3-氨基-苯并[b]噻吩-2-羧酸乙酯 | 34761-09-6

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 3-氨基-苯并[b]噻吩-2-羧酸乙酯
• 中文别名: 3-氨基苯并[B]噻吩-2-乙酸乙酯
• 英文名称: ethyl 3-aminobenzothiophene-2-carboxylate
• 英文别名: ethyl 3-aminobenzo[b]thiophene-2-carboxylate；3-aminobenzothiophene-2-carboxylic acid ethyl ester；ethyl 3-amino-1-benzothiophene-2-carboxylate
• CAS: 34761-09-6
• 化学式: C₁₁H₁₁NO₂S
• mdl: MFCD00661903
• 分子量: 221.28
• InChiKey: XZSFZYVMRZLUOJ-UHFFFAOYSA-N

物化性质

• 熔点：
  ca 82℃ subl.
• 沸点：
  373.4±22.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Ethyl 3-aminobenzothiophene-2-carboxylate
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.
Ethyl 3-aminobenzothiophene-2-carboxylate
Ingredient name:
CAS number: 34761-09-6

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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: C11H11NO2S
Molecular weight: 221.3

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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, 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：

  3-氨基-苯并[b]噻吩-2-羧酸乙酯 在 三氯氧磷 作用下， 反应 4.75h， 生成 4-chlorobenzo[4,5]thieno[2,3-d]pyrimidine
  参考文献：
  名称：

  Synthesis and evaluation of apoptosis induction of thienopyrimidine compounds on KRAS and BRAF mutated colorectal cancer cell lines

  摘要：

  Monoclonal antibodies (MoAb) and tyrosine kinase inhibitors (TKI) targeting the EGFR (Epidermal Growth Factor Receptor) pathways are currently used in colorectal cancer treatment. Despite the improvement of median overall survival, resistance is observed notably due to KRAS and BRAF gene mutations. We synthesized four series of thienopyrimidines whose scaffold is structurally close to TKI used in clinical practice. We evaluated apoptosis induced by these compounds using flow cytometry on KRAS and BRAF mutated cell lines. Our results confirm that the mutated cell lines (HCT116 and HT29) are more resistant to apoptosis than the non-mutated cell line (Hela). Interestingly, among the 13 compounds tested, three of them (5b, 6b and 6d) and gefitinib exhibited a noteworthy pro-apoptotic effect, especially on mutated cell lines with an IC50 value between 70 and 110 mu M. These three compounds seem particularly attractive for the development of novel treatments for colorectal cancer patients harboring EGFR pathway mutations. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.034
• 作为产物：
  描述：

  2-溴硫代苯酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 23.0h， 生成 3-氨基-苯并[b]噻吩-2-羧酸乙酯
  参考文献：
  名称：

  유기 광전자 소자용 화합물, 이를 포함하는 유기 광전자 소자 및 상기 유기 광전자 소자를 포함하는 표시장치

  摘要：

  这段文字的中文翻译如下： 这涉及一种用于有机光电子器件的化合物，包括该化合物的有机光电子器件以及包含该有机光电子器件的显示装置，提供了用于有机光电子器件的化合物，其用化学式1表示。在化学式1中，A，A'，X，R到R'，L到L'如规范中所定义。

  公开号：

  KR20150017817A

文献信息

• Synthesis and Structure-Activity Relationship Studies of 2-(1,3,4-Oxadiazole-2(3<i>H</i>)-thione)-3-amino-5-arylthieno[2,3-<i>b</i>]pyridines as Inhibitors of DRAK2
  作者：Piotr Leonczak、Ling-Jie Gao、Anna Teresa Ramadori、Eveline Lescrinier、Jef Rozenski、Steven De Jonghe、Piet Herdewijn

  DOI：10.1002/cmdc.201402234

  日期：2014.11

  recent years, DAPK‐related apoptosis‐inducing protein kinase 2 (DRAK2) has emerged as a promising target for the treatment of a variety of autoimmune diseases and for the prevention of graft rejection after organ transplantation. However, medicinal chemistry optimization campaigns for the discovery of novel small‐molecule inhibitors of DRAK2 have not yet been published. Screening of a proprietary compound

  近年来，DAPK相关的凋亡诱导蛋白激酶2（DRAK2）已成为治疗各种自身免疫性疾病和预防器官移植后移植排斥的有希望的靶标。但是，尚未发现用于发现DRAK2新型小分子抑制剂的药物化学优化方案。导致了苯并噻吩类似物的发现专有化合物文库的筛选，其中显示的亲和常数（ķ d 0.25μ）值中号。芯支架的变化时，可以得到一系列5- arylthieno [2,3-的取代模式的b ]与强的结合亲和力的吡啶（ķ d = 0.008μ中号代表最有力的代表）。这些化合物还显示出在功能生化DRAK2酶测定有前途的活性，与IC 50值的0.029μ中号为最有效的同类。最有效的化合物的选择性分析表明，它们在DAPK激酶家族中缺乏选择性。但是，效力较低的类似物之一是DRAK2的选择性配体，可以用作合成选择性有效的DRAK2抑制剂的起点。
• 1,2-Benzisothiazoles. Part II. Reactions of 3-chloro-1,2-benzisothiazole with carbanions
  作者：D. E. L. Carrington、K. Clarke、R. M. Scrowston

  DOI：10.1039/j39710003903

  日期：——

  intermediates in those reactions which lead to benzo[b]thiophen derivatives. Support for this mechanism comes from the reaction of o-cyanothiophenol in aqueous sodium hydroxide with ethyl bromoacetate, chloroacetone, phenacyl chloride, chloroacetonitrile, or bromonitromethane to give respectively 2-ethoxycarbonyl-, 2-acetyl-, 2-benzoyl-, 2-cyano-, and 2-nitro-3-aminobenzo[b]thiophen.

  戊烷-2,4-二酮与3-氯-1,2-苯并噻唑在乙醇钠存在下反应形成2-乙酰基-3-氨基苯并[ b ]噻吩。在相似的条件下，乙酰乙酸乙酯和丙二酸二乙酯各自主要得到3-氨基苯并[ b ]噻吩-2-羧酸乙酯。在稍加修改的条件下，丙二酸二乙酯还会提供一些预期的（1,2-苯并噻唑-3--3-基）丙二酸二乙酯，而氰基乙酸乙酯仅形成（1,2-苯并噻唑-3-基）氰基乙酸乙酯，而与条件无关。 。有人提出一种机制，涉及那些导致苯并[ b]的反应中，S-取代的邻氰基硫酚作为可能的中间体。]噻吩衍生物。该机理的支持来自氢氧化钠水溶液中的邻氰基硫酚与溴乙酸乙酯，氯丙酮，苯甲酰氯，氯乙腈或溴硝基甲烷的反应，分别得到2-乙氧基羰基-，2-乙酰基，2-苯甲酰基-，2-氰基-和2-硝基-3-氨基苯并[ b ]噻吩。
• Accepting the Invitation to Open Innovation in Malaria Drug Discovery: Synthesis, Biological Evaluation, and Investigation on the Structure–Activity Relationships of Benzo[<i>b</i>]thiophene-2-carboxamides as Antimalarial Agents
  作者：Marco Pieroni、Elisa Azzali、Nicoletta Basilico、Silvia Parapini、Michal Zolkiewski、Claudia Beato、Giannamaria Annunziato、Agostino Bruno、Federica Vacondio、Gabriele Costantino

  DOI：10.1021/acs.jmedchem.6b01685

  日期：2017.3.9

  Malaria eradication is a global health priority, but current therapies are not always suitable for providing a radical cure. Artemisinin has paved the way for the current malaria treatment, the so-called Artemisinin-based Combination Therapy (ACT). However, with the detection of resistance to ACT, innovative compounds active against multiple parasite species and at multiple life stages are needed.

  消灭疟疾是全球卫生的重中之重，但是当前的治疗方法并不总是适合提供彻底的治疗方法。青蒿素为目前的疟疾治疗铺平了道路，所谓的基于青蒿素的联合疗法（ACT）。但是，随着对ACT的抗性的检测，需要对多种寄生虫物种具有多种生命周期且具有活性的创新化合物。葛兰素史克最近披露了内部图书馆的表型筛选结果，发表了400种抗疟药化学型的集合，称为“疟疾箱”。对数据集进行分析后，我们开展了一项药物化学研究活动，以定义一种释放化合物的结构-活性关系，该关系体现了苯并噻吩-2-羧酰胺核心。制备了35种化合物，本文报道了恶性疟原虫，毒性和代谢稳定性。
• Synthesis of [1]benzothieno[3,2-<i>d</i>]pyrimidines substituted with electron donating substituents on the benzene ring
  作者：Alexander J. Bridges、Hairong Zhou

  DOI：10.1002/jhet.5570340412

  日期：1997.7

  2-fluorobenzonitriles were converted to the corresponding 3-amino[1]benzothiophenecarboxylic acid esters, which in turn were annulated with formamidine or various equivalents to produce the desired tricyclic benzothienopyrimidines. Various methoxy and nitro/amino substituents were placed on the phenyl ring, requiring several different strategies to prepare the desired benzothiophenes. Several different pyrimidone annulations

  将各种2-氟苄腈转化为相应的3-氨基[1]苯并噻吩羧酸酯，然后将其与甲am或各种等价物进行环化，生成所需的三环苯并噻吩并嘧啶。将各种甲氧基和硝基/氨基取代基置于苯环上，需要几种不同的策略来制备所需的苯并噻吩。还需要几种不同的嘧啶酮环化。还描述了在四步一锅式低温锂化过程中使用富电子的2-溴苄腈来生产高度富电子的氨基[1]苯并噻吩羧酸酯。7-氨基-8-氟[1]苯并噻吩并[3,2 - d ]嘧啶-4（3 H）的合成）-一种相对简单，但是合成相应的7-氨基-8-protio类似物非常困难，并且需要多种方法才能找到成功的方法。
• New Efficient Synthesis of 2-Substituted Benzothieno[3,2-<i>d</i>]pyrimidin-4(3<i>H</i>)-ones via a Tandem Aza-Wittig Reaction
  作者：Ming-Wu Ding、Sheng-Zhen Xu、Yang-Gen Hu

  DOI：10.1055/s-2006-950364

  日期：——

  with aryl isocyanates, reacted with secondary amines, phenols, or alkanols in the presence of a catalytic amount of potassium carbonate or sodium alkoxide to give 2-substituted benzothieno[3,2-d]pyrimidin-4(3H)-ones 6 in good yields. The reaction of carbodiimides 4 with primary amines RNH 2 (R ≠ H, Me) in the presence of sodium ethoxide selectively produced one regioisomer 8 via a base-catalyzed cyclization

  1-Aryl-3-[2-(ethoxycarbonyl)benzothien-3-yl]carbodiimides 4，由亚氨基正膦3与芳基异氰酸酯的氮杂-维蒂希反应获得，在催化量的存在下与仲胺、酚或烷醇反应碳酸钾或醇钠以良好的收率得到 2-取代的苯并噻吩并[3,2-d]嘧啶-4(3H)-酮 6。碳二亚胺 4 与伯胺 RNH 2 (R ≠ H, Me) 在乙醇钠存在下的反应通过碱催化的环化机制选择性地产生一种区域异构体 8。然而，当伯胺 RNH 2 (R = H, Me) 在不存在乙醇钠的情况下通过直接环化机制使用时，获得了不同的区域异构体 9。