的各种模型化合物。吸引和排斥相互作用的相互作用导致围绕连接于1,2,3-三唑部分的1和4位的单键周围的旋转约束，因此应能够在较高的低聚物中诱导明确定义的构象偏好和聚合物，即折叠剂。通过使用DFT计算，NMR光谱实验和X射线晶体学，合成并表征了所有化合物在所有三种聚集状态下（即气相，溶液中和固态）的优选构象，并对其进行了表征， 分别。根据对单个连接基序构象行为的一般理解，在不影响其独特折叠特性的情况下，由不同基序制备了异质结构。因此，这项工作提供了一种折叠架构造套件，该套件应能够设计出具有特定形状和所包含功能的各种Clickamer。NMR光谱
• SMALL MOLECULE REGULATORS OF STEROID RECEPTOR COACTIVATORS AND METHODS OF USE THEREOF
  申请人：BAYLOR COLLEGE OF MEDICINE

  公开号：US20170290830A1

  公开（公告）日：2017-10-12

  Small molecule regulators of steroid receptor coactivator (SRC) family proteins are provided, as well as methods for their use in treating or preventing SRC-related diseases. The SRC-related diseases can include cancer, metabolic disorders, human immunodeficiency virus, neurodegenerative disorders, and/or inflammatory diseases. Also provided are methods for regulating SRC family proteins in a cell.

  提供了小分子调节类固醇受体共激活子（SRC）家族蛋白的方法，以及它们在治疗或预防SRC相关疾病中的应用。SRC相关疾病可以包括癌症、代谢紊乱、人类免疫缺陷病毒、神经退行性疾病和/或炎症性疾病。还提供了在细胞中调节SRC家族蛋白的方法。
• [EN] INHIBITORS OF HIV-1 NEF FOR THE TREATMENT OF HIV DISEASE<br/>[FR] INHIBITEURS DE HIV-1 NEF POUR LE TRAITEMENT D'UNE INFECTION PAR LE VIH
  申请人：UNIV PITTSBURGH COMMONWEALTH SYS HIGHER EDUCATION

  公开号：WO2020081856A1

  公开（公告）日：2020-04-23

  A compound of formula I, or a stereoisomer, tautomer, or pharmaceutically acceptable salt thereof: Formula I wherein X1 is benzimidazolyl, substituted benzimidazolyl, azabenzimidazolyl, substituted azabenzimidazolyl, pyrazolyl, or substituted pyrazolyl; X2 is aryl, substituted aryl, arylalkyl, substituted arylalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, substituted heteroarylalkyl, cycloalkyl, substituted cycloalkyl, (cycloalkyl)alkyl, substituted (cycloalkyl)alkyl, heterocycloalkyl, substituted heterocycloalkyl, (heterocycloalkyl)alkyl, substituted (heterocycloalkyl)alkyl, alkyl, substituted alkyl, alkoxycarbonyl, substituted alkoxycarbonyl, dialkylaminocarbonyl, substituted dialkylaminocarbonyl, (heterocycloalkyl)carbonyl, or substituted (heterocycloalkyl)carbonyl; X3 is alkyl, substituted alkyl, alkenyl, substituted alkenyl, heterocycloalkyl, substituted heterocycloalkyl, (heterocycloalkyl)alkyl, substituted (heterocycloalkyl)alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, substituted heteroarylalkyl, cycloalkyl, substituted cycloalkyl, (cycloalkyl)alkyl, or substituted (cycloalkyl)alkyl; and X4 is hydroxy, amino, alkyl, or hydrogen.

  化合物的化学式I，或其立体异构体、互变异构体或药用可接受的盐：化学式I中X1为苯并咪唑基、取代的苯并咪唑基、氮代苯并咪唑基、取代的氮代苯并咪唑基、吡唑基或取代的吡唑基；X2为芳基、取代的芳基、芳基烷基、取代的芳基烷基、杂芳基、取代的杂芳基、杂芳基烷基、取代的杂芳基烷基、环烷基、取代的环烷基、(环烷基)烷基、取代的(环烷基)烷基、杂环烷基、取代的杂环烷基、(杂环烷基)烷基、取代的(杂环烷基)烷基、烷基、取代的烷基、烷氧羰基、取代的烷氧羰基、二烷基氨羰基、取代的二烷基氨羰基、(杂环烷基)羰基或取代的(杂环烷基)羰基；X3为烷基、取代的烷基、烯烃基、取代的烯烃基、杂环烷基、取代的杂环烷基、(杂环烷基)烷基、取代的(杂环烷基)烷基、芳基、取代的芳基、芳基烷基、取代的芳基烷基、杂芳基、取代的杂芳基、杂芳基烷基、取代的杂芳基烷基、环烷基、取代的环烷基、(环烷基)烷基或取代的(环烷基)烷基；X4为羟基、氨基、烷基或氢。
• Heterocyclic hydrazones for use as anti-cancer agents
  申请人：——

  公开号：US20030166658A1

  公开（公告）日：2003-09-04

  The invention relates to novel 2-benzimidazolyl-, 2-benzoxazolyl- and 2-benzothiazolyl hydrazones that are derived from 2-formylpyridine, 2-acylpyridines, acetyldiazines and acetyl(iso)quinolines. The invention also relates to a novel method for producing 2-benzimidazolyl-, 2-benzoxazolyl- and 2-benzothiazolyl hydrazones and to their use as useful anti-cancer therapeutic agents. The novel compounds are also active against multidrug-resistant cancer cells.

  该发明涉及从2-甲醛基吡啶、2-酰基吡啶、乙酰二嗪和乙酰(异)喹啉衍生的新型2-苯并咪唑基、2-苯并噁唑基和2-苯并噻唑基腙。该发明还涉及生产2-苯并咪唑基、2-苯并噁唑基和2-苯并噻唑基腙的新方法，并将其用作有效的抗癌治疗剂。这些新型化合物还对多药耐药癌细胞具有活性。