5-氨磺酰基-2-甲氧基苯甲酸 | 22117-85-7

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: 5-氨磺酰基-2-甲氧基苯甲酸
• 中文别名: 2-甲氧基-5-氨磺酰基苯甲酸；2-甲氧基-5-氨磺酰苯甲酸；2-甲氧基-5-磺酰苯甲酸；2-甲氧基-5-磺酰胺基苯甲酸
• 英文名称: 2-Methoxy-5-sulfamoylbenzoic acid
• 英文别名: 5-sulfamoyl-o-anisic acid
• CAS: 22117-85-7
• 化学式: C₈H₉NO₅S
• mdl: MFCD00129997
• 分子量: 231.229
• InChiKey: SQAILWDRVDGLGY-UHFFFAOYSA-N

物化性质

• 熔点：
  220 °C
• 沸点：
  482.5±55.0 °C(Predicted)
• 密度：
  1.492±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 稳定性/保质期：

  如果按照规格使用和储存，则不会分解。请避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2935009090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  保持贮藏器密封，并将其放入一个紧密封装的容器中。储存时，请确保存放在阴凉、干燥的地方。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Methoxy-5-sulfamoylbenzoic acid
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
2-Methoxy-5-sulfamoylbenzoic acid
Ingredient name:
CAS number: 22117-85-7

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H9NO5S
Molecular weight: 231.2

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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

制备方法与用途

5-氨基磺酰基-2-甲氧基苯甲酸

5-氨磺酰基-2-甲氧基苯甲酸又被称为2-甲氧基-5-氨磺酰基苯甲酸，是舒必利的重要中间体。舒必利属于抗精神病药物。

制备方法 原料及配比

• 苯酰：1千克
• 25% 氨水：1.7千克

合成步骤

1. 将按比例计算的25%氨水加入氨化反应釜中。
2. 打开冷却水进出阀，并在搅拌下缓缓加入苯酰，确保温度保持在20℃以下。加完后立即盖好投料口以防止氨气溢出。
3. 关闭进出冷却水阀门，缓慢打开进出蒸汽阀门，使釜内温度维持在70-75℃约1.5小时，反应结束后通过吹拂法排出氨，并回收利用。
4. 之后关闭蒸汽进出阀，重新开启冷却水进出阀，将釜内温度降至30±2℃。
5. 打开真空泵并注入盐酸，向反应液中加入适量的盐酸以调节pH值至1.0-1.5，并控制加酸速度确保温度不超过50℃。酸析完成后提升温度至98±2℃并保温15分钟，然后继续搅拌使温度降至常温。
6. 停止搅拌，关闭冷却水进出阀，在静置过程中（可微开进出冷却水阀门以保持温度在25～35℃）静置2小时。
7. 静置结束后进行离心分离，滤饼用水冲洗至pH值为3-4后打碎放入烘箱中，在83-87℃下干燥22小时。最终收率为65-75%。

用途

主要用于有机合成中间体以及作为舒必利的合成原料。

反应信息

• 作为反应物：
  描述：

  5-氨磺酰基-2-甲氧基苯甲酸 在 氢溴酸 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 生成 2-羟基-5-氨基磺酰基苯甲酸
  参考文献：
  名称：

  Treatment of chronic inflammatory joint disease with arylsulfonamides

  摘要：

  公开了一种使用以下结构的芳基磺酰胺来治疗慢性炎性关节疾病的方法：Z--SO.sub.2 NR.sup.1 R.sup.2其中R.sup.1和R.sup.2从氢、低烷基、低烯基、环烷基、苯基、低烷基苯基、2或3吡咯基、2或3-(N-低烷基吡咯基中选择，或者R.sup.1和R.sup.2一起可以形成吡咯基或哌啶基杂环氨基基团，Z是从取代或未取代的四唑基、1,3,4-噻二唑基、1,2,4-三唑基、苯并噻唑基、苯并咪唑基、咪唑基、吡啶基、4,6-二甲基嘧啶基、苯或萘中选择的芳基。

  公开号：

  US04990523A1
• 作为产物：
  描述：

  邻甲氧基苯甲酸 在 chlorosulphuric acid 、 氨 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 生成 5-氨磺酰基-2-甲氧基苯甲酸
  参考文献：
  名称：

  Synthesis and D2 dopaminergic activity of pyrrolidinium, tetrahydrothiophenium, and tetrahydrothiophene analogs of sulpiride

  摘要：

  All of the existing dopamine receptor models recognize the amine nitrogen of agonist and antagonist drugs as playing a crucial role in receptor interactions. However, there has been some controversy as to which molecular form of the amine, charged or uncharged, is most important in these interactions. We have synthesized and examined the biological activity of permanently charged and permanently uncharged analogues of the dopaminergic antagonist, sulpiride. Sulpiride and the permanently charged pyrrolidinium (6,7) and tetrahydrothiophenium (9) analogues were able to antagonize the inhibitory effect of apomorphine on the K+-induced release of [3H]acetylcholine from striatal slices. In contrast, the permanently uncharged tetrahydrothiophene analogue 8 was inactive at concentrations up to 100 microM. Additionally, both sulpiride and the tetrahydrothiophenium analogue were able to displace [3H]spiperone from D2 binding sites, while the tetrahydrothiophene analogue was unable to produce any significant displacement. These results are consistent with our previous observations on permanently charged chlorpromazine analogues and provide further evidence that dopaminergic antagonists bind in their charged molecular forms to anionic sites on the D2 receptor.

  DOI：

  10.1021/jm00124a024

文献信息

• Macrocyclic compounds as inhibitors of viral replication
  申请人：Blatt M. Lawrence

  公开号：US20050267018A1

  公开（公告）日：2005-12-01

  The embodiments provide compounds of the general formulas I-XIX, as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating flaviviral infection, including hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.

  该实施例提供了一般式I-XIX的化合物，以及包括药物组合在内的组合物，其中包括一种主体化合物。该实施例还提供了治疗方法，包括治疗黄病毒感染的方法，包括丙型肝炎病毒感染的方法和治疗肝纤维化的方法，这些方法通常涉及向需要的个体施用一种主体化合物或组合物的有效量。
• Novel benzamides as selective and potent gastric prokinetic agents. 1. Synthesis and structure-activity relationships of N-[(2-morpholinyl)alkyl]benzamides
  作者：Shiro Kato、Toshiya Morie、Katsuhiko Hino、Tatsuya Kon、Shunsuke Naruto、Naoyuki Yoshida、Tadahiko Karasawa、Junichi Matsumoto

  DOI：10.1021/jm00167a020

  日期：1990.5

  With the purpose of obtaining more potent and selective gastric prokinetic than metoclopramide (1), a new series of N-[(2-morpholinyl)alkyl]benzamides (17-52) were synthesized and their gastric prokinetic activity was evaluated by determining effects on the gastric emptying of phenol red semisolid meal and of resin pellets solid meal in rats and mice. The morpholinyl moiety was newly designed after

  为了获得比甲氧氯普胺（1）更有效和选择性的胃动力，合成了一系列新的N-[（2-吗啉基）烷基]苯甲酰胺（17-52），并通过测定对胃泌素的作用来评估其胃动力。大鼠和小鼠胃中酚红半固体粉和树脂颗粒固体粉的胃排空。考虑到西沙必利（2）的侧链结构后，新设计了吗啉基部分，并与甲氧氯普胺和西沙必利的4-氨基-5-氯-2-甲氧基苯甲酰基偶联时产生了所需的活性。苯甲酰基的取代基的改性显着影响了活性。特别是，
• Benzoyl-piperazine derivatives
  申请人：Jolidon J. Synese

  公开号：US20050209241A1

  公开（公告）日：2005-09-22

  The invention relates to compounds of formula wherein the substituents are described herein. The compounds may be used in the treatment of illnesses based on the glycine uptake inhibitor, such as psychoses, pain, neurodegenerative disfunction in memory and learning, schizophrenia, dementia and other diseases in which cognitive processes are impaired, such as attention deficit disorders or Alzheimer's disease.

  本发明涉及具有以下通式的化合物 其中取代基如本文所述。这些化合物可用于治疗基于抑制甘氨酸摄取的疾病，如精神疾病、疼痛、记忆和学习方面的神经退行性功能障碍、精神分裂症、痴呆症以及认知过程受损的其他疾病，例如注意力缺陷障碍或阿尔茨海默病。
• Sulfonic acid esters
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04242507A1

  公开（公告）日：1980-12-30

  A novel process for the amidation or esterification which comprises reacting a compound having a carboxy group with a compound having an amino or imino group which can be acylated or with a compound having a hydroxy group in the presence of a sulfonic acid ester of the formula: R.sub.1 --SO.sub.2 --OR.sub.2 wherein R.sub.1 is an organic group and R.sub.2 O-- is a residue of a strongly acidic N-hydroxy compound as a condensation agent, and a novel sulfonic acid ester useful as such a condensation agent and a process for the preparation thereof.

  一种用于酰胺化或酯化的新型过程，包括在有机硫酸酯存在下，将具有羧基的化合物与可酰化的氨基或亚氨基基团的化合物，或具有羟基的化合物反应，其中所述有机硫酸酯的化学式为：R.sub.1 --SO.sub.2 --OR.sub.2，其中R.sub.1是有机基团，R.sub.2 O--是强酸性N-羟基化合物的残基作为缩合剂，以及一种作为这种缩合剂有用的新型磺酸酯和其制备方法。
• Discovery of N-substituted sulfamoylbenzamide derivatives as novel inhibitors of STAT3 signaling pathway based on Niclosamide
  作者：Xuebao Wang、Kaiqi Wu、Longcheng Fang、Xiaojiao Yang、Nan Zheng、Zongxuan Du、Ying Lu、Zixin Xie、Zhiguo Liu、Zhigui Zuo、Faqing Ye

  DOI：10.1016/j.ejmech.2021.113362

  日期：2021.6

  Signal transducer and activator of transcription 3 (STAT3) has been confirmed as an attractive therapeutic target for cancer therapy. Herein, we designed and synthesized a series of N-substituted Sulfamoylbenzamide STAT3 inhibitors based on small-molecule STAT3 inhibitor Niclosamide. Compound B12, the best active compound of this series, was identified as an inhibitor of IL-6/STAT3 signaling with an

  信号转导和转录激活因子 3 (STAT3) 已被证实是一种有吸引力的癌症治疗靶点。在此，我们在小分子 STAT3 抑制剂氯硝柳胺的基础上，设计并合成了一系列 N 取代磺氨酰苯甲酰胺 STAT3 抑制剂。化合物 B12 是该系列中活性最好的化合物，被鉴定为 IL-6/STAT3 信号传导的抑制剂，IC 50在 STAT3 过表达的 MDA-MB-231、HCT-116 和 SW480 肿瘤细胞系中 0.61–1.11 μM，通过抑制 Tyr705 残基的 STAT3 磷酸化和 STAT3 下游基因的表达，诱导细胞凋亡和抑制癌细胞迁移. 此外，体内研究表明，化合物 B12 在 30 mg/kg (ig) 的剂量下抑制了裸鼠中 MDA-MB-231 异种移植肿瘤的生长，比阳性对照氯硝柳胺具有更好的抗肿瘤活性。更重要的是，B12 是一种口服生物可利用的抗癌剂，是进一步开发的有希望的候选者。

表征谱图