4-溴苯并[b]噻吩-2-羧酸 | 5194-37-6

• 物质功能分类: 医药中间体 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 4-溴苯并[b]噻吩-2-羧酸
• 中文别名: 4-溴苯并噻吩2-羧酸；4-溴苯并[B]噻吩-2-甲酸
• 英文名称: 4-bromobenzo[b]thiophene-2-carboxylic acid
• 英文别名: 4-Bromo-1-benzothiophene-2-carboxylic acid
• CAS: 5194-37-6
• 化学式: C₉H₅BrO₂S
• 分子量: 257.107
• InChiKey: LAYNZUFIYSYHIV-UHFFFAOYSA-N

物化性质

• 熔点：
  265
• 沸点：
  429.7±25.0 °C(Predicted)
• 密度：
  1.813±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  1
• 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

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，避光、干燥密闭保存。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4-Bromo-1-benzothiophene-2-carboxylic acid
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 4-Bromo-1-benzothiophene-2-carboxylic acid
CAS number: 5194-37-6

---

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.

---

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.

---

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.

---

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, refrigerated.
Storage:

---

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.

---

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: C9H5BrO2S
Molecular weight: 257.1

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen bromide, sulfur oxides.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-溴苯并[b]噻吩-2-羧酸 在 氯化亚砜 作用下， 以 乙醚 、 苯 为溶剂， 反应 0.25h， 生成 4-bromobenzothiophene-2-N-methylcarboxamide
  参考文献：
  名称：

  Sharma, K. S.; Lata, Suman, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 1, p. 38 - 41

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴苯并[b]噻吩-2-羧酸甲酯 在 水 、 lithium hydroxide 作用下， 生成 4-溴苯并[b]噻吩-2-羧酸
  参考文献：
  名称：

  苯并[b]噻吩 1,1-二氧化物衍生物作为强效 STAT3 抑制剂的设计、合成和生物学评价

  摘要：

  作为信号转导和转录激活因子 (STAT) 家族的成员，STAT3 在细胞增殖、迁移、存活和分化等多种生物学途径中发挥着关键作用。由于肿瘤中的异常持续激活，抑制 STAT3 已成为治疗各种癌细胞的有吸引力的方法。在此，我们报告了一系列基于苯并[b]噻吩 1,1-二氧化物支架的新型 STAT3 抑制剂，并评估了它们的抗癌效力。其中，化合物8b对癌细胞表现出最好的活性。化合物8b诱导细胞凋亡并阻断细胞周期。同时，8b减少细胞内 ROS 含量并导致线粒体膜电位丧失。进一步的研究表明，8b显着阻断了 STAT3 磷酸化，并且 STAT3 依赖性双荧光素酶报告基因实验表明，化合物8b对 STAT3 介导的萤火虫荧光素酶活性具有显着抑制作用。分子模型研究表明，化合物8b以良好的构象占据了具有 SH2 结构域的口袋。

  DOI：

  10.1111/cbdd.13939

文献信息

• MONOMERS CAPABLE OF DIMERIZING IN AN AQUEOUS SOLUTION, AND METHODS OF USING SAME
  申请人：Barany Francis

  公开号：US20140194383A1

  公开（公告）日：2014-07-10

  Described herein are monomers capable of forming a biologically useful multimer when in contact with one, two, three or more other monomers in an aqueous media. In one aspect, such monomers may be capable of binding to another monomer in an aqueous media (e.g. in vivo) to form a multimer, (e.g. a dimer). Contemplated monomers may include a ligand moiety, a linker element, and a connector element that joins the ligand moiety and the linker element. In an aqueous media, such contemplated monomers may join together via each linker element and may thus be capable of modulating one or more biomolecules substantially simultaneously, e.g., modulate two or more binding domains on a protein or on different proteins.

  本发明描述了在水中介质中与一个、两个、三个或更多其他单体接触时能够形成具有生物学用途的多聚体的单体。在一方面，这样的单体可能能够在水介质中（例如，体内）与另一个单体结合形成多聚体（例如，二聚体）。考虑的单体可能包括一个配体部分、一个连接元素和一个连接器元素，连接器元素连接配体部分和连接元素。在水介质中，这样的考虑单体可能通过每个连接元素相互连接，因此可能能够实质上同时调节一个或多个生物分子，例如，调节蛋白质上的两个或多个结合域，或者调节不同蛋白质上的结合域。
• HETEROCYCLIC COMPOUNDS, PROCESS FOR PREPARATION OF THE SAME AND USE THEREOF
  申请人：SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES

  公开号：US20170158680A1

  公开（公告）日：2017-06-08

  The present invention provides a heterocyclic compound represented by the formula (I), its stereoisomers, or a pharmaceutically acceptable salt thereof, pharmaceutical compositions thereof, and their use in preparing a medicament for the prevention and/or treatment of central nervous system disease.

  本发明提供了一种由公式（I）表示的杂环化合物，其立体异构体，或其药用可接受的盐，其药物组合物，以及它们用于制备预防或治疗中枢神经系统疾病的药物。
• A Continuous Protodecarboxylation of Heteroaromatic Carboxylic Acids in Sulfolane.
  作者：Ulf Tilstam

  DOI：10.1021/op300125p

  日期：2012.8.17

  equivalent of DBU could successfully be transferred to benzo[b]thiophene-2-carboxylic acid derivatives if a prolonged reaction time was used. (2) Picolinic acid could also be decarboxylated in sulfolane with 3% water, and thiophene-2-carboxylic acid was smoothly decarboxylated with DABCO instead of DBU. (3) Benzoic acid derivatives were either inert or decomposed under the reaction conditions.

  已经发现了一种通用的，可扩展的用于吲哚-2-羧酸脱羧的方法。在环丁砜中使用一当量的DBU，将吲哚-2-羧酸衍生物在316不锈钢管反应器中在300°C下20分钟内干净地脱羧。以良好的产率获得了相应的吲哚衍生物。还发现吲哚-2-羧酸（1）可以在纯的环丁砜或环丁砜中与3％的水在300℃下在20分钟内脱羧。（1）一当量DBU的脱羧反应可成功转移至苯并[ b]如果使用延长的反应时间，则]噻吩-2-羧酸衍生物。（2）吡啶甲酸也可用3％的水在环丁砜中脱羧，噻吩-2-羧酸可用DABCO代替DBU平稳脱羧。（3）苯甲酸衍生物在反应条件下是惰性的或分解的。
• Dihydroimidazo[2,1-b]thiazole and dihydro-5h-thiazolo[3,2-A]pyrimidines as antidepressant agents
  申请人：——

  公开号：US20030166628A1

  公开（公告）日：2003-09-04

  The present invention relates to certain novel substituted dihydroimidazo[2,1-b]thiazole and dihydro-5H-thiazolo[3,2-a]pyrimidine compounds of Formula (I) including pharmaceutically acceptable salts thereof in which have affinity for 5-HT 1A receptors and which inhibits neuronal reuptake of 5-hydroxytryptamine and/or noradrenaline, to processes for their preparation, to pharmaceutical compositions containing them and to their use in the treatment of depression, anxiety, psychoses (for example schizophrenia), tardive dyskinesia, obesity, drug addiction, drug abuse, cognitive disorders, Alzheimer's disease, obsessive-compulsive behaviour, panic attacks, social phobias, eating disorders such as bulimia, anorexia, snacking and binge eating, non-insulin dependent diabetes mellitus, hyperglycaemia, hyperlipidaemia, stress, as an aid to smoking cessation and in the treatment and/or prophylaxis of seizures, neurological disorders such as epilepsy and/or in which there is neurological damage such as stroke, brain trauma, cerebral ischaemia, head injuries and haemorrhage.

  本发明涉及某些新颖的Formula (I)中的取代二氢咪唑[2,1-b]噻唑和二氢-5H-噻唑[3,2-a]嘧啶化合物，包括其对5-HT1A受体具有亲和力并抑制5-羟色胺和/或去甲肾上腺素的神经再摄取的药用盐，以及其制备方法，含有它们的药物组合物，以及它们在治疗抑郁症、焦虑症、精神病（例如精神分裂症）、迟发性运动障碍、肥胖症、药物成瘾、药物滥用、认知障碍、阿尔茨海默病、强迫性行为、恐慌发作、社交恐惧症、进食障碍（如暴食症、厌食症、吃零食和暴饮暴食）、非胰岛素依赖型糖尿病、高血糖、高脂血症、压力、作为戒烟辅助以及治疗和/或预防癫痫发作、癫痫等神经系统疾病以及存在神经损伤的情况（如中风、脑外伤、脑缺血、头部损伤和出血）中的用途。
• Discovery of fluorescent coumarin-benzo[b]thiophene 1, 1-dioxide conjugates as mitochondria-targeting antitumor STAT3 inhibitors
  作者：Guiping Cai、Wenying Yu、Dongmei Song、Wenda Zhang、Jianpeng Guo、Jiawen Zhu、Yuhao Ren、Lingyi Kong

  DOI：10.1016/j.ejmech.2019.04.024

  日期：2019.7

  STAT3 has been extensively studied as a potential antitumor target. Though studies on regulating STAT3 mainly focus on the inhibition of STAT3 phosphorylation at Tyr705 residue, the phosphorylation at Ser727 residue of STAT3 protein is also closely associated with the mitochondrial import of STAT3 protein. N, N-diethyl-7-aminocoumarin is a fluorescent mitochondria-targeting probe. In this study, a

  STAT3已被广泛研究为潜在的抗肿瘤靶标。尽管关于调节STAT3的研究主要集中在抑制Tyr705残基上的STAT3磷酸化，但是STAT3蛋白的Ser727残基上的磷酸化也与STAT3蛋白的线粒体导入密切相关。N，N-二乙基-7-氨基香豆素是一种荧光的线粒体靶向探针。在这项研究中，通过将N，N-二乙基-7-氨基香豆素荧光团与苯并[ b ]噻吩1，1-二氧化物部分相连，开发了一系列STAT3抑制剂。所有设计的化合物均显示出对癌细胞有效的抗增殖活性。代表性化合物7a主要通过荧光可见的线粒体中积累。化合物7a在Tyr705和Ser727残基均抑制STAT3磷酸化。化合物7a抑制STAT3磷酸化，而对STAT1，JAK2，Src和Erk1 / 2的磷酸化水平没有影响，表明化合物7a具有良好的选择性。此外，化合物7a下调STAT3靶基因Bcl-2和Cyclin D1的表达，增加ROS的产生并显着降低线