4-肼基苯磺酰胺 | 4392-54-5

• 物质功能分类: 化学试剂 - 有机试剂 - 磺酸盐/亚磺酸盐
• 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: 4-肼基苯磺酰胺
• 中文别名: 对氨磺酰基苯肼；4-磺酰胺基苯肼
• 英文名称: 4-aminosulfonylphenylhydrazine
• 英文别名: 4-hydrazinobenzenesulfonamide；p-hydrazinobenzenesulfonamide；4-hydrazineylbenzenesulfonamide；4-hydrazinyl benzene sulfonamide；4-Hydrazinylbenzenesulfonamide
• CAS: 4392-54-5
• 化学式: C₆H₉N₃O₂S
• mdl: MFCD00625132
• 分子量: 187.222
• InChiKey: NBJSNAGTUCWQRO-UHFFFAOYSA-N

物化性质

• 熔点：
  158-1590C
• 沸点：
  434.7±47.0 °C(Predicted)
• 密度：
  1.497±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  -20°C冷冻库

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Hydrazinobenzenesulfonamide
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: 4-Hydrazinobenzenesulfonamide
CAS number: 4392-54-5

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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, refrigerated.
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: C6H9N3O2S
Molecular weight: 187.2

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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

用途：该产品用于医药中间体的制备，主要用来生产赛利可西。

反应信息

• 作为反应物：
  描述：

  4-肼基苯磺酰胺 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 17.75h， 生成 塞来西布
  参考文献：
  名称：

  Synthesis and in vivo evaluation of [18F]-4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide as a PET imaging probe for COX-2 expression

  摘要：

  Synthesis of [F-18]4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide ([F-18]celecoxib), a selective COX-2 inhibitor, is achieved via a bromide to [F-18]F- exchange reaction. Synthesis of the precursor for radiolabeling was achieved from 4'-methylacetophenone in four steps with 22% overall yield. Under non-radioactive conditions, fluorination was achieved using TBAF in DMSO at 135 degrees C in 80% yield. Synthesis of [F-18]celecoxib was achieved using [F-18]TBAF in DMSO at 135 degrees C in 10 +/- 2% yield (EOS) with > 99% chemical and radiochemical purities. The specific activity was 120 +/- 40 mCi/mu mol (EOB). [F-18]celecoxib was found to be stable in ethanol, however, de[F-18]fluorination (6.5%) was observed after 4 h in 10% ethanol-saline solution. Rodent PET studies show bone labeling indicating in vivo de[F-18]fluorination of [F-18]celecoxib. PET studies in baboon indicated a lower rate of de[F-18]fluorination than rat and retention of radioactivity in brain regions consistent with the known distribution of COX-2. A radiolabeling method that can generate consistent high specific activity is needed for routine human use. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.11.033
• 作为产物：
  描述：

  磺胺 在 盐酸 、 sodium nitrite 、 tin(ll) chloride 作用下， 以 水 为溶剂， 反应 4.0h， 生成 4-肼基苯磺酰胺
  参考文献：
  名称：

  3-Hydrazinoisatin-based苯磺酰胺作为新型碳酸酐酶抑制剂，具有抗癌活性：合成，体外生物学评估和计算机模拟。

  摘要：

  在这里，我们描述了设计和合成两个系列的酰胺基酰胺，其特征在于通过肼连接基连接到苯磺酰胺基团的N-未取代的（4a-c）或N-取代的（7a-o）靛红部分（作为尾巴）。所有制备的磺酰胺（4a-c和7a-o）均显示出对跨膜肿瘤相关人碳酸酐酶（hCA，EC 4.2.1.1）同工型，IX和XII的有效抑制活性，KI范围为（8.3-65.4 nM）和（11.9-72.9 nM）。此外，根据US-NCI方案，评估了六种磺酰胺（7e，7i，7j，7m，7n和7o）对一组六十种癌细胞系的抗增殖活性。化合物7j和7n是该测定法中最有前途的对应物，显示出对多种细胞系的广谱抗增殖活性。还，在集落形成试验中，磺酰胺7n以浓度依赖的方式显着抑制了HCT-116细胞的克隆形成性。此外，进行了分子建模研究，以了解hCA亚型II和IX活性位点内目标基于伊斯汀的磺酰胺类药物（4a-c和7a-o）的合理结合相互作用和亲和力。

  DOI：

  10.1016/j.ejmech.2019.111768

文献信息

• Design, synthesis and evaluation of benzenesulfonamide-substituted 1,5-diarylpyrazoles containing phenylacetohydrazide derivatives as COX-1/COX-2 agents against solid tumors
  作者：Xiao-Yuan Lu、Zhong-Chang Wang、Ting Wei、Xiao-Qiang Yan、Peng-Fei Wang、Hai-Liang Zhu

  DOI：10.1039/c6ra02168a

  日期：——

  phenylacetohydrazide derivatives have been designed, synthesized and evaluated for their biological activities as selective COX-2 inhibitors with anticancer potential. In vitro the bioassay results revealed that some of them displayed potent inhibitory activity in the enzymatic and cellular assays. Among them, compound 48 showed the most powerful and potent selective inhibitory activity (IC50 = 82.21 μM

  已经设计，合成并评估了新型的含苯乙酰肼衍生物的苯磺酰胺取代的1,5-二芳基吡唑类化合物作为具有抗癌潜力的选择性COX-2抑制剂的生物活性。在体外，生物测定结果表明，其中一些在酶和细胞测定中显示出有效的抑制活性。其中，化合物48显示出最有力和有效的选择性的抑制活性（IC 50 = 82.21μM为COX-1和IC 50 = 0.37μM为COX-2），相媲美的控制正化合物塞来考昔（40.29μM，0.15μM） 。抗增殖试验结果表明该化合物48在体外对A549细胞具有强大的抗增殖活性，IC 50值为0.78μM。然后，我们对化合物48进行了PI染色测定和细胞凋亡分析，发现其有效引起A549细胞凋亡。进一步进行对接模拟以将化合物48定位在COX-2活性位点中以确定可能的结合模型。建立3D-QSAR模型是为了将来合理设计选择性COX-2抑制剂。
• Synthesis of novel hybrids of pyrazole and coumarin as dual inhibitors of COX-2 and 5-LOX
  作者：Fa-Qian Shen、Zhong-Chang Wang、Song-Yu Wu、Shen-Zhen Ren、Ruo-Jun Man、Bao-Zhong Wang、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2017.07.020

  日期：2017.8

  In our previous study, we designed a series of pyrazole derivatives as novel COX-2 inhibitors. In order to obtain novel dual inhibitors of COX-2 and 5-LOX, herein we designed and synthesized 20 compounds by hybridizing pyrazole with substituted coumarin who was reported to exhibit 5-LOX inhibition to select potent compounds using adequate biological trials sequentially including selective inhibition

  在我们先前的研究中，我们设计了一系列吡唑衍生物作为新型COX-2抑制剂。为了获得新型的COX-2和5-LOX双重抑制剂，我们在此设计并合成了20种化合物，方法是将吡唑与取代的香豆素杂交，据报道，该香豆素具有5-LOX抑制作用，并使用包括选择性抑制在内的充分生物学试验依次选择有效的化合物。 COX-2和5-LOX的表达，体外抗增殖，细胞凋亡和细胞周期。其中，最有效的化合物11g（ COX-2的IC 50 = 0.23±  0.16μM，5-LOX的IC 50 = 0.87±0.07μM， 针对A549的IC 50 = 4.48±0.57μM）与阳性对照相比具有初步优势。控制塞来昔布（ 对于COX-2，IC 50 = 0.41± 0.28μM， 对于A549 ，IC 50 = 7.68± 0.55μM）和Zileuton（ 对于5-LOX，IC 50 = 1.35± 0.24μM）。进一步的研
• Discovery of novel aminophosphonate derivatives containing pyrazole moiety as potential selective COX-2 inhibitors
  作者：Bo Zhang、Xiu-Ting Hu、Kang-Min Zhou、Yu-Shun Yang、Hai-Liang Zhu

  DOI：10.1016/j.bioorg.2020.104096

  日期：2020.9

  Cyclooxygenase is critical for maintaining physiological functions, whereas overexpression of COX-2 was closely implicated in various cancers. In this study, a series of novel aminophosphonate derivatives containing pyrazole moiety were synthesized with their anti-cancer activity evaluated. In vitro assays of the target compounds showed that Z21 displayed excellent COX-2 inhibitory activity against COX-2 (IC50 = 0

  环氧合酶对于维持生理功能至关重要，而COX-2的过度表达与多种癌症密切相关。在这项研究中，合成了一系列含有吡唑部分的新型氨基膦酸酯衍生物，并评估了其抗癌活性。目标化合物的体外分析表明，Z21对COX-2表现出出色的COX-2抑制活性（IC 50  = 0.22±0.04 µM），对MCF-7细胞具有抗增殖活性（IC 50  = 4.37±0.49 µM）。通过流式细胞术和聚合酶链反应证实了化合物Z21的凋亡诱导。进一步的研究表明，化合物Z21通过线粒体依赖性途径诱导MCF-7细胞凋亡，并参与G2期细胞周期停滞。总体而言，这些结果为COX-2抑制剂的治疗药物设计提供了一些新见识，并表明了选择性COX-2抑制与抗肿瘤活性之间的联系。
• SAR study of 4-arylazo-3,5-diamino-1<i>H</i>-pyrazoles: identification of small molecules that induce dispersal of <i>Pseudomonas aeruginosa</i> biofilms
  作者：Charlotte U. Jansen、Jesper Uhd、Jens B. Andersen、Louise D. Hultqvist、Tim H. Jakobsen、Martin Nilsson、Thomas E. Nielsen、Michael Givskov、Tim Tolker-Nielsen、Katrine M. Qvortrup

  DOI：10.1039/d1md00275a

  日期：——

  4-arylazo-3,5-diamino-1H-pyrazoles as a novel group of anti-biofilm agents. Here, we report a SAR study based on 60 analogues by examining ways in which the pharmacophore can be further optimized, for example, via substitutions in the aryl ring. The SAR study revealed the very potent anti-biofilm compound 4-(2-(2-fluorophenyl)hydrazineylidene)-5-imino-4,5-dihydro-1H-pyrazol-3-amine (2).

  通过筛选 50 000 种小分子化合物的集合，我们最近将 4-arylazo-3,5-diamino-1 H -pyrazoles 鉴定为一组新型抗生物膜剂。在这里，我们报告了一项基于 60 种类似物的 SAR 研究，通过检查可以进一步优化药效团的方法，例如通过芳环中的取代。SAR 研究揭示了非常有效的抗生物膜化合物 4-(2-(2-fluorophenyl)hydrazineylidene)-5-imino-4,5-dihydro-1 H -pyrazol-3-amine ( 2 )。
• Novel aminotriazolone compounds, method for preparing same and pharmaceutical compositions containing same
  申请人：——

  公开号：US20040029875A1

  公开（公告）日：2004-02-12

  A compound of formula (I): 1 wherein: R 1 and R 2 represent hydrogen or a group as defined in the description, R 3 represents hydrogen or alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl or heterocycloalkyl, R 4 represents a group of formula (II): 2 wherein W and B are as defined in the description, R 5 represents hydrogen or alkyl, A represents a group selected from -A 2 -, -A 1 -A 2 -, -A 2 -A 1 - and -A 1 -A 2 -A 1 -, V is as defined in the description.

  一种化合物的化学式（I）： 其中： R1和R2代表氢或描述中定义的基团， R3代表氢或烷基，烯基，炔基，芳基，杂芳基，环烷基或杂环烷基， R4代表化学式（II）的基团： 其中W和B如描述中定义， R5代表氢或烷基， A代表从-A2-，-A1-A2-，-A2-A1-和-A1-A2-A1-中选择的基团， V如描述中定义。