4-肼基-5,6,7,8-四氢[1]苯并噻吩并-[2,3-d]嘧啶 | 40106-45-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 中文名称: 4-肼基-5,6,7,8-四氢[1]苯并噻吩并-[2,3-d]嘧啶
• 中文别名: 4-肼-5,6,7,8-四氢[1]苯并噻唑[2,3-D]嘧啶
• 英文名称: 4-hydrazinyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine
• 英文别名: 4-hydrazineyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine；4-Hydrazino-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine；5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-ylhydrazine
• CAS: 40106-45-4
• 化学式: C₁₀H₁₂N₄S
• mdl: MFCD00454415
• 分子量: 220.298
• InChiKey: RLYKRTXCPRRQST-UHFFFAOYSA-N

物化性质

• 熔点：
  202-203 °C(Solv: 1,4-dioxane (123-91-1))
• 沸点：
  461.3±55.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  92.1
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319
• 储存条件：
  -20°C，避光，惰性气体

SDS

Name:	4-Hydrazino-5 6 7 8-tetrahydro[1]benzothieno[2 3-d]pyrimidine Material Safety Data Sheet
Synonym:	None Known
CAS:	40106-45-4

Section 1 - Chemical Product MSDS Name:4-Hydrazino-5 6 7 8-tetrahydro[1]benzothieno[2 3-d]pyrimidine Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
40106-45-4	4-Hydrazino-5,6,7,8-tetrahydro[1]benzo	97+	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Harmful if inhaled.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. 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 appropriate foam.

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

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store under an inert atmosphere.

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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# 40106-45-4: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: yellow
Odor: slight
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 177-179 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: C10H12N4S
Molecular Weight: 220.30

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 40106-45-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Hydrazino-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine - 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: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 6 Keep under nitrogen.
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# 40106-45-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 40106-45-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 40106-45-4 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：

  4-肼基-5,6,7,8-四氢[1]苯并噻吩并-[2,3-d]嘧啶 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 2-(5-tert-butylisoxazol-3-ylamino)-N'-(5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)acetohydrazide
  参考文献：
  名称：

  Design and Synthesis of New Thiophene/Thieno[2,3-d]pyrimidines along with Their Cytotoxic Biological Evaluation as Tyrosine Kinase Inhibitors in Addition to Their Apoptotic and Autophagic Induction

  摘要：

  这项工作描述了新设计的噻吩和噻吩并[2,3-d]嘧啶衍生物的合成及其对激酶酶的抗癌活性，以及它们在癌细胞中激活自噬和凋亡细胞死亡的潜力。设计的化合物被扫描其对激酶的亲和力。结果显示亲和力范围为46.7%至13.3%。进行了分子对接研究，然后筛选这些化合物的抗增殖效果。有趣的是，化合物8和5对MCF-7和HepG-2表现出比参考标准更高的细胞毒效应。对化合物在HT-29和HepG-2上诱导凋亡和/或坏死的评估显示，三种化合物与未处理的对照HT-29细胞相比诱导了显著的早期凋亡，四种衍生物与未处理的HepG-2细胞相比更显著。我们进一步研究了四种化合物对HT-29、HepG-2和MCF-7细胞中自噬过程的影响，使用流式细胞术进行检测。与凋亡结果类似，化合物5在所有化合物中显示了最高的自噬诱导作用。对合成化合物对激酶的潜在抑制活性进行了评估。筛选的化合物显示的抑制活性范围为41.4%至83.5%。记录了显著抑制活性的化合物进一步研究其对FLT3激酶的特异性抑制活性。值得注意的是，化合物5展现了对FLT3最高的抑制活性。

  DOI：

  10.3390/molecules27010123
• 作为产物：
  描述：

  5,6,7,8-四氢-[1]-苯并噻吩[2,3-d]嘧啶-4(1h)-酮 在 一水合肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 4-肼基-5,6,7,8-四氢[1]苯并噻吩并-[2,3-d]嘧啶
  参考文献：
  名称：

  Design and Synthesis of New Thiophene/Thieno[2,3-d]pyrimidines along with Their Cytotoxic Biological Evaluation as Tyrosine Kinase Inhibitors in Addition to Their Apoptotic and Autophagic Induction

  摘要：

  这项工作描述了新设计的噻吩和噻吩并[2,3-d]嘧啶衍生物的合成及其对激酶酶的抗癌活性，以及它们在癌细胞中激活自噬和凋亡细胞死亡的潜力。设计的化合物被扫描其对激酶的亲和力。结果显示亲和力范围为46.7%至13.3%。进行了分子对接研究，然后筛选这些化合物的抗增殖效果。有趣的是，化合物8和5对MCF-7和HepG-2表现出比参考标准更高的细胞毒效应。对化合物在HT-29和HepG-2上诱导凋亡和/或坏死的评估显示，三种化合物与未处理的对照HT-29细胞相比诱导了显著的早期凋亡，四种衍生物与未处理的HepG-2细胞相比更显著。我们进一步研究了四种化合物对HT-29、HepG-2和MCF-7细胞中自噬过程的影响，使用流式细胞术进行检测。与凋亡结果类似，化合物5在所有化合物中显示了最高的自噬诱导作用。对合成化合物对激酶的潜在抑制活性进行了评估。筛选的化合物显示的抑制活性范围为41.4%至83.5%。记录了显著抑制活性的化合物进一步研究其对FLT3激酶的特异性抑制活性。值得注意的是，化合物5展现了对FLT3最高的抑制活性。

  DOI：

  10.3390/molecules27010123

文献信息

• Thieno[2,3-d]pyrimidines as Potential Chemotherapeutic Agents
  作者：Vishnu Ji Ram

  DOI：10.1002/ardp.19793120105

  日期：——

  A series of new thieno[2,3‐d]pyrimidine derivatives with a carbocyclic ring fused at positions 5 and 6 have been synthesised in order to study their pesticidal activity. Some of the compounds exhibit significant biological activity.

  为了研究其杀虫活性，合成了一系列在 5 和 6 位具有稠合碳环的噻吩并 [2,3-d] 嘧啶衍生物。一些化合物表现出显着的生物活性。
• [EN] COMPOUNDS, THEIR SYNTHESES, AND THEIR USES<br/>[FR] COMPOSÉS, LEUR SYNTHÈSE ET LEURS UTILISATIONS
  申请人：UNIV LOUISVILLE RES FOUND

  公开号：WO2010019861A1

  公开（公告）日：2010-02-18

  Embodiments of the present invention provide compounds (such as Formula (I) compounds, Formula (II) compounds, and various embodiments thereof). Compositions comprising those compounds are also provided. Methods for their preparation are included. Also, uses of the compounds are included, such as administering and treating diseases (e.g., cancer and infections).

  本发明实施例提供化合物（如式（I）化合物、式（II）化合物及其各种实施例）。还提供包含这些化合物的组合物。包括它们的制备方法。此外，还包括化合物的用途，如给药和治疗疾病（例如癌症和感染）。
• Molecular dynamics-based discovery of novel phosphodiesterase-9A inhibitors with non-pyrazolopyrimidinone scaffolds
  作者：Zhe Li、Xiao Lu、Ling-Jun Feng、Ying Gu、Xingshu Li、Yinuo Wu、Hai-Bin Luo

  DOI：10.1039/c4mb00389f

  日期：——

  Viamolecular dynamics-based virtual screening, 15 novel phosphodiesterase-9A inhibitors with five non-pyrazolopyrimidinone scaffolds were discovered.

  通过基于分子动力学的虚拟筛选，发现了具有五种非吡唑吡嘧啶骨架的15种新型磷酸二酯酶-9A抑制剂。
• Computer-aided identification, synthesis and evaluation of substituted thienopyrimidines as novel inhibitors of HCV replication
  作者：Marcella Bassetto、Pieter Leyssen、Johan Neyts、Mark M. Yerukhimovich、David N. Frick、Andrea Brancale

  DOI：10.1016/j.ejmech.2016.07.035

  日期：2016.11

  technique was applied to the study of the HCV NS3 helicase, with the aim to find novel inhibitors of the HCV replication. A library of approximately 450000 commercially available compounds was analysed in silico and 21 structures were selected for biological evaluation in the HCV replicon assay. One hit characterized by a substituted thieno-pyrimidine scaffold was found to inhibit the viral replication with

  基于结构的虚拟筛选技术已应用于HCV NS3解旋酶的研究，目的是寻找HCV复制的新型抑制剂。在计算机上分析了大约450000种可商购化合物的文库，并选择了21种结构用于HCV复制子测定的生物学评估。发现一个以取代的噻吩并嘧啶骨架为特征的命中物以亚微摩尔范围的EC 50值和良好的选择性指数抑制病毒复制。设计并合成了不同系列的新型噻吩并嘧啶衍生物。几个新结构显示出在低或亚微摩尔范围内的抗病毒活性。
• Design, synthesis and anticancer evaluation of thieno[2,3-d]pyrimidine derivatives as dual EGFR/HER2 inhibitors and apoptosis inducers
  作者：Souad A. Elmetwally、Khaled F. Saied、Ibrahim H. Eissa、Eslam B. Elkaeed

  DOI：10.1016/j.bioorg.2019.102944

  日期：2019.7

  tyrosine kinase family is one of the most important targets in current cancer therapy regimens. In this study, we have designed and synthesized a series of thieno[2,3-d]pyrimidine derivatives as an EGFR and HER2 tyrosine kinase inhibitors. All the synthesized compounds were evaluated in vitro for their inhibitory activities against EGFRWT; and the most active compounds that showed promising IC50 values

  许多激酶的失调与癌症的发展直接相关，酪氨酸激酶家族是当前癌症治疗方案中最重要的靶标之一。在这项研究中，我们设计并合成了一系列噻吩并[2,3-d]嘧啶衍生物，作为EGFR和HER2酪氨酸激酶抑制剂。在体外评估所有合成的化合物对EGFRWT的抑制活性。并测试了对EGFRWT表现出有希望的IC50值的最具活性的化合物对突变EGFRT790M和HER2激酶的抑制活性。此外，测试了这些化合物对四种癌细胞系（HepG2，HCT-116，MCF-7和A431）的抗肿瘤活性。化合物13g，13h和13k对所检查的细胞系表现出最高活性，IC50值为7.592±0。相当于厄洛替尼的32至16.006±0.58 µM（IC50为4.99±0.09至13.914±0.36 µM）。此外，选择了最有效的抗肿瘤药（13k）进行进一步研究，以确定其对MCF-7细胞系中细胞周期进程和细胞凋亡的影响。结果表明，该化合物阻滞了细胞周期的G2