2-氨基-N-(1-苯乙基)-苯甲酰胺 | 85592-80-9

• 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: 2-氨基-N-(1-苯乙基)-苯甲酰胺
• 中文别名: 2-氨基-N-(1-苯乙基)-苯胺
• 英文名称: 2-amino-N-(1-phenylethyl)benzamide
• CAS: 85592-80-9
• 化学式: C₁₅H₁₆N₂O
• mdl: MFCD00115985
• 分子量: 240.305
• InChiKey: KBRHMOXICLSVTL-UHFFFAOYSA-N

物化性质

• 熔点：
  107-110oC
• 沸点：
  453.5±38.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少量）、甲醇（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  55.1
• 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：
  2924299090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-n-(1-phenylethyl)benzamide
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: 2-Amino-n-(1-phenylethyl)benzamide
CAS number: 85592-80-9

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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: C15H16N2O
Molecular weight: 240.3

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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：

  2-氨基-N-(1-苯乙基)-苯甲酰胺 在 红铝 作用下， 以 甲苯 为溶剂， 以94%的产率得到2-[(1-Phenyl-ethylamino)-methyl]-phenylamine
  参考文献：
  名称：

  4-氨基-N-（1-苯乙基）苯甲酰胺类似物的合成和抗惊厥活性。

  摘要：

  为了研究该化合物的结构与抗惊厥活性之间的关系，制备了一组与4-氨基-N-（1-苯基乙基）苯甲酰胺有关的酰胺和胺。1氨基的酰化和烷基化导致抗惊厥活性几乎完全丧失。在4-氨基和1的芳环之间插入亚甲基会导致抗惊厥药力的轻微增加和毒性的显着增加。1中酰胺羰基的氢化物还原还产生具有抗电击引起的惊厥的ED50稍低的化合物，而在转子法中的TD50则低得多。1-苯基乙基1的修饰也降低了抗惊厥药的效力。

  DOI：

  10.1021/jm00390a016
• 作为产物：
  描述：

  2-硝基-正(1-苯乙基)苯甲酰胺 在 palladium on activated charcoal 氢气 作用下， 生成 2-氨基-N-(1-苯乙基)-苯甲酰胺
  参考文献：
  名称：

  Sirtuin Inhibiting Compounds

  摘要：

  本文提供了治疗或预防癌症和自身免疫疾病的组合物和方法。组合物包括抑制sirtuin的化合物，降低sirtuin的活性，如SIRT1或Sir2。示例方法包括将细胞或分子与抑制sirtuin的化合物接触，降低sirtuin的活性，从而缩短细胞的寿命，杀死细胞或使其对包括放射治疗和化疗在内的某些细胞应激变得敏感。其他方法包括治疗表达sirtuin的病原体。

  公开号：

  US20090137681A1

文献信息

• Convenient and sequential one-pot route for synthesis of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives
  作者：Mehdi Asadi、Shiva Masoomi、Seyed Mostafa Ebrahimi、Mohammad Mahdavi、Mina Saeedi、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1007/s00706-013-1110-8

  日期：2014.3

  AbstractA new and efficient synthetic process has been developed for preparation of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives. The related products were synthesized through reaction of isatoic anhydride, amines/anthranilic acids, and carbon disulfide (CS2) in the presence of potassium hydroxide in ethanol at reflux. Graphical abstract

  摘要已经开发出一种新的有效的合成方法来制备2-硫代氧杂喹唑啉酮和喹唑啉基苯并噻嗪二酮衍生物。在乙醇中，在氢氧化钾存在下，通过等角酸酐，胺/邻氨基苯甲酸和二硫化碳（CS 2）反应合成相关产物。 图形概要
• Synthesis of <i>N</i>-Unsubstituted and <i>N</i>3-Substituted Quinazoline-2,4(1<i>H</i>,3<i>H</i>)-diones from <i>o</i>-Aminobenzamides and CO₂ at Atmospheric Pressure and Room Temperature
  作者：Lin Zhang、Qian Chen、Linlin Li、Nana Ma、Jie Tian、Hao Sun、Qian Xu、Yuanyong Yang、Chun Li

  DOI：10.1021/acs.orglett.3c00614

  日期：2023.4.14

  The unprecedented metal-free synthesis of both N-unsubstituted and N3-substituted quinazoline-2,4(1H,3H)-diones from o-aminobenzamides and CO2 under atmospheric pressure at room temperature is developed. This protocol easily allows for variations of functional groups (including alkyl, aryl, and heterocycle groups) at the N3-position to accommodate the construction of many important drugs and bioactive

  开发了在大气压和室温下从邻氨基苯甲酰胺和 CO 2空前无金属合成N-未取代和N 3-取代喹唑啉-2,4(1 H ,3 H ) -二酮的方法。该协议很容易允许N 3 位的官能团（包括烷基、芳基和杂环基团）发生变化，以适应许多重要药物和生物活性化合物的构建。该反应具有生态友好、底物范围耐受性和多功能性的特点，甚至可以在克级实施。
• Application of <i>N</i>,<i>N</i>-Dimethylethanolamine as a One-Carbon Synthon for the Synthesis of Pyrrolo[1,2-<i>a</i>]quinoxalines, Quinazolin-4-ones, and Benzo[4,5]imidazoquinazolines <i>via</i> [5 + 1] Annulation
  作者：Meiqi Geng、Minzhao Huang、Jinqiang Kuang、Weiwei Fang、MaoZhong Miao、Yongmin Ma

  DOI：10.1021/acs.joc.2c02079

  日期：2022.11.4

  synthetic chemistry. In this report, a Cu(II)-catalyzed green and efficient synthesis of pyrrolo[1,2-a]quinoxaline, quinazolin-4-one, and benzo[4,5]imidazoquinazoline derivatives was developed, employing N,N-dimethylethanolamine (DMEA) as a C1 synthon. Green oxidant O2 is critical in these transformations, facilitating the formation of a key intermediate─a reactive iminium ion. The method conducted

  N-杂环的合成是合成化学的重要组成部分。在本报告中，采用N,N-二甲基乙醇胺开发了 Cu(II) 催化绿色高效合成吡咯并[1,2 - a ]喹喔啉、喹唑啉-4-酮和苯并[4,5]咪唑并喹唑啉衍生物(DMEA) 作为 C1 合成子。绿色氧化剂 O 2在这些转化过程中至关重要，它促进了关键中间体的形成——活性亚胺离子。在温和条件下进行的方法与多种功能组兼容，为以前开发的协议提供了一个有吸引力的替代方案。
• Design and synthesis of sirtinol analogs as human neutrophil elastase inhibitors
  作者：Tsong-Long Hwang、Jing-Yi Lin、Liang-Mou Kuo、Ganesh Kumar Dhandabani、Pei-Wen Hsieh

  DOI：10.1016/j.bmcl.2023.129544

  日期：2024.1

  attenuates acute lung injury and hepatic injury mediated by lipopolysaccharide or trauma hemorrhage. Therefore, 1 was chosen as the model structure to obtain more potent anti-HNE agents. In the present study, we synthesized a series of sirtinol analogues and determined their inhibitory effects on HNE. Structure-activity relationship (SAR) studies showed that swapping the imine and methyl groups of the sirtinol

  人中性粒细胞弹性蛋白酶 (HNE) 过度表达在人类观察到的大多数急性炎症和 α1-抗胰蛋白酶缺乏综合征中起着至关重要的作用，触发中性粒细胞入侵并激活巨噬细胞炎症和蛋白水解作用，从而导致组织损伤。操纵 HNE 水平稳态可能有助于治疗中性粒细胞炎症。先前的研究表明，sirtinol ( 1 ) 对 HNE 有特定的影响，可有效减轻脂多糖或创伤出血介导的急性肺损伤和肝损伤。因此，选择1作为模型结构以获得更有效的抗HNE药物。在本研究中，我们合成了一系列sirtinol类似物并确定了它们对HNE的抑制作用。构效关系 (SAR) 研究表明，将Sirtinol 支架的亚胺和甲基分别替换为二氮烯和羧基，可增强 HNE 抑制效力。化合物29在 SAR 研究中表现出最高的效力，并对 HNE 和蛋白酶 3 显示出双重抑制作用，IC 50值分别为 4.91 和 20.69 µM。此外，在基于细胞的测定中， 29被证实对抑制
• Structure–Activity Relationship and Molecular Docking of Quinazolinones Inhibiting Expression of COX-2, IL-1β, iNOS, and TNF-α through NF-κB Pathways
  作者：Sutthichat Kerdphon、Nopawit Khamto、Kittisak Buddhachat、Jatuporn Ngoenkam、Pussadee Paensuwan、Sutatip Pongcharoen、Thishana Singh、Puttinan Meepowpan、Jira Jongcharoenkamol

  DOI：10.1021/acsmedchemlett.3c00098

  日期：2023.9.14

  The quinazolinone scaffold is found in natural products and biologically active compounds, including inflammatory inhibitors. Major proteins or enzymes involved in the inflammation process are regulated by the amount of gene expression. Quinazolinone derivatives were investigated and developed against the inflammatory genes cyclooxygenase-2 (COX-2), interleukin-1β (IL-1β), tumor necrosis factor-α (TNF-α)

  喹唑啉酮支架存在于天然产物和生物活性化合物中，包括炎症抑制剂。炎症过程中涉及的主要蛋白质或酶受基因表达量的调节。研究并开发了喹唑啉酮衍生物，以对抗脂多糖中的炎症基因环氧合酶-2 (COX-2)、白细胞介素-1β (IL-1β)、肿瘤坏死因子-α (TNF-α) 和诱导型一氧化氮合酶 (iNOS) (LPS) 刺激的 RAW 264.7 巨噬细胞系。使用实时定量聚合酶链式反应（RT-qPCR）测量 mRNA 表达。 62.5 μM 喹唑啉酮化合物通过抑制核因子 κB (NF-κB)，证明抗 COX-2 和抗 IL-1β mRNA 表达分别降至 0.50% 和 3.10% 基因表达。进行分子对接以解释结合位点与所开发的化合物之间的相互作用以及喹唑啉酮部分的构效关系。