2-甲磺酰氨基苯硼酸 | 756520-78-2

• 物质功能分类: 原料药 - 人工合成抗感染类药 - 磺胺类药及增效剂
• 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-甲磺酰氨基苯硼酸
• 中文别名: 2-甲磺氨基苯硼酸；2-(甲基磺酰胺基)苯硼酸
• 英文名称: (2-(methylsulfonamido)phenyl)boronic acid
• 英文别名: [2-(methanesulfonamido)phenyl]boronic acid
• CAS: 756520-78-2
• 化学式: C₇H₁₀BNO₄S
• mdl: MFCD02179471
• 分子量: 215.038
• InChiKey: RPRMOEFOTPSWBO-UHFFFAOYSA-N

物化性质

• 熔点：
  116-120°C

计算性质

• 辛醇/水分配系数(LogP)：
  0.15
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  95
• 氢给体数：
  3
• 氢受体数：
  5

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
• WGK Germany：
  3
• 海关编码：
  2935009090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Methylsulfonylaminophenylboronic acid
Synonyms: 2-Methanesulfonylaminophenylboronic acid

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H319: Causes serious eye irritation
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Methylsulfonylaminophenylboronic acid
CAS number: 756520-78-2

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.
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
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H10BNO4S
Molecular weight: 215.0

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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-甲磺酰氨基苯硼酸 在 palladium diacetate 、 sodium carbonate 、 potassium carbonate 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-[2-(2-methanesulfinylpyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide
  参考文献：
  名称：

  2,7-二取代-吡咯并[2,1- f ] [1,2,4]三嗪：旧模板的新变体及其在体内具有抗肿瘤活性的间变性淋巴瘤激酶（ALK）抑制剂的发现中的应用

  摘要：

  一种新型的2,7-二取代-吡咯并[2,1- f ] [1,2,4]三嗪支架已被设计为一种新的激酶抑制剂平台，可模仿众所周知的二氨基嘧啶基序的生物活性构象。这种新型吡咯并[2,1- f ] [1,2,4]三嗪支架的设计，合成和验证将描述为间变性淋巴瘤激酶（ALK）抑制剂。重要的是，适当的效能和选择性决定簇的引入导致发现了在变性间变性大细胞淋巴瘤（ALCL）动物模型中口服有效的几种先进的先导。鉴定出显示出优异功效的铅抑制剂（30），并且将进行深入的体外/体内表征。

  DOI：

  10.1021/jm200758k
• 作为产物：
  描述：

  2-氨基苯硼酸 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以16%的产率得到2-甲磺酰氨基苯硼酸
  参考文献：
  名称：

  Fused heterotricyclic compounds as inhibitors of 17beta-hydroxysteroid dehydrogenase 3

  摘要：

  融合杂三环化合物，使用这种化合物治疗激素敏感性疾病如前列腺癌的方法，以及含有这种化合物的药物组合物。

  公开号：

  US20050192310A1

文献信息

• FLAP MODULATORS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：US20150259357A1

  公开（公告）日：2015-09-17

  The present invention relates to compounds of Formula (I), or a form thereof, wherein ring A, R 1 , R 2 , R 3 , R 3 ′, L, W, and V are as defined herein, useful as FLAP modulators. The invention also relates to pharmaceutical compositions comprising compounds of Formula (I). Methods of making and using the compounds of Formula (I) are also within the scope of the invention

  本发明涉及式（I）的化合物，或其形式，其中环A，R1，R2，R3，R3'，L，W和V如本文所定义，可用作FLAP调节剂。该发明还涉及包含式（I）化合物的药物组合物。制备和使用式（I）化合物的方法也属于本发明的范围。
• Identification and Preliminary Structure-Activity Relationship Studies of 1,5-Dihydrobenzo[e][1,4]oxazepin-2(3H)-ones That Induce Differentiation of Acute Myeloid Leukemia Cells In Vitro
  作者：Laia Josa-Culleré、Thomas Cogswell、Irene Georgiou、Morgan Jay-Smith、Thomas Jackson、Carole Bataille、Stephen Davies、Paresh Vyas、Thomas Milne、Graham Wynne、Angela Russell

  DOI：10.3390/molecules26216648

  日期：——

  Acute myeloid leukemia (AML) is the most aggressive type of blood cancer, and there is a continued need for new treatments that are well tolerated and improve long-term survival rates in patients. Induction of differentiation has emerged as a promising alternative to conventional cytotoxic chemotherapy, but known agents lack efficacy in genetically distinct patient populations. Previously, we established a phenotypic screen to identify small molecules that could stimulate differentiation in a range of AML cell lines. Utilising this strategy, a 1,5-dihydrobenzo[e][1,4]oxazepin-2(3H)-one hit compound was identified. Herein, we report the hit validation in vitro, structure-activity relationship (SAR) studies and the pharmacokinetic profiles for selected compounds.

  急性髓系白血病（AML）是最具侵略性的血液癌症类型，目前仍然需要新的治疗方法，这些方法应具有良好的耐受性，并能提高患者的长期生存率。诱导分化已经成为一种有希望替代传统细胞毒性化疗的方法，但已知的药物在遗传上不同的患者群体中缺乏疗效。之前，我们建立了一种表型筛选方法，用以识别能够在一系列AML细胞系中刺激分化的 small molecules(小分子)。利用这种策略，我们识别出了一种1,5-二氢苯并[e][1,4]恶嗪-2(3H)-酮的击中化合物。本文中，我们报告了该击中化合物的体外验证、结构-活性关系（SAR）研究以及选定化合物的药代动力学特征。
• Identification of Thieno[3,2-<i>d</i>]pyrimidine Derivatives as Dual Inhibitors of Focal Adhesion Kinase and FMS-like Tyrosine Kinase 3
  作者：Hanna Cho、Injae Shin、Hojong Yoon、Eunhye Jeon、Jiwon Lee、Younghoon Kim、SeongShick Ryu、Chiman Song、Nam Hoon Kwon、Youngji Moon、Sunghoon Kim、Nam Doo Kim、Hwan Geun Choi、Taebo Sim

  DOI：10.1021/acs.jmedchem.1c00459

  日期：2021.8.26

  Focal adhesion kinase (FAK) is overexpressed in highly invasive and metastatic cancers. To identify novel FAK inhibitors, we designed and synthesized various thieno[3,2-d]pyrimidine derivatives. An intensive structure–activity relationship (SAR) study led to the identification of 26 as a lead. Moreover, 26, a multitargeted kinase inhibitor, possesses excellent potencies against FLT3 mutants as well

  粘着斑激酶 (FAK) 在高度侵袭性和转移性癌症中过度表达。为了鉴定新型 FAK 抑制剂，我们设计并合成了各种噻吩并[3,2- d ]嘧啶衍生物。一项深入的构效关系 (SAR) 研究确定了26 个先导化合物。此外， 26是一种多靶点激酶抑制剂，对 FLT3 突变体和 FAK 具有优异的功效。令人欣喜的是， 26显着抑制顽固的 FLT3 突变体，包括导致耐药性的 F691L。重要的是，在 MDA-MB-231 异种移植小鼠模型中， 26在细胞凋亡诱导、锚定非依赖性生长抑制和肿瘤负荷减轻方面优于 PF-562271。此外， 26还能使 MV4-11 异种移植小鼠模型中的肿瘤生长消退，表明它可以有效对抗急性髓系白血病 (AML)。最后，在使用 MDA-MB-231 的原位小鼠模型中， 26显着阻止了原位肿瘤向淋巴结的转移。总而言之，结果表明26对高侵袭性癌症和复发性 AML 具有潜在的治疗价值。
• New Highly Potent NLRP3 Inhibitors: Furanochalcone Velutone F Analogues
  作者：Ruijia Zhang、Feng Hong、Min Zhao、Xiaoying Cai、Xueqin Jiang、Neng Ye、Kaiyue Su、Na Li、Minghai Tang、Xu Ma、Hengfan Ni、Lun Wang、Li Wan、Lijuan Chen、Wenshuang Wu、Haoyu Ye

  DOI：10.1021/acsmedchemlett.1c00597

  日期：2022.4.14

  inhibitors. Among them, compound 14c exerted remarkable inhibitory activity with an IC50 value in the nanomolar range (251.1 nM) and was approximately 5-fold more potent than velutone F. Moreover, the synthesis method of 14c was simple, easy to handle, and scalable. Compound 14c could suppress NLRP3 inflammasome activation by attenuating ASC speck formation. Most importantly, compound 14c reduced peritoneal

  NLRP3 炎症小体现已成为许多炎症相关疾病最有吸引力的药物靶点之一。Velutone F 是一种天然的 NLPR3 抑制剂，在我们之前的研究中发现，由于其植物丰度低、活性弱和合成路线复杂，其应用受到限制。为了满足这些需求，velutone F 的结构优化产生了一系列新型 NLRP3 抑制剂。其中，化合物14c具有显着的抑制活性，IC 50值在纳摩尔范围内（251.1 nM），比velutone F强约5倍。此外，14c的合成方法简单、易于操作且可扩展. 化合物14c可以通过减弱 ASC 斑点形成来抑制 NLRP3 炎性体激活。最重要的是，在 LPS 引发的小鼠模型中，化合物14c减少了小鼠腹膜中性粒细胞的流入和脾脏中 MSU 诱导的腹膜炎中的 IL-1β。总之，化合物14c是发现 NLRP3 炎性体抑制剂的潜在先导化合物。
• Benzimidazole Modulators of VR1
  申请人：Player Mark R.

  公开号：US20070259936A1

  公开（公告）日：2007-11-08

  The invention is directed to compounds of Formula (I): to pharmaceutical compositions containing such compounds and to methods of treatment using them.

  这项发明涉及到式（I）的化合物，以及包含这些化合物的药物组合物，以及使用它们的治疗方法。