3-噻吩-3-苯甲酸 | 20608-89-3

• 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: 3-噻吩-3-苯甲酸
• 中文别名: 3-(3-噻吩基)-苯甲酸
• 英文名称: 3-(3-thienyl)benzoic acid
• 英文别名: 3-(Thiophen-3-yl)benzoic acid；3-thiophen-3-ylbenzoic acid
• CAS: 20608-89-3
• 化学式: C₁₁H₈O₂S
• 分子量: 204.249
• InChiKey: JYLQNWVVMDHMRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  177 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(Thiophen-3-yl)benzoic acid
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: 3-(Thiophen-3-yl)benzoic acid
CAS number: 20608-89-3

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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.
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: C11H8O2S
Molecular weight: 204.2

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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, 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-fluorobenzenesulfonylhydrazide 、 3-噻吩-3-苯甲酸 在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 17.0h， 以90%的产率得到2-fluoro-N'-(3-(thiophen-3-yl)benzoyl)benzenesulfonohydrazide
  参考文献：
  名称：

  Discovery of Acylsulfonohydrazide-Derived Inhibitors of the Lysine Acetyltransferase, KAT6A, as Potent Senescence-Inducing Anti-Cancer Agents

  摘要：

  A high-throughput screen designed to discover new inhibitors of histone acetyltransferase KAT6A uncovered CTX-0124143 (1), a unique aryl acylsulfonohydrazide with an IC50 of 1.0 mu M. Using this acylsulfonohydrazide as a template, we herein disclose the results of our extensive structure-activity relationship investigations, which resulted in the discovery of advanced compounds such as 55 and 80. These two compounds represent significant improvements on our recently reported prototypical lead WM-8014 (3) as they are not only equivalently potent as inhibitors of KAT6A but are less lipophilic and significantly more stable to microsomal degradation. Furthermore, during this process, we discovered a distinct structural subclass that contains key 2-fluorobenzenesulfonyl and phenylpyridine motifs, culminating in the discovery of WM-1119 (4). This compound is a highly potent KAT6A inhibitor (IC50 = 6.3 nM; K-D = 0.002 mu M), competes with Ac-CoA by binding to the Ac-CoA binding site, and has an oral bioavailability of 56% in rats.

  DOI：

  10.1021/acs.jmedchem.9b02071
• 作为产物：
  描述：

  3-噻吩硼酸 、 间溴苯甲酸 在 乙二胺四乙酸 、 potassium carbonate 、 palladium dichloride 作用下， 反应 1.0h， 以86%的产率得到3-噻吩-3-苯甲酸
  参考文献：
  名称：

  Pd-EDTA是水中铃木-宫浦反应的有效催化剂

  摘要：

  PdCl 2 -EDTA络合物1是在20-100°C的水中，芳基和杂芳基卤化物与芳基（杂芳基）硼酸的Suzuki-Miyaura反应的有效催化剂。芳基碘化物和溴化物进行交叉耦合，其周转数（TON）高达97,000，周转频率（TOF）高达582,000 h -1。

  DOI：

  10.1016/j.tetlet.2005.06.085

文献信息

• Efficient and Recyclable Catalyst of Palladium Nanoparticles Stabilized by Polymer Micelles Soluble in Water for Suzuki-Miyaura Reaction, Ostwald Ripening Process with Palladium Nanoparticles
  作者：Irina Beletskaya、Alexander Kashin、Irina Khotina、Alexey Khokhlov

  DOI：10.1055/s-2008-1078430

  日期：2008.6

  Pd-nanoparticle size because the small nanoparticles dissolve to form larger nanoparticles in the course of reaction as well as in the presence of the only reagent, ArI. In the latter case, additionally, the formation of very small, not completely dissolved Pd nanoparticles, obviously having a high catalyst activity, is observed. This observation, together with the catalyst activity data might have an implication

  研究了由PS-PEO共聚物和N-十六烷基氯化吡啶作为表面活性剂形成的含Pd水溶性胶束催化ArX (I, Br)与Ar'B(OH) 2 的Suzuki-Miyaura交叉偶联反应在水和甲醇中。该反应在温和条件下（温度高达 50°C）进行，催化剂可以通过超滤回收（5 次）而不会损失其催化活性。观察到这种现象，包括 Pd 纳米颗粒尺寸的增加，因为小纳米颗粒在反应过程中以及在唯一的试剂 ArI 存在下溶解形成更大的纳米颗粒。此外，在后一种情况下，观察到非常小的、未完全溶解的 Pd 纳米粒子的形成，显然具有高催化剂活性。这个观察，
• Carboxamide compounds and their use as antagonists of a human 11cby receptor
  申请人：——

  公开号：US20040063686A1

  公开（公告）日：2004-04-01

  Compounds of formula (I) in which: each A is independently hydrogen, C1-6alkyl optionally substituted by hydroxyl, C1-6alkoxy, C1-6alkenyl or C1-6acyl group or a halogen atom or hydroxyl, CN or CF3 group; R3 is hydrogen, methyl or ethyl; R4 is an optionally substituted aromatic carbocyclic or heterocyclic ring; Z is an O or S atom, or an NH or CH2 group, or a single bond, at the 3 or 4 position of R4 relative to the carbonyl group; R5 is an optionally substituted aromatic carbocyclic or heterocyclic ring, or an optionally substituted, saturated or unsaturated, carbocyclic or heterocyclic ring; and Q is (a) Where X, Y, R1 and R2 are as defined in claim 1; are antagonists of a human 11CBy receptor. 1

  化合物的公式(I)如下：其中：每个A都是独立的氢，C1-6烷基，可选择性地被氢氧基，C1-6氧烷基，C1-6烯基或C1-6酰基或卤素原子或氢氧基，CN或CF3基替代；R3是氢，甲基或乙基；R4是一个可选择性替代的芳香环或杂环；Z是O或S原子，或NH或CH2基，或与羰基相对的R4的3或4位置上的单键；R5是可选择性替代的芳香环或杂环，或可选择性替代的饱和或不饱和的芳香环或杂环；Q是(a)其中X，Y，R1和R2如权利要求1所定义；是人类11CBy受体的拮抗剂。
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：AMURA THERAPEUTICS LTD

  公开号：WO2009112839A1

  公开（公告）日：2009-09-17

  A first aspect of the invention relates to a compound of formula (I), or a pharmaceutically acceptable salt, hydrate, complex or pro-drug thereof, wherein: R3 is selected from cyclopentyl and cyclohexyl; R9 is a substituted 5 or 6-membered aryl or heteroaryl group or a 6,5- or 6,6-fused biaryl or heterobiaryl group. Compounds of formula (I) exhibit surprisingly high dual efficacies for human cathepsin S and K and are useful for the treatment of rheumatoid arthritis, osteoarthritis, chronic obstructive pulmonary disease (COPD), atherosclerosis, cardiovascular diseases which exhibit significant damage and remodeling of extracellular matrix (ECM) and chronic pain.

  本发明的第一个方面涉及公式(I)的化合物，或其药学上可接受的盐、水合物、复合物或前药，其中：R3选自环戊基和环己基；R9是取代的5或6成员芳基或杂芳基或6,5-或6,6-融合的双芳基或双杂芳基。公式(I)的化合物表现出对人类卡特普汀S和K的惊人双重功效，并可用于治疗类风湿性关节炎、骨关节炎、慢性阻塞性肺病（COPD）、动脉粥样硬化、心血管疾病，这些疾病表现出显着的细胞外基质（ECM）的损伤和重塑以及慢性疼痛。
• [EN] FURO [3, 2-B] PYRR0L-3-0NES AS CATHEPSIN S INHIBITORS<br/>[FR] FURO[3,2-B]PYRROL-3-ONES EN TANT QU'INHIBITEURS DE CATHÉPSINE S
  申请人：AMURA THERAPEUTICS LTD

  公开号：WO2009112826A1

  公开（公告）日：2009-09-17

  A first aspect of the invention relates to a compound of formula (I), or a pharmaceutically acceptable salt, hydrate, complex or pro-drug thereof, wherein: one of R3 and R4 is H, and the other is selected from C1-6-alkyl, C1-6-haloalkyl, C1-6- alkoxy, and C6-12-aralkyl; or R3 and R4 are each independently selected from C1-6-aIkyl and halo; R9 is a substituted 5 or 6-membered aryl or heteroaryl group or a 6,5- or 6,6-fused biaryl or heterobiaryl group. Compounds of formula (I) exhibit surprisingly high efficacies for human cathepsin S, excellent selectivity verses other mammalian cathepsins and are useful for treatment of diseases such as rheumatoid arthritis, multiple sclerosis, myasthenia gravis, transplant rejection, diabetes, Sjogrens syndrome, Grave's disease, systemic lupus erythematosis, osteoarthritis, psoriasis, idiopathic thrombocytopenic purpura, allergic rhinitis, asthma, atherosclerosis, obesity, chronic obstructive pulmonary disease and chronic pain.

  本发明的第一个方面涉及式（I）的化合物，或其药学上可接受的盐，水合物，复合物或前药，其中：R3和R4中的一个为H，另一个选自C1-6烷基，C1-6卤代烷基，C1-6烷氧基和C6-12芳基烷基; 或R3和R4各自独立地选自C1-6烷基和卤素; R9是取代的5或6成员芳基或杂芳基或6,5-或6,6-融合的双芳基或双杂芳基。式（I）的化合物表现出对人类卡特普辛S的惊人高效性，对其他哺乳动物卡特普辛具有优异的选择性，并可用于治疗风湿性关节炎，多发性硬化症，重症肌无力，移植排斥反应，糖尿病，Sjogrens综合症，Grave病，系统性红斑狼疮，骨关节炎，银屑病，特发性血小板减少性紫癜，过敏性鼻炎，哮喘，动脉粥样硬化，肥胖症，慢性阻塞性肺疾病和慢性疼痛等疾病的治疗。
• [EN] CARBOXAMIDE COMPOUNDS AND THEIR USE AS ANTAGONISTS OF A HUMAN 11CBY RECEPTOR<br/>[FR] COMPOSES DU CARBOXAMIDE ET LEUR UTILISATION COMME ANTAGONISTES D'UN RECEPTEUR 11CBY HUMAIN
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2002010146A1

  公开（公告）日：2002-02-07

  Compounds of formula (I) in which: each A is independently hydrogen, C1-6alkyl optionally substituted by hydroxyl, C1-6alkoxy, C1-6alkenyl or C1-6acyl group or a halogen atom or hydroxyl, CN or CF3 group; R3 is hydrogen, methyl or ethyl; R4 is an optionally substituted aromatic carbocyclic or heterocyclic ring; Z is an O or S atom, or an NH or CH2 group, or a single bond, at the 3 or 4 position of R4 relative to the carbonyl group; R5 is an optionally substituted aromatic carbocyclic or heterocyclic ring, or an optionally substituted, saturated or unsaturated, carbocyclic or heterocyclic ring; and Q is (a) Where X, Y, R1 and R2 are as defined in claim 1; are antagonists of a human 11CBy receptor.

  化合物的公式（I），其中：每个A是独立的氢、C1-6烷基（可选择性地被羟基、C1-6烷氧基、C1-6烯基或C1-6酰基或卤原子或羟基、CN或CF3基替代）、R3是氢、甲基或乙基、R4是可选择性取代的芳香环烃或杂环烃环、Z是O或S原子、或NH或CH2基、或与羰基相对于R4的3或4位置的单键、R5是可选择性取代的芳香环烃或杂环烃环、或可选择性取代的饱和或不饱和的芳香环烃或杂环烃环；Q是（a）式，其中X、Y、R1和R2如权利要求1所定义；是人类11CBy受体的拮抗剂。