2-氨基-4-(2-噻吩基)噻吩-3-羧酸乙酯 | 243669-48-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 中文名称: 2-氨基-4-(2-噻吩基)噻吩-3-羧酸乙酯
• 中文别名: 乙基5′-氨基-2,3′-联噻吩-4′-羧酸盐
• 英文名称: ethyl 5’-amino-[2,3’-bithiophene]-4’-carboxylate
• 英文别名: ethyl 5′-amino-[2,3′-bithiophene]-4′-carboxylate；ethyl 5'-amino-2,3'-bithiophene-4'-carboxylate；5'-amino-[2,3']bithiophenyl-4'-carboxylic acid ethyl ester；2-Amino-3-ethoxycarbonyl-4-thienylthiophen；Ethyl 2-Amino-4-(2-thienyl)thiophene-3-carboxylate；ethyl 2-amino-4-thiophen-2-ylthiophene-3-carboxylate
• CAS: 243669-48-9
• 化学式: C₁₁H₁₁NO₂S₂
• mdl: MFCD00115120
• 分子量: 253.346
• InChiKey: AKFDBWIUWIWHRK-UHFFFAOYSA-N

物化性质

• 熔点：
  85 °C
• 沸点：
  389.3±42.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)
• 溶解度：
  26.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2934999090

SDS

Name:	Ethyl 2-amino-4-(2-thieny)thiophene-3-carboxylate Material Safety Data Sheet
Synonym:	None Known
CAS:	243669-48-9

Section 1 - Chemical Product MSDS Name:Ethyl 2-amino-4-(2-thieny)thiophene-3-carboxylate Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
243669-48-9	Ethyl 2-amino-4-(2-thieny)thiophene-3-	97+%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause irritation of the digestive tract.
Inhalation:
Causes respiratory tract irritation.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 243669-48-9: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 84 - 87 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C11H11NO2S2
Molecular Weight: 253.34

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong acids, strong bases, acid chlorides.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 243669-48-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 2-amino-4-(2-thieny)thiophene-3-carboxylate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 22 Do not breathe dust.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 243669-48-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 243669-48-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 243669-48-9 is not listed on the TSCA inventory.
It is for research and development use only.

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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-(2-噻吩基)噻吩-3-羧酸乙酯 在 盐酸 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 4.0h， 生成 ethyl 2-(chloromethyl)-4-oxo-5-thiophen-2-ylthieno[2,3-d]pyrimidine-3-carboxylate
  参考文献：
  名称：

  Hosni, Hanaa M.; Basyouni, Wahid M.; El-Nahas, Hanan A., Journal of Chemical Research, Miniprint, 1999, # 11, p. 2775 - 2794

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙酰基噻吩 、 氰乙酸乙酯 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以83%的产率得到2-氨基-4-(2-噻吩基)噻吩-3-羧酸乙酯
  参考文献：
  名称：

  含噻吩衍生物的吡啶，吡喃和噻唑的合成及其抗肿瘤作用

  摘要：

  2-乙酰基噻吩与芳族醛，丙二腈或氰基乙酸乙酯的多组分反应得到吡喃衍生物4a - 4f和吡啶衍生物5a - 5f。另一方面，2-乙酰基噻吩与元素硫和丙二腈或氰基乙酸乙酯的反应得到了噻吩衍生物6a和6b。分别。化合物6a和6b进行了一系列杂环反应，得到噻唑和噻吩衍生物。评估了所有产品对人胃癌，胃癌（NUGC和HR），人结肠癌（DLD1），人肝癌（HA22T和HEPG2），人乳腺癌（MCF），鼻咽癌（HONE1）细胞系的抗肿瘤活性。 。化合物4e，4f，5e，5f，7b，8b，10e，10f，11e，11f，14d-f，15d-f，16a，b和18b对癌细胞系表现出最佳的细胞毒性作用，IC 50在nM范围内。此外，7b，10e，14d，15e和16b对虾幼虫没有毒性。最有效的化合物对癌细胞系的抗增殖细胞活性表明，在所测试的化合物中，化合物5f和10e的活性最高。

  DOI：

  10.1007/s00044-016-1654-3

文献信息

• NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS
  申请人：Carroll William A.

  公开号：US20090018114A1

  公开（公告）日：2009-01-15

  The present application relates to cannabinoid receptor ligands containing compounds of formula (I) wherein A, R 1 , R 2 , and R 3 are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  本申请涉及含有式(I)化合物的大麻素受体配体，其中A、R1、R2和R3如规范中所定义。本申请还涉及包含这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。
• Discovery of Novel, Highly Potent, and Selective Matrix Metalloproteinase (MMP)-13 Inhibitors with a 1,2,4-Triazol-3-yl Moiety as a Zinc Binding Group Using a Structure-Based Design Approach
  作者：Hiroshi Nara、Akira Kaieda、Kenjiro Sato、Takako Naito、Hideyuki Mototani、Hideyuki Oki、Yoshio Yamamoto、Haruhiko Kuno、Takashi Santou、Naoyuki Kanzaki、Jun Terauchi、Osamu Uchikawa、Masakuni Kori

  DOI：10.1021/acs.jmedchem.6b01007

  日期：2017.1.26

  and -14) and tumor necrosis factor-α converting enzyme (TACE). Furthermore, the inhibitor was shown to protect bovine nasal cartilage explants against degradation induced by interleukin-1 and oncostatin M. In this article, we report the discovery of extremely potent, highly selective, and orally bioavailable fused pyrimidine derivatives that possess a 1,2,4-triazol-3-yl group as a novel ZBG for selective

  在对喹唑啉衍生物1和三唑衍生物2与基质金属蛋白酶（MMP）-13催化结构域的配合物的X射线晶体结构进行叠加研究的基础上，得到了一系列新型的具有1,2,4-嘧啶基的稠合嘧啶化合物。设计了三唑-3-基作为锌结合基团（ZBG）。在本文所述和评估的化合物中，31f对MMP-13（IC 50= 0.036 nM）和相对于其他MMP（MMP-1，-2，-3，-7，-8，-9，-10和-14）的选择性（大于1,500倍）和肿瘤坏死因子-α转换酶（TACE）。此外，已证明该抑制剂可保护牛鼻软骨外植体免受白介素-1和制瘤素M诱导的降解。在本文中，我们报告了发现一种具有1,2的极强效，高选择性和口服生物利用度的融合嘧啶衍生物的发现。 ，4-三唑-3-基作为选择性抑制MMP-13的新型ZBG。
• In Vitro and In Vivo Anti-Breast Cancer Activities of Some Newly Synthesized 5-(thiophen-2-yl)thieno-[2,3-d]pyrimidin-4-one Candidates
  作者：Abd El-Galil E. Amr、Alhussein A. Ibrahimd、Mohamed F. El-Shehry、Hanaa M. Hosni、Ahmed A. Fayed、Elsayed A. Elsayed

  DOI：10.3390/molecules24122255

  日期：——

  hydrate or anthranilic acid to afford acetohydrazide 4 and benzo[d][1,3]oxazin-4-one 5, respectively. Condensation of 4 with aromatic aldehydes or phenylisothiocyanate yielded Schiff base derivatives 6,7, and thiosemicarbazise 10, which were treated with 2-mercaptoacetic acid or chloroacetic acid to give the corresponding thiazolidinones 8, 9, and phenylimino-thiazolidinone 11, respectively. Treatment

  本研究以乙基酯衍生物环化制备的噻吩噻吩并[2,3-d]嘧啶酮衍生物2为起始原料，制备并测试了一些新型噻吩噻吩并嘧啶酮衍生物2-15作为抗癌药物。 1 与甲酰胺。用氯乙酸乙酯处理2得到噻吩并嘧啶酮N-乙酸乙酯3，其与水合肼或邻氨基苯甲酸反应分别得到乙酰肼4和苯并[d][1,3]恶嗪-4-酮5。4 与芳香醛或异硫氰酸苯酯缩合得到席夫碱衍生物 6,7 和氨基硫脲 10，它们用 2-巯基乙酸或氯乙酸处理，分别得到相应的噻唑烷酮 8、9 和苯基亚氨基-噻唑烷酮 11。4 用乙酰乙酸乙酯或乙酸/乙酸酐处理分别得到吡唑 12 和乙酰基乙酰肼 13 衍生物。后一种化合物13与环乙酸乙酯或丙二腈反应，分别得到14和15。在这项工作中，我们研究了合成的噻吩并嘧啶酮衍生物对 MCF-7 和 MCF-10A 癌细胞的抗癌活性。此外，体内实验表明，与对照动物模型相比，合成的化合物在治疗的第 8 天显着降低了肿瘤生长。此外，合成的衍生物显示出对
• [EN] THIENOPYRIMIDINE DERIVATIVES AS POTASSIUM CHANNEL INHIBITORS<br/>[FR] UTILISATION DE DERIVES DE LA THIENOPYRIMIDINE COMME INHIBITEURS DES CANAUX POTASSIQUES
  申请人：XENTION DISCOVERY LTD

  公开号：WO2004111057A1

  公开（公告）日：2004-12-23

  The present invention provides thienopyrimidine compounds which are potasium channels inhibitors. Pharmaceutical compositions comprising the compounds and their use in the treatment of arrhythmia are also provided.

  本发明提供了硫代嘧啶类化合物，它们是钾通道抑制剂。还提供了包含这些化合物的药物组合物，以及它们在治疗心律失常中的用途。
• Synthesis of Some New Substituted Thieno[2,3-d]pyrimidine Derivatives as Antimicrobial Agents
  作者：M. F. El-Shehry、H. M. Hosni、A. E. Amr、A. A. Ibrahim、Ahmed A. Fayed、D. H. Elnaggar

  DOI：10.1134/s1070363219070247

  日期：2019.7

  A series of thieno-pyrimidine derivatives are synthesized from 5′-amino-2,3′-bithiophene-4′-carboxylate via the corresponding intermediate N-benzoylated carboxamide derivatives. The target compounds are tested for antibacterial and antifungal activity. Some of the synthesized compounds demonstrate potent antibacterial activity with LD50 comparable with the reference drug indomethacin.

  由5'-氨基-2,3'-联噻吩-4'-羧酸盐通过相应的中间体N-苯甲酰化羧酰胺衍生物合成了一系列噻吩并嘧啶衍生物。测试目标化合物的抗菌和抗真菌活性。一些合成的化合物对LD 50表现出强大的抗菌活性，可与参考药物消炎痛相媲美。