4-氯-5-甲基-6-苯基噻吩[2,3-D]嘧啶 | 306934-78-1

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 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-氯-5-甲基-6-苯基噻吩[2,3-D]嘧啶
• 英文名称: 4-chloro-5-methyl-6-phenylthieno[2,3-d]pyrimidine
• CAS: 306934-78-1
• 化学式: C₁₃H₉ClN₂S
• mdl: MFCD02179828
• 分子量: 260.747
• InChiKey: LRTKDTZXCFGPEU-UHFFFAOYSA-N

物化性质

• 熔点：
  131-132
• 沸点：
  407.1±40.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 海关编码：
  2934999090

SDS

Name:	4-Chloro-5-methyl-6-phenylthieno[2 3-d]pyrimidine 97% Material Safety Data Sheet
Synonym:
CAS:	306934-78-1

Section 1 - Chemical Product MSDS Name:4-Chloro-5-methyl-6-phenylthieno[2 3-d]pyrimidine 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
306934-78-1	4-Chloro-5-methyl-6-phenylthieno[2,3-d	97%	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
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 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.

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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# 306934-78-1: 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: 131 - 132 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: C13H9ClN2S
Molecular Weight: 261

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, amines.
Hazardous Decomposition Products:
Hydrogen chloride, chlorine, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 306934-78-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Chloro-5-methyl-6-phenylthieno[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
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# 306934-78-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 306934-78-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 306934-78-1 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-氯-5-甲基-6-苯基噻吩[2,3-D]嘧啶 在 potassium fluoride dihydrate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  人法呢基焦磷酸合酶基于硫代嘧啶的单膦酸酯（ThP-MP）抑制剂的药理学定位。

  摘要：

  人法呢基焦磷酸合酶（hFPPS）是甲羟戊酸途径中的关键调节酶，催化C-15异戊二烯类法呢基焦磷酸（FPP）的生物合成。FPP在执行大量细胞功能的小GTP酶的翻译后异戊烯化中起关键作用。尽管hFPPS是溶骨性疾病的公认治疗靶标，但目前可用的双膦酸酯类药物表现出不良的细胞摄取能力，并分布到非骨骼组织中。最近的药物发现工作主要集中在hFPPS的变构抑制和发现潜在用于治疗非骨骼疾病的非双膦酸酯药物上。一系列基于硫代嘧啶的单膦酸酯（ThP-MPs）的先导性优化导致鉴定出具有纳摩尔浓度抑制hFPPS的类似物。它们与酶的变构口袋的相互作用通过晶体学表征，并且结果提供了对变构抑制的药效团要求的进一步见解。

  DOI：

  10.1021/acs.jmedchem.6b01888
• 作为产物：
  描述：

  5-甲基-6-苯基噻吩[2,3-D]嘧啶-4-醇 在 三氯氧磷 作用下， 反应 5.0h， 以79%的产率得到4-氯-5-甲基-6-苯基噻吩[2,3-D]嘧啶
  参考文献：
  名称：

  Thieno[2,3-d]pyrimidine als Glutamatantagonisten

  摘要：

  尽管Kainat受体在大脑中的功能目前尚未完全阐明，但它们在文献中越来越多地被定义为开发新型抗癫痫药物的新靶点。我们合成的噻吩并嘧啶类化合物被检测了其对Kainat受体亚型GluR5和GluR6的拮抗作用。效果最佳的是一种4-乙氧基噻吩并[2,3-d]嘧啶，它在GluR6受体上的IC50值为68 μM。

  DOI：

  10.1691/ph.2008.8600

文献信息

• Thieno[2,3-d]pyrimidine als Glutamatantagonisten
  作者：Briel、Rybak、Kronbach、Unverferth

  DOI：10.1691/ph.2008.8600

  日期：——

  Obwohl die Funktion von Kainat-Rezeptoren im Hirn aktuell noch nicht vollständig geklärt ist, werden diese in der Literatur zunehmend als neue Zielobjekte bei der Entwicklung originärer Antiepileptika definiert. Die von uns synthetisierten Thienopyrimidine wurden auf eine antagonistische Wirkung an den Kainat-Rezeptor-Subtypen GluR5 und GluR6 untersucht. Die beste Wirkung erzielte ein 4-Ethoxy-thieno[2,3-d]pyrimidin mit einem IC50 von 68 μM am GluR6-Rezeptor. Thieno[2,3-d]pyrimidines as antagonists of the glutamate receptors Although the function of the kainate receptors in the brain is still not clear, they are increasingly defined as targets in the development of new classes of anti-epileptics. The thienopyrimidines described in this report were tested for their antagonistic effect at the kainate receptor subtypes GluR5 and GluR6. The highest effectiveness was obtained by a 4-ethoxy-thieno[2,3-d]pyrimidin with an IC50 = 68 μM at the GluR6 receptor.

  尽管Kainat受体在大脑中的功能目前尚未完全阐明，但它们在文献中越来越多地被定义为开发新型抗癫痫药物的新靶点。我们合成的噻吩并嘧啶类化合物被检测了其对Kainat受体亚型GluR5和GluR6的拮抗作用。效果最佳的是一种4-乙氧基噻吩并[2,3-d]嘧啶，它在GluR6受体上的IC50值为68 μM。
• The Discovery and Development of Thienopyrimidines as Inhibitors of <i>Helicobacter pylori</i> That Act through Inhibition of the Respiratory Complex I
  作者：Alex K. Mugengana、Nicole A. Vita、Autumn Brown Gandt、Kevin Moran、George Agyapong、Lalit K. Sharma、Elizabeth C. Griffith、Jiuyu Liu、Lei Yang、Ekaterina Gavrish、Kirk E. Hevener、Michael D. LaFleur、Richard E. Lee

  DOI：10.1021/acsinfecdis.0c00300

  日期：2021.5.14

  binding and poor solubility. Although lead compounds in the series demonstrated efficacy in an ex vivo infection model, the compounds had no efficacy in a mouse model of H. pylori infection. Additional optimization of pharmacological properties of the series to increase solubility and free-drug levels at the sequestered sites of H. pylori infection would potentially result in a gain of in vivo efficacy. The

  由于对当前广谱三联疗法的耐药性增加，幽门螺杆菌感染的成功治疗变得越来越困难。在寻找针对幽门螺杆菌的窄谱药物时，高通量筛选确定了两种结构相关的噻吩并嘧啶化合物，它们选择性地抑制幽门螺杆菌而不是肠道微生物群的共生成员。建立噻吩并嘧啶对幽门螺杆菌的构效关系 (SAR)，这项研究采用了四系列修改，其中探索了对噻吩并嘧啶核心的系统取代，最终从两个原始命中优化的侧链元素合并到先导化合物中。在本系列的开发过程中，作用模式研究将幽门螺杆菌的呼吸复合物 I 亚基 NuoD 确定为噻吩并嘧啶铅的靶标。由于这种酶复合物对于 H. pylori 中的 ATP 合成至关重要，因此生成了H. pylori NuoB-NuoD 结合界面的同源模型，以帮助合理化 SAR 并指导该系列的进一步开发。从这些研究中，出现了具有增强的抗幽门螺杆菌效力的先导化合物、改进的安全指数和良好的总体药代动力学特征，但蛋白质结合率高和溶解度
• N-aryl-thienopyrimidin-4-amines and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cai Xiong Sui

  公开号：US20070099877A1

  公开（公告）日：2007-05-03

  Disclosed are N-aryl-thienopyrimidin-4-amines and analogs thereof, represented by the Formulae I-II: wherein Ar and R 1 -R 4 are defined herein. The present invention relates to the discovery that compounds having Formulae I-II are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  揭示了N-芳基噻吩吡嘧啶-4-胺及其类似物，由以下的式子I-II表示：其中Ar和R1-R4在此有所定义。本发明涉及发现具有式子I-II的化合物是半胱氨酸蛋白酶的激活剂和凋亡诱导剂。因此，本发明的半胱氨酸蛋白酶激活剂和凋亡诱导剂可用于诱导在各种临床病况中发生细胞死亡，这些病况中存在细胞不受控制的生长和异常细胞的扩散。
• Thieno[2,3-d]pyrimidines and -[1,3]oxazines as glutamate antagonists and investigations on the inhibitory potency toward human leukocyte elastase
  作者：Detlef Briel、Anastasiya Rybak、Christiane Kronbach、Klaus Unverferth、Camino M. González Tanarro、Michael Gütschow

  DOI：10.1002/jhet.375

  日期：——

  Thieno[2,3‐d][1, 3]oxazin‐4‐one 2 (R = C2H5) was identified as new a potent inhibitor (IC50 = 17 μM) of this receptor subtype. The inhibitory potency of 2 (R = C2H5) against human leukocyte elastase was also examined. The compound was characterized as a noncovalent inhibitor with an IC50 value of 8.8 μM. J. Heterocyclic Chem., (2010).

  一系列稠合的噻吩衍生物，即，噻吩并[2,3-代表d ]嘧啶，噻吩并[2,3- d ] [ 1，3 ]恶嗪和噻吩并[2,3- d ] [ 1，3 ]合成了具有共同的5-甲基-6-苯基取代模式的噻嗪。目标化合物，例如，7或8，被设计为2-氨基-4-甲基-5-苯基噻吩-3-羧酸乙酯，在GluR6红藻氨酸受体的拮抗剂的环状类似物。噻吩并[2,3- d ] [ 1，3 ]恶嗪-4-酮2（R = C 2 H ^5）被确定为新的强效抑制剂（IC 50 = 17μ中号这个受体亚型的）。还检查了对人白细胞弹性蛋白酶的抑制力2（R = C 2 H 5）。将该化合物表征为具有IC非共价抑制剂50 8.8μ值中号。J.杂环化​​学。（2010）。
• Aryloxypropanolamines, methods of preparation thereof and use of aryloxypropanolamines as medicaments
  申请人：4SC AG

  公开号：EP1947103A1

  公开（公告）日：2008-07-23

  This invention relates to novel aryloxypropanolamines. The invention also relates to the pharmaceutically acceptable salts and solvates containing said compounds, methods for the preparation thereof and to respective synthesis intermediates. Said compounds have agonistic activity at β3 adrenergic receptors and are useful for treatment of ailments influenced by activation of β3 adrenergic receptors.

  本发明涉及新型芳氧基丙醇胺。该发明还涉及含有所述化合物的药学上可接受的盐和溶剂化物，其制备方法以及相应的合成中间体。所述化合物在β3肾上腺素能受体上具有激动作用，并且可用于治疗受到β3肾上腺素能受体激活影响的疾病。