3-苄基氨基磺酰基-苯甲酸 | 7326-77-4

• 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-苄基氨基磺酰基-苯甲酸
• 中文别名: 3-苄基磺酰苯甲酸
• 英文名称: 3-[(4-phenylmethyl)aminosulfonyl]benzoic acid
• 英文别名: 3-Benzylsulfamoyl-benzoic acid；3-(benzylsulfamoyl)benzoic acid
• CAS: 7326-77-4
• 化学式: C₁₄H₁₃NO₄S
• mdl: MFCD00622724
• 分子量: 291.328
• InChiKey: IPSYRXPRMAIAKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 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-Benzylsulfamoyl-benzoic 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-Benzylsulfamoyl-benzoic acid
CAS number: 7326-77-4

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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: C14H13NO4S
Molecular weight: 291.3

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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-苄基氨基磺酰基-苯甲酸 在 sodium tetrahydroborate 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.33h， 生成 N-benzyl-3-formylbenzenesulfonamide
  参考文献：
  名称：

  β-Amino-thiols Inhibit the Zinc Metallopeptidase Activity of Tetanus Toxin Light Chain

  摘要：

  Tetanus neurotoxin is a 150-kDa protein produced by Clostridium tetani, which causes the lethal spastic paralytic syndromes of tetanus by blocking inhibitory neurotransmitter release at central synapses. The toxin light chain (50 kDa) has a zinc endopeptidase activity specific for synaptobrevin, an essential component of the neuroexocytosis apparatus. Previous unsuccessful attempts to block the proteolytic activity of this neurotoxin with well-known inhibitors of other zinc proteases led us to study the design of specific inhibitors as a possible drug therapy to prevent the progressive evolution of tetanus following infection. Starting from the synaptobrevin sequence at the level of the cleavage site by tetanus neurotoxin (Gln(76)-Phe(77)), a thiol analogue of glutamine demonstrated inhibitory activities in the millimolar range. A structure-activity relationship performed with this compound led us to determine the requirement for the correct positioning of the thiol group, the primary amino group, and a carboxamide or sulfonamide group on the side chain. This resulted in the design of a beta-amino-(4-sulfamoylphenyl)glycine-thiol, the first significantly efficient inhibitor of tetanus neurotoxin with a K-i value of 35 +/- 5 mu M.

  DOI：

  10.1021/jm981015z
• 作为产物：
  描述：

  苯甲酸 在 氯磺酸 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 3-苄基氨基磺酰基-苯甲酸
  参考文献：
  名称：

  苯乙酸和三氟甲基苯基取代的苯甲酰胺衍生物作为潜在的PPARδ激动剂的合成，对接和评价

  摘要：

  背景：过氧化物酶体增殖物激活受体（PPAR）δ是一种类固醇，属于类固醇或核激素受体超家族。PPARδ的活化导致脂肪代谢，而不是人体能量代谢所需的葡萄糖。PPARδ代表用于治疗代谢综合征（MS）的新兴药理学靶标。已经合成了许多选择性和有效的PPARδ激动剂，在治疗与MS相关的各种疾病（包括2型糖尿病和炎症）方面具有潜在作用。 目的：本工作旨在合成和评估一些新型的苯乙酸和三氟甲基苯基取代的苯甲酰胺衍生物作为潜在的PPARδ激动剂的抗糖尿病和抗炎活性。 方法：这项工作涉及合成新的氨磺酰基苯甲酰胺衍生物，并通过分子对接研究对其进行评估，以确定在PPARδ蛋白结合位点最合适的构象的结合相互作用。根据计算机研究的结果，测试了所选化合物在动物模型中的抗糖尿病和抗炎活性。 结果：在合成的分子中，化合物7具有较高的抗糖尿病活性，化合物19具有较高的抗炎活性。发现实验结果与计算机模拟结果一致。如Lipinsk

  DOI：

  10.2174/1570180814666170327164443

文献信息

• Chemokine receptor binding heterocyclic compounds
  申请人：——

  公开号：US20020147192A1

  公开（公告）日：2002-10-10

  Tertiary amines containing a multiplicity of heteroaromatic substituents are useful as chemokine receptor modulators.

  含有多种杂环取代基的三级胺可用作化学受体调节剂。
• Synthesis, Docking and Evaluation of Phenylacetic Acid and Trifluoro-methylphenyl Substituted Benzamide Derivatives as Potential PPARδ Agonists
  作者：Ajmer Singh Grewal、Viney Lather、Deepti Pandita、Garima Bhayana

  DOI：10.2174/1570180814666170327164443

  日期：2017.10.3

  PPARδ agonists had been synthesized with a potential role in the treatment of various disorders associated with MS including type 2 diabetes and inflammation. Objective: The present work was designed to synthesize and evaluate the antidiabetic and anti-inflammatory activity of some newer phenylacetic acid and trifluoromethylphenyl substituted benzamide derivatives as potential PPARδ agonists. Methods:

  背景：过氧化物酶体增殖物激活受体（PPAR）δ是一种类固醇，属于类固醇或核激素受体超家族。PPARδ的活化导致脂肪代谢，而不是人体能量代谢所需的葡萄糖。PPARδ代表用于治疗代谢综合征（MS）的新兴药理学靶标。已经合成了许多选择性和有效的PPARδ激动剂，在治疗与MS相关的各种疾病（包括2型糖尿病和炎症）方面具有潜在作用。 目的：本工作旨在合成和评估一些新型的苯乙酸和三氟甲基苯基取代的苯甲酰胺衍生物作为潜在的PPARδ激动剂的抗糖尿病和抗炎活性。 方法：这项工作涉及合成新的氨磺酰基苯甲酰胺衍生物，并通过分子对接研究对其进行评估，以确定在PPARδ蛋白结合位点最合适的构象的结合相互作用。根据计算机研究的结果，测试了所选化合物在动物模型中的抗糖尿病和抗炎活性。 结果：在合成的分子中，化合物7具有较高的抗糖尿病活性，化合物19具有较高的抗炎活性。发现实验结果与计算机模拟结果一致。如Lipinsk
• New Purines with Antiplatelet Activity
  作者：Katrin Märschenz、Klaus Rehse

  DOI：10.1002/ardp.200500189

  日期：2006.3

  collagen with IC50 values between 3 and 10 μmol/L in the Born test. ADP, PAF, and adrenaline were used as specific aggregation inducers to examine the mechanism of the anti‐aggregating activity. An astonishing pattern of activities in the nanomolar, with 6m, 7b, 8 and even subnanomolar range, with 6b, was observed. Compound 6b inhibited the platelet aggregation induced by ADP with an IC50 = 0.45 nM (6m: 3

  四种嘌呤 - 2,6 - 二胺，4a, b, 5a, b，十九种 N-（嘌呤 - 2 - 基）苯甲酰胺 6a - q, 7b 和一种 N-（嘌呤 - 2 - 基） -2 - 呋喃甲酰胺 8首次制备并测试它们对血小板聚集的抑制作用。6a、b、h、m、o、p六种化合物在Born试验中抑制胶原诱导的血小板聚集，IC50值在3～10μmol/L之间。ADP、PAF和肾上腺素被用作特异性聚集诱导剂来检查抗聚集活性的机制。观察到惊人的纳米摩尔级活动模式，6m、7b、8 甚至亚纳摩尔范围（6b）。化合物6b以IC50 = 0.45 nM（6m：3.5 nM；8：30 nM）抑制ADP诱导的血小板聚集。化合物 7b 显示出对诱导剂肾上腺素的拮抗作用，IC 50 = 1.8 nM (6o: 20 nM; 8: 30 nM)。
• CHEMOKINE RECEPTOR BINDING HETEROCYCLIC COMPOUNDS
  申请人：Bridger Gary

  公开号：US20080090846A1

  公开（公告）日：2008-04-17

  Tertiary amines containing a multiplicity of heteroaromatic substituents are useful as chemokine receptor modulators.

  含有多种杂环芳基取代基的三级胺可用作趋化因子受体调节剂。
• US6835731B2
  申请人：——

  公开号：US6835731B2

  公开（公告）日：2004-12-28