3,4-二氨基苯磺酰胺 | 2360-20-5

• 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: 3,4-二氨基苯磺酰胺
• 中文别名: 3，4-二氨基苯磺酰胺
• 英文名称: 3,4-diaminobenzenesulfonamide
• CAS: 2360-20-5
• 化学式: C₆H₉N₃O₂S
• mdl: MFCD00277940
• 分子量: 187.222
• InChiKey: QULXUUQWVHVHSM-UHFFFAOYSA-N

物化性质

• 熔点：
  160(dec.)
• 沸点：
  475.9±55.0 °C(Predicted)
• 密度：
  1.522±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2935009090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H317,H319

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3,4-Diaminobenzenesulfonamide, diHCl
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: 3,4-Diaminobenzenesulfonamide, diHCl
CAS number: 2360-20-5

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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: C6H11Cl2N3O2S
Molecular weight: 259.9

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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 chloride, sulfur 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：

  3,4-二氨基苯磺酰胺 在 盐酸 、 溶剂黄146 、 sodium nitrite 作用下， 生成 (9ci)-1H-苯并噻唑-5-磺酰胺
  参考文献：
  名称：

  Sulfonamides in the Benzimidazole, Benzothiazole and Benzotriazole Series

  摘要：

  DOI：

  10.1021/ja01233a053
• 作为产物：
  描述：

  4-氯-3-硝基苯磺酰氯 在 ammonium hydroxide 、 tin(II) chloride dihdyrate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 5.0h， 生成 3,4-二氨基苯磺酰胺
  参考文献：
  名称：

  苯并咪唑衍生物作为有效的和同工型选择性肿瘤相关的碳酸酐酶IX / XII抑制剂。

  摘要：

  我们描述了一系列带有磺酰胺官能团（4a-d，7a-c和10）以及异羟肟酸（15a-b），羧酸（16a-b），羧酰胺（17a-b）的2-芳基苯并咪唑衍生物的合成）和硼酸（22a-b和26）的功能，它们可作为人的碳酸酐酶（hCA，EC 4.2.1.1）抑制剂。对新合成的苯并咪唑衍生物针对4种生理相关的CA同工型（hCA I，II，IX和XII）进行了评估，尤其是含磺酰胺的苯并咪唑对KI的范围在KI值范围内的肿瘤相关CA IX和XII表现出令人感兴趣的抑制活性。分别为5.2-29.3 nM和9.9-41.7 nM。值得注意的是，化合物4c是最有效和选择性最高的CA IX（KI = 6.6 nM）和XII（KI = 9）。9 nM）抑制剂，相对于胞质CA I和II同工型具有显着的选择性比，范围在3.4-25.20之间。另外，具有KIX的微摩尔效价较低，具有异羟肟酸（15a-b）或羧酸（16a-b）官能度的化合物对CA

  DOI：

  10.1016/j.bioorg.2019.103544

文献信息

• Synthesis and Antistaphylococcal Activity of<i>N</i>-Substituted-1<i>H</i>-benzimidazole-sulphonamides
  作者：M. Orhan Püsküllü、Sulhiye Yıldız、Hakan Göker

  DOI：10.1002/ardp.200900199

  日期：2009.11.19

  evaluated for antibacterial activity against Staphylococcus aureus and methicillin‐resistant S. aureus (MRSA). Certain compounds inhibit bacterial growth with low MIC (μg/mL) values. The most active compounds 30, 31, and 32 have the lowest MIC values with 0.39 to 0.19 μg/mL. Among the compounds having sulfonamido moities, 16, 23, and 24 exhibited the strongest antibacterial activity with 1.56 μg/mL MIC values

  合成了一系列 N-取代-1H-苯并咪唑-5(6)-磺酰胺和 3-(5,6-二氯-1H-苯并咪唑-2-基)-N-取代苯磺酰胺并评估其对金黄色葡萄球菌的抗菌活性和耐甲氧西林金黄色葡萄球菌 (MRSA)。某些化合物以低 MIC (μg/mL) 值抑制细菌生长。活性最强的化合物 30、31 和 32 的 MIC 值最低，为 0.39 至 0.19 μg/mL。在具有磺酰氨基部分的化合物中，16、23 和 24 表现出最强的抗菌活性，MIC 值为 1.56 μg/mL。
• Substituted benzimidazoles and imidazo-[4,5]-pyridines
  申请人：——

  公开号：US20040214857A1

  公开（公告）日：2004-10-28

  2-Aryl substituted benzimidazoles and imidazo[4,5]pyridines are disclosed as inhibitors of Cds1 and useful as adjuvants to chemotherapy or radiation therapy in the treatment of cancer.

  2-芳基取代苯并咪唑和咪唑[4,5]吡啶被披露为Cds1的抑制剂，并在癌症治疗中作为化疗或放疗的辅助剂。
• Synthesis of Fused Imidazoles and Benzothiazoles from (Hetero)Aromatic <i>ortho</i>-Diamines or <i>ortho</i>-Aminothiophenol and Aldehydes Promoted by Chlorotrimethylsilane
  作者：Dmitriy Volochnyuk、Sergey Ryabukhin、Andrey Plaskon、Andrey Tolmachev

  DOI：10.1055/s-2006-950289

  日期：2006.11

  New convenient conditions for benzimidazole and benzothiazole syntheses are described. A set of benzimidazoles, 3H-imidazo[4,5-b]pyridines, purines, xanthines and benzothiazoles was readily prepared from (hetero)aromatic ortho-diamines or ortho-aminothiophenol and aldehydes using chlorotrimethylsilane in DMF as a promoter and water-acceptor agent, followed by oxidation with air oxygen.

  描述了苯并咪唑和苯并噻唑合成的新便利条件。一组苯并咪唑、3H-咪唑并[4,5-b]吡啶、嘌呤、黄嘌呤和苯并噻唑很容易由（杂）芳族邻二胺或邻氨基苯硫酚和醛在 DMF 中使用三甲基氯硅烷作为促进剂和水受体制备剂，然后用空气氧氧化。
• Novel Fluorene Derivatives, Composition Containing Said Derivatives and the Use Thereof
  申请人：MAILLIET Patrick

  公开号：US20080153837A1

  公开（公告）日：2008-06-26

  This invention relates to derivatives of 4-(benzimidazol-2-yl)fluorene and 4-(azabenzimidazol-2-yl)fluorene, to pharmaceutical compositions comprising such derivatives, and to methods of treatment of disorders related to Hsp90 protein activity, comprising administering such derivatives.

  这项发明涉及4-(苯并咪唑-2-基)芴和4-(氮杂苯并咪唑-2-基)芴的衍生物，涉及包含这些衍生物的药物组合物，以及涉及治疗与Hsp90蛋白活性相关的疾病的方法，包括给予这些衍生物。
• In silico Optimization of a Fragment-Based Hit Yields Biologically Active, High-Efficiency Inhibitors for Glutamate Racemase
  作者：Katie L. Whalen、Anthony C. Chau、M. Ashley Spies

  DOI：10.1002/cmdc.201300271

  日期：2013.8.8

  A novel lead compound for inhibition of the antibacterial drug target, glutamate racemase (GR), was optimized for both ligand efficiency and lipophilic efficiency. A previously developed hybrid molecular dynamics–docking and scoring scheme, FERM‐SMD, was used to predict relative potencies of potential derivatives prior to chemical synthesis. This scheme was successful in distinguishing between high‐

  一种用于抑制抗菌药物靶标谷氨酸消旋酶 (GR) 的新型先导化合物针对配体效率和亲脂效率进行了优化。先前开发的混合分子动力学对接和评分方案，FERM-SMD，用于在化学合成之前预测潜在衍生物的相对效力。该方案成功地以最少的实验结构信息区分了高亲和力和低亲和力的粘合剂，节省了过程中的时间和资源。对来自模式生物枯草芽孢杆菌的GR 的体外效力增加了大约四倍。与母体支架相比，铅衍生物的抗菌效力提高了 2 到 4 倍。此外，对枯草芽孢杆菌的特异性优于大肠杆菌和金黄色葡萄球菌取决于添加到父支架上的取代基。最后，使用细菌细胞壁裂解试验深入了解了这些化合物在体内达到目标酶的能力。这项研究的结果是GR的具有以下特征的一个新颖的小分子抑制剂：ķ我= 2.5μ中号，LE = 0.45千卡摩尔-1 原子-1，利普= 6.0，MIC 50 = 260微克毫升-1针对枯草芽孢杆菌，EC 50，对枯草芽孢杆菌的裂解=520