5-甲酸基-4-甲基噻吩-2-硼酸 | 352530-25-7

• 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 - 有机杂环化合物 - 噻吩类
• 中文名称: 5-甲酸基-4-甲基噻吩-2-硼酸
• 中文别名: 5-硼-3-甲基噻吩-2-羧醛
• 英文名称: (5-formyl-4-methylthiophen-2-yl)boronic acid
• CAS: 352530-25-7
• 化学式: C₆H₇BO₃S
• mdl: MFCD03093890
• 分子量: 169.997
• InChiKey: QEIXJCOHLUKRPO-UHFFFAOYSA-N

物化性质

• 熔点：
  118-120°C
• 沸点：
  404.2±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  85.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
5-Borono-3-methylthiophene-2-carboxaldehyde
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.
5-Borono-3-methylthiophene-2-carboxaldehyde
Ingredient name:
CAS number: 352530-25-7

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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.
Store in closed vessels, under −20◦C.
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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C6H7BO3S
Molecular weight: 170.0

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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, 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：

  5-甲酸基-4-甲基噻吩-2-硼酸 在 四(三苯基膦)钯 、 氨 、 sodium carbonate 、 三乙胺 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 97.34h， 生成 (+/-)-4-(2-amino-5-(5-((dimethylamino)methyl)-4-methylthiophen-2-yl)pyridin-3-yl)-2-(1-(2-(trifluoromethyl)phenyl)ethoxy)benzamide
  参考文献：
  名称：

  Design of Potent and Selective Hybrid Inhibitors of the Mitotic Kinase Nek2: Structure–Activity Relationship, Structural Biology, and Cellular Activity

  摘要：

  We report herein a series of Nek2 inhibitors based on an aminopyridine scaffold. These compounds have been designed by combining key elements of two previously discovered chemical series. Structure based design led to aminopyridine (R)-21, a potent and selective inhibitor able to modulate Nek2 activity in cells.

  DOI：

  10.1021/jm201683b

文献信息

• [EN] PYRROLONE MELANIN CONCENTRATING HORMONE RECEPTOR-1 ANTAGONISTS<br/>[FR] ANTAGONISTES DE RÉCEPTEUR D'HORMONE CONCENTRANT LA MÉLANINE 1 DE TYPE PYRROLONE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2010042674A1

  公开（公告）日：2010-04-15

  The present application provides compounds, including all stereoisomers, solvates, prodrugs and pharmaceutically acceptable forms thereof according to Formula I wherein R1, Formula Ia, R4, R5, Formula Ib, R3, R3a, W, D, R2a, R2b and R2c are defined herein. Additionally, the present application provides pharmaceutical compositions containing at least one compound according to Formula I and optionally at least one additional therapeutic agent. Finally, the present application provides methods for treating a patient suffering from an MCHR-1 modulated disease or disorder such as, for example, obesity, diabetes, depression, anxiety or intestinal inflammation, by administration of a therapeutically effective dose of a compound according to Formula I.

  本申请提供了根据公式I提供的化合物，包括所有立体异构体、溶剂合物、前药和药用可接受形式，其中R1、公式Ia、R4、R5、公式Ib、R3、R3a、W、D、R2a、R2b和R2c在此处定义。此外，本申请提供了含有至少一种根据公式I的化合物和可选至少一种额外治疗剂的药物组合物。最后，本申请提供了治疗患有MCHR-1调节性疾病或紊乱的患者的方法，例如肥胖、糖尿病、抑郁症、焦虑或肠道炎症，通过给予根据公式I的化合物的治疗有效剂量。
• Discovery of a potent, highly selective, and orally bioavailable inhibitor of CDK8 through a structure-based optimisation
  作者：Mingfeng Yu、Yi Long、Yuchao Yang、Manjun Li、Theodosia Teo、Benjamin Noll、Stephen Philip、Shudong Wang

  DOI：10.1016/j.ejmech.2021.113391

  日期：2021.6

  is viewed as a therapeutic target for the treatment of the disease. Accordingly, the search for small-molecule inhibitors of CDK8 is being intensified. Capitalising on our initial discovery of AU1-100, a potent CDK8 inhibitor yet with a limited degree of kinase selectivity, a structure-based optimisation was carried out, with a series of new multi-substituted pyridines rationally designed, chemically

  CDK8 在多种类型的人类癌症中失调，被视为治疗该疾病的治疗靶点。因此，正在加紧寻找 CDK8 的小分子抑制剂。利用我们最初发现的 AU1-100，一种有效的 CDK8 抑制剂，但激酶选择性有限，我们进行了基于结构的优化，对一系列新的多取代吡啶进行了合理设计、化学制备和生物学评估。这种努力最终确定了42，这是一种更有效的 CDK8 抑制剂，具有优异的运动学选择性和口服生物利用度。42抗增殖作用的机制对 MV4-11 细胞进行了研究，表明该化合物可以阻止 G1 细胞周期并引发细胞凋亡。估计42的肝毒性和心脏毒性的风险较低。这些发现值得进一步研究42作为靶向癌症治疗剂。
• A convenient synthesis of 4(5)-(hetero)aryl-1H-imidazoles via microwave-assisted Suzuki–Miyaura cross-coupling reaction
  作者：Sophie Vichier-Guerre、Laurence Dugué、Sylvie Pochet

  DOI：10.1016/j.tetlet.2014.09.104

  日期：2014.11

  A simple and rapid access to a variety of 4(5)-arylated imidazoles via palladium-catalyzed Suzuki–Miyaura cross-coupling reaction is described. Coupling parameters were screened for efficient C-4 arylation of N-unprotected 4-iodoimidazole with a broad range of boronic acids under microwave irradiation. Twenty-one imidazole derivatives were synthesized in modest to excellent yields in short reaction

  描述了通过钯催化的Suzuki-Miyaura交叉偶联反应快速简便地获得各种4（5）-芳基咪唑的方法。在微波辐射下，筛选了用于N-未保护的4-碘咪唑与各种硼酸的有效C-4芳基化的偶联参数。在短的反应时间内以适中至优异的产率合成了二十一种咪唑衍生物。
• Utilization of an Active Site Mutant Receptor for the Identification of Potent and Selective Atypical 5-HT_2C Receptor Agonists
  作者：Joseph Carpenter、Ying Wang、Gang Wu、Jianxin Feng、Xiang-Yang Ye、Christian L. Morales、Matthias Broekema、Karen A. Rossi、Keith J. Miller、Brian J. Murphy、Ginger Wu、Sarah E. Malmstrom、Anthony V. Azzara、Philip M. Sher、John M. Fevig、Andrew Alt、Robert L. Bertekap、Mary Jane Cullen、Timothy M. Harper、Kimberly Foster、Emily Luk、Qian Xiang、Mary F. Grubb、Jeffrey A. Robl、Dean A. Wacker

  DOI：10.1021/acs.jmedchem.7b00385

  日期：2017.7.27

  additionally report the discovery and optimization of a novel class of nonbasic heterocyclic amide agonists of 5-HT2C. SAR investigations around the screening hits provided a diverse set of potent agonists at 5-HT2C with high selectivity over the related 5-HT2A and 5-HT2B receptor subtypes. Further optimization through replacement of the amide with a variety of five- and six-membered heterocycles led to the identification

  5-HT 2C受体的拮抗作用是药理学减轻体重的最深入研究和临床证明的机制之一。对密切相关的5-HT 2A和5-HT 2B受体的选择性至关重要，因为已证明它们的活化会导致不良的副作用和重大的安全隐患。在此通讯中，我们报告了一种新的筛选范例的开发，该范例利用了活性位点突变体D134A（D3.32）5-HT 2C受体来鉴定非典型激动剂结构。我们还报告了5-HT 2C的新型非碱性杂环酰胺激动剂的发现和优化。围绕筛选结果的SAR调查为5-HT提供了多种有效的激动剂2C具有对相关5-HT 2A和5-HT 2B受体亚型的高选择性。通过用各种五元和六元杂环取代酰胺进行进一步优化，导致鉴定出6-（1-乙基-3-（喹啉-8-基）-1 H-吡唑-5-基）哒嗪-3-胺（69）。老鼠口服给药69可减少随意采食模型中的食物摄入量，而选择性5-HT 2C拮抗剂可完全逆转这种情况。
• PYRROLONE MELANIN CONCENTRATING HORMONE RECEPTOR-1 ANTAGONISTS
  申请人：Zhao Guohua

  公开号：US20110195986A1

  公开（公告）日：2011-08-11

  The present application provides compounds, including all stereoisomers, solvates, prodrugs and pharmaceutically acceptable forms thereof according to Formula I wherein R 1 , R 4 , R 5 , R 3 , R 3a , W, D, R 2a , R 2b and R 2c are defined herein. Additionally, the present application provides pharmaceutical compositions containing at least one compound according to Formula I and optionally at least one additional therapeutic agent. Finally, the present application provides methods for treating a patient suffering from an MCHR-1 modulated disease or disorder such as, for example, obesity, diabetes, depression, anxiety or intestinal inflammation, by administration of a therapeutically effective dose of a compound according to Formula I.

  本申请提供了按照式I定义的化合物，包括所有立体异构体、溶剂合物、前药和药学上可接受的形式，其中R1、R4、R5、R3、R3a、W、D、R2a、R2b和R2c在此定义。此外，本申请提供了含有至少一种式I化合物和可选的至少一种额外治疗剂的制药组合物。最后，本申请提供了通过给予式I化合物的治疗有效剂量来治疗患有MCHR-1调节性疾病或失调的患者的方法，例如肥胖症、糖尿病、抑郁症、焦虑症或肠道炎症。