3-苯磺酰氨基苯甲酸 | 28547-15-1

• 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-苯磺酰氨基苯甲酸
• 中文别名: 3-(苯磺酰基氨基)苯甲酸；3-苯磺酰基氨基-苯甲酸
• 英文名称: 3-(phenylsulfonamido)benzoic acid
• 英文别名: 3-(phenylsulfonyl)aminobenzoic acid；3-[(Phenylsulfonyl)amino]benzoic acid；3-(benzenesulfonamido)benzoic acid
• CAS: 28547-15-1
• 化学式: C₁₃H₁₁NO₄S
• mdl: MFCD00531524
• 分子量: 277.301
• InChiKey: RELBUFSHELNQKC-UHFFFAOYSA-N

物化性质

• 熔点：
  203-204 °C
• 沸点：
  492.3±47.0 °C(Predicted)
• 密度：
  1.451±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2935009090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Benzenesulfonylaminobenzoic acid
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-Benzenesulfonylaminobenzoic acid
CAS number: 28547-15-1

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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: C13H11NO4S
Molecular weight: 277.3

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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, 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-苯磺酰氨基苯甲酸 在 N,N'-羰基二咪唑 、 盐酸羟胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N-hydroxy-3-(phenylsulfonamido)benzamide
  参考文献：
  名称：

  异羟肟酸与苯磺酰胺：开发广谱金属-β-内酰胺酶抑制剂的有效支架

  摘要：

  鉴于金属β-内酰胺酶（MβLs）介导的β-内酰胺抗生素耐药性严重威胁人类健康，我们与苯磺酰胺一起设计并合成了19种异羟肟酸，对四种测试的MβLs ImiS、L1、VIM-2和IMP-1（IMP-1 上的6、13和18以及 VIM-2 上的 18除外），IC 50值分别在 0.6–9.4、1.3–27.4、5.4–43.7 和 5.2–49.7 µM 范围内，并恢复了头孢唑啉和美罗培南的抗菌活性，导致抗生素的 MIC 降低了 2-32 倍。化合物17对 L1 显示出可逆的竞争性抑制作用， K i值为 2.5 µM，并显着降低被表达 L1 的大肠杆菌感染的小鼠脾脏和肝脏中的细菌负荷。对接研究表明17通过磺酰胺基团的氧原子与VIM-2和CphA的Zn(II)紧密结合，但通过异羟肟酸基团的氧原子与L1的Zn(II)配位。这些研究表明，异羟肟酸与苯磺酰胺是开发 MβL 抑制剂的有效支架。

  DOI：

  10.1016/j.bioorg.2020.104436
• 作为产物：
  描述：

  3-氨基苯甲酸甲酯 在 sodium hydroxide 作用下， 以6.62 g (89%)的产率得到3-苯磺酰氨基苯甲酸
  参考文献：
  名称：

  Arylsulfonylaminobenzene derivatives and the use thereof as factor Xa

  摘要：

  本发明涉及用于治疗动脉和静脉血栓性闭塞性疾病、炎症、癌症和神经退行性疾病的非肽因子Xa抑制剂。因子Xa抑制剂提供结构化合物：##STR1##或其药学上可接受的盐；其中R.sup.1是烷基、取代烷基、环烷基、芳基、取代芳基、杂环芳基或取代杂环芳基；R.sup.2是氢、烷基、环烷基或芳基中的一种；R.sup.3是氢、羟基或烷氧基中的一种；R.sup.4是--NH.sub.2、苯基或吡啶基中的一种，其中所述苯基和所述吡啶基可以选择地取代为卤素、羟基、羟基烷基、烷氧基、氨基、单烷基氨基、二烷基氨基、氨基烷基、单烷基氨基烷基和/或二烷基氨基烷基中的一种或两种；X是--CH.sub.2--或--C(O)--中的一种；n为零到十一；但是当R.sup.4为--NH.sub.2时，R.sup.3为氢且n不为零；同时当R.sup.3为羟基或烷氧基时，R.sup.4不为--NH.sub.2，且n不为零。

  公开号：

  US05741819A1

文献信息

• Novel sulfonamides as L-CPT1 inhibitors
  申请人：Bleicher Konrad

  公开号：US20060276494A1

  公开（公告）日：2006-12-07

  The invention is concerned with novel sulfonamide derivatives of formula (I) wherein R 2 , R 3 , R 4 , A, X, Y 1 , Y 2 , Y 3 , Y 4 and Z 1 are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds inhibit L-CPT1 and can be used as medicaments.

  这项发明涉及式(I)的新型磺胺衍生物， 其中R 2 ，R 3 ，R 4 ，A，X，Y 1 ，Y 2 ，Y 3 ，Y 4 和Z 1 如描述和索赔中所定义，并且其生理上可接受的盐和酯。这些化合物抑制L-CPT1，可用作药物。
• [EN] BENZIMIDAZOLECARBOXAMIDES AS INHIBITORS OF FAK<br/>[FR] BENZIMIDAZOLECARBOXAMIDES CONSTITUANT DES INHIBITEURS DE LA KINASE D'ADHÉRENCE FOCALE
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2010126922A1

  公开（公告）日：2010-11-04

  This invention relates to benzimadolecarboxamides of formula (I) which are inhibitors of focal adhesion kinase, and as such are useful for treating proliferative diseases.

  这项发明涉及式(I)的苯并咪唑羧酰胺，它们是黏附斑激酶的抑制剂，因此可用于治疗增殖性疾病。
• Sequential C–S and S–N Coupling Approach to Sulfonamides
  作者：Kai Chen、Wei Chen、Bing Han、Wanzhi Chen、Miaochang Liu、Huayue Wu

  DOI：10.1021/acs.orglett.0c00183

  日期：2020.3.6

  A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. A broad range of sulfonamides bearing different reactive functional groups were obtained in good to excellent yields through sequential C-S and S-N coupling that does not require metal catalysts.

  描述了涉及硝基芳烃，（杂）芳基硼酸和焦亚硫酸钾的一锅三组分反应，生成磺酰胺。通过不需要金属催化剂的连续CS和SN偶联，获得了具有不同反应性官能团的多种磺酰胺，收率好至极好。
• [EN] NOVEL SULFONE AMIDE DERIVATIVES CAPABLE OF INHIBITING BACE<br/>[FR] NOUVEAUX DERIVES SULFONAMIDE CAPABLES D'INHIBER BACE
  申请人：LG LIFE SCIENCES LTD

  公开号：WO2005030709A1

  公开（公告）日：2005-04-07

  The present invention relates to novel derivatives of sulfone amide of Formula 1 as defined in this disclosure which inhibit the activity of BACE (or beta-secretase). These sulfone amide derivatives are useful for the treatment and prevention of Alzheimer's disease and related diseases caused by production of beta-amyloid, by inhibiting the activity of BACE.

  本发明涉及本公开中定义的式1的磺酰脒衍生物，该衍生物抑制BACE（或β-分泌酶）的活性。这些磺酰脒衍生物可用于治疗和预防由β-淀粉样蛋白产生引起的阿尔茨海默病及相关疾病，通过抑制BACE的活性。
• Design and Synthesis of Small Molecule Glycerol 3-Phosphate Acyltransferase Inhibitors
  作者：Edward A. Wydysh、Susan M. Medghalchi、Aravinda Vadlamudi、Craig A. Townsend

  DOI：10.1021/jm900251a

  日期：2009.5.28

  mass is growing rapidly, particularly in the United States. Glycerol 3-phosphate acyltransferase (GPAT) catalyzes the rate-limiting step of glycerolipid biosynthesis, the acylation of glycerol 3-phosphate with saturated long-chain acyl-CoAs. In an effort to produce small molecule inhibitors of this enzyme, a series of benzoic and phosphonic acids was designed and synthesized. In vitro testing of this series

  肥胖症和其他与甘油三酯含量增加相关的疾病的发病率正在迅速增长，尤其是在美国。甘油 3-磷酸酰基转移酶 (GPAT) 催化甘油脂生物合成的限速步骤，即甘油 3-磷酸与饱和长链酰基辅酶 A 的酰化。为了生产这种酶的小分子抑制剂，设计并合成了一系列苯甲酸和膦酸。该系列的体外测试导致鉴定了几种化合物，特别是 2-(壬基磺酰胺基)苯甲酸 ( 15g )，在完整线粒体分析中具有中等 GPAT 抑制活性。