2-氨基-4,5,6,7-四氢-7-氧代苯并[b]噻吩-3-甲腈 | 98899-30-0

• 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-氨基-4,5,6,7-四氢-7-氧代苯并[b]噻吩-3-甲腈
• 中文别名: 2-氨基-4,5,6,7-四氢-7-氧代-苯并[b]噻吩-3-甲腈
• 英文名称: 2-amino-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile
• 英文别名: 2-Amino-4,5,6,7-tetrahydro-7-oxobenzo[b]thiophene-3-carbonitrile；2-amino-7-oxo-5,6-dihydro-4H-1-benzothiophene-3-carbonitrile
• CAS: 98899-30-0
• 化学式: C₉H₈N₂OS
• mdl: MFCD01858636
• 分子量: 192.241
• InChiKey: XMZNDMVUUNFZEB-UHFFFAOYSA-N

物化性质

• 熔点：
  212-215℃
• 沸点：
  473.6±45.0 °C(Predicted)
• 密度：
  1.40

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  95.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-4,5,6,7-tetrahydro-7-oxobenzo[b]thiophene-3-carbonitrile
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: 2-Amino-4,5,6,7-tetrahydro-7-oxobenzo[b]thiophene-3-carbonitrile
CAS number: 98899-30-0

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H8N2OS
Molecular weight: 192.2

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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, 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：

  2-氨基-4,5,6,7-四氢-7-氧代苯并[b]噻吩-3-甲腈 在 三氯氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.42h， 生成 4-chloro-6,7-dihydro[1]benzothieno[2,3-d]pyrimidin-8-one
  参考文献：
  名称：

  Microwave-Assisted and Conventional Synthesis of Benzothieno [3,2-e] [1,3,4] triazolo[4,3-c]pyrimidines: A Comparative Study

  摘要：

  苯并噻吩[2,3-d]嘧啶（2,3,4）和苯并噻吩[3,2-e][1,3,4]三唑并[4,3-c]嘧啶（5a-c）由前体2-氨基-7-氧代-4,5,6,7-四氢-1-苯并噻吩-3-甲腈1通过常规方法和微波辐射技术合成。前体2-氨基-3-氰基噻吩类似物1通过众所周知的Gewald反应合成。在本研究中，发现微波辅助合成比传统的经典加热方法更有效。所有化合物的结构通过光谱和分析数据确定。

  DOI：

  10.5012/jkcs.2014.58.4.388
• 作为产物：
  描述：

  1,3-环己二酮 、 丙二腈 在 sulfur 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-氨基-4,5,6,7-四氢-7-氧代苯并[b]噻吩-3-甲腈
  参考文献：
  名称：

  新型吡喃，吡啶，噻吩和咪唑衍生物的细胞毒性，酪氨酸激酶抑制

  摘要：

  在这项工作中，我们有兴趣使用环己-1,3-二酮与不同试剂的多组分反应来合成具有抗肿瘤活性的吡喃，吡啶，噻吩和咪唑的新衍生物。选择了22种新合成的衍生物并测试了其抗癌效力。这些化合物中的几种对三种人类肿瘤细胞系表现出非常有趣的潜能，分别是NCI-H460（非小细胞肺癌），SF-268（CNS癌症）和MCF-7（乳腺腺癌），尤其是与之相比参考药物阿霉素和5-Fu化合物5b，5c，7b，9b，14a，16c，18a，19c，20B，和22B，被发现是朝向所选择的细胞系中的细胞毒性最化合物。另一方面，7b，14a，16c，19c和22b显示出对酪氨酸激酶的高度抑制作用。针对VEGFR-2，活性化合物14A，16C，和19C，对接到VEGFR-2enzyme内部，以显示所测试的化合物和活性位点的氨基酸之间的相互作用。

  DOI：

  10.1002/jhet.4010

文献信息

• Discovery of new thiophene, pyrazole, isoxazole derivatives as antitumor, c-Met, tyrosine kinase and Pim-1 kinase inhibitors
  作者：R. M. Mohareb、K. M. H. Hilmy、Y. A. Elshehawy

  DOI：10.4314/bcse.v32i2.9

  日期：——

  The reaction of cyclohexan-1,3-dione (1) with ethyl orthoformate (2) in acetic acid gave the 2-(ethoxymethylene)cyclohexane-1,3-dione (3). The latter compound was used for further heterocyclization reactions to give thiophene, pyrazole and pyran derivatives. The cytotoxicity of the newly synthesized compound against the six cancer cell lines NUGC, DLDI, HA22T, HEPG2, HONE1 and MCF showed that compounds 5, 10c, 10d, 13b, 14a, 18b, 18d, 18e and 20b were the most potent compounds. On the other hand, the toxicity of these compounds against shrimp larvae indicated that compounds 7a, 10c, 13b, 14a, 18b and 18d were non toxic against the tested organisms. Inhibition of the most potent compounds towards the tyrosine kinases c-kit, FIT-3, Vascular Endothelial Growth Factor Receptor (VEGFR)-2, Estimated Glomerular Filtration Rate (EGFR) and Platelet-Derived Growth Factor Receptor (PDGFR) revealed that compounds 5, 10c, 10d, 13b, 18b, 18d, 18e and 20b were of the highest inhibitory effect. The Pim-1 kinase test revealed that compounds 10d, 18b and 20b were of the highest inhibitory effect. In addition, the c-Met enzymatic activities showed that compounds 10c, 10d, 18b, 18e, 19 and 20b showed higher potencies against c-Met kinase than the reference foretinib. On the other hand, compounds 7a, 7b, 10d, 13a, 13b, 14a, 14b, 16a, 16b, 17, 18a-f, 19 and 20 showed higher inhibition towards PC-3 cell line than the reference SGI-1776. Compounds 10c and 18b were of common potencies and their molecular docking was described.

  环己烷-1,3-二酮（1）与乙基邻福尔马酸酯（2）在醋酸中反应生成了2-(乙氧基亚甲基)环己烷-1,3-二酮（3）。后者化合物用于进一步的杂环化反应，生成噻吩、吡唑和吡喃衍生物。新合成化合物对六种癌细胞系NUGC、DLDI、HA22T、HEPG2、HONE1和MCF的细胞毒性显示化合物5、10c、10d、13b、14a、18b、18d、18e和20b是最有效的化合物。另一方面，这些化合物对虾幼虫的毒性测试表明，化合物7a、10c、13b、14a、18b和18d对所测试生物无毒。对酪氨酸激酶c-kit、FIT-3、血管内皮生长因子受体（VEGFR）-2、估计肾小球滤过率（EGFR）和血小板源性生长因子受体（PDGFR）的最有效化合物的抑制作用显示，化合物5、10c、10d、13b、18b、18d、18e和20b具有最高的抑制效果。Pim-1激酶测试表明化合物10d、18b和20b具有最高的抑制效果。此外，c-Met酶活性显示，化合物10c、10d、18b、18e、19和20b对c-Met激酶的活性高于参考化合物foretinib。另一方面，化合物7a、7b、10d、13a、13b、14a、14b、16a、16b、17、18a-f、19和20对PC-3细胞系的抑制作用高于参考化合物SGI-1776。化合物10c和18b具有相似的效力，其分子对接已被描述。
• Convenient and Efficient Synthesis of 11-Amino-2,8-substituted-2,3,8,9-tetrahydrobenzo[4,5]thieno[2,3-<i>b</i>]quinolinone Derivatives
  作者：Zhong-Xia Wang、Li-Zhuang Chen、Bei Li、Guang-Fan Han

  DOI：10.1002/jhet.2200

  日期：2015.11

  2‐amino‐5‐substituted‐7‐oxo‐4,5,6,7‐tetrahydrobenzo[b]thiophene‐3‐carbonitrile derivatives 1. The intermediate enamines 2 were prepared by reaction of compounds 1 and 5‐substituted‐1,3‐cyclohexanedione with hydrochloric acid as catalyst. The title compounds 11‐amino‐2,8‐substituted‐2,3,8,9‐tetrahydrobenzo[4,5]thieno[2,3‐b]quinolinone 3 were synthesized by cyclization of compounds 2 in the presence of K2CO3

  进行了5-取代-1,3-环己二酮，丙二腈和粉状硫的Gewald反应，得到了相应的产物2-氨基-5-取代-7-氧代-4,5,6,7-四氢苯并[ b ]噻吩-3-腈衍生物1。中间体烯胺2是通过化合物1和5-取代的-1,3-环己二酮与盐酸作为催化剂反应制得的。通过在K 2存在下环化化合物2合成标题化合物11-氨基-2,8-取代-2,3,8,9-四氢苯并[4,5]噻吩并[2,3- b ]喹啉酮3 CO 3和Cu 2 Cl 2。所有化合物的结构均通过元素分析，IR，MS和1 H-NMR光谱进行表征。
• Fused thiophene derivatives as kinase inhibitors
  申请人：UCB Pharma SA

  公开号：US08324204B2

  公开（公告）日：2012-12-04

  A series of 5,6-dihydro-1-benzothiophen-7(4H)-one derivatives, and analogues thereof, which are substituted in the 2-position by an optionally substituted morpholin-4-yl moiety, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

  一系列的5,6-二氢-1-苯并噻吩-7(4H)-酮衍生物及其类似物，在2位被一个可选择取代的吗啡啶-4-基团取代，是选择性PI3激酶抑制剂，因此在医学上具有益处，例如在炎症、自身免疫、心血管、神经退行性、代谢、肿瘤、疼痛或眼科疾病的治疗中。
• Fused Thiophene Derivatives as Kinase Inhibitors
  申请人：Alexander Rikki Peter

  公开号：US20100305066A1

  公开（公告）日：2010-12-02

  A series of 5,6-dihydro-1-benzothiophen-7(4H)-one derivatives, and analogues thereof, which are substituted in the 2-position by an optionally substituted morpholin-4-yl moiety, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

  一系列取代了可选取代的吗啡啶-4-基的2位的5,6-二氢-1-苯并噻吩-7（4H）-酮衍生物及其类似物，是PI3激酶酶的选择性抑制剂，因此在医学上具有益处，例如用于治疗炎症、自身免疫、心血管、神经退行性、代谢、肿瘤、疼痛或眼科疾病。
• Farbfotografisches Aufzeichnungsmaterial mit einem Farbabspalter für blaugrüne Farbstoffe, ein mit diesen Farbstoffen erzeugtes Farbbild und die Farbstoffe selbst
  申请人：Agfa-Gevaert AG

  公开号：EP0150319A2

  公开（公告）日：1985-08-07

  Farbstoffe der Formel I können bei Farbdiffusionsübertragungsverfahren bildmäßig aus entsprechenden Farbabspaltern freigesetzt werden. Es handelt sich dabei um lichtechte blaugrüne Farbstoffe mit verbesserten spektralen Eigenschaften und verminderter Empfindlichkeit gegen Reduktionsmittel Die Bedeutung der in der Formel I dargestellten Symbole, (A, A', G, R1, R2, R3 und R4) ist in der Beschreibung angegeben.

  在色彩扩散转移过程中，式 I 所示染料可从相应的分色剂中以图像方式释放出来。 这些染料为蓝绿色染料，具有较好的光谱特性，对还原剂的敏感性较低。 式 I 所示符号（A、A'、G、R1、R2、R3 和 R4）的含义已在说明中给出。