2-氨基-5,6-二氢-4H-环戊烯并噻吩-3-甲腈 | 70291-62-2

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 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-5,6-二氢-4H-环戊烯并噻吩-3-甲腈
• 中文别名: 2-氨基-5,6-二氢-4H-环戊并[b]噻吩-3-甲腈
• 英文名称: 2-amino-5,6-dihydro-4H-cyclopentathiophene-3-carbonitrile
• 英文别名: 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile；2‐amino‐5,6‐dihydro‐4H‐cyclopenta[b]thiophene‐3‐carbonitrile
• CAS: 70291-62-2
• 化学式: C₈H₈N₂S
• mdl: MFCD00121495
• 分子量: 164.231
• InChiKey: RILAXFOADRDGPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  153-154℃
• 沸点：
  379.9±42.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  78
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  6.1
• 危险品标志：
  Xi
• 海关编码：
  2934999090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P280,P305+P351+P338,P311
• 危险品运输编号：
  3439
• 危险性描述：
  H302+H312,H315,H319,H331,H335
• 储存条件：
  -20°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-5,6-dihydro-4h-cyclopenta[b]thiophene-3-carbonitrile
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H331: Toxic if inhaled
H302: Harmful if swallowed
H312: Harmful in contact with skin
Causes skin irritation
H315:
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
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.
Ingredient name: 2-Amino-5,6-dihydro-4h-cyclopenta[b]thiophene-3-carbonitrile
CAS number: 70291-62-2

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H8N2S
Molecular weight: 164.2

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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
UN Number: UN3439 Class: 6.1 Packing group: III
Proper shipping name: NITRILES, TOXIC, SOLID, N.O.S. (2-Amino-5,6-dihydro-4h-cyclopenta[b]thiophene-3-carbonitrile)

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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-5,6-二氢-4H-环戊烯并噻吩-3-甲腈 在 lithium aluminium tetrahydride 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 24.5h， 生成 1-<2-(3-aminomethyl)-5,6-dihydro-4H-cyclopenta-thienyl>pyrrole
  参考文献：
  名称：

  Vega; Soledad Gil; Darias, Pharmazie, 1995, vol. 50, # 1, p. 27 - 33

  摘要：

  DOI：
• 作为产物：
  描述：

  环戊亚基丙二腈 在 三乙烯二胺 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 水 为溶剂， 反应 7.0h， 生成 2-氨基-5,6-二氢-4H-环戊烯并噻吩-3-甲腈
  参考文献：
  名称：

  DABCO水溶液，一种用于快速有机催化Knoevenagel缩合和Gewald反应的有效介质

  摘要：

  在水和1,4-二氮杂双环[2.2.2]辛烷的存在下，几种醛和环状酮与丙二腈和氰基乙酸乙酯进行有效的Knoevenagel缩合反应，从而在相当短的时间内产生各自的ab-不饱和体系。结果，容易获得高收率的结合产物。产物可以逐步地或原位地进行Gewald反应，以在4--7小时内有效地产生它们各自的2-氨基噻吩。

  DOI：

  10.3906/kim-1309-38

文献信息

• Structure–activity relationships for inhibitors of Pseudomonas aeruginosa exoenzyme S ADP-ribosyltransferase activity
  作者：Michael Saleeb、Charlotta Sundin、Öznur Aglar、Ana Filipa Pinto、Mahsa Ebrahimi、Åke Forsberg、Herwig Schüler、Mikael Elofsson

  DOI：10.1016/j.ejmech.2017.11.036

  日期：2018.1

  recombinant ExoS ADPRT domain. Herein, we report structure–activity relationships of this compound class by comparing a total of 51 compounds based on a thieno [2,3-d]pyrimidin-4(3H)-one and 4-oxo-3,4-dihydroquinazoline scaffolds. Improved inhibitors with in vitro IC50 values of 6 μM were identified. Importantly, we demonstrated that the most potent inhibitors block ADPRT activity of native full-length

  在感染期间，革兰氏阴性机会性病原体铜绿假单胞菌利用其III型分泌系统将毒素外切酶S（ExoS）转移到真核宿主细胞的细胞质中。ExoS是一种必不可少的体内毒力因子，可使铜绿假单胞菌避免吞噬作用并最终杀死宿主细胞。ExoS主要通过ADP-核糖基转移酶（ADPRT）活性引起其致病性。我们最近鉴定了具有体外IC 50的新型ExoS ADPRT抑制剂使用重组ExoS ADPRT结构域进行酶促测定时，大约20μM的核酸。在这里，我们通过比较基于噻吩并[2,3- d ]嘧啶-4（3 H）-one和4-oxo-3,4-dihydroquinazoline支架的51种化合物来报告该化合物类别的结构-活性关系。鉴定出体外IC 50值为6μM的改良抑制剂。重要的是，我们证明了最有效的抑制剂在酶促试验中能阻断铜绿假单胞菌分泌的天然全长ExoS的ADPRT活性，IC 50值为1.3μM 。该化合物类别有望成为开发新型抗菌剂的起点。
• [EN] CATHEPSIN C INHIBITORS<br/>[FR] INHIBITEURS DE CATHEPSINE C
  申请人：GLAXO GROUP LTD

  公开号：WO2011025799A1

  公开（公告）日：2011-03-03

  Disclosed are 3-aminopyrrolidines of Formula (I) having pharmacological activity, pharmaceutical compositions containing them, and methods for the treatment of diseases mediated by the cathepsin C enzyme such as chronic obstructive pulmonary disease.

  揭示了具有药理活性的式（I）的3-氨基吡咯烷，包含它们的药物组合物，以及用于治疗由cathepsin C酶介导的疾病（如慢性阻塞性肺病）的方法。
• Novel tetrahydrobenzo[b]thiophen-2-yl)urea derivatives as novel α-glucosidase inhibitors: Synthesis, kinetics study, molecular docking, and in vivo anti-hyperglycemic evaluation
  作者：Hong-Xu Xie、Juan Zhang、Yue Li、Jin-He Zhang、Shan-Kui Liu、Jie Zhang、Hua Zheng、Gui-Zhou Hao、Kong-Kai Zhu、Cheng-Shi Jiang

  DOI：10.1016/j.bioorg.2021.105236

  日期：2021.10

  α-Glucosidase inhibitors, which can inhibit the digestion of carbohydrates into glucose, are one of important groups of anti-type 2 diabetic drugs. In the present study, we report our effort on the discovery and optimization of α-glucosidase inhibitors with tetrahydrobenzo[b]thiophen-2-yl)urea core. Screening of an in-house library revealed a moderated α-glucosidase inhibitors, 5a, and then the following

  α-葡萄糖苷酶抑制剂是一类重要的抗2型糖尿病药物，可抑制碳水化合物消化为葡萄糖。在本研究中，我们报告了我们在发现和优化具有四氢苯并[ b ]噻吩-2-基)脲核心的α-葡萄糖苷酶抑制剂方面的努力。内部文库的筛选揭示了一种缓和的 α-葡萄糖苷酶抑制剂，5a，然后进行以下结构优化以获得更有效的衍生物。与亲本化合物5a (IC 50为 26.71 ± 1.80 μM) 和阳性对照阿卡波糖 (IC 50为 258.53 ± 1.27 μM)相比，大多数这些衍生物对 α-葡萄糖苷酶的抑制活性增加。其中，化合物8r (IC 50  = 0.59 ± 0.02 μM) 和8s (IC 50  = 0.65 ± 0.03 μM) 是最有效的抑制剂，并且表现出优于 α-淀粉酶的选择性。荧光猝灭实验证实了两种化合物与α-葡萄糖苷酶的直接结合。动力学研究表明，这些化合物是非竞争性抑制剂，这与分子对接结果一致，即化
• Pharmacophore modeling, 3D‐QSAR, synthesis, and anti‐lung cancer evaluation of novel thieno[2,3‐ <i>d</i> ][1,2,3]triazines targeting EGFR
  作者：Ranza Elrayess、Yasmine M. Abdel Aziz、Mohamed S. Elgawish、Marwa Elewa、Hosam A. Elshihawy、Mohamed M. Said

  DOI：10.1002/ardp.201900108

  日期：2020.2

  Two series of thieno[2,3‐d][1,2,3]triazine derivatives were designed, synthesized, and biologically evaluated as potential epidermal growth factor receptor (EGFR) inhibitors targeting the non‐small‐cell lung cancer cell line H1299. Most of the synthesized compounds displayed IC50 values ranging from 25 to 58 nM against H1299, which are superior to that of gefitinib (40 µM). 3‐(5,6,7,8‐Tetrahydro‐7

  设计、合成了两个系列的噻吩并 [2,3-d][1,2,3] 三嗪衍生物，并对其作为潜在的表皮生长因子受体 (EGFR) 抑制剂进行了生物评估，以靶向非小细胞肺癌细胞系 H1299 . 大多数合成的化合物对 H1299 的 IC50 值范围为 25 至 58 nM，优于吉非替尼 (40 µM)。3-(5,6,7,8-Tetrahydro-7H-cyclohexa[4:5]thieno[2,3-d]-1,2,3-triazin-4-ylamino)benzo-1,3-diamine ( 6b) 对 H1299 达到最高的细胞毒活性，IC50 值为 25 nM；它能够将 H1299 细胞中的 EGFR 浓度从 7.22 pg/ml 降低到 2.67 pg/ml。在体外，化合物6b对EGFR的IC50值为0.33 nM，优于1.9 nM的吉非替尼和4 nM的厄洛替尼。三维定量构效关系和分子建模研究揭示了化合物
• Discovery of Potent Dual EGFR/HER2 Inhibitors Based on Thiophene Scaffold Targeting H1299 Lung Cancer Cell Line
  作者：Ranza Elrayess、Yasmine M. Abdel Aziz、Mohamed Saleh Elgawish、Marwa Elewa、Asmaa S. A. Yassen、Sameh S. Elhady、Hosam A. Elshihawy、Mohamed M. Said

  DOI：10.3390/ph14010009

  日期：——

  Dual targeting of epidermal growth factor receptor (EGFR) and human EGFR-related receptor 2 (HER2) is a proven approach for the treatment of lung cancer. With the aim of discovering effective dual EGFR/HER2 inhibitors targeting non-small cell lung cancer cell line H1299, three series of thieno[2,3-d][1,2,3]triazine and acetamide derivatives were designed, synthesized, and biologically evaluated. The

  表皮生长因子受体 (EGFR) 和人 EGFR 相关受体 2 (HER2) 的双重靶向是一种经过验证的肺癌治疗方法。为了发现针对非小细胞肺癌细胞系H1299的有效EGFR/HER2双重抑制剂，设计、合成并合成了三个系列的噻吩并[2,3-d][1,2,3]三嗪和乙酰胺衍生物。生物学评估。合成的化合物对 H1299 的 IC50 值范围为 12 至 54 nM，优于 40 µM 的吉非替尼 (2)。合成的化合物中，2-(1H-吡唑并[3,4-b]吡啶-3-基氨基)-N-(3-氰基4,5,6,7-四氢苯并[b]噻吩-2-基)乙酰胺( 21a) 针对 H1299 实现了最高的体外细胞毒活性，原位 IC50 值为 12.5 nM，针对 EGFR 和 HER2 的 IC50 值分别为 0.47 和 0.14 nM，与已批准药物伊马替尼的 IC50 值相当 (1)。我们合成的化合物很有前途，表现出对 EGFR/HER2