2-噻吩甲甲酯-5-硼酸 | 876189-21-8

• 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: 2-噻吩甲甲酯-5-硼酸
• 中文别名: 噻吩-2-羧酸甲酯-5-硼酸
• 英文名称: (5-(methoxycarbonyl)thiophen-2-yl)boronic acid
• 英文别名: 5-Methoxycarbonylthiophene-2-boronic acid；(5-methoxycarbonylthiophen-2-yl)boronic acid
• CAS: 876189-21-8
• 化学式: C₆H₇BO₄S
• mdl: MFCD08443761
• 分子量: 185.996
• InChiKey: VJWFTDBWRPSNFS-UHFFFAOYSA-N

物化性质

• 沸点：
  386.7±52.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  95
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-(Methoxycarbonyl)thiophene-2-boronic acid
Synonyms: Methyl 5-boronothiophene-2-carboxylate

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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: 5-(Methoxycarbonyl)thiophene-2-boronic acid
CAS number: 876189-21-8

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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, 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
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C6H7BO4S
Molecular weight: 186.0

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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：

  2-噻吩甲甲酯-5-硼酸 在 N-溴代丁二酰亚胺(NBS) 、 [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 、 甲苯 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  [EN] NOVEL THIOPHENE COMPOUNDS AND METHOD FOR IN VIVO IMAGING
  [FR] NOUVEAUX COMPOSÉS DE THIOPHÈNE ET PROCÉDÉ POUR IMAGERIE IN VIVO

  摘要：

  本发明涉及公式（I）（C）n-B-（A）m-B-（C）n的新型标记化合物，其中m为0或1，n独立地为0、1、2或3，A、每个B和每个C独立地选自苯基和五元和六元杂芳环，对于末端环B或C还可以选自具有七至十个环成员的双环杂芳融合环，其中至少两个环A到C之间的键可以被羰基（-CO-）取代，其中至少两个环A到C被一个或两个基团R取代，每个环A到C还可以选择地被一个或两个基团R1取代，用于在活体患者中成像淀粉样沉积物和聚集蛋白。该发明还涉及使用公式I的标记或未标记化合物的成像方法，以及未标记化合物在这些方法中的使用。

  公开号：

  WO2013036196A1
• 作为产物：
  描述：

  5-溴噻吩-2-甲酸甲酯 在 双二甲胺基乙基醚 、 异丙基氯化镁 、 硼酸三甲酯 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到2-噻吩甲甲酯-5-硼酸
  参考文献：
  名称：

  使用i-PrMgCl-双[2-（N，N-二甲基氨基）乙基]醚络合物对带有敏感官能团的芳族卤化物进行非低温I / Br-Mg交换。

  摘要：

  [反应：见正文]在环境温度下，在双[2-（N，N-二甲基氨基）乙基]醚存在下，对带有敏感羧酸酯和氰基的碘代和溴代芳烃与异丙基氯化镁进行选择性卤化物-镁交换，得到相应的格氏试剂。使新形成的反应性格氏试剂与亲电子试剂如硼酸三甲酯反应，以良好或优异的产率得到芳基硼酸。

  DOI：

  10.1021/ol052704p

文献信息

• [EN] C-28 AMIDES OF MODIFIED C-3 BETULINIC ACID DERIVATIVES AS HIV MATURATION INHIBITORS<br/>[FR] AMIDES C-28 DE DÉRIVÉS D'ACIDE BÉTULINIQUE MODIFIÉS EN C-3, UTILISÉS COMME INHIBITEURS DE MATURATION DU VIH
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2011153319A1

  公开（公告）日：2011-12-08

  Compounds having drug and bio-affecting properties, their pharmaceutical compositions and methods of use are set forth. In particular, modified C-3 and C-28 betulinic acid derivatives that possess unique antiviral activity are provided as HIV maturation inhibitors. These compounds are useful for the treatment of HIV and AIDS.

  具有药物和生物活性的化合物、其药物组合物及其使用方法。特别是，提供了一种具有独特抗病毒活性的改性C-3和C-28桦木酸衍生物，用作HIV成熟抑制剂。这些化合物可用于治疗HIV和艾滋病。
• [EN] NOVEL THIOPHENE COMPOUNDS AND METHOD FOR IN VIVO IMAGING<br/>[FR] NOUVEAUX COMPOSÉS DE THIOPHÈNE ET PROCÉDÉ POUR IMAGERIE IN VIVO
  申请人：BIOCHROMIX AB

  公开号：WO2013036196A1

  公开（公告）日：2013-03-14

  The present invention relates to novel labelled compounds of formula (I) (C)n-B-(A)m-B-(C)n (I) wherein m is 0 or 1, and n is independently 0, 1, 2 or 3, A, each B and each C are independently selected from phenylene and five- and six-membered heteroaromatic rings, and for a terminal ring B or C also from bicyclic heteroaromatic fused rings having seven to ten ring members, wherein the bond between at least two of the rings A to C may be replaced by a carbonyl group ( -CO- ), wherein at least two of the rings A to C are substituted with one or two groups R, and wherein each ring A to C further optionally is substituted with one or two groups R1, for use in imaging amyloid deposits and aggregated protein in living patients. The invention further relates to imaging methods using labelled or unlabelled compounds of formual I and the use of unlabelled compounds in such methods.

  本发明涉及公式（I）（C）n-B-（A）m-B-（C）n的新型标记化合物，其中m为0或1，n独立地为0、1、2或3，A、每个B和每个C独立地选自苯基和五元和六元杂芳环，对于末端环B或C还可以选自具有七至十个环成员的双环杂芳融合环，其中至少两个环A到C之间的键可以被羰基（-CO-）取代，其中至少两个环A到C被一个或两个基团R取代，每个环A到C还可以选择地被一个或两个基团R1取代，用于在活体患者中成像淀粉样沉积物和聚集蛋白。该发明还涉及使用公式I的标记或未标记化合物的成像方法，以及未标记化合物在这些方法中的使用。
• Development and Characterization of New Inhibitors of the Human and Mouse Hematopoietic Prostaglandin D₂ Synthases
  作者：Angelika N. Christ、Larisa Labzin、Gregory T. Bourne、Hirotada Fukunishi、Jane E. Weber、Matthew J. Sweet、Mark L. Smythe、Jack U. Flanagan

  DOI：10.1021/jm100194a

  日期：2010.8.12

  The hematopoietic prostaglandin D2 synthase has a proinflammatory effect in a range of diseases, including allergic asthma, where its product prostaglandin D2 (PGD2) has a role in regulating many of the hallmark disease characteristics. Here we describe the development and characterization of a novel series of hematopoietic prostaglandin D2 synthase inhibitors with potency similar to that of known

  造血前列腺素D 2合酶在包括过敏性哮喘在内的多种疾病中具有促炎作用，其中其产物前列腺素D 2（PGD 2）在调节许多标志性疾病特征中起作用。在这里，我们描述了一系列新型造血前列腺素D 2合酶抑制剂的开发和表征，其功效与已知抑制剂相似。化合物N-苯甲酰基-5-（3-羟苯基）噻吩-2-羧酰胺（化合物8）和N-（1-氨基-1-氧代-3-苯基丙-2-基）-6-（噻吩-2-基烟酰胺（化合物34）在抑制纯化的酶方面表现出较低的微摩尔效价，而在小鼠原代骨髓来源的巨噬细胞和人巨核细胞系MEG-01S中，只有34种减少的Toll样受体（TLR）诱导的PGD 2产生。重要的是，34证实了抑制PGD的更大的选择性2合成与该位于PGH的下游的其它类花生酸2（PGE 2和前列腺环素（6-酮基PGF的标志物1α）和血栓素（TXB 2））相比，已知的抑制剂HQL -79（化合物1）和2-苯基-5-（1 H-吡唑-3-基
• [EN] SPIROCYCLIC CONTAINING COMPOUNDS AND PHARMACEUTICAL USES THEREOF<br/>[FR] COMPOSÉS CONTENANT DES SPIROCYCLIQUES ET LEURS UTILISATIONS PHARMACEUTIQUES
  申请人：PHARMASCIENCE INC

  公开号：WO2018032104A1

  公开（公告）日：2018-02-22

  The present invention relates to a novel family of covalent kinases inhibitors, compounds of this class have been found to have inhibitory activity against members of the TEC kinase family, particularly ITK and/or TXK, BTK, TEC and/or combinations thereof. The present invention is directed to a compound of Formula I or pharmaceutically acceptable salt, solvate, solvates of salt, stereoisomer, tautomer, isotope, prodrug, complex or biologically active metabolite thereof, for use in therapy.

  本发明涉及一种新型的共价激酶抑制剂家族，该类化合物已发现对TEC激酶家族的成员，特别是ITK和/或TXK，BTK，TEC和/或其组合具有抑制活性。本发明涉及一种具有I式结构的化合物或其药学上可接受的盐、溶剂、盐的溶剂体、立体异构体、互变异构体、同位素、前药、复合物或其生物活性代谢物，用于治疗。
• Design, Synthesis, and Biological Evaluation of Orally Bioavailable CHK1 Inhibitors Active against Acute Myeloid Leukemia
  作者：Tingting Jin、Peipei Wang、Xiubing Long、Kailong Jiang、Pinrao Song、Wenbiao Wu、Gaoya Xu、Yubo Zhou、Jia Li、Tao Liu

  DOI：10.1002/cmdc.202000882

  日期：2021.5.6

  Checkpoint kinase 1 (CHK1) is a central component in DNA damage response and has emerged as a target for antitumor therapeutics. Herein, we describe the design, synthesis, and biological evaluation of a novel series of potent diaminopyrimidine CHK1 inhibitors. The compounds exhibited moderate to potent CHK1 inhibition and could suppress the proliferation of malignant hematological cell lines. The optimized

  检查点激酶 1 (CHK1) 是 DNA 损伤反应的核心成分，已成为抗肿瘤治疗的靶点。在此，我们描述了一系列新型强效二氨基嘧啶 CHK1 抑制剂的设计、合成和生物学评价。这些化合物表现出中度至强效的 CHK1 抑制作用，并能抑制恶性血液细胞系的增殖。优化后的化合物13的CHK1 IC 50值为7.73±0.74 nM，MV-4-11细胞对其敏感（IC 50 =0.035±0.007 μM）。此外，化合物13在体外小鼠肝微粒体中的代谢稳定，并在体内显示出中等的口服生物利用度. 此外，用化合物13处理 MV-4-11 细胞2 小时导致对丝氨酸 296 上 CHK1 自磷酸化的强烈抑制。基于这些生化结果，我们认为化合物13是一种有前途的 CHK1 抑制剂和潜在的抗癌治疗剂。