4-(乙基氨基)-3-硝基苯甲酸甲酯 | 396652-42-9

• 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: 4-(乙基氨基)-3-硝基苯甲酸甲酯
• 英文名称: 4-ethylamino-3-nitro-benzoic acid methyl ester
• 英文别名: 4-ethylamino-3-nitrobenzoic acid methyl ester；Methyl 4-(ethylamino)-3-nitrobenzoate
• CAS: 396652-42-9
• 化学式: C₁₀H₁₂N₂O₄
• mdl: MFCD09862451
• 分子量: 224.216
• InChiKey: PGOWZUNCBPVWPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2922499990

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Methyl 4-(ethylamino)-3-nitrobenzoate
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: Methyl 4-(ethylamino)-3-nitrobenzoate
CAS number: 396652-42-9

---

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: C10H12N2O4
Molecular weight: 224.2

---

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：

  4-(乙基氨基)-3-硝基苯甲酸甲酯 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 40.0 ℃ 、275.79 kPa 条件下， 反应 8.0h， 生成 Methyl 2-(2-ethoxy-2-oxoethyl)-1-ethylbenzimidazole-5-carboxylate
  参考文献：
  名称：

  某些带有酰胺或am基的新型1H-苯并咪唑-5-羧酸甲酯或乙酯的合成及强效抗菌活性。

  摘要：

  合成了一系列在C-2位带有酰胺或am取代的甲基或苯基基团的苯并咪唑-5-羧酸烷基酯衍生物，并评估了其对金黄色葡萄球菌，耐甲氧西林金黄色葡萄球菌（MRSA）的抗菌和抗真菌活性，粪链球菌，耐甲氧西林的表皮葡萄球菌（MRSE），大肠杆菌和白色念珠菌。结果表明，尽管所有简单的乙酰胺基本上都没有活性，但芳族酰胺和am具有强大的抗菌活性。芳族am衍生物13 fh对MRSA和MRSE表现出最佳的抑制活性，其1.56-0.39 microg / mL MIC值。

  DOI：

  10.1016/j.bmc.2004.12.025
• 作为产物：
  描述：

  4-氯-3-硝基苯甲酸 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(乙基氨基)-3-硝基苯甲酸甲酯
  参考文献：
  名称：

  某些带有酰胺或am基的新型1H-苯并咪唑-5-羧酸甲酯或乙酯的合成及强效抗菌活性。

  摘要：

  合成了一系列在C-2位带有酰胺或am取代的甲基或苯基基团的苯并咪唑-5-羧酸烷基酯衍生物，并评估了其对金黄色葡萄球菌，耐甲氧西林金黄色葡萄球菌（MRSA）的抗菌和抗真菌活性，粪链球菌，耐甲氧西林的表皮葡萄球菌（MRSE），大肠杆菌和白色念珠菌。结果表明，尽管所有简单的乙酰胺基本上都没有活性，但芳族酰胺和am具有强大的抗菌活性。芳族am衍生物13 fh对MRSA和MRSE表现出最佳的抑制活性，其1.56-0.39 microg / mL MIC值。

  DOI：

  10.1016/j.bmc.2004.12.025

文献信息

• Substituted Fused Imidazole Derivatives, Pharmaceutical Compositions, and Methods of Use Thereof
  申请人：Mjalli Adnan M. M.

  公开号：US20110201604A1

  公开（公告）日：2011-08-18

  Substituted fused imidazole derivatives, methods of their preparation, pharmaceutical compositions comprising a substituted fused imidazole derivative, and methods of use in treating inflammation are provided. The substituted fused imidazole derivatives may control the activity or the amount or both the activity and the amount of heme-oxygenase.

  提供了替代融合咪唑衍生物、其制备方法、包含替代融合咪唑衍生物的药物组合物，以及在治疗炎症中使用的方法。这些替代融合咪唑衍生物可能控制血红素氧合酶的活性或数量，或者同时控制活性和数量。
• Heterocyclic modulators of nuclear receptors
  申请人：——

  公开号：US20030212111A1

  公开（公告）日：2003-11-13

  Compounds, compositions and methods for modulating the activity of nuclear receptors are provided. In particular, heterocyclic compounds are provided for modulating the activity of farnesoid X receptor (FXR), liver X receptor (LXR) and/or orphan nuclear receptors. In certain embodiments, the compounds are thiazolidinone derivatives.

  提供了用于调节核受体活性的化合物、组合物和方法。具体来说，提供了用于调节法尼索醇X受体（FXR）、肝X受体（LXR）和/或孤儿核受体活性的杂环化合物。在某些实施例中，这些化合物是噻唑啉酮衍生物。
• The discovery of new scaffold of plant activators: From salicylic acid to benzotriazole
  作者：Kang Chang、Jian-Qin Chen、Yan-Xia Shi、Mei-Jian Sun、Peng-Fei Li、Zhen-Jiang Zhao、Wei-Ping Zhu、Hong-Lin Li、Yu-Fang Xu、Bao-Ju Li、Xu-Hong Qian

  DOI：10.1016/j.cclet.2017.02.004

  日期：2017.4

  Abstract Started from salicylic acid (SA) and related commercialized plant activators, based on molecular three-dimensional shape and pharmacophore similarity comparison (SHAFTS), a new lead compound benzotriazole was predicted and a series of benzotriazole derivatives were designed and synthesized. The bioassay showed that benzotriazole had high activity against a broad spectrum of diseases including

  摘要从水杨酸（SA）和相关的商业化植物活化剂开始，基于分子三维形状和药效团相似度比较（SHAFTS），预测了一种新的铅化合物苯并三唑，并设计和合成了一系列苯并三唑衍生物。生物测定表明，苯并三唑在体内对多种疾病（包括真菌和卵菌）具有高活性，但在体外则无活性。并且在1'-位和5'-位引入适当的基团对于该活性是有利的。因此，它们具有被开发为新型植物激活剂的潜力。
• Substituted fused imidazole derivatives, pharmaceutical compositions, and methods of use thereof
  申请人：Mjalli Adnan M. M.

  公开号：US08759535B2

  公开（公告）日：2014-06-24

  Substituted fused imidazole derivatives, methods of their preparation, pharmaceutical compositions comprising a substituted fused imidazole derivative, and methods of use in treating inflammation are provided. The substituted fused imidazole derivatives may control the activity or the amount or both the activity and the amount of heme-oxygenase.

  本发明提供了替代融合咪唑衍生物，它们的制备方法，包括替代融合咪唑衍生物的药物组合物以及在治疗炎症方面使用的方法。这些替代融合咪唑衍生物可以控制血红素氧化酶的活性或数量或活性和数量。
• Design and synthesis of 1H-benzo[d]imidazole selective HDAC6 inhibitors with potential therapy for multiple myeloma
  作者：Linfu Liu、Liyuan Zhang、Xuxi Chen、Kang Yang、Hao Cui、Rui Qian、Shanshan Zhao、Liqun Wang、Xiaolan Su、Manyu Zhao、Mengzhu Wang、Zan Hu、Tao Lu、Yong Zhu、Qing-Qing Zhou、Yuqin Yao

  DOI：10.1016/j.ejmech.2023.115833

  日期：2023.12

  with the benzimidazole group serving as a specific linker for these inhibitors. Notably, compound 30 has exhibited outstanding HDAC6 inhibitory activity (IC50 = 4.63 nM) and superior antiproliferative effects against human multiple myeloma cells, specifically RPMI-8226. Moreover, it has been shown to induce cell cycle arrest in the G2 phase and promote apoptosis through the mitochondrial pathway. In a

  Pan-HDAC抑制剂对多发性骨髓瘤表现出显着的抑制活性，然而，其临床应用却因严重的毒副作用而受到阻碍。相比之下，选择性 HDAC6 抑制剂已被证明可有效治疗多发性骨髓瘤。属于 1 H-苯并[ d ]咪唑异羟肟酸类的化合物已被鉴定为新型 HDAC6 抑制剂，其中苯并咪唑基团充当这些抑制剂的特定连接体。值得注意的是，化合物30 对人多发性骨髓瘤细胞（特别是 RPMI-8226）表现出出色的 HDAC6 抑制活性（IC 50 = 4.63 nM）和卓越的抗增殖作用。此外，它已被证明可以诱导细胞周期停滞在 G2 期，并通过线粒体途径促进细胞凋亡。在骨髓瘤 RPMI-8226 异种移植模型中，化合物30作为独立药物给药时表现出显着的体内抗肿瘤功效 (T/C = 34.8%)，且没有可观察到的细胞毒性。这些发现强调了化合物30作为治疗多发性骨髓瘤的有前途的治疗剂的巨大潜力。