2-苯磺酰基氨基苯甲酸 | 34837-67-7

• 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-苯磺酰基氨基苯甲酸
• 英文名称: 2-(phenylsulfonamido)benzoic acid
• 英文别名: o-benzenesulphonamidobenzoic acid；2-[(phenylsulfonyl)amino]benzoic acid；o-benzenesulfonamidobenzoic acid；N-Phenylsulfonylanthranilsaeure；2-benzenesulfonamidobenzoic acid；N-benzenesulfonyl-anthranilic acid；N-Benzolsulfonyl-anthranilsaeure；2-Benzolsulfamino-benzoesaeure；2-(benzenesulfonamido)benzoic acid
• CAS: 34837-67-7
• 化学式: C₁₃H₁₁NO₄S
• mdl: MFCD00429933
• 分子量: 277.301
• InChiKey: KIAHUXDVSURYKM-UHFFFAOYSA-N

物化性质

• 熔点：
  223 °C
• 沸点：
  478.4±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: 2-Benzenesulfonamidobenzoic 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: 2-Benzenesulfonamidobenzoic acid
CAS number: 34837-67-7

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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：

  2-苯磺酰基氨基苯甲酸 在 dipotassium hydrogenphosphate 、 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以74%的产率得到2-氨基二苯甲酮
  参考文献：
  名称：

  通过芳基迁移对羧酸进行脱氧丙烯酸化。

  摘要：

  已经实现了前所未有的芳香族羧酸脱氧芳基化反应，从而可以构建增强的不对称二芳基酮库。协同的光氧化还原催化作用和磷烷基自由基化学反应可在温和的反应条件下，通过1,5-芳基迁移，精确裂解更强的CO键并形成较弱的CC键。此新协议独立于底物氧化还原电势，电子和取代基效应。在氧化还原中性条件下，它提供了60种合成通用的邻氨基和邻羟基二芳基酮的通用且有希望的途径。此外，以令人满意的产率，它也为全合成喹诺酮生物碱，（±）-yaequinolone A2和viridicatin衍生物提供了一条简洁的途径。

  DOI：

  10.1002/chem.201903816
• 作为产物：
  描述：

  2-(苯磺酰胺基)苯酸甲酯 在 potassium tert-butylate 、 水 作用下， 以 乙醚 为溶剂， 生成 2-苯磺酰基氨基苯甲酸
  参考文献：
  名称：

  小分子甘油三磷酸酰基转移酶抑制剂的设计与合成

  摘要：

  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。

  DOI：

  10.1021/jm900251a

文献信息

• Hydroxamic acid with benzenesulfonamide: An effective scaffold for the development of broad-spectrum metallo-β-lactamase inhibitors
  作者：Jia-Qi Li、Cheng Chen、Min Yao、Le-Yun Sun、Han Gao、Jiazhu Chigan、Ke-Wu Yang

  DOI：10.1016/j.bioorg.2020.104436

  日期：2020.12

  Given that β-lactam antibiotic resistance mediated by metallo-β-lactamases (MβLs) seriously threatens human health, we designed and synthesized nineteen hydroxamic acids with benzenesulfonamide, which exhibited broad-spectrum inhibition against four tested MβLs ImiS, L1, VIM-2 and IMP-1 (except 6, 13 and 18 on IMP-1, and 18 on VIM-2), with an IC50 value in the range of 0.6–9.4, 1.3–27.4, 5.4–43.7 and

  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。
• [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。
• [EN] SMALL MOLECULE INHIBITORS OF MCL-1 AND USES THEREOF<br/>[FR] PETITES MOLÉCULES INHIBITRICES DE MCL-1 ET LEURS UTILISATIONS
  申请人：UNIV MICHIGAN REGENTS

  公开号：WO2016172218A1

  公开（公告）日：2016-10-27

  This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having benzoic acid structure which function as inhibitors of Mcl-1 protein, and their use as therapeutics for the treatment of cancer and other diseases.

  这项发明属于药物化学领域。具体来说，该发明涉及一类具有苯甲酸结构的新型小分子，其作为Mcl-1蛋白的抑制剂，并且它们作为治疗癌症和其他疾病的药物的用途。
• Studies of heterocyclic compounds. X. The synthesis and properties of some organotin(IV)-oxygen and-nitrogen heterocycles
  作者：Craig A. Obafemi、A.B. Ejenavi、D.O. Kolawole、J.K. Oloke

  DOI：10.1016/s0020-1693(00)83479-9

  日期：1988.1

  Some representative six-membered heterocyclic organotin(IV)-nitrogen and -oxygen compounds were prepared by the condensation of dialkyltin oxides with hydroxycarboxylic acids, substituted aminocarboxylic acids and diols and characterized by infrared and mass spectra. The compounds were screened against nine species of bacteria and five species of fungi.

  通过氧化二烷基锡与羟基羧酸，取代的氨基羧酸和二醇的缩合反应，制备了一些代表性的六元杂环有机锡（IV）氮和氧化合物，并通过红外光谱和质谱进行了表征。筛选了针对9种细菌和5种真菌的化合物。
• 一种由芳香羧酸合成邻氨基芳香酮的方法
  申请人：南京大学

  公开号：CN109824530B

  公开（公告）日：2021-09-28

  一种由芳香羧酸制备邻氨基芳香酮的方法，它是以2‑芳基磺酰胺基芳香羧酸为原料，三苯基膦作为脱氧剂，在蓝光灯照射下，在1,4‑二氧六环溶液中，氩气气氛下，在磷酸氢二钾存在下，以[Ir(dF(CF3)ppy)2(dtbbpy)]PF6为光催化剂，得到邻氨基芳香酮化合物；所述的光催化剂[Ir(dF(CF3)ppy)2(dtbbpy)]PF6如下结构：。