2-氨基-5-甲基-4-苯基噻吩-3-羧酸乙酯 | 4815-37-6

• 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-甲基-4-苯基噻吩-3-羧酸乙酯
• 中文别名: 2-氨基-5-甲基-4-苯噻吩-3-甲酸乙酯
• 英文名称: ethyl 2-amino-5-methyl-4-phenylthiophene-3-carboxylate
• CAS: 4815-37-6
• 化学式: C₁₄H₁₅NO₂S
• mdl: MFCD01763475
• 分子量: 261.345
• InChiKey: SXONDAWSQJWZEO-UHFFFAOYSA-N

物化性质

• 熔点：
  92 °C

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.214
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090

SDS

Name:	Ethyl 2-amino-5-methyl-4-phenylthiophene-3-carboxylate 97% Material Safety Data Sheet
Synonym:
CAS:	4815-37-6

Section 1 - Chemical Product MSDS Name:Ethyl 2-amino-5-methyl-4-phenylthiophene-3-carboxylate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4815-37-6	Ethyl 2-amino-5-methyl-4-phenylthiophe	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Moisture sensitive.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: 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.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
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.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 4815-37-6: Personal Protective Equipment Eyes: Not available.
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: 72 - 74 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: C14H15NO2S
Molecular Weight: 261

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, exposure to moist air or water.
Incompatibilities with Other Materials:
Strong oxidizing agents, oxidizing agents, acids, acid chlorides, halogenated agents, halogens.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide, ammonia.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 4815-37-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 2-amino-5-methyl-4-phenylthiophene-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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 4815-37-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 4815-37-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4815-37-6 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-5-甲基-4-苯基噻吩-3-羧酸乙酯 在 tetraphosphorus decasulfide 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 24.5h， 生成 Ethyl 2-(6-methyl-5-phenylthieno[2,3-d]pyrimidin-4-yl)sulfanylacetate
  参考文献：
  名称：

  Synthesis and biological evaluation of substituted (thieno[2,3-d]pyrimidin-4-ylthio)carboxylic acids as inhibitors of human protein kinase CK2

  摘要：

  A novel series of substituted (thieno[2,3-d]pyrimidin-4-ylthio)carboxylic acids has been synthesized and tested in vitro towards human protein kinase CK2. It was revealed that the most active compounds inhibiting CK2 are 3-{[5-(4-methylphenyl)thieno[2,3-d]pyrimidin-4-yl]thio}propanoic acid and 3-{[5-(4-ethoxyphenyl)thieno[2,3-d]pyrimidin-4-yl]thio}propanoic acid (IC50 values are 0.1 mu M and 0.125 mu M, respectively). Structure activity relationships of 28 tested thienopyrimidine derivatives have been studied and binding mode of this chemical class has been predicted. Evaluation of the inhibitors on seven protein kinases revealed considerable selectivity towards CK2. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.025
• 作为产物：
  描述：

  2-Cyan-3-phenyl-pent-2-ensaeure-aethylester 在 sulfur 、 二乙胺 作用下， 以 乙醇 为溶剂， 生成 2-氨基-5-甲基-4-苯基噻吩-3-羧酸乙酯
  参考文献：
  名称：

  Synthesis and antimicrobial activity of novel 2-(pyridin-2-yl)thieno[2,3-d]pyrimidin-4 (3H)-ones

  摘要：

  在本研究中，合成了一些新的2-(吡啶-2-基)噻吩[2,3-d]嘧啶-4(3H)-酮衍生物（IIa-o）。目标化合物（IIa-o）是通过2-氰基、3-氰基和4-氰基吡啶与各种2-氨基-3-乙氧基噻吩（Ia-e）进行酸催化缩合合成的。所有噻吩衍生物均通过Gewald反应合成。新合成化合物的结构通过紫外-可见光谱、傅里叶变换红外光谱、^1H-NMR和质谱分析得到了确认。所有合成化合物均被评估其针对各种革兰阳性和革兰阴性细菌及真菌菌株的抗微生物活性。在合成的化合物中，发现IIa、IIb、IId、IIe和IIm具有活性。

  DOI：

  10.3906/kim-1012-888

文献信息

• [EN] THIENOPYRIDONE DERIVATIVES AS AMP-ACTIVATED PROTEIN KINASE (AMPK) ACTIVATORS<br/>[FR] DÉRIVÉS DE THÉNOPYRIDONE COMME ACTIVATEURS DE LA PROTÉINE KINASE DÉPENDANTE DE L'AMP (AMPK)
  申请人：MERCK PATENT GMBH

  公开号：WO2009124636A1

  公开（公告）日：2009-10-15

  The present invention relates to compounds of formula (I) wherein R1, R2 and R3 are as defined in claim 1, including pharmaceutical compositions thereof and for their use in the treatment and/or prevention of diseases and disorders modulated by AMP agonists. The invention is also directed to intermediates and to a method of preparation of compounds of formula (I).

  本发明涉及式(I)的化合物，其中R1、R2和R3如权利要求1所定义，包括其药物组合物以及用于治疗和/或预防由AMP激动剂调节的疾病和紊乱的用途。该发明还涉及中间体和式(I)化合物的制备方法。
• THIENOPYRIDONE DERIVATIVES AS AMP-ACTIVATED PROTEIN KINASE (AMPK) ACTIVATORS
  申请人：Cravo Daniel

  公开号：US20110034505A1

  公开（公告）日：2011-02-10

  The present invention relates to compounds of formula (I) wherein R1, R2 and R3 are as defined in claim 1 , including pharmaceutical compositions thereof and for their use in the treatment and/or prevention of diseases and disorders modulated by AMP agonists. The invention is also directed to intermediates and to a method of preparation of compounds of formula (I).

  本发明涉及式（I）化合物，其中R1、R2和R3如权利要求1所定义，包括其药物组合物以及用于治疗和/或预防由AMP激动剂调节的疾病和紊乱的用途。该发明还涉及中间体和式（I）化合物的制备方法。
• Design and synthesis of novel protein kinase CK2 inhibitors on the base of 4-aminothieno[2,3-d]pyrimidines
  作者：Olga V. Ostrynska、Anatoliy O. Balanda、Volodymyr G. Bdzhola、Andriy G. Golub、Igor M. Kotey、Olexander P. Kukharenko、Andrii A. Gryshchenko、Nadiia V. Briukhovetska、Sergiy M. Yarmoluk

  DOI：10.1016/j.ejmech.2016.03.004

  日期：2016.6

  research work has resulted in a number of new ATP-competitive CK2 inhibitors that have been identified among 4-aminothieno[2,3-d]pyrimidine derivatives. The most active compounds obtained in the course of the research are 3-(5-p-tolyl-thieno[2,3-d]pyrimidin-4-ylamino)-benzoic acid, 5e (NHTP23, IC50 = 0.01 μM), 3-(5-phenyl-thieno[2,3-d]pyrimidin-4-ylamino)-benzoic acid, 5g (NHTP25, IC50 = 0.065 μM) and 3

  我们先前研究工作的扩展已导致在4-氨基噻吩并[2,3-d]嘧啶衍生物中鉴定出许多新的与ATP竞争的CK2抑制剂。在研究过程中获得的活性最高的化合物是3-（5-对甲苯基-噻吩并[2,3-d]嘧啶-4-基氨基）苯甲酸5e（NHTP23，IC 50  = 0.01μM）， 3-（5-苯基-噻吩并[2,3-d]嘧啶-4-基氨基）-苯甲酸，5g（NHTP25，IC 50  = 0.065μM）和3-（6-甲基-5-苯基-噻吩并[2 ，3-d]嘧啶-4-基氨基）-苯甲酸，5n（NHTP33，IC 50 = 0.008μM）。研究了测试的4-氨基噻吩并[2,3-d]嘧啶衍生物的结构-活性关系，并提出了它们与CK2 ATP受体位点的结合方式。讨论了分子内氢键对化合物结构的负面影响。
• Therapeutically Active Fused Pyrimidine Derivatives
  申请人：Brookings Daniel Christopher

  公开号：US20140309222A1

  公开（公告）日：2014-10-16

  A series of monocyclic or bicyclic diamine-substituted thieno[2,3-d]pyrimidine and isothiazolo[5,4-d]pyrimidine derivatives are beneficial in the treatment and/or prevention of various human ailments, including inflammatory, autoimmune and oncological disorders; viral diseases; and organ and cell transplant rejection.

  一系列单环或双环二胺取代的噻吩[2,3-d]嘧啶和异噻唑[5,4-d]嘧啶衍生物在治疗和/或预防各种人类疾病方面具有益处，包括炎症性、自身免疫和肿瘤性疾病；病毒性疾病；以及器官和细胞移植排斥。
• [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。