4-苯基甲酰氨苯基硼酸 | 330793-45-8

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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-苯基甲酰氨苯基硼酸
• 中文别名: 4-苯基氨甲酰基苯硼酸
• 英文名称: (4-(phenylcarbamoyl)phenyl)boronic acid
• 英文别名: 4-phenylaminocarbonylphenylboronic acid；4-(phenylcarbamoyl)phenylboronic acid；{4-[(phenylamino)carbonyl]phenyl}boronic acid；[4-(anilinocarbonyl)phenyl]boronic acid；4-(anilinocarbonyl)phenylboronic acid；[4-(phenylcarbamoyl)phenyl]boronic acid
• CAS: 330793-45-8
• 化学式: C₁₃H₁₂BNO₃
• mdl: MFCD04115683
• 分子量: 241.054
• InChiKey: DAUSGSRIYCUJDK-UHFFFAOYSA-N

物化性质

• 熔点：
  210-216°C
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

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：
  2931900090
• 危险性防范说明：
  P264,P271,P302+P352,P305+P351+P338,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  保持冷静

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-Phenylaminocarbonylphenylboronic acid
Product Name:
Synonyms: N-Phenyl 4-boronobenzamide

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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.
4-Phenylaminocarbonylphenylboronic acid
Ingredient name:
CAS number: 330793-45-8

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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: C13H12BNO3
Molecular weight: 241.1

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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.

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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：

  4-苯基甲酰氨苯基硼酸 在 N-碘代丁二酰亚胺 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(4-amino-7-iodothieno[3,2-c]pyridin-3-yl)-N-phenylbenzamide
  参考文献：
  名称：

  发现噻吩并[3,2 - c ]吡啶-4-胺作为新型布鲁顿酪氨酸激酶（BTK）抑制剂

  摘要：

  设计，合成和表征了一系列以噻吩并[3,2 - c ]吡啶-4-胺骨架为核心骨架的新型BTK抑制剂。在本文中，二十一种化合物在体外显示出对BTK酶的不同抑制活性，而化合物14g对BTK酶显示出最有效的抑制活性，IC 50值为12.8 nM。而且，化合物14g显示出相对良好的激酶选择性，并且随后在体内评估了其PK特性。这项工作确定了thieno [3,2 - c ] pyridin-4-amine衍生物是新型的BTK抑制剂，并验证了thieno [3,2 - c ] pyridin-4-amine支架在药物设计中的价值。

  DOI：

  10.1016/j.bmc.2015.05.043
• 作为产物：
  描述：

  4-羧基苯硼酸 、 苯胺 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 生成 4-苯基甲酰氨苯基硼酸
  参考文献：
  名称：

  从芳基脲到联芳基酰胺再到氨基喹唑啉：发现新型有效的TRPV1拮抗剂。

  摘要：

  铅VR1拮抗剂1中芳基环的哌嗪生物等位取代导致了联芳基酰胺系列的产生。B环SAR的发展导致构象受限的类似物70。所得氨基喹唑啉70代表一种新型VR1拮抗剂，与先导系列的类似化合物相比，具有更高的体外效价和口服生物利用度。

  DOI：

  10.1016/j.bmcl.2006.07.010

文献信息

• Pyrazolopyrimidines as therapeutic agents
  申请人：Abbott Laboratories

  公开号：US20020156081A1

  公开（公告）日：2002-10-24

  The present invention provides compounds of Formula I, 1 including pharmaceutically acceptable salts and/or prodrugs thereof, where G, R 2 , and R 3 are defined as described herein.

  本发明提供了公式I的化合物，包括其药学上可接受的盐和/或前药，其中G、R2和R3的定义如本文所述。
• Universal Solid-Phase Approach for the Immobilization, Derivatization, and Resin-to-Resin Transfer Reactions of Boronic Acids
  作者：Michel Gravel、Kim A. Thompson、Mark Zak、Christian Bérubé、Dennis G. Hall

  DOI：10.1021/jo0106501

  日期：2002.1.1

  amides, anilides, and ureas, respectively. Ugi multicomponent reactions on DEAM-PS-supported aminobenzeneboronic acids, derivatization of multifunctional arylboronic acids, and sequential reactions can also be carried out efficiently. These new DEAM-PS-supported arylboronic acids can be employed directly into resin-to-resin transfer reactions (RRTR). This type of multiresin process helps eliminate time-consuming

  含硼酸的分子广泛用于生物学，医学和合成领域。然而，这些化合物往往难以通过溶液相方法处理。在此，该问题通过用于官能化硼酸的衍生化的第一种通用固相方法的开发来解决。该方法基于使用二乙醇胺树脂锚，该锚通过避免在酯化过程中彻底去除水的需要而促进了硼酸的固定。通过在室温下在无水溶剂中简单搅拌，可以在数分钟内将多种硼酸固定在N，N-二乙醇氨基甲基聚苯乙烯（DEAM-PS，1）上。通过（1）DEAM-PS负载的对甲苯基硼酸的（1）NMR分析显示了形成具有假定的NB配位的双环二乙醇胺硼酸酯的证据。通过紫外光谱研究了DEAM-PS树脂对相同型号硼酸的水解裂解。水解和附着显示在快速达到的平衡下发生，并且需要大量过量的水（> 32当量）以实现从DEAM-PS实际定量释放硼酸。尽管它们对水和醇具有相对的敏感性，但可以用甲酰基，溴甲基，羧基或氨基官能化的DEAM-PS结合的芳基硼酸以良好或极高的收率转化成各种胺，酰
• Discovery of Evobrutinib: An Oral, Potent, and Highly Selective, Covalent Bruton’s Tyrosine Kinase (BTK) Inhibitor for the Treatment of Immunological Diseases
  作者：Richard D. Caldwell、Hui Qiu、Ben C. Askew、Andrew T. Bender、Nadia Brugger、Montserrat Camps、Mohanraj Dhanabal、Vikram Dutt、Thomas Eichhorn、Anna S. Gardberg、Andreas Goutopoulos、Roland Grenningloh、Jared Head、Brian Healey、Brian L. Hodous、Bayard R. Huck、Theresa L. Johnson、Christopher Jones、Reinaldo C. Jones、Igor Mochalkin、Federica Morandi、Ngan Nguyen、Michael Meyring、Justin R. Potnick、Dusica Cvetinovic Santos、Ralf Schmidt、Brian Sherer、Adam Shutes、Klaus Urbahns、Ariele Viacava Follis、Ansgar A. Wegener、Simone C. Zimmerli、Lesley Liu-Bujalski

  DOI：10.1021/acs.jmedchem.9b00794

  日期：2019.9.12

  Bruton's tyrosine kinase (BTK) inhibitors such as ibrutinib hold a prominent role in the treatment of B cell malignancies. However, further refinement is needed to this class of agents, particularly in terms of adverse events (potentially driven by kinase promiscuity), which preclude their evaluation in nononcology indications. Here, we report the discovery and preclinical characterization of evobrutinib

  Bruton的酪氨酸激酶（BTK）抑制剂如ibrutinib在B细胞恶性肿瘤的治疗中起着重要作用。但是，此类药物需要进一步改进，特别是在不良事件（可能由激酶混杂引起的不良事件）方面，这使其无法在非肿瘤适应症中进行评估。在这里，我们报告evobrutinib的发现和临床前表征，evobrutinib是一种具有高激酶选择性的有效的专性共价抑制剂。Evobrutinib表现出足够的临床前药代动力学和药效动力学特征，可在功效模型中进行体内评估。此外，依武鲁替尼对BTK的选择性高于表皮生长因子受体和其他Tec家族激酶，这表明脱靶相关不良反应的可能性较低。
• [EN] PHENYL OR HETEROARYL AMINO ALKANE DERIVATIVES AS IP RECEPTOR ANTAGONIST<br/>[FR] DERIVES DE PHENYL- OU HETEROARYLAMINO-ALCANES COMME ANTAGONISTES DU RECEPTEUR IP
  申请人：BAYER HEALTHCARE AG

  公开号：WO2004043926A1

  公开（公告）日：2004-05-27

  The present invention relates to a phenyl or heteroaryl amino alkane derivatives which are useful as an active ingredient of pharmaceutical preparations. The phenyl or heteroaryl amino alkanes of the present invention have IP receptor antagonistic activity, and can be used for the prophylaxis and treatment of diseases associated with IP receptor antagonistic activity. Such diseases include urological diseases or disorder as follows: bladder outlet obstruction, overactive bladder, urinary incontinence, detrusor hyper-reflexia, detrusor instability, reduced bladder capacity, frequency of micturition, urge incontinence, stress incontinence, bladder hyperreactivity, benighn prostatic hypertrophy (BPH), prostatitis, urinary frequency, nocturia, urinary urgency, pelvic hypersensitivity, urethritis, pelvic pain syndrome, prostatodynia, cystitis, or idiophatic bladder hypersensitivity. The compounds of the present invention are also useful for treatment of pain including, but not limited to inflammatory pain, neuropathic pain, acute pain, chronic pain, dental pain, premenstrual pain, visceral pain, headaches, and the like; hypotension; hemophilia and hemorrhage; and inflammation, since the diseases also is alleviated by treatment with an IP receptor antagonist.

  本发明涉及一种苯基或杂环烷基氨基烷衍生物，其作为药物制剂的活性成分是有用的。本发明的苯基或杂环烷基氨基烷具有IP受体拮抗活性，并可用于预防和治疗与IP受体拮抗活性相关的疾病。这些疾病包括泌尿系统疾病或障碍，如：膀胱出口梗阻、膀胱过度活跃、尿失禁、膀胱逼尿肌过度反射、膀胱逼尿肌不稳定、膀胱容量减少、排尿频率增加、急迫性尿失禁、压力性尿失禁、膀胱高反应性、良性前列腺增生（BPH）、前列腺炎、尿频、夜尿频、尿急、盆腔过敏、尿道炎、盆腔疼痛综合征、前列腺疼痛综合征、膀胱炎或特发性膀胱过敏。本发明的化合物还可用于治疗疼痛，包括但不限于炎症性疼痛、神经病性疼痛、急性疼痛、慢性疼痛、牙痛、经前疼痛、内脏疼痛、头痛等；低血压；血友病和出血；以及炎症，因为这些疾病也可以通过IP受体拮抗剂治疗而得到缓解。
• 噻吩并[3,2-c]吡啶类化合物、其制备方法及 应用
  申请人：南京勇山生物科技有限公司

  公开号：CN104945411B

  公开（公告）日：2018-07-31

  本发明涉及一类噻吩并[3,2‑c]吡啶类化合物及其应用，其具有式（I）结构。本发明的结构如式（I）所示的化合物对布鲁顿激酶活性具有很好的抑制作用，本发明还涉及此类化合物在预防和/或治疗因BTK（Bruton酪氨酸激酶）活性抑制而改善的疾病中的应用。